🎧 Psst — Open this issue on the Substack App to hear the audio version

• 🌞 The day my (undiagnosed) anxiety disorder developed

• 🙊 Why moving fast and moving forward aren't the same thing (and how I came to love OHIO)

• 🛠️ The succession plan you need to start now — and how to do it

• 🔪 Some dark art

• 🎶 A song stuffed with all the things you want

• 🔮 "You" Will Likely Not End With "You"

• 🔥 Your Burning Question: How to close a business without calling it giving up

• ➕ Some killer memes, some lighter and heavier things from the internet, and an acronym I’m gifting to you from the ghost of my CEO past

I was thirteen, sitting in a portable classroom that smelled like pencil shavings and the ghost of a hundred bologna sandwiches, when my science teacher said something that rattled my brain…

“One day, the sun is going to die.” 😳

He continued, “not tomorrow or for billions of years. But it will happen. It will burn through its fuel, swell into something monstrous, and eventually go dark. ⚫️ And as a result, the earth will go with it.” 🌎

(I’m paraphrasing. Maybe he didn’t say it so dramatically, but I remember the feeling being just as intense).

I was staring at the little diagram in my textbook, the depiction of a star going from yellow to red to nothing, and feeling something crack inside me as I visualized clips of all the things that would cease to (eventually) be. 😱

The ocean, my favorite t-shirt, the Eiffel Tower (I hadn’t even seen it yet), and oh my god, even Devon Sawa! 🧒

The concept that everything humans ever built or created on this planet would eventually just be expansive stardust hanging in the vastness of space, was unsettling!(Frankly, it still is). 🌌

And what if scientists had it wrong? What if it happened today? Or next week? What if they were mistaken on the timeline? 🔥

Thirteen-year-olds aren’t supposed to think about heat death. We’re supposed to think about who we’re sitting with at lunch, 🥪 and whether our jeans are the “right kind” of jeans (and/or whether Devon Sawa might think I was cute if he met me). 🤩

All of that felt moot that day. And I couldn’t unknow it.

While everyone seemed to absorb this absolutely insane new fact and carry on about their day, I carried the heft of it home on the bus. 🚌

🔭 Zooming In & Out

What melted my brain the most was that I couldn’t help but keep sliding back and forth between this type of perspective telescope.

Zooming out far enough where everything shrinks. 🦠

My homework. The latest argument with my best friend. The brand label of my jeans. All of it a rounding error against a (5 billion year) countdown clock. ⌚ Thinking about it for too long made everything start to feel so insignificant that it was hard to make anything matter. Including little old me.

But zoom back in, 🔎 and the opposite is true.

If nothing lasts, everything is a gift because it expires. Your lifetime. The chance to build, experience, create, love. That’s the whole meaning of it right there. Every day is a significant opportunity — which means every hour is too. Every minute. 🤯

Once we spend our time, it’s gone. 💨

There are no second chances. There is no second sun. ☀️

🌀 [insert the exact moment my undiagnosed anxiety disorder developed here] 🌀

The concept of time and space, finality and legacy, life and death really sunk into my being that day in class. As a result, I developed a keen sense of urgency that hasn’t left me since.

And that urgency has pretty much dominated how I execute in business and in life, sometimes to a fault. 😬

Escape Velocity 🚀

While building RAW, my executive team used to make fun of me because I’d repeat the phrase “this is a critical, pivotal time.”

Everything was critical and pivotal to me (almost) every day. Ha!

It became so frequent in our chats that they even turned it into an acronym — “CPT.” Asking me (half joking) whether or not this next task was a CPT (#funny but also #rude). 😆

I was moving fast. Breaking things. Sometimes even breaking my team as a result. 😬

For me, once I had looked through that proverbial telescope way back when, I could never stop toggling between the two views: zoomed out, 🔭 where nothing matters; zoomed in, 🔎 where this — today, this decision, this conversation, this task — is all there is.

Everything was and is important (not to mention, the zoomed in version of things was much more comfortable than full-blown nihilism).

🪐 Anyone else ever think about the fact that we're all just spinning on a rock in an endless, expanding universe, surrounded by nothingness while worrying about our MRR? ✨

I’d bet that builders like you also toggle between the macro and the micro, but you probably live in the zoomed-in view. 🤷‍♀️

Moving, deciding, taking action — because time is too precious to waste, and reading the instructions, or waiting for them, seems even more wasteful.

(I get it. We’re on the same wavelength.) 🛰️

On the flip side, the builders who delay and drag their feet — on the launch, the next hire, the conversation they keep meaning to have, or worse, the business they’ll build “someday” 🐌 — keep their world small. 🐜 And as time ticks on (tomorrow’s never promised), it might eventually become too late. 👴

Here’s the beautiful thing about moving fast 🏃‍♀️ — energy forms around you. 💫
The more you execute, the more experience, relationships, and opportunities you rack up, which lead to more of all three. Your universe only keeps expanding. ✨

There’s a built-in accountability that comes with time running down. ⌛️

How are you spending yours?

So yeah, I had a lot of CPTs. Because I believe today's fragments and small everyday actions make up the entirety of whatever "much bigger" thing you're creating. Every action, decision, and contribution — stacked on top of each other, stuffed into the crevices — makes up the whole of it.

I think the difference between builders isn’t just in how they execute, or how fast they move. It’s in how much care they take making sure the pieces going into that larger container are quality. 🫙

And those differences leave a mark — on your team, your customers, and the world at large. 🌏

This month, I want to talk about Legacy — the view from way out on the telescope — and Execution — what’s in frame when you zoom all the way in. Because I’ve come to believe they’re not two separate topics. They’re the same conversation, at different distances.

Legacy is the view from space. 🪐 Execution is what you’re doing today to meet it. 📆

Let’s get into it. 👇

🙊 Quiet Part Out Loud: Urgency Isn’t Always the Best Execution Strategy

I’ve grown up a lot since my days of naming almost everything a “Critical, pivotal time.” 😆

And partially that was due to my executive team’s encouragement to slow down, measure twice 📐 and cut once ✂️ (thanks, Vy). The tension between my running fast and their ability to make me stop and think through the objectives and outcomes is what made us a dynamic and winning team. 🏆

The truth is things weren’t always critical. It wasn’t always pivotal. We weren’t curing cancer or sending people to the moon.

A lot of the time, it was just me, speeding forward because I had goals that I created for our growth. And I wanted them done sooner than later because, time (or maybe anxiety? Or both? 🤷‍♀️). I gave our team artificial deadlines (usually with razor thin margins for error) to make them happen.

Checking those goals off the list on time was so satisfying, it made me feel like we were indeed moving onward.

But I also remember stressing people out. Moving too fast and breaking things I didn’t mean to (or want to) break including team members, relationships and maybe even trust. 😣

Moving fast isn’t always the same thing as moving forward. Sometimes it sets you several paces backward, in fact.

The lesson I learned above all is that urgency and execution can look identical from the outside.

But they aren’t.

I’ve sat on the other side of the rubble a few too many times and it’s shifted my work strategy (or maybe I’ve just slowed down with age 👵). As I’ve matured in leadership and experience I’ve come to realize that while a sense of urgency is a fantastic trait, and a bias toward action is absolutely necessary — urgency for the sake of urgency, without a thoughtful plan can be reckless. 🧨

You can have all the urgency in the world and still finish the day having produced nothing but a handful of half-done things. You could be working on 30 different things that are all the wrong types of things for your ultimate objective. 🌪️

You must zoom out to truly focus in. 🔭

⚾️ I love OHIO

Have you heard the term OHIO? (not the Gen-z phrase that means lame). It’s a different type of acronym that stands for: Only Handle It Once. (Who knew there was an acronym for my internal OS?).

I read it as: Spend the time now. Fully fuse it together. Finish it. Make sure it’s sound, so you don’t need to re-do it or re-jig it later.

To me, OHIO is the practice of avoiding starting a pile of problems for “future you.”

There’s less adrenaline rush tied to working this way, and sometimes it might even feel boring or tedious or daunting. But after having a hand in building 10 different companies, investing in 18 and watching all the different versions of (unnecessary) fire drills over the years 👨‍🚒 — I’ve learned the best task is one that you can call, (at least) 99% done.

The version of urgency I run on now looks nothing like the version I started with at 24. It’s quieter. It has fewer exclamation points. It asks “does this actually need to happen today, or does it just feel like it does?” Can we sit and think before we execute? Can we test a few more times before we blast off? 🚀

I’m a big fan of calm deadlines these days, where things get done fast, but with thoughtful, well-crafted pieces that fit into the grander picture. 🧩

🔥 Little Fires Everywhere

When you haven’t decided what actually matters, what’s priority, what is the best and highest use of your time or what you’re actually aiming at, everything matters equally, and sometimes everything feels like a thousand burning fire balls (a CPT, if you will). ☄️

Take it from me — that type of chaos is exhausting, and you will burn yourself down quickly working this way. 💨

I built an entire company partially fueled by CPT energy, and I’m not saying it didn’t work — clearly, it was effective. I don’t argue with the fact that this might just be what’s required of any bootstrapping founder for at least a period of time.

But reflecting on it, I ask at what expense?

My nervous system burnt to crisp? A worn down team? A jam-packed schedule with no time to rest?

So if you’re the founder who’s proud of how fast you move, how many fires you put out, how “on it” you always are — I’d just gently ask: does it have to be so intense? Are you building the right thing in the first place? For the long term you and the version of your company? 🏆 Is everything a fire? What could you prevent instead? 🐻🌲

Move with urgency, yes. Take action, absolutely. Just make sure it’s pointed at something that is reflecting the impression you want to leave on the people around you and the world at large. 🌎

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🛠️ Usable Things: To Build Your Legacy, and Make Yourself Replaceable (on purpose)

Here’s the paradox — the same sense of LFG that gets a business off the ground 🚀 is often the thing silently making sure it can never run without you.

When you’re bootstrapping, you are the company. You’re the ops manual, the org chart, the customer relationships, and the password manager, all stuffed into one exhausted (and likely overly caffeinated) human. ☕️ Who has time to plan for a version of the business that doesn’t need you, when the version that exists right now can barely survive with you? 🥴

Here’s what I encourage you to consider: The best time to build a business that can survive without you is before you desperately need it to.

Not because you’re planning to leave or because something’s wrong. But because a business that only works when you’re in the room isn’t a business — it’s a very demanding job you invented for yourself. 💼

🤫 I’ll say the super duper quiet part now, the one wrapped deeper inside this issue: As an owner who may be responsible for many families' livelihoods (not just your own), you also need a will. A trust, if it makes sense for your situation. A power of attorney, and a healthcare directive — the whole dark folder of documents nobody wants to think about, 📂 because thinking about them means admitting you’re mortal. 🪦

(My husband and I are in the middle of this process now, and man, it’s sobering. We’ve had to decide who would care for our kids, dogs, manage assets, liquidate investments — oof. It’s heavy). The more you’re responsible for — the more this should be on your radar. 📡

Most founders I know have more documentation for their company vacation policy than for what happens to their family, or their company, if they get hit by a bus next week. 🚌⚡️

Might sound morbid. But it’s a real liability you should be thinking about.

I’m not going to spend this usable tools section walking you through estate law — that’s not my lane (and this is not legal or financial advice), and frankly, it’s one good search and an estate attorney away from OHIO. But what I can talk to you about — because I’ve lived it, built it, and rebuilt it (more than once) — is the version of succession planning that lives inside your actual business. The kind you can start today, for free, with the tools already open in one of your desktop tabs…

Here are some tips and tools that can help:

📝 Document like someone else has to run this tomorrow.
You can’t pass forward something that only lives in your head. Every process, every vendor relationship, every “oh, I just know to do it this way” — write it down, step by step. Include the tools, materials, accounts, and passwords needed. These are the keys that let others do it without you. Pass it over. Watch them do it. Add the parts you forgot. Note the nuances. Revisit often. Install AI into what you can.

• 🧰 Tools: Loom or Tango — record yourself doing the task once and it auto-generates a walkthrough, capturing the “oh, and also” steps you’d forget to type out. Or good old Google Docs — fast, free, and likely already in your workspace.

🔑 Get out of single points of failure.
If only you know the login, only you can approve the invoice, only you can talk to your biggest client — you haven’t built a business, you’ve built a bottleneck with a logo. Cross-train. Share access (securely). Make sure at least one other human could keep the lights on for two weeks if you need a break (what a thought), or god forbid something worse.

• 🧰 Tools: A shared password manager like 1Password (I love this product). Everyone gets their own master login to the accounts you set, plus a designated emergency-access contact. Fifteen minutes to set up. A lot of peace of mind. Someone leaves your team — you cut access in two seconds.

🧍‍♂️🧍‍♀️ Build your org chart before you have the org.
Even at a team of one, sketch out the roles the business will eventually need — not the people, the functions. Sounds premature. It’s not. Group like skills and similar tasks together and you’ll start to see job descriptions form. It’s the difference between growing on purpose and growing by accident.

• 🧰 Tools: Just a spreadsheet. Columns for Function, Current Owner (probably you), and Who Could Cover This in a Pinch. Skills and Experience required. Revisit quarterly.

💌 Decide, on paper, what happens if you can’t decide.
Who has authority if you’re unreachable? Who signs? Who calls the shots for 48 hours while you’re offline? Not dramatic. Just what adults with something to protect do.

This is the version of legacy that has nothing to do with being remembered, and everything to do with being replaceable — in the best sense. A business that depends entirely on you won’t drive a legacy. Build the thing so it can outlive the version of you that built it.

You want a level of craftsmanship that stands the test of time. 🗿

🧰 More tips & tools:

• ⚖️ For the actual legal stuff: Trust & Will, or a referral to a local estate attorney if your situation has any complexity (ask your network — a banker recommended mine). This is the one item on this list I’d spend real money on. Least fun, most important line item you’ll pay for this year — for context, this process is costing us $5k.

  • If you opt out of this — (and god forbid something horrible happens) you might want to read up on the probate process. Brutal.

  • If you don’t have a ton of budget right now, you could write your wishes down on a single sheet of paper. Keep it safe. According to my estate attorney, it can suffice in the absence of a legal Will or Trust document, but it can’t save you from probate.
    

• ✍️ For deciding who signs when you can’t: If you’re incorporated, revisit your operating agreement or bylaws for exactly this scenario. If you don’t have one — or it’s five years dusty — you know what to do.
  

• 💰 For how your business might live on: Planning to sell one day? You’ll want to prepare in a number of ways. But namely, clean financials, IP ownership and documentation of that ownership + a clear tax strategy. ⚠️ If you’re not currently set up to take advantage of QSBS, you might leave a big chunk of legacy on the table. Your CPA can help you with all of it.

Also, no affiliate links here — just stuff I think is worth your precious time.

☠️ I’m dying…

🎶 A Song Stuffed with Experience

Musical artist R Lee is trying to fly under the radar with his new project, Born Runner — but I found him. [insert maniacal laugh here] 😈

After years and years of producing music for film, television, and ads, Mr. Lee (who is apparently trying to be a ghost online) 👻 has quietly dropped several punchy jams under the moniker Born Runner.

This month I'm highlighting his song "How U Want It." The synthy bass, grungy guitar, and grainy vocals take me straight back to the late '90s — poolside, the smell of Sun-In Lemon Fresh hair lightener, a glossy Seventeen magazine sitting next to the Pepsi the Spice Girls told me to buy. 🥤 A different time.

This song gives me back some energy from my youth while simultaneously reminding me that there’s so much left to taste in life.

Enjoy this one — stuffed with experience and crisp execution. ✅

🎨 Some Dark Arts

Digital artist Morgan Sorensen goes by the pen name See Machine. His work is deeply human — mortality, loss, the ways we quietly inflict pain on ourselves 🔪 — rendered with the kind of mechanical precision that makes the darkness feel earned rather than performed. ☠️ Pieces like Ego Death and Posthumous Radiance sit uncomfortably close to this month’s theme, which is either a coincidence or proof he’s been staring at the same telescope I have. 👀

Still, Sorensen has a sense of humor about all of it. His bio reads: “Don’t bring me to parties, I’m clearly a real bummer.” 😆

Though the work is dark and macabre (he’s clearly a Scorpio), 🦂 I find it honest, thoughtful, and empathetic underneath the skulls and altars. Sorensen starts every piece in pencil before moving it digital — you can feel that hand-built patience in the linework, even once it’s fully rendered.

Check out more of Morgan’s work on his website.

🔮 Future Cast: “You” Will Likely Not End With “You”

Here’s where legacy stops being a metaphor and starts getting genuinely strange.

People are already uploading themselves. Not their businesses — themselves. Their voice, their mannerisms, years of text messages and voice memos and video, all fed into AI systems designed to let the people they love keep talking to them after they’re gone. 😳

Note: If you haven’t seen the mini series Years and Years (HBO, 2019) it does an incredible job of predicting what this actually looks like. This show has haunted me. I think about it often. Recommend!

There are already startups built entirely around this. Grief tech. 💀 Digital afterlives. 👻 AI models trained on a deceased parent’s emails so their kid can still ask them for advice. 💻 Companies letting you record hours of yourself now, 🎙️ specifically so a future version of “you” can keep showing up at Sunday dinner long after you can’t. 🕯️

Sit with that for a second, because I had to. 🫥

Here’s what I think is coming:

👻 “Digital estate” might becomes a real line item.
Right now your will covers your house and your savings account. Soon it’ll need to cover your data — do you want a version of you trained on your texts talking to your grandkids in 40 years? Who owns that decision? Who owns the model?

🧬 Legacy stops being a look-back and starts being a product.
For generations, legacy meant: what did you leave behind. Soon, for some people, it’ll mean: what did you leave running. An interactive version. A presence that persists, that can be asked new questions it never got to answer in life.

💔 Grief tech becomes a genuine ethical minefield.
Is talking to an AI trained on your late father comforting, or does it quietly rob you of the closure that comes from an ending actually being an ending? I don’t think we know yet. I think the first generation to really live through this at scale is going to teach the rest of us something we can’t currently see.

🏗️ For builders specifically: this is either an enormous emerging category, or an ethical third rail, or (most likely) both at once. If you’re building anywhere near memory, identity, data permanence, or grief — the next few years are going to be foundational for how this entire space gets shaped. Tread thoughtfully though. This is the rare corner of tech where “move fast” should probably lose to “move correct.”

I don’t know exactly how I feel about a version of me still answering emails in sixty years (let my tired soul rest). Some days it sounds like a comfort. Some days it sounds like the opposite of the whole point — that things are supposed to end, and the ending is what makes the middle matter. 🌗

But I know it’s coming, one way or another. And I’d rather we talk about it now, with our eyes open, than back into it by accident.

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🪶 Lighter & Heavier 🪨 things from the internet…

😆 Lighter…

🐮 Wardrobe for when you’re in a hurry

📺 When you wish the sun would quit - this one makes me laugh out loud

📱 People who weren’t looking ahead

🖇️ Things we’ll all likely leave behind

💋 A Long Kiss goodbye

🥲 Heavier…

🚶‍♂️ A long walk with Al

🪑 A conversation I could never have with my kids (without sobbing) —Bravo, dad!

💜 A poem that will give you a lump in your throat

🗓️ End of Summer Calendar

🪽 9.9 | Cherub’s Creator Angel Summit - We’re hosting 100 creators for a one-day summit educating on angel investing, startup equity, and ownership. Creator? Apply.

🗽 9.7-9.11 | I’ll be in NYC, wanna grab coffee? Hit reply.

🥾 9.17 | Find Profit & Sustainability: 6-Week Small Business Bootcamp at the ERC in Temecula kicks off this day. If you’re in the I.E you can join me for Free

🔥 Your Burning Questions

“How do you actually let go of a business that isn’t working, that you’ve spent so much time and energy on without feeling like you’re just giving up?”

— Anonymous builder, Long Beach, CA

Oh, this one’s close to home. 🫠

I want to gently push back on the framing first, because I think the word “giving up” is doing a lot of damage in that sentence. Giving up implies you quit on something that still had a pulse. 🫀 What you’re actually describing — deciding to close something that isn’t working — is closer to making a call. And making the call, (even the hard one), is still execution. It’s just execution pointed at an ending instead of a launch. 🏁

Here’s how I think about it:

🔍 1. Separate the sunk cost from the signal.

Ask yourself honestly: am I staying because the data says this is close to working, or because I’ve already put so much in that stopping feels unbearable? Those are two completely different reasons to keep going, and only one of them is a good one. Time, money, identity — all of it makes closing something feel like losing a piece of yourself. It’s not. It’s just accounting. (But it might feel like that for a while).

📉 2. Get specific about what “not working” actually means.

Vague dread (“this doesn’t feel right anymore”) and hard evidence (“revenue has declined three quarters running and I can’t identify a fixable cause”) require completely different responses. The first might mean you need a break, a pivot, or a new co-pilot. The second might mean it’s time.

Don’t let the emotional version stand in for the data version — get clear on which one you’re actually dealing with.

🗓️ 3. Set a real deadline, not a vibe.

“I’ll give it a little longer” is how projects limp along for years past their expiration date. Pick an actual date. Pick actual metrics. If you hit the date and the metrics aren’t there, you’ve already made the decision — you’re just executing on a call your past self made with a clearer head.

🪦 4. Let it have an ending, on purpose.

Don’t just quietly stop posting, stop showing up, let the thing fade into vapor. Close it deliberately. Tell your customers. Tell your team, if you have one. Write the last chapter instead of just letting the pages stop turning. A defined ending is what lets you actually walk away from something — an undefined one will just haunt you.

🧱 5. Take the receipts with you.

Nothing you built was wasted if you extract what it taught you. The systems you built, the audience you found, the thing you learned about yourself under pressure — that’s not lost when the business closes. That’s the actual legacy of the thing. The business was just the vehicle.

I saw a video clip recently from a chat Chamath Palihapitiya gave at a college campus, and it really resonated.

Take a look:

Here’s the truth nobody tells you when you’re deep in the identity of Founder: not everything is supposed to be forever, and that’s not a failure of the thing — that’s just what things are. The sun isn’t going to burn forever either, and nobody calls that a tragedy. It’s just the shape of things having a beginning, a middle, and an end. 🌖

Sunset it with your chin up (if that’s what you decide to do). That’s not giving up, that’s executing on your next phase. Letting something finish it’s burn.

P.S., If you, dear reader are sitting with a version of this decision right now — hit reply. I mean it. I’ve closed things before, and I’m happy to talk you through it.

📫 NEXT LETTER: 🤝Networking 🤝 & 🧱 Building Relationships 🧱

For the longest time, I thought my legacy would be RAW Artists, and RAW Artists alone. I poured every grain of my being — for better, (and at times for worse) — into it for 11 years straight.

I wasn’t thinking much about succession planning. I was building with blind momentum, for the long haul. 👵

It wasn’t until my own supermassive black hole (COVID) that I was forced to reckon with the ending and refocus the whole telescope. ⚫️

At the time, my small slice of the universe was experiencing multiple deaths simultaneously: the death of the company as I’d built it, the death of my identity as an every-day-in-the-office CEO, and the death of all the hopes and plans I’d pinned to my envisioned future. 🪦 🥀

I had to ask myself: Who was I if my company might not exist anymore? If I didn’t have a team? If we had to scrap it all? What does starting over even look like? What would my legacy even be, if not that?

That was a hard hole to sit in. 🕳️ (Don’t worry, I eventually climbed out).

Here’s what that collapse taught me: the zoomed-out view — the death of a star, a company, a chapter, a version of yourself — is both inevitable as a result of being alive and sometimes completely beyond your control. (You never know when a bus, an asteroid, or a global pandemic might strike.) ⚡️

And sometimes it’s not the full stop ending you thought it would be. Sometimes it’s the perfect opportunity for the beginning of something new. 🌱

Which is exactly why the zoomed-in view is important. Putting energy into the things that are in front of you right now. The things that compound your skills and sharpen your mind every day. 🗓️ No one can take what you’ve learned away from you.

Move fast. Have a sense of urgency. Decide. Take action. Build. GO! 🚦

As long as you’re healthy, capable, and have a desire to create a brighter future — start now. ⏰

Not tomorrow. 🕰️

But also be intentional. Think things through. 🤔 Be mindful of the quality (or lack thereof) you’re leaving in your wake.

Because nobody truly has “build legacy” on their to-do list.

More likely, you have a daily list of tasks. ✅
Answer emails, do that thing you’ve been dreading, ship the other thing, keep your word, build a relationship. Follow up. Repair the small tear before it becomes a giant rip. 🩹

You do all of that on a random Wednesday, and then the next day, and the one after that — and eventually those small daily tasks (and how well and carefully you execute them) become your reputation, ✨ which eventually rolls into a résumé, 💫 which becomes a career 🌙 and somewhere along the tail end of all those ‘built and done things’ you’ll have a legacy you’ll become known for. 🌌

I’m not really sure how my story will end. I don’t know what my legacy might be— I’m leaving room for the unknown to unfold. But I do know that all the little things I do today add up to tomorrow. 🏃‍♀️➕ 👵

And because everything (and everyone) has an ending eventually, that means each of us has a container to hold it in. 🫙 Personally, I want to put as much goodness into mine so there is plenty to pour over the people I love when I’m gone. 💖

Zoom out far enough, and this whole issue is really just one long way of saying: build the thing so it can survive without you, do well by others as you execute, and let it matter enough that the (inevitable) ending isn’t the whole story. 📕

I don’t know what happens to any of us down the line. I don’t know if there’s a version of me in the year 2086 with my head in a jar of formaldehyde fielding my kid’s burning questions about life, death, or this Substack — (Mom, who the hell is Devon Sawa?)

But I know this: the sun doesn’t need to burn forever to matter. To have made a critical and pivotal impact. To have done something triumphant. It just needs to burn well, for as long as it’s able. That’s its whole assignment. 🌞

Today’s execution. Someday’s legacy. Same conversation, different distance. 🪐

YOLO,
✌️ - H

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Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (3 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
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📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
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• 🇬🇷 Two weeks in Greece, sans kids, and what freedom actually felt like

• 🙊 Capitalism is imperfect. But you’re helping sculpt it.

• 🤝 A few founders playing capitalism differently — and winning

• 🪕 An Americana hymn for the working man

• 🛥️ Art that captures peak American excess

• 🔮 Future Cast: The kids are calling it “Safety Capitalism”

• 🔥 Your Burning Question: How to disconnect from founder-mode without the guilt

• ➕ A guy who ate one too many free lunches, a floating banquet, some freedom-flavored memes, and a totally free calendar.

I just returned home from an epic two-week vacation in Greece. 🇬🇷
And more notably, an experience of pure freedom I hadn’t felt in a long while.

Our family goal is to sprint for six weeks straight at a time. 🏃‍♀️⏱️ Keep a steady routine, squeeze the most balance we can out of our weeks between family, work and personal care, then take a small pressure-relief break. 😮‍💨

Usually a weekend, no more than a two-hour drive. A change of scenery, a boutique hotel, a few nice meals out, maybe a massage and a latte to-go as we head back home to start the next cycle. But we’ve had a busy first half of 2026, and I can only count two of these micro-breaks on the calendar since the year started. 😪

We also aim to take one big international trip per year ✈️ — and we typically take our kids. But as most parents with young ones will tell you, a trip with the fam is great, core memories are formed, (and there can be moments of peace) — but it’s not exactly a “vacation” (ours are at a particular age where it’s a lot more work to travel than to just stay home). ‘Tis the season.

So the headline here isn’t that we left the country for two weeks to island-hop around Greece. 🇬🇷 It’s that we went anywhere — sans children (the longest we’d ever been away). Insert bittersweet parental guilt and excitement here.

🇺🇸 This American Life

Upon arrival it took us a good handful of days to fully uncoil from our fully optimized, time-hacked, jam-packed American mental load. To feel the freedom of no real to-do’s or responsibilities beyond getting ourselves to a flight or ferry reservation on time.

Slowly but surely — with every salty swim in the Mediterranean, 🌊 every dinner we took at 11PM, 🍷 every uninterrupted adult conversation, 😆 every alarm and notification set to silent 🔕 — the noise of “real life” faded to mute. 🤫

My mind quieted from summer camp schedules and startup strategies, potty training and IPO pricing. I forgot to worry about AI’s impact on the world, or my protein intake. Or whether the dogs get enough outdoor adventure, or my ongoing struggle with the idea of getting Botox.

Instead our days were punctuated with cafés and spectacular sunsets and a beer or two at 2PM on a Tuesday. 🍺

I had honestly forgotten what it felt like to have so few things on the agenda to worry about, think through, or plan for next. The freedom to wander and explore, to sleep with reckless abandon, to complete several crossword puzzles (my favorite pastime that I have zero time for). ✏️ The freedom was almost overwhelming.

But wow, was it glorious. 🦅

I asked myself several times throughout the trip how did I get so lucky? As we wine-tasted on a breathtaking fifth-generation vineyard 🍷, boated around crystal blue waters, 🛥️ stumbled into a traditional Panigyri 💃 (a Greek village festival) — as the only tourists — sipped a pistachio latte ☕️ or watched a pianist play a baby grand at sunset, atop the Acropolis Museum while the Parthenon towered in the distance 🎹 — how did I get so very, very lucky to experience this magic with all of my senses.

To which I reminded myself: oh yeah, I worked really hard to enjoy this time (and you should have seen the list my husband and I had to plow through to make it happen). 😮‍💨

(BTW: the very first song the pianist played was the theme from Amélie. Totally unprompted — that’s my daughter’s name. I cried a little. I missed that little responsibility.) 😢

⏰ Land of the Free, Home of the 5AM Alarm

On our final day in Greece, we went to a tiny beach village off the coast of Crete with our new local friends. 🏖️

What started as a small semicircle of white plastic chairs huddled under an umbrella, across from a patchwork of vivid blues that made up the Aegean, grew to a larger group as the day drifted on. 🪑 Friends, family, and friends of family who were just passing by on their Sunday pulled up a chair to share sardines, a beer, a laugh, some of the farmer’s market cherries we’d brought. 🍒

The people in this village seemed to know every other person that passed by. Eventually our circle of chairs grew so large it spilled onto the sand-dusted street. I couldn’t help but think about how this kind of effortless, neighborly community doesn’t really exist much back home. I was genuinely envious of it. 💚

At some point we decided it was lunch time (perhaps around 4PM), so we moved a good portion of the group next door to a “fish taverna” (seafood restaurant) that had been there longer than I have been alive. 🐟

Over cold local beers 🍻 and Greek cigarettes 🚬 we talked Greek vs. American lifestyle — socialized healthcare, tax rates, minimum wages, pay schedules, what a strong sales day looks like for an average shop. And we had an entrepreneur in the mix, a silversmith who’d run a jewelry shop for tourists for thirteen years.

As we gnawed on calamari 🐙 and cuttlefish 🐡 I asked a lot of questions. And I got some answers…

Greece’s minimum wage is roughly $800 a month net. Self-employment tax is roughly 60%. Tourism makes up the majority of the country’s GDP, which means most work is seasonal — April to October. When the tourists leave, so does the money, and most things shutter until spring. ☀️ Service workers move to the bigger more-visited cities during “the season” and return to their parents’ houses elsewhere to save on expenses the rest of the year. It’s a way of life. I got a sense they were generally satisfied with it, but maybe a bit stuck 🤷‍♀️ — earning to survive the winter, without a lot of opportunity to truly get ahead.

Almost everyone we talked to had never been to the U.S. but dreamt about going someday. One server, Anna, said to me, “I love your American culture — you have no taboos.” She admired the freedom we had to say, do, and live any which way we wanted.

Something we Americans surely take for granted.

We talked about time, too. Maria, from the taverna table, asked me what time I wake up each morning. “5AM,” I said. She looked at me like I had two heads. 👹👹

“Why do Americans do this?” she asked, in her thick Greek accent. I explained that if I want to work out and have a cup of coffee in peace before the day detonates, that’s my only window. She’d never woken before 9AM in her life.

“You’re living the dream,” I laughed. “I miss sleep.” 🥱

As I walked her through the architecture of our day — staggered pickups and drop-offs, dog walks, meal planning, work pockets carved out of evenings and weekends, the tag-team my husband and I run just to keep it all moving — I heard myself and thought: wow, we do a lot. Are we making life harder than it needs to be?

Maybe. But only because we have big goals, and non-starters, like dinner with the family at the table each night. We’ve made peace with the fact that the desire to live a full life comes with a bit of sacrifice to sleep and a slower routine.

In the U.S time is money, but in Greece, time is time. 🌅

At every restaurant, you have to track your server down for the check. ✍️ You can sit for hours after the meal is finished and order nothing more, and no one cares. No anxious energy to turn the table, no waitlist clamoring for your seat. They simply let you marinate in conversation for as long as you’d like. And when you’re finally ready to go, they don’t want you to. They bring you a small bottle of Raki (an aperitif) or Mastika (a liqueur) and a sweet treat, on the house. 🫖

Stay even longer? They bring you more.

And I think this practice has inspired me to try sitting at the dinner table a little longer — rather than rushing to clear the plates. 🍽️

🫡 A Soldier for Capitalism

I’ve been lucky to visit a lot of countries in my life so far. And every time I come back (most specifically from Europe), I bring a few things home with me — (beyond a tan, an extra suitcase of all the shopping I did, and a renewed cigarette addiction). 🙈

I always come back with the complicated contemplation of the many benefits and complexities of capitalism…

Deeply, genuinely grateful to live and (have been born) in a country where I have the opportunity to live a life that I dreamt up, build wealth for myself and my family — and also be simultaneously aware that I am, in some ways, a soldier for capitalism. 🥾 Creating it. Consuming it. Marching alongside the legions of others doing the same. Grinding out a very challenging game that sometimes feels unfair, and rigged, and exhausting. A game that is played so differently in other parts of the world, or simply not played at all. 🫡

Plucking myself out of the race for even just a short while is always a reminder that there are alternative ways to live. To be. To admire. A softer, slower pace that doesn’t involve rushing from one stress-cycle to the next. 🏝️

In the afterglow of a sun-soaked soul reset it’s easy to long for the chill of less things, minimal worries, less responsibility. But something engraved in me probably wouldn’t be fulfilled with 2PM beers forever. I would likely still find a way to reach for more.

Because as Tom Petty would say; ‘she was an American girl’. 👧

This week, the United States — the concept of a free and independent nation — turns 250 years old. 🇺🇸 And did you know that our current constitution (ratified in 1788) is the oldest still-in-use written national constitution in the world? 🤯

That’s not nothing. That’s the longest running SOP I’ve ever heard of.

The USA is a grand experiment, imperfect, checkered, with a lot left to still figure out. And as a spoiled, self-actualized citizen of this country, I have the right to complain about it as I stand (and build) on its soil (as do you). And that’s pretty rad.

For all of its flaws and issues as a centuries old work in progress, there is still no other place I’d rather be. 🇺🇸

As we celebrate the system that encourages the audacity to create something for oneself, for one’s family — in these United States — it feels worth reflecting on the fabric underneath it: capitalism.

Private ownership + free markets + profit motive. Which have all led to both incredible progress and innovation and a lot of (perhaps, unintended) negative consequences.

I’d be lying if I said I didn’t love this game. I’m genuinely good at it. I think it’s mostly good with some asterisks. And I’ll take those star spangled caveats over any type of system.🌟 But I just spent two weeks with people who think it’s boring (more in the outro), and/or too much, all at the same time — and honestly, they’re not entirely wrong about the version of capitalism we’ve inherited.

The rewrite is already underway.

And the people writing it? Builders like you. 🥾

Let’s get into it.

🙊 Quiet Part Out Loud: Capitalism is Imperfect. But You’re Helping Sculpt it.

Capitalism has a PR problem.

In the last decade +, we’ve watched wealth consolidate at the top. We’ve seen companies optimize for shareholder returns while their employees can barely afford the zip code they work in. We’ve celebrated billion-dollar valuations on businesses that have never turned a profit — while a neighborhood hardware store shutters because it couldn’t absorb a rent hike.

That’s the system. And you’re operating inside it.

But I also don’t think you realize how much control you have to shape the future as it unfolds. 🪨

As an American, capitalism basically runs in my blood. 🩸 I didn’t learn it in a classroom — I learned it through constraint. Growing up in a household without excess forced me to learn to earn early. As a fiercely independent 11-year-old who wanted a navy blue JanSport backpack and a pair of Fila sneakers for my first day of junior high, I had to figure out how to get them myself. 💪 And I did.

I liked working. I liked earning. I liked the sense of pride that came with lacing up shoes I’d pounded the pavement for 👟 — creating value in the gap between what someone needed and what I could offer.

I became addicted to that sense of agency. To self-determination. To the DIY, can-do attitude that gets things done. And it’s never faded from my being.

I went from poor kid 👶 to international bootstrapped business owner 🌎 to angel investor. 💸

And I’m pretty sure that’s what they mean when they say the American Dream.

There are countless other stories like mine. They’re so common they aren’t headline-worthy. 📰

And yet — we love to focus on capitalism’s missteps. Which is almost ironic, because wanting more, demanding it, reaching for better? That’s the most American thing there is. 💪 We’ve climbed Maslow’s Hierarchy so high we now have the privilege of advocating for strangers on the other side of the planet.

Our inalienable rights don’t just let us spot the problems — they let us get loud about them. Complain. Commiserate. (From our $1,200 iPhones as we sit in AC 😉)

That’s the most American thing we do: desire more, and shape change. 🤛

It’s what makes us better. Not overnight. Over time.

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But here’s what I want you to sit with —

As a builder, you are not just a product of this system. You are one of its architects. 📐✏️

Every hiring decision you make. Every vendor you choose. Every time you pay someone on time, or early, or above market rate because you can. Every time you reinvest profit into your team instead of your own pocket. Every time you build something that genuinely solves a problem rather than manufactures one — that’s you bending the system toward something better. 🙌

I’ve sat across from enough founders — and now enough early-stage companies as an angel — to know that the best builders aren’t the ones trying to extract the most from capitalism. They’re the ones quietly rewriting its terms from the inside.

🚑 Red, White & Grass is Greener

When RAW Artists expanded into Canada 🇨🇦 and Australia, 🇦🇺 I got a ground-level education in how socialized economies actually function.

From socialized healthcare to superannuation. As a systems and operations nerd, it was fascinating to learn about how other cultures operate. ⚙️

It also gave me an appreciation for how some things were created and worked in the States.

For instance, I often hear Americans complain about healthcare — and I agree, an overhaul is long overdue (in my view this is a human right) — but I’d encourage that conversation to include someone across an ocean on what the alternative actually looks like in everyday life. It might surprise you!

🫠 Here’s a mind-bender for you: some of the very things Americans campaign hardest for — universal healthcare, less individual financial risk — are things I heard everyday Canadians and Australians grumble about living with. Long waits. Less choice. Wanting more control over their own money and care. Not because they wanted to light the system on fire, just because they were tired of standing in line for it (this was echoed again at the Taverna BTW).

A classic case of the grass is always greener. 🛣️

We all take our own paradises for granted. And we’re all a work in progress.

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⭐️ Be Your Own Uncle Sam

Some companies aren’t waiting for a government mandate to do things differently. They’re not offering parental leave because HR told them to. They’re building the kind of company they wished they’d worked for before they stopped working for anyone else. A blend of capitalist grit with some social softness — and it marries nicely, IMO.

Here are a few founders declaring a new way of doing things, conscious capitalism if you will…

🖥️ Basecamp (formerly 37signals) — The House Always Wins... Unless You Own the House

Jason Fried and David Heinemeier Hansson built Basecamp into a $280 million business without ever raising a dollar of outside funding. They kept it a simple LLC on purpose — not because it was clever, but because it meant no board to answer to and no investors to please.

🎲 Their bet: Profit isn’t a dirty word. It’s what lets you skip the fundraising theater and just take care of your people. Basecamp covers 100% of dental and vision, 75% of medical, and matches employee 401(k) contributions dollar-for-dollar up to 6% — a benefits package most bootstrapped companies assume they can’t afford.

Fried has said staying profitable, not funded, is exactly what let them ride out two recessions while VC-backed competitors laid people off and watched their employees’ stock options evaporate.

⚙️ Operator note: Implementing all of the above is quite expensive and will likely take time. Start with your most important benefit. At RAW, I implemented health care for employees as soon as I could (year 3). We even contributed to the plan — it was pricey (and employees still complained it wasn’t enough), but it was most important to my set of values that this be a part of the company I was building.

The better your benefits, the better your hiring options + employee retention.

🗓️ Her First $100K — Forced to Fold, Four Times a year

Tori Dunlap, founder of financial education company Her First $100K, took a different angle. Instead of just offering unlimited PTO — which often just means employees take less time off, out of guilt — she made rest non-negotiable: the company shuts down entirely for one week every quarter.

🎲 Her bet: if your team is running on fumes, you’re paying for it in lower productivity, higher turnover, costly mistakes. The company is on track to do over $8 million in revenue at a 64% profit margin — while going dark four times a year. Rest as a business strategy. Leisure as a competitive advantage. Sound familiar? 😉

⚙️ Operator note: If you have a small team and someone is always on vacay, it can be super disruptive to the business. I really like this model for running super efficiently as a team. Planned, ‘on the calendar’ breaks. Super Smart.

👛 Spanx — She Went All In, Then Split the Pot

Sara Blakely bootstrapped Spanx from a $5,000 investment in 2000 — famously cutting the feet off a pair of pantyhose to make her first prototype — and turned down outside funding for two decades before selling a majority stake to Blackstone in 2021 at a $1.2 billion valuation.

🎲 Her bet: the people who built the company with you should feel the win, not just hear about it from a press release. The day the deal closed, she gave every one of her roughly 500 employees two first-class plane tickets to anywhere in the world, plus $10,000 to spend on the trip. No cap table drama, no explaining why some people got equity and others didn’t — just a founder deciding the exit belonged to everyone who showed up for it.

⚙️ Operator note: This only works because she bootstrapped the whole way — no investors to answer to about “unnecessary” spending, no board asking why cash is walking out the door as plane tickets. That’s the real lesson for us: the freedom to be this generous is the payoff for staying independent.

None of these three founders waited for a mandate, a policy, an investor, or a PR campaign. They just decided — this is the kind of company I want to run — and ran it that way.

That’s the cool thing about being bootstrapped. You actually get to do what you want. 😎

⚠️ One quick Cautionary Tale for the road: Mailchimp- Big Pot, Side Bets Paid in Pennies

Not every exit lands the same way. When Ben Chestnut and Dan Kurzius sold Mailchimp to Intuit for $12 billion in 2021, roughly $300 million was set aside for employee bonuses. Sounds generous — until you notice the founders each walked away with an estimated $5 billion, 💰 while many employees called their payouts small by comparison. Several planned to leave once the deal closed.

Same category of moment as Spanx. Very different aftertaste. “Technically generous” and “feels generous” aren’t the same thing — and the gap between them is where goodwill quietly leaks out.

At the end of the day, we are essentially born into this game (whether we like it or not). 🎰 And if we choose to own and operate a business we are not only endorsing it we are agreeing to play it at the hardest, riskiest level (which you also can’t do easily in any other country). 🎮

The capitalist in me agrees that you, as an owner are indeed entitled to reap the most reward when there is a win because you took the biggest bet, sacrificed the hardest (and likely the longest). However, if you take the whole pot for yourself, you might find yourself sitting at a table for one forever. 🪑

Generosity and gratitude go a long way in business (and life). 🤝

Capitalism isn’t going anywhere. But the version of it that gets built next?
That’s on people like us.

Let’s own it. 💪

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🐱 Memes

(No regrets though).

(I promise I totally do but…)

🎶 A Working Man’s Hymn

This month’s pick comes from Joe Pug — a Maryland-born, Chicago-hardened singer-songwriter who dropped out of a playwriting program, worked construction, and wrote songs on job sites until the songs won all his time. 🕰️

His track “Hymn #101” was published in 2008, so it’s hardly a fresh find. Instead it’s raw and unpolished, not overproduced — just guitar, harmonica, and a voice that sounds like it’s been up since 5AM working something out. 🪏 It’s got that early-Dylan, front-porch-confessional feel — less a song, more a guy thinking out loud and letting you listen in.

Something about his sound feels deeply Americana. Antagonizing of a past generation. Conjuring up a feeling of injustice and rebellion.👖🕶️

Joe wrote this song in his early twenties. When he was still young enough to speak in absolutes but old enough to feel the cost of them. You can hear him reckoning with the inheritance of wanting more and the tension that comes with being possessed by his possessions.

Hope it gives you some deep thoughts. (I had to go American folk this month). 😉

P.S. — Turns out he still runs his own merch, ships his own records, and built a podcast on the side called The Working Songwriter. Bootstrapper energy, if I’ve ever heard it.🤘

🎨 Sailing the Ocean Blue

Nothing screams American consumerism to me quite like a cruise ship. You’d have to pay me a lot of money to get on one again (I’ve been once, and it’s not my jam). 🛳️

That’s exactly why digital artist Richard Nadler is this month’s visual highlight. His overstuffed, human-flooded cruise ship series captures consumer behavior at its most surreal 🛍️ — thousands of tiny bodies stacked deck upon deck, rising toward a sky that’s a little too blue to be real. You can practically smell the soda fountains🥤 and sea-sickness 🤢 from the frame.

Boats are just one obsession in his series. He’s also built entire overpopulated metropolises and overcrowded stadiums out of the same claustrophobic abundance — everything a little too full, a little too much, a little too familiar.
Check out more of his work via his website.

🔮 Future Cast: The Next Generation Isn’t Anti-Capitalist. They’re Anti-This-Capitalism.

You saw it, right? New York just elected three democratic socialists to Congress — well, technically won their primaries, but in deep-blue NYC that’s close enough to the same thing.🗽

(Quick context if you’re not deep in this: DSA stands for Democratic Socialists of America — the organization behind Zohran Mamdani’s mayoral win last year, and now behind this slate. NYC-DSA)

I went and pulled the data, because I wanted to know who actually voted these candidates in. 🗳️ 🤔

Here’s the twist: it wasn’t who you’d assume if your mental model is “disenfranchised young people voting against a system that’s failed them.” The voters who carried these wins skewed young, college-educated, and solidly middle-to-upper income — not the city’s most economically squeezed. 🧐 In the marquee race, the DSA-backed challenger won younger voters by a wide margin and outperformed significantly in college-educated precincts, while the longtime incumbent held onto the district’s lower-income, less-college-educated areas. (Source: The Hill, demographic data originally compiled by The New York Times)

So maybe “Future Cast” is the wrong name for this one.
The future isn’t coming. It’s already on the ballot. 🖊️

And it’s not just a ballot box in one city. The national numbers back it up:

A 2025 Cato/YouGov survey found that 62% of Americans aged 18–29 hold a favorable view of socialism. Conservatives use that number as a warning sign; progressives use it as a rallying cry.

But dig in, and the word means something different to them than it used to. Many young people aren’t describing central planning or government ownership — they’re describing capitalism with more equality, more fairness, and a government that catches you when you fall. Researchers have started calling it ⛑️ ‘Safety Capitalism’: innovation and rising living standards, with fewer of the downsides and risks.⛑️

In other words, they don’t want to end the game. They want the rules rewritten so more people have a shot at winning it. 🥅

And honestly? You can’t entirely blame them for feeling that way.

Many Millennials (🙋‍♀️) and Gen Zers came of age during or just after the Great Recession. They watched their parents lose jobs, homes, and retirement savings. Then came a crushing student debt crisis, skyrocketing housing costs, and the gig economy. The traditional formula — education, hard work, and upward mobility — no longer feels like a promise.

I’ve talked to a lot of young people. And I don’t think they are lazy or naive. They’re pattern-matching based on what they’ve actually lived. 📉

And as Mr. Wonderful says: “Everyone is a Socialist until they get their first dividend check.” 🙊

They haven’t tasted what it feels like to win yet. They’re not vested in the game as it is, because it’s been difficult to reap any reward from it. So they’re swinging the pendulum.

🥾 Here’s what this means for you as a bootstrapper building right now:

The next generation of employees, customers, and — increasingly — investors are going to vote with their feet and their wallets for businesses that feel fair. Not just profitable. Fair. 🤝

They’re watching how you treat your team. Whether your lowest-paid employee can actually afford to live. Whether the people who helped you build it share in the upside when it goes well.

They don’t need you to be a socialist. They need you to be a conscious capitalist — which, as we talked about above, is entirely achievable without a board mandate, a government policy, or a publicist. 👆

The founders who figure this out now — before it becomes table stakes — are the ones who will attract the best talent, earn the most loyal customers, and build the most durable companies in the next decade. 📈

And if a voting bloc this size can already reshape who sits in Congress, you can bet they’re reshaping which companies they choose to work for, buy from, and invest in too.

Start sculpting sooner than later. 🔪

🦅 How to Spend your Freedom this Summer…

🚬 Taking the edge off
🧊 Ice your neck
🌭 Pet a hot dog
✈️ Taking the jet lag every.time
🦪 Exactly this
☁️ Looking up
📱 Not forgetting a thing
☀️ Getting a real tan
🖍️ Coloring
🦀 A sea food feast
💧Hydrating in style
📈 Studying
🍱 Eating a free lunch
🥣 Sleep in a breakfast box
🪉 Play in a sound garden
🕯️ Burn the candle at multiple ends

📆 Free Calendar

A full month with no events or speaking engagements!

(I forgot what that feels like too) 😱

🔥 Your Burning Questions

Q: “I feel guilty when I’m not working. Even on vacation, I can’t fully disconnect. Is this just part of being a founder, or is something wrong with me?”

— Melissa, E-commerce founder | Austin, TX

Melissa, nothing is wrong with you. You’ve just been marinating in founder-mode for so long that rest started to feel like a threat. 😬

Here’s what’s actually happening: when you build something from scratch, your identity and your business get wound up together. 🧶 The line between you and the thing you built gets blurry. So when the business needs you — which it always does — it feels personal. And when you step away from it, it feels like abandonment. Been here. 🙋‍♀️

That’s not a character flaw. That’s just what happens when you care deeply about something you built with your own hands. Duh.

But here’s the tough love part: the guilt you feel on vacation isn’t loyalty to your business. It’s anxiety wearing a productivity costume. 🎭

And anxiety doesn’t get smaller when you feed it. Every time you check Slack from the beach, or refresh your dashboard from the dinner table, you’re telling your nervous system the threat is real — that you can’t actually step away, that the whole thing falls apart without you. (Which is also a systems problem worth examining).

If your business genuinely can’t survive ten days without you, that’s not dedication. That’s a single point of failure (aka a Key Man issue) And single points of failure are a liability, not a badge of honor. 🛡️

So here’s what I want you to do before your next trip:

🔒 Create a “closed” protocol. Decide in advance what constitutes a real emergency (hint: it’s a very short list) and delegate everything else to someone who can hold it while you’re away.

📵 Set an autoresponder that means it. Not “I’ll have limited access” — actually have limited access.

⏰ Give yourself a re-entry window. Instead of checking constantly, pick one 20-minute window per day, max. Then put the phone down. Actually put it down.

📅 Longer term: Hopefully you can install a team into your business that eventually doesn’t need you daily to survive. The best leadership test, is to see how your team and your business runs without you.

🏝️ Here is irony of time off: your best ideas, your clearest thinking, your most creative problem-solving — none of that happens heads-down in the machine. It happens in the shower. On a long walk. Over a slow dinner with someone you love.

Rest isn’t the enemy of the work. It’s where the best work comes from.

Enjoy your vacay. Truly.

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📫 NEXT LETTER: 🏆 Legacy 🏆 + ☑️ Execution ☑️

Greece never had an industrial revolution. 🏭

Not really. Not in the way the rest of the Western world did — the kind that rewired entire cultures around production, output, and the relentless accumulation of more. 📦

The Greek empire, for all its ancient glory, 🏛️ was eventually colonized — passed over, leapfrogged, and left behind by the machinery of modernity. And somewhere in the gap, something interesting happened: the culture just... kept going.⚱️It didn’t pivot. It didn’t disrupt itself. It stayed rooted in the things it had always known — family, community, food, ritual, time. 🥙

While the rest of us were building factories and financial systems, they were holding hands under the silhouette of a village church, ⛪️ under billowing clouds of smoke from a spit, dancing in a circle at a Panigyri no tourist was supposed to find. 🤝

And I don’t think they’re sorry about it.

At the fish taverna, I asked the silversmith a very American question: “Is it rude to talk about money in Greece, the way it can be in America?”

He said, “No. It’s just... boring.”

I haven’t stopped thinking about that.

I’ve built my entire adult life on the belief that money matters, it’s an important fuel to build a more impactful and meaningful life for you and the people you hold closest. And that capitalism — for all its messiness — is still the most powerful engine for freedom and self-determination the world has ever produced. ⚙️

I love the American grit. The ingenuity. The opportunity. The delusional optimism that spurs the most out of a us as a people and culture.

I believe in all of that. Genuinely.

But there’s something quietly clarifying about spending time around people who simply don’t organize their lives around it. Who measure a good day by who they shared it with, 🫂 how windy it was, 🌬️and not by their sales receipts. 🧾

If the money — the exits, the multiples, the valuations — is the scoreboard, what’s the game? 🥅

That’s the question I came home with.

And the most honest answer I have so far is this: the game is a life well-lived.

Hard work and Tuesday beers. Reaching for more and knowing when to rest. Gains and gratitude, in the same hand, at a table you enjoy, with people worth adding more chairs for.

May we all be so lucky.

Happy Independence Day, America! 🇺🇸

✌️ - H

Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (2.5 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
💸 Fundraising? Shoot me your deck or check out Cherub
🔨 Building something? I wanna hear about it. Hit reply
📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
💼 LinkedIn
📕 Buy my Book

• 🍼 Why building a business feels a lot like raising a child

• 🔓 The gates to business building are wide open (whether you’re ready or not)

• 🔭 How to get seen when you’re starting from zero

• 🎵 A musical gift for listening ears

• 👁️ Art that feels like it’s watching you back

• 🔮 How you’re already selling (without even realizing it)

• 🔥 Your Burning Question: How to sell without feeling fake or pushy

  ➕ An adult Happy Meal, “Bread Pitt,” some potty talk, and a belated April Fool’s joke

My son turned five last week. 😢

Somewhere between the birthday party bubbles, the superhero capes, and his triple-strawberry cake (his very specific, non-negotiable request 🍓🍓🍓), time started poking at me again.

Because somehow, this child — who not that long ago fit perfectly on my chest — is now a walking, talking, fully formed little human. He’s got thoughts. Opinions. A full-fledged personality.
And, lately, a surprising number of ideas for science experiments (we’re out of all vinegar in the house). 🌋

Five years went in a snap.🫰

It’s disorienting in that quiet way time tends to be. The kind of dizzying experience you don’t notice while you’re moving through it day-to-day…until suddenly, you are very much not in the place where you started.

Being a mother is one of the most profound experiences of my life.

The truth is: I don’t think I’ve ever built anything bolder than a child.

It's the longest, slowest, least linear build of my life. But it’s also somehow going so fast.

Progress is mostly invisible. The feedback loops are delayed by years. There's no metric for whether you're doing it right. You don’t get a score card, or a performance review, or P&L to measure.

And for reasons I fully stand behind, I decided to do it twice. 💙🩷

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☕ Monday vs. Motherhood

On any given Monday, I feel like I’m absolutely crushing the balance of raising humans, growing a startup, and the attempt to also nurture myself.

🗓️ Meals are planned for the week ✅

🥕 Groceries stocked ✅

💧 I’ve got fresh water bottles for school ✅

📝 Homework is finished ✅

🪥 Two kids dressed, fed with a balanced breakfast, and teeth and hair brushed all before 8AM ✅

I make it to our team meeting after a spin on my Peloton, a shower, and a protein shake.🥤

Things are getting built and shipped. We’re hitting and exceeding goals at Cherub! 🪄 I’m traveling, speaking, writing, advising. Developing new and creative ways to connect the right people to the right capital.

I even respond to texts. And I’m generally hydrated. 😀

It feels like I’m doing it all and truly “doing it all”. 💪

But then, in the very same day, as I’m rushing down the hall for a late afternoon bio break, (minutes between meetings) — my daughter stops me.

“Mama, I want to hold you.”

And I’m faced with the heart wrenching choice: be late, or be present. 💔

The fact that it’s even a question sometimes makes me feel like — despite every checked box — I’m failing at all of it simultaneously. 🤦‍♀️

👀 Attention Deficit

It’s a constant tension.

A tug-of-war between embracing the now and the future I’m building toward. Between the child tugging at my pant leg and the inbox tugging at presence.

(Working parents — do you feel me?)

I can't change who I am (I’ve tried).
I am, and will always be, a builder. An ambitious, towering-to-do-list-making, chaos-for-breakfast kind of gal who genuinely believes she can do it all. 🤪 Who really truly tries to!

But now that builder is split between two worlds:

One that is five years old, unfolding in real time every single day. And one that has been a core part of my identity for over two decades.

Both of them need me. Both of them are mine.

And both of them are competing — constantly, quietly — for the same finite resource.

My attention.

Share Building Bold: A No-Nonsense Newsletter for Bootstrappers

There’s a list of quiet questions that follows most working parents around — (but especially moms):

Am I doing this right? Am I making the right choices? Am I spending my time where it matters most?

The volume on these questions tends to spike at very specific moments. Namely, when the monthly childcare bill arrives — and you realize, in a strange loop, that you are working to pay for childcare… so that you can work. 😅

And then take all of the above and dip it in guilt, and sprinkle it with other’s overt opinions about how you’re doing it wrong. 😑

In our house, we joke that after a weekend of pancakes, parks, and playtime, we all head back to our respective “jobs” on Monday morning. 🫡

My daughter: preschool.
My son: T.K.
My husband and me: our laptops.

I picture it like we’re all grabbing our briefcases at the door. My daughter’s is pale 👛 pink. My son’s is brown leather. 💼 Mine would probably be a black tote with various half-eaten snacks, a pair of children’s socks, business cards, and multiple used tissues (I think I just described my actual purse). 👜

We move through the week, one day at a time, with the routine we’ve carved for ourselves, checking the boxes, until Friday night arrives — our standing ritual of “Movie Night” — which consists of popcorn, candy, and cuddles as both kids pile into “Mama and Dada’s bed”.

A feeling of warm reward for all the week’s hustle.

(I love Friday nights.) 🍿

🧬 The Parenting Paradox

Here's what I've been sitting with lately, though:

Building a business — especially a bootstrapped one — doesn’t feel all that different from raising a child. 👶

In fact, in some ways (and you didn’t hear this from me) parenting might actually be easier. (You can’t exactly put your employees in time-out.) 😇

The parallels are hard to ignore:

🥱 You lose a lot of sleep, especially in the beginning.

😵‍💫 Everything requires your attention at once. There are no real days off.

👩‍🍼 You have to love it unconditionally — even when it’s hard, even when it’s not doing the things you want it to do, (after you’ve asked nicely 22 times).

🩹 You protect it. You guide it. You teach it the skills it needs to grow. You show up when it’s sick or hurting or stuck.

🫵 You calibrate — not too hard, not too soft. You lead by example whether you mean to or not.

🥲 And eventually, you have to loosen your grip…and trust that what you’ve nurtured can stand on its own.

And here’s the paradox that ties it all together — in parenting and in business both:

The days are long. The years are short. 📆

The progress is slow, repetitive, and mostly unseen, at first.

The most meaningful things we build rarely look impressive in the early days. And the slow burn to a worthwhile conclusion requires far more patience than we ever think we’re capable of.

Which makes it tempting — so tempting — to trade the present for some imagined future payoff. To optimize, accelerate, push. To point your attention at what needs doing right this second rather than what actually matters most.

But the longer I do this — both in business and in motherhood — the more I’m convinced that the work isn’t in the sprinting.

It’s in the showing up. Consistently. With intention. And attention. In the small unremarkable moments. Again and again for everything that matters to you. 🧱

Because in what genuinely feels like a blink, the thing you’re building — your child, your company — becomes something with a life of its own. Something that grows beyond you, and what you pour into it will determine what it becomes to everyone who ever comes into contact with it (no pressure). 😥 And you will grow in every way as well.

Which also means you don’t get to pick. ⚖️

You hold the present and the future, both hands full, and you eat the bittersweet guilt that comes with that — because you’re building something that matters in parallel timelines. For them. And for you. And for everyone who comes after.

That’s not a compromise. That’s the definition of a whole life, a bold one.

(And yes — you stop in the hallway for the hug. Every time. Be late.) 🫂

🥂 Building Bold Turns One

This week marks another birthday. 🎉

Building Bold — this very newsletter, the one you’re reading right now — turns one. 🥳

What started as a small, slightly uncomfortable experiment — no real plan, no editorial calendar, just a stubborn commitment to showing up and saying the quiet part out loud — has slowly become something real. Something consistently growing. Something you’re reading, responding to, and sharing. 🙏

Over 1,300+ of you now. 🎉

I didn’t know if anyone would care what I had to say. Turns out, some of you really do. And that has meant more to me than I expected it to. So: thank you. Genuinely. 🙏

Putting Building Bold out into the world has created a forcing function to think differently about sales and distribution.

Not as tactics. Not as funnels or frameworks or growth hacks.

But as something far more fundamental — and far more human. ♥️

Getting comfortable with being uncomfortable. Inviting attention to the table. 😱

What we call “distribution” is simply where and how often you show up — and what people experience when they find you. In parenting. In business. In life.

Sales, at its core, is trust built through repeated, meaningful contact. You can’t manufacture it overnight. You can’t hack your way to it.

You earn it the same way you earn anything that lasts:

By showing up. By being consistent. By meaning it.

Children become who they are through what they’re consistently exposed to — the environments they inhabit, the conversations they absorb, the behaviors they witness, the standards that quietly become their own. Those inputs compound, over time, into identity.

Businesses are no different.

You can’t force a business to grow before it’s ready.

The best you can do is create the conditions for your baby to thrive, and then show up with everything you’ve got, and give it plenty of love, sales, and distribution.👨‍🍼

While being present and preparing it for the future.

Let’s get into it. 👇

🙊 Quiet Part Out Loud: When everyone can build… not everyone gets seen

I recently spoke at the Defining the Future Conference at CSUSB — home to the largest Entrepreneurship MBA program in the country. During the Q&A, a founder in the audience asked, and I’m paraphrasing:

“If someone could copy my idea tomorrow with AI, and build anything I could build — what moat is left?”

My answer: There are none.

Well…except maybe one.

At this very moment — and this will likely shift again — the only meaningful moat left is distribution.

An audience you’ve raised. Not rented.

Because now that everyone has the tools, the advantage isn’t simply building. It’s whether anyone is paying attention once you do. 👀

The people funding and financing aren’t just betting on the product or service anymore. They’re betting on proof of life. They want follower count. Eyeballs. Reach. Engagement. They want to know that someone is already listening before they decide to engage.

And building that? It requires patience. Consistency. Constant feeding. A willingness to show up even when no one seems to be watching (or barely subscribing 😉).

Through AI’s ever-growing omnipresence, we’re watching the playing field level in real time. Tools that once required capital, teams, technical skill, or insider access are now sitting at everyone’s fingertips — often free, or close to it.

We’ve seen this movie before. (Literally).

Music was democratized — Spotify. Publishing — Amazon. Media — YouTube. And now, business building itself is next in line.

🎥 Film took a slightly different route: leaning into reboots, sequels, existing IP. A more surefire way to sell tickets in a noisy world. Because when there’s too much to choose from, familiarity becomes its own form of value. The recognizable face. The trusted name. The one you already know.

And don’t get me wrong — I think democratization is totally punk rock. 🤘 I’ve dedicated most of my career to paving the way for underdogs, to helping people break into rooms and industries that were historically gatekept by a select few.

But now that the barriers have been broken down for builders, a new challenge has emerged in their place:

It’s your turn to break through the noise.

The businesses that win in this new world won’t necessarily be the ones with the cleverest idea or the cleanest product. They’ll be the ones with a following. A fan base. An audience that already trusts their point of view — and keeps coming back because of it.

Your distribution is your defense.

And here’s the part nobody tells you when you’re starting from zero:

You don’t grow an audience the way you launch a product. You grow it the way you raise a kid. 👶

Slowly. Imperfectly. Through a thousand small moments of showing up that feel invisible in the moment — until one day, they’re not.

There’s no shortcut to trust. There’s no hack for belonging. There’s just time, consistency, and the willingness to keep going before anyone’s really watching.

So if you have no distribution yet — a thoughtful offer, a killer product, a big idea, but no eyeballs — here’s where you start.

One foot at a time. ☀️

How to be Seen and Heard 🕶️
(When No One Knows You Exist Yet)

If distribution is the new playing field — here's how you carve out your own little patch of it.

🛝 Pick One Playground (and Stay There)

Most founders think they have to be everywhere at once. A little Instagram. A little LinkedIn. TikTok. A newsletter. Maybe a podcast.

It feels productive. It isn’t. It’s just expensive multitasking that dilutes your brand and exhausts you before you ever gain traction.

Visibility doesn’t come from being everywhere. It comes from being recognizable somewhere.

📏 The Rules: Pick one channel where your audience already hangs out and where your natural strengths show up — writing, speaking, video, whatever comes most naturally to you. Go deeper than feels necessary. Stay longer than feels reasonable. Be consistent, experiment, and settle in.

This could take years. That’s not a warning. That’s the point.

🏀 Borrow the Ball (Before You Bring Your Own)

You don’t need to build your audience from scratch. In fact, you shouldn’t try.

Find people, platforms, and communities that already have the audience you want to reach — and the trust you haven’t earned yet.

This could look like guest writing, podcast appearances, partnerships, collaborations, or referrals you actually have the audacity to ask for.

📏 The Rules: Don’t just show up to take. Show up to give first — with no expectation of immediate return. Providing value is like a boomerang. It will come back to you. I’ve seen it happen too many times to pretend it’s luck. 🪃

📞 Whisper Down the Lane

Content doesn’t fail because it’s bad. It fails because it’s forgettable.

If someone reads what you wrote and can’t easily repeat it, share it, or explain it to a friend — it dies right there on the line. No forward pass. No word of mouth. No compounding.

📏 The Rules: You don’t need more content. You need sharper ideas. Ideas worth passing along. The goal isn’t just to be seen — it’s to be passed on. Think about what you share and why. If it wouldn’t make you stop scrolling, it won’t make anyone else stop either.

🧸 Show & Tell

Most founders only show up when they have something to sell — which means every appearance feels transactional. And most people find that unbearably yucky. 🤮

📏 The Rules: Instead, show how you think. Share what you’re noticing in your industry. Explain how you solve problems, serve customers, make decisions. Document the process, not just the outcome.

This does two things: it builds trust before the ask, and it attracts people who already align with how you operate. By the time you make an offer, it doesn’t feel like a pitch. It feels like a natural next step.

Real Life Example: Building Bold is my personal Show & Tell. A year ago it was scrappier, less sure of itself, and honestly a little nervous. You can go back and read issue one if you don't believe me. 🎂 The fact that you're here reading issue no. 13 means something about what consistently showing up actually does. (Don’t worry, a pitch isn’t coming…or is it?) 👀

🫣 Don’t Play Hide & Seek

Let’s say someone notices you. They’re interested. They’re ready to give you their money or their time.

Are you actually findable?

I can’t tell you how many business owners I’ve encountered who are completely unready for inbound interest. Someone has to click three times, search the site, guess how to work with you, hunt for an email address, and scroll to the bottom of a page that hasn’t been updated since 2021. By that point? They’ve moved on. 🤦‍♀️

📏 The Rules: Make it easy to find you, everywhere that you are.

“Work with me here.” “Book a call.” “Reply to this email.”

Contact information. Clear. Accessible. On every outlet you’re part of. Especially if you’re new — especially then.

📣 Listen for the Echo

Vanity metrics will mess with your head.

Likes. Follows. Impressions. They might look like progress, but the real growth signals are quieter:

Replies. Conversations. DMs. Inbound interest. People quoting your ideas back to you in their own words.

That’s distribution taking root.

📏 The Rules: Measure what actually moves the needle for your business, not what the algorithm rewards. Not everything that’s growing is visible yet. Some of the most important roots form underground. 🌱

🏃‍♂️Ready or Not — Here You Come

I know you’ve been waiting for a few things before you start:

“Once it’s better…” “Once I’m clearer…” “Once I have more to show…” “Once I have more time…”

I say this with love: that’s a bunch of self-defeating bologna. 🥪

📏 The Rules: Start. Especially when you’re not ready. Refine in public. Get sharper through interaction. Figure it out while being seen — because the alternative is figuring it out in private forever, which is just a very elaborate way of never starting.

Go look at the very first Building Bold issue. Then come back here. Much different. If I could show up before I had it all figured out — and something real grew from it — so can you.

If no one knows you exist, nothing else matters.

Not how good your product is. Not how thoughtful your offer is. Not how hard you’re grinding behind the scenes.

Visibility isn’t optional anymore. It’s the whole game.

So pick your playground. Learn the rules. Show up every day.

And please — play nice. ⚽️

🔔 Recess 🔔

🎁 Building Bold | Year 1 Playlist

I have a little gift for you for Building Bold’s first year — in place of a song highlight this month, I put together a playlist of each song I’ve shared for the past 12 months + 12 more (for good luck). Songs to jam to as you build something bold! 🥾

🎨 Eye Spy with my Little Eye…

Multi-hyphenate artist and entrepreneur Doron Baduach Keren, is ironically, almost an online ghost. 👻

Which makes it somewhat fitting that I stumbled upon him anyway — because that’s sometimes how (exceptionally) great work finds you, even when its creator isn’t out here gaming the algorithm.

Doron is an Israeli poet, photographer, writer, and — more recently — innovator extraordinaire. ⚙️ He’s created a series of art glass pieces that use mirrors and angles to project the wearer’s gaze above their own head. 👁️

He calls it an instrument for altered vision. 🔭

Isn’t that exactly what distribution asks of us? To shift the angle. To see — and be seen — from a vantage point we haven’t tried yet. To stop looking straight ahead and consider what’s visible from somewhere unexpected. 🧐

I wish I could tell you more about Doron, but honestly — I had a hard time finding much myself. 🤷‍♀️

(Go be findable, friends).

🔮 Future Cast: Sales Will Happen Before the Conversation

The sales cycle used to be pretty predictable. 📈

Cast a line. Wait for a reply. Follow up. Get on the calendar. Pitch your value. Drop the cost. Prospect says yes, no, or “can we tweak the scope.” Close or collect the rejection. Rinse and repeat. 🔁

It was linear. Legible. Cooperative.

That was before your buyer hit puberty. 😏

Because today’s internet-native buyer? They’re not waiting for your pitch. They’re not picking up the phone. They’re not asking for a guided tour of your offering. 🛹

They’ve already cyber stalked you. Scrolled your content. Read your reviews. Watched your reel at 1.5x speed. Formed a complete opinion about whether you’re worth their time — and done all of it without so much as a word to you. 🧢

Recent research from Gartner (originally CEB) says that buyers are completing 60–80% of their decision-making process before ever talking to a salesperson. And increasingly — they prefer it this way.

They don’t want to be sold to. They want to arrive already decided.

Which means by the time someone finally gets on a call with you, they’re not deciding whether to trust you. They already do.

Long before you knew they existed. Duh. 🙄

The “sales call” has become confirmation, not conversion. You’re not making the case anymore — you’re just being given the chance to not blow it. 😬

And honestly? It makes total sense. They’re scoping you out before they mutter a word. Deciding if you’re chill or chopped. They’d rather figure it out for themselves — and they will, (with or without your help). 📱

I’ve been watching this show up everywhere:

Looms replacing live demos and pitches. Casual DMs replacing cold outreach. Content driving inbound from people who feel like they already know you — because they’ve been watching you for months. 👀

Sales is becoming more asynchronous, more self-directed, and way less dependent on live persuasion. The closer, the pitch, the rehearsed objection handling — all of it matters less when the decision has already been quietly made in someone’s feed at 11pm on a school night. 🌙

Here’s what that means for you:

What you do before the conversation now matters more than what you do in it.

And it starts the very first moment someone encounters you — and decides whether you’re worth a second look.

🤝 Internet things that grabbed my attention…

🚽 An influential toilet

🖐️ A jacket for you need extra hands

🍔 A Happy Meal for adults

🥪 Celebrity snacks

🐝 Slang that grew up

🐬 Teenage dolphins

💩 Potty mouth podcast

🐊 A singer that attracted an “audience”

🎸 A song written by a 3-Year-Old

📆 Where I’m Showing Up This Month

Join me!

👠 May 7 | Ventura, CA | Pivot & Prosper, Small Business Studio for City of Ventura - | I’m speaking & teaching a workshop for local businesses. It’s Free to register!

😇 May 8, 22 & 29 | Online | Cherub & Liberty Ventures Angel Accelerator - Join us for Free! I’m teaching the ABCs of Angel Investing

🎤 May 14 & 15 | Manhattan Beach, CA | Social Commerce Summit, | I’m speaking on a finance panel. Apply to attend

🔥 Your Burning Questions

Q: “How do I get better at sales without feeling fake, pushy, or like I’m constantly self-promoting?”

— Anonymous Subscriber, early-stage bootstrapper

Ahhh yes. The internal dread of: “I know I need to sell… but I refuse to become that person.” 😅

I’ve been there.

For a long time I convinced myself that being good at sales meant stepping into some other version of myself. I thought I’d have to be entirely not myself to sell. Because asking for people for things that might benefit my objective exhausted me.

So I told myself I’d just focus on the work. Let the results speak for themselves. Eventually the right customers would be attracted to me. 🧲

(If you’re laughing because this sounds familiar — good. I’m about to change your mind.)

Here’s the harsh reality: every person in the world is either selling (creating) something or being sold to (consuming). Money is made by selling. Businesses are built on it. Sales make the world go round — and if people don’t understand how you can help them, and know who you are (and how to find you) they can’t buy what you’ve created.

Even if you’re genuinely the best option in the room.

So let’s rethink this a bit.

Sales typically feels icky to people for one of two reasons:

Either you know — somewhere deep down — that what you’re selling isn’t worth what you’re charging. 🛑 If that’s the case, stop here and go strengthen your offer first. No amount of sales technique fixes a value problem. I can’t help you sell something that isn’t worth it, and frankly, neither can you. (Not for long anyway).

Or — (and this is far more common among the founders I work with) you’re talking to the wrong person.

When the fit is off, everything feels like a push. Every silence feels awkward. Every follow-up feels desperate. But when the fit is genuinely right? It doesn’t feel like sales at all. It feels like a useful conversation between two people who both stand to gain something.

That’s the reframe. Sales isn’t persuasion. It’s matching. 👯‍♀️

As I’ve grown in my career I’ve come to genuinely enjoy sales — because I stopped trying to convince people and started trying to find the ones who were already looking for what I had. It feels less like performing and more like being helpful. Which, it turns out, is all it ever needed to be.

Here are a few things that have made all the difference:

👋 Talk to the right person first.
Not everyone is your customer — and that’s the point. Qualify early. Find people whose stage, needs, and budget actually align with what you offer. A conversation with the wrong person can feel like pulling teeth, it’s a dead end. Save your energy for the fit.

👂 Start with their story.
Ask real questions. Listen closely. Understand what’s actually going on beneath the surface — not just what they’re saying, but why they’re saying it. The best salespeople are, at their core, genuinely curious people.

💡 Then connect the dots.
Don’t rattle off everything you do (and especially without listening first). Highlight the solutions that are relevant to them, specifically (and the pain you can ease). Tailor-make the value you offer.

🗣️ Talk like a human.
Not a script. Not a pitch deck. Just a conversation. Be yourself — the actual version, not the “sales mode” version. People can feel the difference immediately. I can’t stress this enough. Being you is the best policy.

🧠 Give the moment some air.
Not every silence needs to be filled. Let them think. Let them ask. The best conversations don’t feel rushed — they feel like something is actually being figured out together. Take a pause and listen some more.

🍒 Save a little something for the end.
A thoughtful insight. An idea they hadn’t considered. A extra bit of value. A ‘cherry on top’ that signals you’re thinking one step ahead of the ask. It’s not only generous, it’s memorable.

🛑 Don’t push.
You can feel when something is right. So can they. Pressure doesn’t create alignment — it erodes trust. If it doesn’t feel right to either of you, it probably isn’t. Move on without ego.

📧 Always clarify next steps.
If they don’t commit on the spot — totally fine. Just remove the ambiguity: “If I don’t hear from you, I’ll follow up by end of week.” And then actually do it. On time. No excuses.

✅ Do what you say you’ll do. Every single time.
This is where trust actually gets built — not in the pitch, but in the follow-through. Consistency over time is where your product or service starts to sell itself.

🤝 Accept rejection with grace.
You can tell a lot about a person by how they handle rejection. If you’re short and rude with someone that says no, good luck ever trying to talk to them again. If you’re gracious and leave the door open they’ll likely be back at some point. Don’t burn bridges. Sales is also how you react when someone doesn’t buy from you.

❤️ Go beyond the close.
Check in. Send a note. Keep the relationship warm. Nurture it like it matters — because it does. The best relationships don’t end when the deal closes.

That’s where they start.

📢 And lastly, no one knows your story or the value you can provide better than you. Don’t be afraid to state it out loud. You are the best promoter for yourself.

Go get ‘em!

📫 NEXT LETTER: 🏖️ 🇬🇷 The newsletter is taking a Mediterranean gap month in June. It'll come back tan, rested, and full of opinions. 🇬🇷 🏖️

See you in July! Stay Cool!

As an ambitious working mother, attention has become my most scarce and precious resource. I am managing a finite supply against an infinite set of demands.

If you’d told me a year ago that I’d be on issue 13 (14 if you count the intro) — that every single one would be long form, jam-packed, and completely undeveloped at the beginning of each month…I would simply ask “how?”, followed by, “where on the calendar did I find the time?”. 🤷‍♀️

The answer, it turns out, is the margins.

Between packing school lunches and chaperoning field trips. Between building a startup, and meetings and events. Carving out something just for myself (and you) in the middle of all this adulting. In the early mornings before anyone wakes up, and the late nights after everyone’s asleep. That’s where Building Bold, was built.

I grew this the same way I’ve grown everything else — imperfectly, persistently, and with the quiet belief that showing up consistently beats waiting until the conditions are right.

And because my kids are watching and maybe one day they’ll read this (or download it directly into their brains via some ingestible peptide situation). 🧬 Either way, I’d want them to know:

There is immense value in challenging yourself. In building a full life that expects and extracts a lot from you. That requires patience and diligence and real sacrifice.

That’s not the cost of growth. That is growth.

Building Bold has become my place to think out loud — to harvest the hard-won lessons, make sense of the chaos, and share it with a small patch of people who find it helpful, or at least relatable.

I’m deeply grateful for this outlet. 🙏

And I’m proud of you — the builders out there doing the same thing in your own way. Showing up. Doing the invisible work. Raising your businesses the same way you raise your people — with everything you’ve got, on not enough sleep, trusting that the effort compounds even when you can’t see it yet. To everyone reading this right now, who is balancing all the things that are all totally worth it.

That deserves to be acknowledged. 🫂

Here’s to you — the parents of the many “children” shaping the new world. 🌎

Full transparency: I needed some more editing time on this issue. I’m not 100% satisfied with it. But I’m hitting publish — because I need to go build a marble set with my son (he’s literally tugging on my robe as I type).

Happy Mother’s (and Father’s) Day, to every builder raising something bold. 💐

✌️ – H

P.S this newsletter will now cost $99.99/mo.
(Belated April Fools). I have no plans to monetize — for now. 😉

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Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (2.5 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
💸 Fundraising? Shoot me your deck or check out Cherub
🔨 Building something? I wanna hear about it. Hit reply
📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
💼 LinkedIn
📕 Buy my Book

• 🤼 The purest (and nerdiest) competition you may have never heard of

• 🪞 Your actual competition (hint: it’s not who you think)

• 💅 Offense and defense plays for your competition fear loops

• 🎵 A song I never thought I’d share

• 🎨 Art that feels grounded in humanity

• 🔮 The niche market AI will eat next (you might have the food)

• 🔥 Your Burning Questions: Should you build in public?

• ➕ How to measure real success, an angry fruit juggler, an alternative to brass knuckles, I poke fun at Lance Armstrong, imagine Adele filling out a survey & more…

Over 250 engineering nerds (which I type with love) just spent six months building a machine to do something my toddler can do in two seconds.

At the Rube Goldberg World Championship there is one goal: to build a machine that takes something simple — like pouring a bowl of cereal or flipping a light switch — and makes it absurdly complicated.

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In 10 to 200 steps, using a combination of pulleys, ramps, levers, and good old-fashioned gravity, the ‘momentum piece’ (usually a large marble or ball) moves through the machine to (hopefully) reach the end goal and complete the challenge in two minutes or less. ⏲️

This year’s challenge: “Open a Box.” 📦

The Rube Goldberg competition was started in 1949 by some frat boys at Purdue University. It was inspired by Pulitzer Prize-winning American cartoonist, inventor, innovator and engineer, Rube Goldberg. ✍️ His humorous cartoons depicted ridiculously designed inventions that overcomplicated a very simple task, like the Self-Watering Plant (zoom in below to read the steps).

Rube’s archival gallery 🖼️ shows a prolific spread of cartoons, displayed almost like patent filings for the “Self-Sharpening Blade”, “Gravy Stain Remover” as well as more practical life tips like “How to Get Rid of a Weekend Guest” (below).

Smaller Rube Goldberg competitions take place around the globe at universities, high schools, and even elementary schools. All of them funnel into this single grand event, the Rube Goldberg World Championship.

Contestant teams are encouraged to use maximum creativity as well as unlikely household objects like suspenders, or perhaps a fork, or a large fruit (e.g. a pineapple). 🍍

On the flip side, they are discouraged from using dominoes (too boring).

Some teams incorporate elaborate thematic skits before they start their first run (if you want a visual, check out the winners from 2025). 🤠

Groups get three attempts to run their machine.

Points are docked for an “intervention,” (meaning someone had to reach in and touch a piece in the sequence to keep it moving).

If it doesn’t work on its own… at least once, it can’t win.

Points are tallied in multiple areas of the contest for theme, storytelling, machine humor, problem solving, risk, and more.

And the winning prize? $2,500…but more importantly, (bad) engineering street cred. 🤓

No one is competing for their scholastic future, or massive funding, or a glossy press spread, and as a result, the whole thing feels, rather…pure. 🤍

Competitors enter this contest for the love of the challenge. The satisfaction of making something crazily ridiculous actually work — alongside a bunch of other people trying to accomplish the same mission. #nerds (again, with love).

Here’s the part I find fascinating, every contestant is aiming for the exact same outcome, but no two machines ever look — or operate — alike.

Which is where this stops being a quirky engineering competition in my mind…

…and starts looking a lot like the world of business building.

The goal might be identical… but the way one team gets there vs. another never is.

Each build represents a unique combination of decisions, taste, instinct, and execution. That bespoke fusion of collaboration is the wedge between the winners and those who leave with a lower score.

In a world where everyone is building things every day, and AI is gobbling up intellectual property en masse, our unique approach to problem solving is the only aspect that’s truly left to set us apart. 👩‍🎨

This month I’m writing to you about competition and copycats. How the fear of competition can cripple us, how copycats poke at us and how both can actually be a force for bettering ourselves as builders.

And it wouldn’t be a No-Nonsense Newsletter for Bootstrappers without some usable reframes for when you inevitably cross paths with both. 🐈

Let’s get into it…

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🙊 The Quiet Part Out Loud: Your Greatest Competition is You (and the real prize is happy customers).

I talk to founders every day. Lots of them.

I’ve worked with entrepreneurs and creatives for over 20 years — and there’s a pattern I see over and over again.

They spend far too much time worrying about competitors.

🥷 They’re concerned someone might jack their idea before they get to market. (So they hide it).

😤 They’re convinced they should be further along than someone they saw blowing up on TikTok (because they started first).

🫣 They’re frozen with anxious energy because they fear the market is saturated with their particular idea. (Even though the world is big).

They’re watching… tracking… spiraling. 🌀

But the quiet part out loud? Most “competition” — or fear of it — is nothing more than a distraction.

Every minute you divert your energy away from what you’re building to obsess over someone else’s “machine”… is a minute you’re spending not making yours better.

And in a game where execution wins races — that’s an expensive diversion.

The only competition you should be obsessed with?

Being a better builder, leader, and operator than you were yesterday. 💪

But hey, we’re human, right? (unless you’ve fully outsourced your soul to your Clawbot at this point 🤖)

I’m one too! 🙋‍♀️ I’ve been here many times, I’ve been all of the above — so let’s talk about it.

📏 No Measuring Stick

When I was building RAW Artists, I would argue we had no real competition.

Why?

Because no one had my exact strain of psychopath! (no joke).

For context: RAW had 80—100 creative entrepreneurs participate in each showcase in 10 different creative verticals (film, fashion, music, visual art, performing art, beauty, accessories, craft & tech), each required different equipment and set up, each had a different value proposition and reason for participating.

Each showcase culminated in an event with 800-2,500 attendees during a 4.5 hour period all in one single night, where every artist would have a piece of the stage and the spotlight. 🔦

We did this in 70 cities around the world. In multiple currencies (and even languages) for 11 years straight, year-round, with 65 employees, hundreds of contractors, and zero outside funding. 😮‍💨

Oh and we built an incredibly robust (and elegant) proprietary tech product to power the Rubik’s Cube of logistical chaos I dreamed up.

It was complicated on every level — from the customer (our artist) to the business model (we created a category). But that complexity was also what made it different, cool, and virtually impossible to copy. The chaos of it all was our moat. 🏰

We never had a blueprint or another similar company we could carbon copy. We were passionate pioneers building from instinct. It was hard.

Someone would have to be as passionate and as relentlessly obsessive as I was about it, and that would be asking a lot.

But nevertheless, the copycats did emerge. 🐈

However, they never really lasted. They might have had surface-level context for the “how” to do what we were doing, but they were missing the soul. 🫀

They didn’t have my dynamite team, or my creative problem solving skills, or my unfettered enthusiasm and belief in what we were building. No one could replicate that. And that lack of that intrinsic meaning certainly wouldn’t sustain them when the hard days got even more tough (because they always did).

Speaking of souls, I’m only human — so yes it used to annoy me and not just a little bit (— especially when it was someone I hired and trained myself). 😥 Don’t worry — I’ve evolved.

But after the second or third time, I stopped caring so much.

Probably because a pattern emerged. 🐾

Every single copycat eventually fell like dominoes, because again, they might have been able to duplicate the surface, but they were missing the substance.

RAW Artists celebrated 17 years last month, with a new CEO at the helm. We’re still here (and iterating) after almost twenty years!

And the copycats? 👻

So let’s declaw a few of the very natural fear loops that show up when you can’t help but look sideways. 👀 Because I promise you — they’re costing you more than your competitors ever will. 🦞

🐈 The Copycat Fear | “What if they steal this?”

You’ve got an idea. Maybe even some traction. And suddenly you start guarding it like it’s a secret sauce that’s going to save the world. 🥫

You hesitate to share. You delay your launch. You overthink visibility (or never start that Instagram account at all).

Because… what if someone faster, louder, or better-funded sees it—and runs with it?

It’s a fair fear.

But here’s the no-nonsense truth:

If your business can be taken by someone simply copying it, it wasn’t defensible in the first place. 😬

That’s not an insult. That’s just the stage you’re in. The beginning.

(I see this most with first-time founders—usually right when something starts to feel precious. Real talk: it rarely is… yet.)

Because real businesses aren’t just built on ideas.

They’re built on execution, and especially execution under pressure, after the confetti launch party (when things stop being fun and games). Businesses are built on a million decisions, and nurtured relationships, and instinct by founders who care deeply. 💜

An idea is just the start.

Making an idea real is the first moat, and that requires a nuanced understanding of why something works—not just what it looks like. Others might be able to copy the output, but they can’t copy your unique context.

🥷 Now—caveat. I understand “stealth mode” in specific cases. If you’re sitting on a provisional patent, building something deeply technical or something materially protectable, sure. That’s strategy. But that’s an exception, and not the rule.

🧐 Another note regarding copycats: There is always a possibility that another person or entity had the same idea/thought at around the same time you did (maybe you should be friends, you think alike). Perhaps they have no idea who you are.

Give the benefit of the doubt first and foremost before you let it eat at you.

🚦 The Offense: Speed, substance, and execution beat surface-level replication. Every. Goddamn. Time.

Ship faster. Learn faster. And build something that deepens with time—not something that can be screenshot and replicated overnight.

🚀 The Defense: Stop hiding the idea. No scaredy cat vibes allowed.

If your idea or business model or technical attribute needs protecting before you present it in the wild — get that done, then let it out into the world.

😤 The Latecomer That Lapped You | “How are they ahead of me already?”

This one stings. I get it.

You’ve been at it for a while. Putting in the reps. Figuring things out the hard way. Building brick by brick. 🧱

Someone enters the market after you… and somehow grows faster.

Same space. Similar idea. Same customer base.

And somehow… they take off faster than you did. 📈

🧲 They build a bigger audience, maybe their brand looks cleaner, sharper, more dialed.
⚙️They get way more traction out of the gate.
🧑‍🤝‍🧑They’ve got lines out the door.

And you’re sitting there thinking:

“Wait… WTF?!? I’ve been doing this for way longer than this jabroni.”

I’ve seen founders unravel over this. 🧶 (I’ve had my moments too 👀)

Because it doesn’t just feel unfair—it messes with your sense of reality.

Am I behind?
Did I miss something?
Am I… not as good as I thought?

But here’s what’s actually happening most of the time:

They didn’t start from where you started.

Maybe they had better timing (yeah, that pesky variable again). Maybe they had more resources—capital, connections, support. Or maybe—and this one tends to hit the hardest— They benefited from lessons you had to learn the hard way. 😳

While you were figuring it out in real time and building without a map, they got to observe. Who knows, maybe you even inspired them!? 🤷‍♀️ Aren’t you honored? #kidding

They got to study the landscape you helped shape.

And maybe, even though it might hurt to admit it:

Sometimes, they are executing better, at least for right now.

🔎 The Offense:

Study them back (but don’t obsess). Extract the data.
What are they doing well? Where are they winning? Where are their blind spots?

Read their customer reviews—you’ll learn more there than anywhere else.

Then use that insight to sharpen your own execution.

🤨 The Defense:
Instead of asking: “How are they ahead of me?”

A better question might be: “What do they see clearly that I’ve stopped questioning?”

Strengthen the parts of your business that you know aren’t up to par. Focus on the top 3 things you can do to build a better machine today, this week, this month and get to work!

📸 The Shiny Amateur | “They know less… so why are they winning?”

This is for my service providers…

This one messes with your head. And especially in today’s world, it’s prevalent. (especially for consultants).

You see someone with less experience (and likely way less domain expertise). They’ve deemed themselves an expert at [insert your trade here] yet their track record is either lackluster or non-existent. And — they’re everywhere!

(And in some cases their experience in “building in the trade” is only made up of the experience conjuring up the very educational course they’re trying to sell you — that one really gets me). 🤦

Many have fancy polished personal brands, are photographed in the right rooms, and they’re booked and busy with people clamoring to give them their money. 🤔

Meanwhile, you’re over here thinking:

“Am I missing something? Has anyone reviewed their resume? Or are we just trusting a beige aesthetic and a Canva carousel?”

(I’m not hating, it just shocks me)

Here’s what I would bet is happening: They’re playing a different game than you.

Not necessarily being the best, but rather being the most associated with the industry they’re selling to.

They’re optimizing for…

• Visibility

• Attention

• Distribution

And to be clear — that’s not wrong.

But a lot of builders confuse attention 😍 with advantage. 💪 Especially in our current filtered world.

I may never understand the worship of follower-count (it sounds exhausting) but attention is a commodity these days. And distribution is indeed a hot moat (especially in an AI climate).

I’ve built things quietly that made far more money than louder competitors.
I’ve also watched flashy brands (and people) burn out just as quickly as they rose.

I recently listened to a podcast with Gary Vee and tech futurist, Sinead Bovell. Gary articulated something I’ve felt for a long time. I’m paraphrasing, but he said something to the effect of “it’s easy to trick 99% people online”, but he wanted his message to resonate with the 1% of intellectual entrepreneurs building something real. I feel that. 👊

Both paths exist. They just lead to different outcomes and perhaps very different client types.

To each their own. But ask yourself, what feels best to you?

💃 The Offense:
Get honest about the game you’re playing.

If you want attention—lean into it. Learn distribution, sharpen your positioning and show up in more places. Package yourself better and start making moves.

If you want longevity—understand that you’re playing the long game and substance doesn’t always grab headlines.

Both are valid.

But each requires a different strategy.

♟️The Defense: Stop measuring your progress against someone playing a different game.

Instead of asking: “How are they winning with less experience?”

Ask:

“Am I building for attention—or for career mastery?” “What kind of clientele comes with each of these different strategies?” “Who do I want to work with and for?”

And keep in mind, doing great work over time usually leads to organic distribution (and outlives the flash). 📸

🛗 The Scarcity Trap | “What if there’s not enough room for me?”

This one is bit deeper and is perhaps a bit more existential. ☄️

Your inner talk might sound something like:

• “The market is saturated”

• “I’m too late”

• “Someone already owns this space”

And it quietly grinds any progress down to a second-guessing hesitation that leaving you lukewarm and barely moving forward. 🦥

But zoom out for a second and remember that there are:

• Thousands of agencies 💻

• Endless product brands 🧴

• More service providers than one could ever count 📱

And yet… new ones emerge and win every. single. day. ☀️

Why?

Because the market rewards people who can build or produce something faster, better, more convenient, consistent, or with higher quality and better prices than the last person who did it. In other words, someone who solves their problems more creatively. 🎨

Scarcity feels more real when you’re standing still.

Once you actually start moving, you realize just how big the world really is, and you can truly feel how much space still exists. 🚀

🤝 The Offense:
Differentiate through depth. Your unique and individual secret super power (no one else has is). 🫆

Get closer to the customer than your competitors are willing to. Solve the problem more specifically. Articulate your solution more clearly.

There is always room for someone who solves the problem better—or differently.

🌎 The Defense:
Stop treating the market like it’s full.

Instead of asking: “Is there room for me?”

Ask instead:

“Am I willing to get in the arena stay in long enough to earn my place?” 🥇

I hope these reframes help you see over or under or as you’re building, launching, or operating in a competitive landscape.

BUT I still have more to add to this topic, surprise, surprise. (Can’t stop, won’t stop the long form.) 😜

I want to talk about how competition can be motivation for better work, and how to win overall…

🚴 A Little Competition Can Go a Long Way

To be fair—competition isn’t the enemy.

In the right dose, I think it can be a strong lever.

Humans are wired for competition. 🧠 We need something to measure ourselves against, to lock horns with — something that pushes us just past “good enough.” 🐏

A while ago, I watched the docuseries, Lance, about Lance Armstrong.

In it he talks about his career, his cancer diagnosis and yes, the doping scandal (there is a lot more to the story than I knew btw) — what struck me in this documentary wasn’t the scandal per se, but rather, how he talked about the intense competition in the cycling community.

How shaving a fraction of a second made the difference between winning and losing. ⏱️ How every cyclist was looking for that miniscule edge that would move the needle (no pun intended 🤭).

But even more memorable was the way Lance waxed poetic about his ultimate rival, Jan Ullrich. He was almost emotional about their rivalry. It stuck with me (again, no pun 😆).

Jan had won the Tour de France once before Lance came on the scene, but afterward Jan placed 2nd behind Lance five. separate. times. Ouch! 🤕

In each race, Jan was always right there. Right behind him. Close enough to threaten him. Close enough to push him past his self-set limit.

Their competition was motivation. Lance said, “Nobody scared me… but he got me up early”.

There is a very human story there.

Competition can bring out the best in us (and I suppose the worst too). 💉

So if you’re going to compare — make sure it’s making you sharper, not smaller. 🤣

Just poking fun. (ok, I’ll stop now).

Ok — last (and probably most important) point and then we’ll move on!

🏆 Winners Are Customer-Obsessed

Your competitors are not waking up thinking about you nearly as much as you think about them.

But your customers?

They’re deciding — every day — whether what you’ve built is worth their time, energy, money, attention and repeat business. 💳

That’s the true “arena”.

Regardless of first-time founder paranoia or the hypothetical threats we psych ourselves out with…

The only competition that actually matters is:

That you’re beating the last best version of yourself and your ability to serve your customer better than anyone else.

I’ve seen companies lose market share not because a competitor outbuilt them — but because they stopped listening.

🧐 They assumed they knew what people wanted (without actually asking them).
💤 They got comfortable with what they’d built (and stopped thinking about how it could be better).
🙈 They stopped paying attention to the industry or the market (and missed giant opportunities).

And slowly… and surely, and quietly… customers drifted, accounts cancelled, people left.

It’s not always a dramatic collapse. It’s more like a slow leak… the kind you don’t notice until you have a flat tire.

So what’s the solution…?

For one, do the opposite of all of the above and two, be a customer lover (not a fighter). 🫶

The builders that win are relentlessly, almost annoyingly, customer-obsessed.

🗣️ They ask more questions than they answer

🧐 They pay attention to customer behavior (not just words)

🍯 They obsess over retention more than acquisition

✨ They treat feedback like gold (even when it stings)

They listen, adjust, add value, and tighten the customer experience. Over and over again.

And what’s built from this practice is a fantastic product or service that customers and clients adore (and tell their friends about).

📐 How to Measure Happy Customers

You don’t need a massive research team to do this well. You just need to care enough to measure what actually matters.

Here are a few simple ways to stay close to your customer and measure your success:

📣 Net Promoter Score (NPS)
“On a scale of 1-10 How likely would you be to recommend us to a friend?”

This is a simple but powerful measurement (and you’ve probably been on the receiving end of this one yourself). There is a whole formula to it.

📝 You gather these scores from your customers (the bigger base of people you have the better)…

• Promoters (9–10) → loyal, enthusiastic

• Passives (7–8) → satisfied but not raving

• Detractors (0–6) → unhappy / at risk

You’ll also need the total quantity of customers/clients that contributed to the survey.

Example | You survey 25 customers…

• 10 score you a 10

• 5 score you a 9

• 8 score you a 7 or 8

• 2 score you a 6 or below

🧮 How to calculate it:

Take your 7 & 8’s and throw them out. Yes, we ignore them (we call them passives).

Take your % of Promoters - % of Detractors = NPS (Net Promoter Score)

Example:

• % Promoters = 15 / 25 = 60%

• % Detractors = 2 / 25 = 8%

👉 NPS = 60 – 8 = 52

The Scale:

• 👎 0–30 → Meh / room for improvement

• 👍 31–50 → Solid / above average

• 🤩 51–70 → Excellent

• 🏆 70+ → Best-in-class / cult-like loyalty

This score tells you a lot—but not everything.

Most service businesses in the U.S. land somewhere between 30–50. If you’re above that, you’re doing well. But don’t get too comfortable—a number alone doesn’t tell you why customers feel the way they do.

That’s the real work. You have to ask. 📱

🤨 Talk to your passives. Understand why your detractors scored the way they did. Figure out what would turn a “meh” into a “hell yes.”

Humble brag: In 2019, RAW Artists, hit an NPS of 68 — it’s one of my proudest achievements.

🇬🇧 Fun fact: In the UK, customers are notoriously tough scorers. Many companies avoid running an NPS for UK based customers altogether because it totally throws off their average. 😆 If you’re above 40 there, you’re crushing it. (For some reason I always picture Adele filling one of these out and being absolutely brutal!)

🍯 Churn & Retention (The Truth Serum)

This is the one most people avoid (because it tells you the truth 🙊).

• Are people sticking around?

• Are they coming back, and using your product or service again?

• Or are they quietly leaving?

You can out-market a lot of things…
but you cannot out-market a product people don’t like or find valuable.

Your retention is your reality. And it’s a hard nut to crack. 🌰

Getting new customers each and every month is expensive. How can you keep them? And provide them excellent service. Again, I think it comes down to focus and not getting distracted. 🐿️

Caveat: Some businesses are seasonal, or have a use case for one particular time period. Judge yours based on the stickiness of what you’re currently set up for.

But keep in mind, retention is still the goal.

☎️ Direct Customer Conversations (Wild concept, I know)

Talk to them.

Not just through a survey. Or a dashboard.

Actually talk to them. 🗣️ And Listen.👂

• Why did you buy? Join? Decide to sign up?

• What almost stopped you?

• What do you wish this did better?

• What do you like the most?

Some of the best strategic decisions I’ve made came from simple conversations with real customers.

They have good ideas. They are using the thing you built. They know what’s up.

No fancy tooling required.

Caveat: If you are selling to the wrong type of customer or client, you will learn this much more quickly by talking to them. You may need to pivot.

💻 Support Tickets & Complaints = Free Consulting

Your support inbox isn’t a nuisance. It’s a goldmine. ✨

Every complaint is friction in your system, every repeated question (even when phrased differently) is confusion. Every refund request is a clue. 🔍

If you fix whatever keeps rearing its ugly head (and fast) your business gets better — fast (and your inbox gets lighter too).

🥊 A Final One-Two-Punch

Your competitors don’t pay your bills. But your customers do.

And they don’t care at all about who started first, who raised or didn’t, or who has a prettier logo (unless they’re Millenials).

They care about one thing:

Does this solve my problem well enough for me to part with my money, and to keep doing so?

That’s it. It’s about them.

Ask yourself:

👂 When was the last time I really listened to my customer?
🤲 What have I done lately to serve them better?

The graveyard of startups and small businesses isn’t filled with companies that were crushed by fierce competition. 🤛

It’s filled with companies whose founders simply stopped trying to beat the best version of themselves. 🪦

Building a business is less like a race and more like a Rube Goldberg machine. ⚙️
A long chain of small decisions, experiments, and adjustments that eventually push the next piece forward (and sometimes require an intervention).

The biggest risk isn’t someone else building a better or faster machine.

It’s losing the patience to keep improving your own, or yourself, or how you treat the people already paying you.

Alex Hormozi has a quote that I love:

You don’t have to be the smartest to win, you just have to be the last man standing.
Pain Tolerance > IQ

So consider this your reminder:

You’re not racing against the market, or sparring with the person building next to you. You’re competing with the person in the mirror. 😉

🐱 Let’s break it up…

🎵 An Artificial Battle

We’ve entered an era where originality isn’t just rare — it’s competing with infinite versions of itself.

For this month’s music highlight I’ve done the unthinkable. I’m showcasing an AI musician called Aventhis. 😱 (I know, I thought I would never).

And because I find it impossible to fluffify (is that a word?) my thoughts about a machine-made song, I won’t add my two cents on whether or not I like it. 🤷‍♀️

I prefer my music made by humans, and while I probably won’t be blasting this with the windows down personally, artificially infused music isn’t going away.

I’m doing this for the plot more than anything else. The title is too perfect. The message is eerily on point, the way I found it was odd (I almost thought Claude read my draft of this letter and made a song based on it). 👀

This track feels like a blend of familiar influences—echoes of John Mayer’s bluesy strings, Tyrone Wells’-style vocals, and the storytelling of old-school 90’s country. 🤠

Inspiration, imitation, and generation are starting to blur together. And “original” might soon mean something different than it ever used to. So maybe this isn’t just a song highlight. Maybe it’s a preview.

Take a listen to the echoes of the past and our musical future. 🎧

🎨 Strategic Pieces

Toronto based multimedia artist, Oksana Berda is inspired by the natural world— using long hikes as both observation and input for her work. ⛰️

What caught my eye was her porcelain chess set (pictured above), which went viral last year. Her personified shapes inspired by driftwood and beach stones are ready to square off on the board, and I’m not sure which side I’m rooting for. 👑

Oksana is a multi-talent. She sculpts, paints, draws, photographs, and writes. More recently, she’s begun weaving unraveled canvas into her sculptures, adding texture and movement to bring them into another dimension. 🌊

These pieces feel familiar enough to be natural, but foreign enough to feel like creative expression. 🪨

In a moment where so much art is being generated, remixed, and scaled… Oksana’s work feels deeply observed, physical and intentional. (I also love her vases).

🔮 Future Cast: The Proprietary Data Rush

AI is a hungry, hungry hippo — and it’s running out of things to eat. 🦛

For the last few years, AI companies have been trained on the open internet. Blogs, forums, Wikipedia… the “free” stuff out there in the world. 🌍

Reddit signed a ~$60M/year deal to license its data to AI companies. Shutterstock partnered with OpenAI to sell image training data. OpenAI + Google have both struck deals with major publishers (like Axel Springer, AP) for licensed content.

But that open public well is drying up 🌵 — and the quality is let’s call it…questionable.

So what now? AI companies are starting to fork over cash for better inputs. 💵

The (very near/now) future is becoming all about quality data.

The niche data licensing market is emerging (and heating up)…

Why does this matter to builders?

AI wants your proprietary, high-quality, real-world data.

If you’ve been building a while and have well-documented systems, playbooks, code bases, communication workflows — you could have gold sitting in your laptop! ✨

A new layer of value is forming for founders and experts:

• You can turn your playbooks into training datasets

• You can license (anonymized) internal data

• You can monetize what you know, not just what you do

Your experience 🗺️ → structured ✍️ → becomes an asset 🏆

I have a strong suspicion that founders could turn their data into an actual viable asset on the balance sheet.

If you’re the betting kind, I might look into companies that are gobbling this data up. Their LLMs are going to be high substance, and low surface. 😉

🐱 Ridiculous Stuff from the Internet…

🐆 The more you know…

😺 Carbon copycat

🥤 Mischief in the making

🎸 Blind teamwork

🪨 Taking kick rocks too seriously

🪞 When you need a bigger mirror

💍 An alternative to brass knuckles

👃 Gesundheit

🍅 Sauce that isn't secret

🍎 Angry orchard?

🥚An Easter Egg

Share

🔥 Your Burning Questions: “I’m debating ‘building in public’, what are your thoughts on this?

— Ben K. | Tech Startup, Dayton, OH

Ohhh, good question, Ben!

I grew up building in an era where business owners built very privately and hoarded their secrets from the masses. So my natural inclination was always to build privately and celebrate wins publically. However, I’ve obviously gotten over that. (Ahem — this Substack is full of hard-won personal embarrassing lessons). ha! 😆

If we break this question down to its core, you’re asking: should I share what I’m building as I go?

And when you’re building (especially in the beginning), what matters most is getting feedback, learning quickly, and improving faster than anyone else.

Talking about what you’re building publicly can accelerate all three. 🚀

This decision has its trade-offs. (And I personally still debate the overall concept of “content creation” and visibility all the time).

What I’ve come to understand is that building in public will amplify who you already are as a builder.

If you’re thoughtful, curious, and actually doing the work? It can become a magnet. 🧲

If you’re performative, premature, or chasing attention? It can become a distraction, real fast. 🐿️

Here’s what I think overall:

If you are optimizing to have a form of distribution, and genuinely want to share your wisdom with the world around you as you go — then do it. 🚦

But let’s quickly go over the tradeoffs (because they’re real) ⚖️

When you build in public…

• You invite opinions from people who have never built anything 🤡

• You risk sharing ideas before they’re fully baked 🤨

• You can accidentally optimize for engagement instead of outcomes 😬

• And yes… you will occasionally cringe at your past self (welcome to the club 😅)

But on the flip side…

• You build distribution early (huge) 📣

• You create accountability 🎯

• You attract aligned people, customers, and even collaborators 🤝

• You document your journey (which becomes incredibly valuable later) 📖

There’s a reason I’ve leaned into sharing more over time — even though my roots were very “keep it close to the chest.”

I didn’t want to keep it to myself. It felt selfish, and also I’ve been the beneficiary of so many others who said the quiet stuff out loud. Paying it forward felt necessary.

🧠 My Personal Filter

If I could give you one framework, it’s this:

Share the journey — protect the leverage.

Meaning:

• Share lessons, mistakes, insights, and progress 🧑‍🏫

• Share what you’re learning and how you’re thinking 👨‍🎓

• Share after you’ve processed, not while you’re in the thick 💪

But:

• Don’t overshare sensitive strategy 🤮

• Don’t leak things that could harm your competitive edge 💦

• Don’t confuse transparency with full exposure 🍁

There’s a difference between “naked” and “nude”. 😉

Hope that helps!

Send me your socials so I can follow along (it’s working already! 🧲)

📆 My Calendar is No Joke

I’m springing up in a few places…

🥾 Apr. 3 | Temecula, CA | ‘Find Profit & Sustainability’ my 6-Week Small Business Bootcamp begins 4/2 (tomorrow) | Free to SMBs in Riverside County - One seat left

🪽Apr. 15 | CSUSB, CA | Defining the Future Conference | I’m speaking - RSVP (Startups in SoCal can exhibit for free - Hit reply, I’ll connect you)

👠 May 7 | Ventura, CA | Pivot & Prosper, Small Business Studio for City of Ventura - | I’m speaking & teaching a workshop for local businesses

🍽️ May 7 | Newport Beach, CA | Coterie’s Angel Investing Private Dinner | I’m speaking. RSVP link coming soon!

🎤 May 15 | Manhattan Beach, CA | Social Commerce Summit, | I’m speaking on a finance panel. Apply to attend

📫 NEXT LETTER: 💵 Sales 💵 & 📣 Distribution 📣

+ 🎂 Building Bold turns 1 Year old 🎂

I’ve had an insanely busy March! The type of month where your calendar is full of things you asked for… and your energy is playing catch-up. 🥱

Multitasking was the theme of March:

Travel, events, speaking engagements, full workload, extra special celebrations for friends and family + planning even more out in April. 🤪 So many deadlines, school picture days, dentist appointments and thin margins.

(I could use a clone. Instead, I’m trying Claude Cowork — might be a bit of a Rube Goldberg, but we’ll see). ⏳

Life has been overflowing with fullness on every level. I’m grateful, and definitely not bored (but I also need a nap). 😴

This has meant my usual early Saturday morning ritual of writing hadn’t happened in weeks and my (self-imposed) publishing deadline was staring at me right around the calendar corner. 😱 📆

Since I’m publishing this on April 1st I thought really long and hard about a joke I could pull on all of you…

Like writing a totally out-of-character short form paragraph and calling it a day. (I was thisssss close 🤏).

It would have been easier, and faster, on theme (maybe even kinda funny?).

But right on cue, I felt that familiar edge kick in — the quiet competitiveness I have with myself.

The voice that says: do better.
Find the time. Stretch the day. Finish what you started. Don’t you dare phone it in!

It’s funny because I’m not competing with anyone else. So this is less pressure, and more honestly, pride.

I was grappling with the version of me that almost felt ok with letting myself off the hook.

But this time, the better version of me won. 💪🏆

So here I am. 👋

A little tired. Extremely thankful. Slightly delirious from the pace of the past few weeks…
But still showing up for this, committed, for you, and for the promise I made to myself when I started this whole thing; to share the real stuff with those who are also wrestling with themselves in the arena. 🤼

Happy Spring, nerds!

✌️ - H

P.S. I will be skipping a month this Summer —because I’m not a machine, I’m a human…who will be enjoying some beaches in Greece. 🇬🇷

No April Fools Joke. But there is an Easter Egg 👆

Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (2.5 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
💸 Fundraising? Shoot me your deck or check out Cherub
🔨 Building something? I wanna hear about it. Hit reply
📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
💼 LinkedIn
📕 Buy my Book

• 🚘 You might have engaged with my grandfather’s work

• ⏱️ Some thoughts on how timing shapes success

• 🛣️ Why a healthy runway is your greatest asset

• 💵 I give you my “Bootstrapper’s Greenprint”

• 🎵 A song that is a subwoofer’s new bestie

• 🎨 Some funny money

• 🔮 The great market downshift

• 🔥 Burning Questions (taking a breather this month)

• ➕ Spreadsheet games, a chicken salad jackpot, the most spot-on Guinness World Record I’ve ever seen — and I finally hit that pesky goal 🏆

  ---

In 1952, my grandfather, Ralph C. Struthers, filed a patent for something he called the Speedmatic. 🚙

It was a throttle-valve control device — an early automotive speed-control system that functioned much like what we now call cruise control. 🛞 Only his was elegant in its specificity:

Press the gas to the exact speed you wanted. Lock it in, allow the car to coast.
Tap the brake — it disengaged.

It was simple, practical and smart.

He invented the Speedmatic because he needed it.

At the time, he had just taken an Executive position at Honeywell located in Washington state. As a native Californian, he was making frequent trips back home to North Hollywood, as he courted the woman who would later become his second wife (my step-grandma? What is the exact term for this in the family tree?). 🤷‍♀️

In those days, the American highway system was expanding. Long-distance car travel was becoming normalized. So were fatigue-related crashes. 💥

My grandfather — an engineer whose brain never stopped turning — decided to solve for that.

My aunt told me a story about how he installed the Speedmatic in the family car. Apparently he’d scooch over in the bench seat, stretch out and close his eyes while his older daughters (including her) took turns steering during long stretches of open highway.

Imagine pulling up next to a 14-year-old, with her hands at ten and two, driving down I-5. (Different era. 😅)

⚙️ Grandpa Ralph

My grandfather was an inventor in the truest sense.

A brilliant engineer. A relentless tinkerer. A man constitutionally incapable of leaving a problem unsolved.

His breadth of work spanned energy technology, electrochemistry, fuel cells and clean energy systems. He was a champion of clean tech (before cleantech was trendy).

Later in life he created in the medical device space. He even patented a plastic pancreas (he was also diabetic).

Grandpa Ralph worked with NASA. 🛰
Held executive roles at engineering firms. 💼
He and his brother owned a manufacturing company, Struthers Manufacturing. 🛠️

He filed hundreds of patents. He was as busy as he was ambitious.

And then, in the early 2000s, Alzheimer’s slowly dismantled the very mind that built all of it.

I’ve always felt that there was something profoundly cruel about that.
A prolific mind, undone by erosion of itself.

I think about that often.

🕰️ Timing (and the myth of “luck”)

So here’s where I correct your thought that I might be a trust fund kid…

Surely — with hundreds of patents, NASA contracts, mid-century innovation — there was generational wealth for the family, right?

Nope. 🙂‍↔️

The Speedmatic didn’t mint a family fortune.

Because my grandfather was early. Too early.

And timing, as it turns out, is often the cornerstone of what we lazily call “luck.”

In Summer 1957, he transferred the Speedmatic patent rights to his brother, Noble, and their family manufacturing company. Noble’s job was to commercialize it (apparently he was the better salesman).

Noble took it to trade shows. Set meetings. Demo’d it everywhere he could. 🤹‍♂️

Turns out, consumer interest was tepid at best.

After about a year of pounding the pavement, Noble called it quits. 👎

My grandfather may have invented the earliest version of cruise control.

But he couldn’t control the market.

📆 The Difference a Year Makes

In 1958 — just one year later — another inventor, Ralph Teetor (yes, same first name), licensed a similar, non-competing system to Chrysler. They branded it Auto-Pilot. 🤯

Auto-Pilot became widely adopted and eventually a ubiquitous feature on all cars in the decades that followed.

There’s no public record of what Mr. Teetor earned for his contributing invention. However, I did some deep research and based on production volume and royalty norms of the era (alongside some inflation-adjusted estimates) the Teetor family could have earned ~$330M in the lifespan of its adoption. #dang 💰 💰 💰

A year’s difference. Maybe a different partnership. Perhaps a bit more stamina.

Maybe a tip of the hat from lady luck would have created an entirely different outcome for the Struthers family for generations to come. 🎩

🌳 Family Lore & What-Ifs

Every family has its mythology. And ours is no exception.

There are whispers that my grandfather’s ideas were “borrowed” without credit. (Teetor’s patent predates his, so probably not by him.) 🕵️‍♂️

Another version suggests Noble did sell it, but secretly, and for far less than it was worth. 🤫

God only knows. 🤷‍♀️

What I do know is that my grandfather believed something went sideways. He felt there was an injustice, and it was stolen in some way. I also heard that he decided to forego legal action.

He was bitter about it (I would be too).

My grandfather had plenty of successful inventions that were adopted commercially and have contributed to clean tech research. In fact, his patents have been cited by Honeywell, General Motors, The Department of Energy, & MIT (just to name a few).

But the Speedmatic, was the one that got away. 😞

This month, I’m writing to you about luck 🍀 and how timing plays a leading role in the wins we have (and how we don’t talk about that much).

I’m also writing to you about money 🤑, and how to best preserve, protect, and invest it so you can allow for longevity. Because longevity is a force multiplier for luck. 🍀

There’s no time like the present.

🚦 So, let’s go…

🙊 The Quiet Part Out Loud: Timing Is Underrated

In business, we often pretend luck doesn’t exist.

We prefer the cleaner narrative: Hard work. Vision. Relentless execution. Years of sacrifice. Grind, grit, and green juice. 🧃 A strict recipe that when baked for 10+ years gives you a unicorn. 🦄

All of the above matters.

These things move the ball down the field.

But sometimes the difference between a billion-dollar company and a bankruptcy filing isn’t talent…

It’s timing. ⏳

🌼 Two Seeds. One Spring.

In the late aughts, two founders believed the world was ready to ditch traditional taxis. 🚖

One launched a sleek black-car service in San Francisco around 2009/2010.
The other launched a ride-sharing startup in 2011.

Both were smart. Technical. Experienced. And both founders saw the same problem.

One company became Uber.
The other was called Sidecar.

You’ve heard of one.
The other quietly shut down in 2015, and sold its assets to General Motors.

Were the founders of Sidecar less capable? Less driven? Less visionary?

Nope.

In fact, Sidecar’s founder, Sunil Paul, had already built and exited Brightmail — acquired by Symantec (now Broadcom) for $370M — years earlier.

He wasn’t new. And he certainly wasn’t green.

Sidecar even introduced peer-to-peer ride matching before Uber did. And that feature later became standard across the entire rideshare industry. 📱

Uber, on the other hand raised more capital. 💰 They scaled much faster. 💨
They expanded city by city with intense urgency.📍

(Have you seen Super Pumped? Recommend! Netflix.)

Uber hit the market at the precise moment smartphones, GPS reliability, investor appetite, and consumer behavior aligned. Like magic. 🪄 Like, the best possible timing. ✨

Two founders planted similar seeds. 🌰

One sprouted in a field of clover. ☘️
The other lay pushing up daisies. 🌼

Same industry. Same era. And very similar intelligence.

I’m positive that there is plenty more nuance to this story (and I would love to know it), but there was a fork in the road that veered Uber toward the glory and Sidecar to a now linkless entity.

Was it pure luck?

No.

Was it pure genius?

Also no.

Uber didn’t just get lucky.
They were positioned to capitalize on luck at scale.

Uber had more speed and more runway. 🛣️

🎲 Is Success a Lottery Ticket?

We love to attribute great outcomes to pure genius. 🧠

We hate to attribute them to timing — because that feels random. 🎲 And random feels terrifying because that means that great outcomes are likely totally and completely unfair.

Being too early for instance, can warrant the same outcome as being flat out wrong. 😥

When you’re all-in on betting on yourself, you don’t want to hear that your efforts could hit — or crap out — and that luck, timing, and forces beyond your control still get a seat at the table

We want to feel in control of our own destiny. We want to believe we can make our own luck but…

📈 Markets can change on a dime.
🪙 Consumer trust can flip.
💰 Capital can flood in — or dry up.
🧱 Infrastructure can rally — or crash.

😷 A global pandemic can come out of nowhere and level your entire 11-year-old business almost overnight (— ok that one was personal 😉)

Having luck and timing on your side is a dance with forces far bigger than you or I.

Why one founder wins and another doesn’t — is probably a combination of a lot of things, or how food scientist and entrepreneur, Riana Lynn puts it…

“It’s about 88% skill and hard work, 12% luck.”

Perhaps that’s why we exalt founders when they hit the entrepreneurial jackpot — an exit, an IPO, an acquisition. 🏆

It looks like a single winning hand.

But behind it?
A thousand shuffled decks. A hundred well-timed bets. More than a few moments where the table could have turned.

So many yeses had to land.
So many players had to stay in the game.
So many hands had to reveal aces at exactly the right moment. ♦️

That’s a lot to get right.

From the outside, it can feel like divine favor. Like the house winked. 🌈

But the truth is less mystical and more strategic.

You can’t control the cards you’re dealt. 🃏
But you can control how you play them. ♠️

You can read the table, manage your stack, know when to press — and when to hold.

As a builder, you’re playing offense and defense simultaneously— protecting downside while positioning for upside — especially when the landscape keeps shifting beneath the felt.

💵 Managing your Stack

The people who keep and compound their windfalls — emotional, financial, or otherwise — aren’t necessarily luckier.

They’re prepared.

They’re organized.

They’ve thought through the “what ifs.”

They probably have a Plan D, E, and F quietly waiting in a drawer.

Here’s a simple gut check:

If your current income disappeared tomorrow… how long could you stand?

Six months?
Twelve?
Longer?

You should always know this number.

Because this is where luck stops being romantic and starts being practical.

🛞 Control What You Can Control

As a bootstrapper, your power lives in your ability to focus on what’s ahead.

💵 Control your money

• Your cash reserves

• Your burn rate

• Your personal lifestyle inflation

🧘‍♀️ Control your mindset

• Your ability to pivot without ego

• Your willingness to play a longer game than your competitors

• Your composure when the forecast shows rain instead of shine

A few honest questions:

🏜️ Can you stay calm when funds are drying up?
🍂 Can you see contraction as a season — not a death sentence?
📊 Can you detach your identity from this quarter’s numbers?
👩‍🎨 Can you solve problems creatively when resources shrink?

Builders who survive cycles build wealth in more than dollars.

They build pattern recognition. 🧩
Emotional range. 🫀
Operational muscle. 💪

And no market correction can confiscate that.

🛣️ The Real Asset: A Healthy Runway

Luck and timing might determine when opportunity strikes. ⚡️

But your financial positioning determines whether you’re still standing when it does. Liquidity buys emotional stability. Runway buys optionality and, funny enough, more time. ⌚️

But don’t be mistaken, a healthy runway isn’t just money in the bank. I see it as:

• 💵 Financial runway - cash + low burn

• ⚙️ Operational runway - systems that don’t snap under pressure

• 🔋 Emotional runway - regulated enough to think clearly (would you make different decisions if you had $500k in the bank?)

• 🏠 Lifestyle runway - personal expenses aligned with the reality of the risk you’re taking

Sometimes staying in the game long enough is the strategy.

The longer you remain in the arena, the more surface area you give timing to work in your favor. ✨

And staying in the green zone is almost always determined by one thing:

How much runway you’ve built — financially and internally.

Set it, steady it (and don’t fall asleep at the wheel).

Share

🫆 My Bootstrapper’s Greenprint

Being a bootstrapped founder often means that you’re starting with the foundation of your own money first. That foundation needs to be solid before we build anything upon it, including a business.

You are the bank, the investor, and you’re betting on yourself. This means, you must get organized, budget and manage carefully.

I started my largest business (17 years ago) with $0 (negative $, probably), and grew it to $MM company.

Here’s my playbook…my Bootstrapper’s Greenprint (see what I did there?).

Because a Greenprint beats a lucky break!

Disclaimer: This is not financial advice. Rather, this is how I’ve looked at (and achieved) my own financial goals as a bootstrapper myself. See your CPA. I’m just a Substacker. 😉

💸 Use the 50/30/20 Rule

Calculate your post-tax monthly income and…

• Spend no more than 50% on Needs = Housing, transportation, utilities, groceries, etc.

• No more than 30% Wants = Subscriptions, entertainment, dining out, etc

• Save 20% (until you can start investing)

For example: If you earn $6,000/mo post-tax…

• Needs = $3,000

• Wants = $1,800

• Savings = $1,200

Move things around until everything fits neatly in one of these buckets.

Have less Needs and Wants? Great, add to savings.

Have excess in Needs or Wants? Cut them down to size.

🥒 If you’re in a financial pickle, and your numbers don’t fit 50/30/20 right now, you’re not broken—start with awareness and a first lever and chip away at what you can.

🤓 I have a spreadsheet template for this (surprise, surprise). Hit reply and I’ll share it with you!

🦋 Recommendation! Monarch is hands down the best household money management app I’ve ever used. (Not a sponsored endorsement. It’s just really good).

🌧️ Next, fill up a “Rainy Day” Fund

I took my monthly “Needs $” bucket 👆 and multiplied it by 6 months and made that my “Rainy Day Fund Goal”. 🌧️ Not a pot of gold—just peace of mind. 🌈

If you lost your income, or had to skip a few paychecks because business was down this is what the Rainy Day Fund is for. If life decides to “life” you, you’re buying some future time to figure it all out.

👧 Note: If you have dependents you might want more security. I upgraded from 6 months to a 12 month goal after I had kids (children are pricey).

So following our above example: A six month Rainy Day Fund would be an $18k Rainy Day Fund Goal and if you’re saving $1,200 (like the example), this would take a little over a year to achieve. Settle in. It’s worth it!

Find a high yield savings account you like to sock it in. 😉

I personally find the feeling of standing on a sturdy financial foundation a great comfort. I can make much better decisions from a place of purpose and growth rather than a scarcity mindset.

✂️ Remember, you can always lean out your lifestyle, bring the cost of your “Needs” or even the “Wants” (those are easier to cut) way down if you want to meet your Rainy Day Fund goal faster. You’re in control of this! But it requires some iron clad sacrifice and some serious discipline.

🧰 Put your Money to Work

Once you’ve filled your Rainy Day Fund to the brim of your goal, flip that $1,200 you were saving into something that can earn you even more money.

Invest it into your business each month, enhance your product, hire a contractor, buy more AI tokens 😜. Use it to grow something that could potentially earn you more money.

Or! Invest it. Maybe in the stock market, crypto, startups, whatever behooves you. Educate yourself on what you’re investing in first. Calculate the length of return. Consult your financial advisor.

I personally like angel investing in startups. It’s definitely more cowboy. 🤠 It’s riskier (and I won’t know if I’m good at it for about 5-7 more years) but I’m ok with a bit more risk for the potential upside of a larger reward later, plus, I’m helping a founder. And founders are my people.

Whatever you do, I say diversify and make your money start working for you.

💳 What if Luck hasn’t been a lady? And you have debt!

Been there (wrote a Substack about it).

Some people might argue this differently, but I say pay off all of your credit card debt and any other high interest debt you have first and foremost. Don’t save a penny until this is done. 🙊 (yep. typed that)

Lean out your lifestyle as much as you can until that toxic steaming pile of debt is paid off.

🔪 Cut up your credit cards. Stop doing fun things. Live kinda miserably until this debt is gone. For just a season. (Sorry, not sorry, I’ve done it — it sucks, but you gotta). 🍜

If the debt is in the business. Do the same. Go to idle. Put austerity measures in place. Wear more hats yourself. Work more hours. Cut the luxuries.

Get creative on ways you can earn more money. Sell assets. Pick up a side hustle.
(I was CEO of a Inc. 5000 company and I was still renting my second room as an Airbnb, moonlighting as a maid, so I could pay off my student loans faster).

You have to find ways to spend less and earn more to escape your deficit hamster wheel.

You will get there eventually. It’s the most unsexy, somewhat depressing state to be in, but you can climb out and still win! 🏆 I promise.

In case you can’t tell, I’m pretty debt averse,😆 but you can leverage debt for your business strategically (I have also done this). Not all debt is bad, and in fact sometimes it’s better than other financing alternatives.

💸 Another Rec: Flex (also not a sponsor, but it is a portco of mine) has an interesting product that helps manage both personal and business finance together. Since these things are so intertwined it’s super helpful for bootstrappers!

They also have 60-day Net terms on their credit product.

🤑 If you have a Windfall…

“The harder I work, the luckier I seem to get”. - Samuel Goldwyn

I say, let luck find you working.

I’ve had some modest windfalls and it’s been a nice financial power boost.

When you have some extra skrilla…(and assuming you have no high-interest credit card debt, and your Rainy Day Fund is filled to the brim) here’s what I’ve done.

I like to imagine these as buckets that once full, can overflow to the bucket below in the following order…

1. 🪣 The Future Self Bucket:

   1. Fill your retirement accounts up to their limits ($7,500/year for 2026 for individuals, if you have a spouse you can double this, $8,600 if you’re 50+).

   2. Maybe pour some into a Self-Directed IRA which you can invest from and realize gains with great tax benefits (I spoke with Alto about how this works on a webinar recently, take a gander)
      

2. 🪣 The Family Bucket:

   1. Contribute to a 529 plan if you have kids

   
   If you still have excess after the above, we fill what I call…
   

3. 🍵🍵🍵The Micro Values Buckets 🍵🍵🍵

These are our choices based on what we value in our family (and took several conversations to arrive at), but it’s a structure that’s set so we don’t have to guess.

We choose to allocate a certain % to…

• ✏️ 20% Education & Enrichment - Learning, conferences, industry events

• 🏡 20% Home & Beautification - Fixing or enhancing something in our living space

• 🏥 20% Health & Comfort - Finally go get that full body scan, lasik, or something that will better us in our own skin

• ✈️ 15% Travel & Experiences - places or things that we want to do/see or go

• 💝 15% Giving & Gifting - We technically do this whether we have “extra” or not, and we do less 501(c)3 donations and more direct giving and gifting to people in our lives that could use it or we want to share with

• 📈 10% Investment & Assets - My husband and I don’t particularly agree on where we should invest our money. I like angel investing, he likes sturdier asset classes. So we split this 10% down the middle and give each other permission to invest as we see fit. It works for us! And it’s built in diversification.

Depending on market conditions we might shift this around a bit.

Money is fuel.⛽️ It gives energy to the things you want to bring to fruition. It can compound your values and the things you want to grow in your life.

As a lifelong entrepreneur I’ve always been attracted to the lifestyle and freedom that comes with paving my own way. It took a bit longer to learn how to earn and organize it so it would multiply (more on that in the outro👇).

As I told you in letter #1 I haven’t reached private-jet-wealth, (and I’m not sure I even want that anyways). But I also promised, I’d share what I’ve learned practically and with no-nonsense.

I hope my Bootstrapper’s Greenprint is helpful to you in some way.🫆

And if it is, go build boldly on top of it. 🎩

🐱 Fiscal Foolery

🎵 The Sound of Reinvention

‼️ This one is NSFW. ‼️

It’s brash. It’s explicit. It shape-shifts between swagger and sorcery. The beat feels like it belongs blasting through oversized subwoofers in a ‘99 Honda Civic — windows down, zero apologies.(You can hear it, can’t you? 😉 ). 🔊

Qveen Herby and rapper, THOT SQUAD join forces to deliver their power anthem, The Fool. Their bravado hip hop beat grabbed my ear drums, and forced me into their risk-taking getaway car.

And on the topic of earning, Qveen Herby is recently 100% independent. She’s in her second act after wrapping up a stint as a label-safe, bubblegum pop poster child. Her new album, Isle of Qveen is fun, fresh, original — and yes, explicit. 🙊

But also, she’s earning every penny because she controls the entire machine. 🎰

🎨 Funny Money

Artist Stacey Lee Webber is a Philadelphia based artist who makes greenbacks her canvas. 🧵 From stitching and embroidering tender notes together to meticulously cutting quarters and dimes, her money pieces don’t only move, they kind of poke fun at how we value money. 🪡

Stacey depicts dead presidents as both circus clowns 🤡 and counter culture emos with face tats.👨‍🎤 And she doesn’t just pick on American notes, she does Euros and Canadian dollars too.

Check her work out if you fancy a deconstructed set of penny earrings or an Andrew Jackson series in a theme of orange things. Her vintage nickel cuff links go for $160.

(BTW- she was just involved in a crazy carjacking situation in New Mexico that made headlines days before I hit send. She’s ok. See her Insta for the story).

🔮 Future Cast: The Great Market Shift

Unless you’re living under a rock, you probably have seen and maybe even physically felt the down shift in the market this past month.

That AI omnipresence I wrote about last Summer is starting to do its thing. 😥

The top researcher (and Harvard PHD) at OpenAI wrote an Op Ed in the NY Times about why she was quitting over her concern for ads in AI. 🤖

An AI safety researcher quit Anthropic with a startling open letter to his colleagues (that went viral) stating bluntly — “The world is in peril.” He says he’s moving to the UK and going to spend his days writing poetry. ✍️

Then, a single Substack briefly rattled the stock market for a day. chart 📉

And to round out the month, Jack Dorsey (former founder/CEO of Twitter - now leading fintech giant, Block) eliminated 40% of his workforce, writing;

“We’re already seeing it internally. A significantly smaller team, using the tools we’re building, can do more and do it better. And intelligence tool capabilities are compounding faster every week.”

Block’s stock jumped 20% in a day after this announcement (now that we have a case study in the ether…watch other companies follow suit). 😬

In my own circle, I’ve seen job losses and layoffs directly attributed to AI this past month.

The conversation that once felt theoretical is becoming visceral. 🫣

I’m not an AI doomer.

But as I wrote last June (after 2.5 years of quietly spiraling about it to myself) there will be a treacherous bridge between where we are and where we’re headed. I believe we’ve stepped onto it this month. 🐊

Our old ways of working are being uprooted. And while the earth shifts under our feet, we must steady ourselves.

I don’t have all the answers. But I do have some recommendations for how to prepare for what’s coming — and what’s already here.

🧠 Give yourself a sanity check
It’s easy to give tools like Claude Code “fangs” 🦷 when you haven’t actually used them. When you do, you’ll likely find: it’s wicked fast, genuinely exciting — and also expensive, technically demanding, and still not that much cheaper than a skilled human (or maybe not at all).

We’re not quite in the era of the layman coding the next DoorDash. Yet. 😮‍💨

🧘 Cool your jets
Things are rarely as good or as bad as we imagine them to be. Try to let go of needing to predict things in one way or another.

🎲 Take some chips off the table
If you have an asset that’s worth something in the current market, you might want to liquidate some. Take some of your winnings off the table (for a rainy day, just in case) and maybe hold for a bit until more is revealed.

🏁 Go a wee bit Faster
What AI tools can you harness in your business or workflow right now to make you faster, leaner, more productive? How can you get in front of your competitors, or simply have a more enjoyable work day? Don’t get lapped because you waited too long.

👋 Use the Human Filter
For the past few years (since OpenAI entered the chat), I’ve been running everything I work on through the same filter: ‘Will this idea, business, product, investment, service, etc. still be viable in a post AI world?’ This questions has been a part of my investment thesis, and part of everything I choose to pour energy into.

I encourage you to point your energy in the direction of things that won’t be obsolete later. Be careful not to accidentally build a sandcastle before the storm.

Instead, focus on human things.

Humans will need to eat, drink, they’ll have babies, they’ll need housing, health care, entertainment, childcare, a haircut, they’ll need and want to gather.

See where I’m going with this?

Think about how you might be able to build and pivot not just for today but for the next decade.

⛅️ The silver lining: As builders, we’re the lucky ones that get to shape the future. Builders are essential to what’s coming.

Get your house in order (and nail a horseshoe above the door). 🚪

Subscribe now

🟢 Things that might make you pinch yourself…

💪 A peek into the future?

🍻 The epitome of a Guinness World Record

☠️ Early April foolin’

🍭 For those who want to leave the top down

👔 A very meta tie

⏱️ A reminder

☁️ One way to store the dishes

💻 My kinda sport

🪽Coming to a sky near you

🔥 I ran out of time this month for Burning Questions (and I’m also running low on them) — Hit reply if you’d like to send some, they help inspire the themes I write to you about each month.

🌼 My Spring Circuit

Join me.

👩‍⚖️ Mar. 11 | Austin, TX | Startup Mania & Pitch Competition presented by Startup Grind | I’m judging the pitch competition + speaking on a panel. More info & Tickets

☁️ Mar. 12 | Austin, TX | ‘Founder Heaven’ presented by Cherub | I’m moderating our investor panels | Free for Founders & Funders - RSVP

👩‍⚖️ Mar. 13 | Austin, TX | Liberty Ventures Pitch Competition | I’m judging | RSVP

🥾 Apr. 3 | Temecula, CA | ‘Find Profit & Sustainability’ my 6-Week Small Business Bootcamp begins 4/3 | Free to SMBs in Riverside County - Waitlist open, 10 seats remaining

🔮 Apr. 16 | CSUSB, CA | Defining the Future Conference | I’m speaking | Register

🍽️ May 7 | Newport Beach, CA | Coterie’s Angel Investing Private Dinner | I’m speaking. RSVP link coming soon!

📫 NEXT LETTER: 🤼‍♀️ Competition 🤼‍♀️ & 🐈 Copy Cats 🐈

I can count on two hands the number of times I saw my grandfather growing up.

Partly because he was busy working. 🔧
Partly because he had seven daughters — who all had children — and even the most ambitious man can’t visit that many households in a year (I think I have like 20+ cousins - too many to count).

My grandfather and I weren’t especially close.

But whenever we spoke — whether in person or via his glitchy “internet phone” that he jimmy rigged in 1998 (not kidding, again, so early) — I used our time wisely. ☎️

I asked big questions.

Like;

“What’s the meaning of life?”
“What do you think will happen during Y2k?”
“How are you talking to me over the internet?”

I noted a few things about him.

He always questioned defaults. He challenged me to think both far and wide about topics. He encouraged me to untangle the ‘why’ of things. 🧐

But most importantly, (and most special to me) he encouraged my own ambitions.

To move to Los Angeles.
To enter the fashion industry.
To keep building my business.
To bet on myself.

Grandpa Ralph passed away in 2019 after a long battle with Alzheimer’s.

Recently, my aunt (the 14-year-old highway driver) shipped me an incredible gift:

Stacks on stacks of his original patents. 📑

Inside the pile: hand-drawn schematics. Margins crowded with penciled notes and math equations. Diagrams of lithium compounds. Patent attorney business cards wedged into the creases. Random phone numbers.

Brittle, yellowed filings spanning from the 1940s through the early 2000s.

All of his many, many ideas that once lived only inside his mind are now in my possession.

Including the patent for Speedmatic. 🫶

Holding them feels like holding a whole life in my hands. Heavy with wins and losses. Proof of a life spent building. Thoughtfully.

I wasn’t handed a trust fund.

But I’d like to think I inherited a legacy of creative thinking, strategic problem solving, and the ability to perhaps see around corners.

My guess is I got that from him.

And maybe that’s worth a whole lot more. 💚

I didn’t grow up with a silver spoon in my mouth. 🥄

If anything, I started from a deeper deficit than many of my peers.

I had to earn my financial literacy.
Learn by white knuckling through my own rookie mistakes.
I had to start from scratch multiple times and get wiser with each new cycle.

And just this month, literally days before publishing this letter, I crossed a pretty significant financial milestone (that pesky goal I’ve been after).

I hit thee number that I’ve pegged as success. 🎯 🧿

I thought it might feel like confetti and champagne. But if I’m being honest?

It just felt… calm.

(All it took was two decades of daily grind, sharpening my skills, hard won lessons, strengthening my mindset and making money moves. AKA staying in the arena. Easy right?). 😅

I’ve had a few lucky breaks that I capitalized on.
I’ve good timing in certain seasons and winter discipline in others.
I leveraged the value of time when I didn’t have anything more to offer.

It wasn’t dumb luck, but there was certainly some serendipity. 🪄

Windfalls make headlines.

But most wealth — especially the bootstrapped kind — is accumulated in quiet seasons over time. In restraint and reinvestment and staying solvent long enough meet your moment.

Fortune may favor the bold. But I think she also favors the patient. 🙏

I feel lucky to have met my moment at least this once (just in time for the market to most likely downgrade me 🤣).

Because if I inherited anything at all —

It’s the refusal to fold.

Let’s keep building. 🍀 🎩 🌈

✌️ H

Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (2.5 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
💸 Fundraising? Shoot me your deck or check out Cherub
🔨 Building something? I wanna hear about it. Hit reply
📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
💼 LinkedIn
📕 Buy my Book

• 🦸 One of the wildest (100% true) dating stories you’ll ever read

• ❤️‍🔥 Passion vs. Purpose🫀— how to tell which one you’re actually chasing

• 🎵 A song that will make you say “ooooh” and “ahhhh”

• 🎨 Maximalist art. Minimalist advertising.

• 🔮 Meet-cutes are back (and GenZ is leading the charge)

• 🔥 Your Burning Questions About how to defuse a ‘Business Partnership Bomb’ that’s about to blow

• ➕ Some things you might love from the internet, “something” that can pour your wine; some related memes; a date you don’t have to get up for & more.

This month’s letter is about passion ❤️‍🔥 vs. purpose🫀 — and the difference between the two. As builders we can often confuse them, or even subconsciously disguise them as one another.

This issue is also about communication.📱 Or more accurately, what happens when we fill in the gaps with assumptions instead of getting clear (with ourselves and others).

There are two stories this month. Two threads, running in parallel. 🧶
(Braiding has been a fun writing challenge).

One story is about saying yes to the wrong thing because it’s familiar, and how being good at something can quietly convince us it’s what we’re meant to do.

The other is what happens when the universe conspires through miscommunication, and the surprising place I found myself as a result.

Both stories subtly taught me the same lesson and I hope they’ll be helpful to you as well. If not, at least I hope you’ll enjoy a laugh.

But first, the scene:

In my early twenties, I was living in Los Angeles, working a corporate job that paid the bills but not much else, and quietly saying yes to every side project that made me feel more myself, useful, capable, and slightly less trapped in cubicle culture. 🪑

Just a few years before, I had discovered (accidentally) that I had a knack for organizing large-scale events. I could wrangle chaos, organize people, curate impactful experiences, and sprinkle a little creative magic over the top. ✨

People took notice.

That’s how I found myself planning a giant Halloween party in the Hollywood Hills for a recently liquidated tech CEO with a mansion and a very specific vision as to who attended said party.

Let me tell you a story…

Disclaimer:
The personal story I’m sharing is 100% true (and still slightly unbelievable). Names, and a few details have been changed to protect privacy.

🏰 A Hollywood Masquerade

In early October of 2008, I got a call from a friend of a friend, who had another friend who had just moved to Los Angeles and wanted to throw a big Halloween bash at his newly leased mansion in the Hollywood Hills.

At the time, I was working at CBS—squarely in that down-and-out phase of life (the period I posted about previously)—so the idea of side hustle money was extremely appealing. 👍

I hadn’t set out to become an event planner I moved to LA to go to fashion school, (and become a fashion designer), but through producing Project Ethos (my first fashion, music and art showcase), I’d developed a reputation for large creative productions.

I was good at events. Big ones didn’t faze me. 😎

Booking great talent. Getting people in the doors. Executing publicly and under pressure. It came pretty naturally to me.

It was fun.

A rush, even.

One I enjoyed.

I might have even said that I was passionate about producing events at one point. ❤️‍🔥

It felt good to create value for the creative community that I held so dear, and it didn’t hurt that others enjoyed it enough to applaud. 👏 The fact that I was launching careers on this platform was incredibly rewarding.

So through the vehicle having of event production skills, I had uncovered a greater purpose.🫀

After my Project Ethos business partnership blew up, I landed in corporate for a while. Meanwhile calls for event projects like this were becoming more and more frequent.

Halloween party? Easy.

I took the meeting.

At the top of October, with less than 30 days to plan, this was a rush job. I didn’t like that, but it wasn’t a deal breaker.

The client—let’s call him Mr. Investor—had recently sold his company in San Francisco and relocated to a massive mansion in the Hollywood Hills. The house, casually, happened to be Pauly Shore’s former place, tucked up behind The Comedy Store. If you know the area, you know the one.

Mr. Investor was blunt. No-nonsense. Sharp. A little sarcastic. And honestly, kind of mean in a way that felt unnecessary. But he was ready to hire me on the spot for a 500-person Halloween party, and I wasn’t in a place to turn down paid work.

The goal: Multiple music experiences. Every facet of the mansion draped in Halloween décor. Photo booth. Food. Full open bar. He wanted it to be a blow out!

None of that scared me. I could do this in my sleep. 🥱

Then he laid out the KPIs (Key Party Indicators 🤓)…

He didn’t want to lift a finger.

He’d invite his friends, but I would handle the entire production—vendors, talent, marketing, ticket sales, operations. And his biggest metric for success wasn’t the financial outcome, or the experience for guests, or even flawless execution.

It was the number of “hot girls” in attendance. 🤦‍♀️ Yes. His words.

(A vanity metric if I’ve ever heard one.)💄

He may have been a bit of an asshole, but my bank account overlooked that.

Despite being immediately turned off by his personality, I said yes.

Before we wrapped the meeting, he dangled the carrot: if this party went well, it could be the start of many more. 🥕 This was essentially an audition to run events at the property full-time! He’d pluck me out of my corporate job and pay me double my salary to do this year-round.

It was enticing. 🤩

On the surface, this opportunity looked like a career break. A grand gig that could change my current trajectory. It had all the markers of something promising — impressive on paper and exciting in theory just enough to ignore the early red flags. 🚩

Even though something about him and our arrangement wasn’t sitting right in my gut, I agreed and I got to work. 🤝

☎️ Pressure Without Purpose

The planning moved fast. Within the first 48 hours vendors were booked. Talent was locked. The concept took shape.

I updated him on the progress, and it was largely radio silence, until it wasn’t. 🦗

His management style was… (at best) aggressive.

Daily phone calls.
Constant pressure.
Zero positive feedback.
Frequent pivots.
And pure obsession with the male-to-female ticket ratio.

Every. Single. Day.

Work I completed would be reopened. Decisions we’d already made were rehashed as he changed his mind. He didn’t trust I knew what I was doing at all.

My compensation was tied to the success of the event, which meant I was fronting an enormous amount of time and emotional energy—and he took all that he could. 😑

Seeing his name pop up in my phone gave me pure anxiety. 😣

I’d leave my desk at CBS to take the calls outside while he droned on about the importance of “the girls” being there. Always the girls.

It was bad.

I don’t remember every detail now (it’s been nearly two decades), but I remember how I felt…

Like a pressure cooker in a pantsuit. Balancing two responsibilities and regretting the day I signed up for this. 🤦‍♀️

💻 Jake Enters The Chat

Mid-October was a dear friend of mine’s birthday. We celebrated over a beach bonfire and some discreet brown bags of beer (a much-needed break to let off some steam). 😮‍💨

I vented to my friends about the situation while the waves crashed on the shore.

The pressure. The constant calls. The feeling that I was sprinting without anything ever being “good enough”. And wondering whether I could indeed pull 500 people to this property.

A friend-of-a-friend named Jake was there. I’d met him a handful of times at various meet-ups with this group. He was a successful celebrity photographer, well-traveled, and very familiar with this particular client type.

We commiserated. He made me feel seen. 🙏

His take was measured: This guy sounds like a dick, but this opportunity could change your life. Don’t quit!

Then he added, “When someone tells me an opportunity could change the trajectory of their career, I want to help. What can I do?”

I asked if he’d help promote the event to his circle. Celebs, models, friends, whomever.

“Done,” he said definitively.

I was genuinely touched. We weren’t close friends—more acquaintances on the fringe of this particular friend group—but his willingness to help stood out.

🦸‍♂️ Zorro

The following Monday (just two days later), an order came through for eight tickets from a Jacob! He had a globe as his avatar in Gmail.

I quickly G Chatted him enthusiastically and with pure glee:
“Jake! You’re the best. OMG! Thank you, thank you!!” 🙏

“It’s my pleasure, there’s more where that came from” he responded.

Wow! Whatta guy.

Over the next few weeks, Jake continued to message me as he helped sell more tickets to the event. He gave me a few brilliant marketing ideas as I continued to talk to him about the dude to girl ratio metric I was aiming for. He brought in more friends. And females. All told, he was responsible for selling over fifty tickets.

I couldn’t believe it. Follow-through, if you’re not familiar, is a rare commodity in Los Angeles. 🤯

We chatted almost every day or two leading up to the party. At one point, I even had a fleeting thought: Is he into me? He’s messaging a lot.

I brushed it off. I’d never gotten that vibe from him before. He’s just helping like he said he would. I went about my business. 🎼 La la ti da.

One of his last messages before the party read:
“Look out for Zorro tonight!” 🦸

I told him I’d be dressed as a Water Bearer—aka an Aquarius—and that I’d see him there. 🫡

🪠 Plunging Purpose

The day of the party arrived.

Setup was a nightmare, but not for lack of preparation.

Mr. Investor was, without exaggeration, a full-blown jerk all day. Every small thing was scrutinized. New tasks appeared with zero notice. At one point, he informed me—five hours before doors—that we’d need three more porta-potties. 📱

And he got upset that I didn’t know how to wire some random speakers he had found in the mansion. 📻 Not only am I not an A/V whiz, but we didn’t plan for this. WTF?

I didn’t know who this guy thought he was, but to me — he was the absolute worst.

I did everything I could to keep my cool. I even ordered an eleventh-hour ice luge that wasn’t in the budget and somehow got it delivered just in time.

Four hours before doors, the event sold out! 🙌
Five hundred tickets, done and dusted (and yes, more girls than boys) 😑
The mansion looked incredible. 🕸️

Still, there was no word of affirmation or praise from Mr. Investor. When I told him the last ticket sold, he muttered stoically, “Good”.

As guests piled in the music thumped, lights danced in the palm trees around the property. It was a party! A good one. A very packed one. It felt like a movie.

I’d done it. And largely, solo.

Success! 🏆

At one point I spotted Jake briefly, I ran up and threw my arms around him. 🫂 He was a welcome sight of comfort for my beat down morale. He was standing with a couple of friends in a surgeon costume—not Zorro—but I didn’t have time to dwell on that.

Because seconds later, Mr. Investor tapped me on the shoulder and told me a toilet was clogged upstairs.

He handed me a plunger. 🪠 Not kidding.

Standing in a trashed bathroom (that smelled worse than it looked), I heaved the plunger in my silver heels trying desperately not to dip the costume dress I’d made in the toilet.

I had a moment of total clarity:

This wasn’t a relationship worth building. Or a client worth suffering for.

I never want to work with this man again.

I had fulfilled my duty. The party was a success, but I was out after this.

Once the puke was pressure washed and the random guy who had fallen asleep in the bushes was woken up, we counted the cash. After expenses, I walked away with a little over $1,000.

Two things were clear:

The stress and torment wasn’t worth the pay—and I wasn’t interested in continuing this arrangement.

This was my first real lesson in the cost of things energetically and emotionally— it really showed me the true value of time. It also edged me closer to defining the difference between passion ❤️‍🔥 and purpose.🫀

Just because I could do something well, that I generally liked doing, didn’t mean that I should. I wanted to point my energy, skill, and time toward something way more meaningful.

Mansion parties? Not it.

🧐 A Date with Jake?

Despite the low monetary pay-off, I had some flowers to give. 💐 Especially to Jake.

“Hope you had fun at the party! I’m taking you to lunch—pick a date,” I typed into our (now super long) GChat thread.

“It was epic! We had a blast! Did you see that guy passed out in the bushes?”

“Yep, had to wake him up myself” I typed. Ha!

We set an early lunch at 11:30 AM for the following week. We both had meetings to work around.

Jake suggested a sushi spot at the Santa Monica airport. He lived near Miracle Mile so it was a little out of the way for him, which struck me as odd, but I had a meeting in Redondo that day, so worked for me!

We inked it!

The next week, about an hour before our lunch, I realized that I hadn’t confirmed the day before (which is out of character for me, I always confirm). And my Redondo meeting had just rescheduled.

I called Jake. No answer.

I left a voicemail:

“Hey, realized I didn’t confirm our lunch today. My Redondo meeting just cancelled, but I’m on my way. Hit me back, so I don’t drive to the West Side if you forgot, no worries if you did, we can always do it another time".”

He never called back. 🤔

I wasn’t going to risk standing a friend up, so I drove out regardless.

I arrived in the vastly empty airport parking lot. It was quiet. The restaurant had barely opened. I walked in to use the restroom.

Wow, I thought. This was a bit romantic for a lunch. Wait… is this a date?
I brushed the thought away again. Nah.

I decided to wait outside to greet Jake. I saw a car circle in the parking lot, but no, that wasn’t Jake’s car. The car parked kind of far away from the entrance. Which gave me enough time to squint and scrutinize the male figure that got out of the car.

No, too tall to be Jake.

As he got closer it seemed like he was walking directly to me.

I was confused. I stared at my BlackBerry avoiding eye contact.

As he approached, he asked, “Heidi?”

“Yes?” I replied as I looked up, completely puzzled.

“Jacob.” He said, as he stuck out his hand to shake mine. “Great to meet you”

Reader, it was not Jake. 😳

🍣 Rolling with Sushi

I shook his hand, doing my best to mask the panic setting in. We walked upstairs to light jazz playing, over crisp white table cloths and triangular folded cloth napkins. A candle flickered in the center of our table.

I immediately excused myself to the restroom. I got halfway there and then realized I had forgotten my BlackBerry at the table, 🤦‍♀️ which I quickly came back for before disappearing again. #totallysmooth

I frantically called my best friend from the sinks. She didn’t pick up.

I left a voicemail:

“I’m in the bathroom of a sushi place in Santa Monica with a guy named Jacob—I thought I was having lunch with Jake, but it’s NOT Jake!! I feel like I’m being punked. Call me back immediately.”

With no second brain to bounce the facts off of I was left to figure this out myself.

[Insert the meme of the confused lady doing calculus in the air here]. #%/-+

And then it clicked. 😳

There were two Jacobs.

Well really…

Jake—the photographer— had indeed attended the party, and yes, he had brought a few friends, but he must’ve never really gone ham on promotion to the extent that I had thought.

Then there was Jacob—a complete stranger—who had bought tickets, messaged me literally 48 hours after Jake and I had chatted, and had unknowingly been on the receiving end of weeks of friendly, overly familiar banter.

He probably thought I was flirting with him. 😱

OMG. I was on a date. How the? What are the odds? Holy 💩! 😆

In that moment I had two choices:

Sit and eat sushi with this stranger - or - reveal the mix-up and embarrass us both!

I chose the former.

After all, it was lunch time, and I was all the way on the West Side and I did owe Jacob lunch, even if it was a very romantic one. 🕯️😬

I compartmentalized what I couldn’t reconcile in the moment, and returned to the table from my prolonged stint in the bathroom. I accepted this as the bizarre story that it was and settled into the fact that I was simply having lunch with someone I met online.

I tried not to let my face show how completely mortified I felt inside. 🫣

So we got to talking. First about the party. Then work. About business building. (My favorite topic.)

He was confident. Kind. Interesting. Well-traveled. Entrepreneurial. Easy to chat with.

A few pangs of moral obligation came over me during our chat.

Was it wrong to say nothing?

Should I just tell him?

Rip the band-aid? 🩹

I didn’t.

Share Building Bold: A No-Nonsense Newsletter for Bootstrappers

Lunch turned into two hours. I eventually forgot how we got there (and that we were perfect strangers). We were genuinely having a good time. In fact, I actually felt a little flicker of a romantic spark between us. 🧨

We exchanged numbers.

As we said goodbye I couldn’t think of much anything else but getting home and digging into how this happened. And calling the actual Jake immediately! (Turns out he was in Cabo or something). 🏝️

Jacob texted hours after we left lunch with a request to meet again soon.

TL;DR we ended up dating!

We proceeded to fall into complete infatuation with each other. 🔥

We spent as much time as we could with each other, and when we weren’t together, we were texting (constantly).

I eventually told him the story of how we actually met. Although, I probably waited too long to do so. 😬 (Because how do you start that conversation with someone you’re really into?!) It never seemed like the right time. 🤦‍♀️

When his mother heard about our origin story, she told him he had to marry me, because we were clearly ‘destined for each other’.

Jacob and I fizzled after a handful of months. 🌬️ Despite my would-be Mother in Law’s proclamation, we weren’t written in the stars.

I can’t remember how it ended exactly.

In any event — despite the whirlwind romance, we weren’t sustainable. We remained friends, though.

Hope you’re well, “Jacob”. 😉

I’ve told this story at dinner parties over the years as a funny tale of pure happenstance, serendipitous miscommunication and ‘can you f*ing believe it?!’ 🤣

It still boggles me how many things had to fit just so, and not happen just right, in order for this mix up to have gone on for over a month, without completely unraveling in advance. 🤯

🌎 If his Gchat icon wasn’t a picture of a globe, but of his face.

👨‍⚕️ If I had questioned Jake at the party as to why he wasn’t Zorro, but a Surgeon.

🦸‍♂️ If I would have actually seen Jacob as Zorro at the party.

📞 If I had confirmed lunch with the actual Jake 24 hours before, or he had picked up when I called on my way.

And all the other tidbits.

All of these little communication points and missed opportunities for reveal that felt —at least for a moment — like they were completely meant for us to meet.

Even still, it came to a dead end. 🪨

(AND BTW: you wouldn’t believe me if I told you their actual names, because they are WAAAAY more unique and way more uncommon than Jake and Jacob).

What a story, huh?

I’ve always wanted to write this one out. Thanks for giving me a reason to.

Also — someone want to turn this into a screenplay? 🎬 Take it. Please.

❤️‍🔥 The Passion You Want ❤️‍🔥

I’m convinced that passion is some type of evolutionary intrinsic feature that helps us not only start but also persist through pain.

As builders we’re often pelted with what feels like impossible circumstances, difficult (even toxic) clients, criticism (and/or clogged “pipes”). And it requires a burning passion ❤️‍🔥 to push through it and keep going despite it all.

Passion will keep you suffering through whatever comes with the things you deem meaningful. It burns hot. Because you couldn’t survive with lukewarm vibes.

I’ve met and worked with business owners that have run out of money, or been severely exhausted, or have every obstacle step in their way, and I’ve seen almost all of them come out the other side. ❤️‍🩹

But, I’ve rarely seen a single builder survive the world of business without a deeply embedded passion for what they are doing.

There is no amount of money, or status, or promise of future success, that motivates the way that loving what you’re building does. ♥️

You want passion. It’s hard to build anything without it.

And what’s even more powerful? Foundational purpose behind what you’re building.

🫀The Purpose You Need🫀

I may have been passionate about events.

But my purpose was well beyond the KPI of satisfying an impossible client (with a shit personality) driven by ego and applause from his friends.

And I knew it. 🫀

Passion wasn’t enough, and it wasn’t the only thing that mattered.

If I was going to say yes to something, (anything for that matter), it would need to be rooted in a more meaningful mission than a string of raging house parties.

🍻🏰 🎵 🤮 🚽

Money didn’t outweigh my purpose either. Double the salary (though super attractive at the time) wasn’t worth it with this nightmare of a boss. Our values = not aligned.

I wasn’t leaving my cubicle anytime soon, by my own choice! And that was empowering.

Both experiences taught me the difference between passion and purpose.

Passion is attraction.❤️‍🔥 But, purpose is compatibility.🫀

You need both — but only one of them truly endures.

And just like with Jake and Jacob, I wouldn’t mistake familiarity for fit.

🙊 The Quiet Part Out Loud: Your Passion ≠ Your Purpose

Just because you love something doesn’t mean it’s what you’re meant to build your life around.

Passion is powerful. 🔥
It’s intoxicating. ☄️
It keeps you up late, 🌙 wakes you up early 🐦, gets you through hard days, and convinces you to say yes before you’ve fully thought it through.

Passion is chemistry. 🧪
That type of “I want all of this” infatuation — that juices you up with dopamine and feels electric and urgent and exciting.

But passion will inevitably fade.

Things will get hard.
And boring.
And annoying.
And maybe even mundane.

The honeymoon, as you know, will (eventually) end.

But purpose? Purpose endures. 🥰

Purpose provides the long-term stamina that reminds you why it’s all worth it — even when it’s repetitive, inconvenient, or quietly unglamorous. 🫀

Confusing the two can keep you stuck in relationships — with work, people, or paths — that slowly drain you instead of deepen you.

😒 You can be great at something and still be misaligned with it.
😥 You can enjoy the rush and still resent the cost.
👻 You can feel needed and still feel empty.

That’s completely human.
But maybe a human that is running on pure twitterpation, and not necessarily unconditional love.

We rarely question passion because the world rewards it loudly.
“You’re so good at this.”
“You’re a natural.”
“You were meant for this.”
”You should totally turn this into a business” 😆 ← I have definitely been this friend.

And before you know it, momentum paired with outside validation has made the decision for you.

But purpose asks the quieter questions:

Does this reflect my values? ♥️
Does this thing I’m building (or thinking about building) grow with me? 💞
Does this still make sense for the life I’m trying to design into the future? 🥰

Sometimes the bravest move isn’t doubling down on the passion that helped you start — it’s admitting that purpose matters more.

Passion can spark the business. Or the path. Or the project (or the relationship). 💋
But purpose is what sustains it.

And choosing self alignment over what looks great on paper?
That’s the boldest kind of love there is.

Love for yourself. 🤗

💗 How to Tell If It’s Passion — or Purpose

A little 5 point test that might help you determine what you’re truly chasing…

1. The “Audience Test” 🍿

I love this quote from Jon Gordon:

“If you were the main character in a movie of your life, what would the audience be screaming at you to do right now?”

You likely already know in your gut🫃what your heart ❤️ is trying to tell you.

But ask yourself:

• Am I energized after spending time on this — or relieved when it’s over?

• Do I keep justifying the downsides because “the upside” sounds impressive?

• Am I hoping it will change once X happens? (More money, better team, less pressure, more respect)

Purpose doesn’t require constant justification.
Passion often does.

2. The Energy Detector 🪄

Instead of listing pros and cons, track energy for one week.

At the end of each workday, jot down:

• 🔋 What gave me energy today?

• 🪫 What drained me disproportionately to its impact?

• 😐 What did I do well but felt oddly hollow?

Patterns emerge fast when you stop intellectualizing and start observing.

Purpose creates net-positive energy over time. Not just bursts of excitement.
Passion creates spikes, usually followed by crashes.

3. The Three-Year Truth Test ⏳

This question is uncomfortable by design:

Ask yourself:

If nothing about this changed for the next three years—same role, same pace, same constraints—would I still choose it?

Not:

• “Could I survive it?”

• “Would it look good to others?”

• “Would I feel foolish walking away?”

But:
Would I choose it again—on purpose?

Purpose can evolve (and it should).
Passion is often conditional.

And conditions are fragile (and constantly changing). Especially when you’re building a business.

4. The Values Mismatch Detector ⚖️

Misalignment doesn’t always show up as failure.
More often, it shows up as resentment.

Ask yourself:

• What values am I quietly compromising to stay here? ⚖️

• Where do I feel irritation or resistance—even when things are “working”?

• What do I complain about on repeat?

Resentment is passion doing the heavy lifting where purpose should be.

5. The Identity Check 👹

This one divorces ego from alignment.

Ask:

• Who is this really for?

  • My past self?

  • Other people’s expectations?

  • A version of me that needed familiarity to feel safe?

  • Or the life I’m actively building now and into the future?

Sometimes passion is just loyalty to an old identity.
Or worse—an identity someone else handed you.

Purpose makes room for who you are becoming.

The Real Difference ➗

One burns hot. 🔥 The other burns long. 🕯️

Passion keeps you chasing potential. ❤️‍🔥
Purpose feels steady. Calm. Sometimes boring. Often repetitive. 🫀

I call this the Groundhog Day Effect. 🕳️

When the days start to look largely the same—when things don’t feel as novel and electric (or chaotic) as they once were, but that sameness feels grounding, and secure, not suffocating—you’re probably building something that compounds for the greater good. Something that creates a better version of yourself.

And while it might feel uncomfortably bland at first, you’ve probably graduating from surface passion to a deeper purpose.

So what if you realize you’re far from your purpose? 🤷‍♀️

🛠️ Maybe you work on it.
If your initial passion burnt you out, take a beat and reassess.
Often, a small tweak or slight pivot can uncover the purpose beneath the minutiae.

If you’re not done yet — wrench on it. Change something.

🤝 Maybe you see other people.
Outsource the parts that no longer light you up.
Hire a CEO or COO. Keep ownership. (I’ve done this — best decision.)

What can you let go of to make room for flow again?

✌️ Maybe you break things off.
Maybe you’ve ignored the red flags, 🚩🚩 made excuses, 🤷 and know — deep down — that this isn’t “the one.”

It might be time for the hardest (and healthiest) conversation of all:

“It’s not me. It’s you.” ☎️

Explore the different routes you can take to find a path back to your purpose.
Give yourself some optionality.

Check out these celebs who did a full 180 on their career path.

It doesn’t need to be all or nothing. But it does require honesty.

Communication is the key to any healthy relationship, including the one with yourself. 🫶

🐱 Let’s Take a (meme) Break…

Hey Cutie, if you’re enjoying Building Bold can you ❤️ this? 👆

🎵 The Onomatopoeia of Connection

Debbii Dawson’s “Chemical Reaction” is a fun, fresh, pop-forward take on the frivolous magic of falling in love. 💖

She lulls you in thinking it’s a folksy country ditty—then flips the switch and punches you straight into a nostalgic, shoulder-shaking groove. 🥊 If this song were an adult beverage, it’d be a Jell-O shot: playful, surprising, and immediately mood-lifting.

A homegrown Minnesotan with Indian roots, Debbii blends genres effortlessly and sparks joy that’s downright gravitational. 🧲

Thanks for the plot twist, Debbii.

🎨 Art Meets Advertising

Graphic designer and collage artist Lisett Ledón, who hails from Spain, crops together layered scenes with a maximalist edge. She’s part illustrator, part collage artist — and entirely unmistakable in style.

My favorite pieces of hers depict oversized limbs and exaggerated poses that stretch, wrap, and spill beyond the frame. Her distortion is intentional as it communicates something truer than realism ever could.

Whether it’s a disproportionate figure of David Lynch in his burning Twin Peaks red room, or a pretzeled Cameron Winter hugging a piano, Lisett doesn’t just depict the talent in her subjects — she amplifies it.

What’s even more impressive is that Lisett has carried this exact voice into the world of big brands — working with Forbes and Mercedes-Benz without sanding down her edges.

It’s a reminder that purpose doesn’t require abandoning passion but rather, learning how to communicate it across contexts.

Check out her merger of passion, purpose (and getting paid for it) via Instagram here.

🔮 Future Cast: The Return of the IRL Meet Cute

I was talking to my college-aged neighbors recently about dating, and AI, and how they “party” this in age (grandma Heidi has questions). 👵

They said something off-the-cuff about how they prefer to meet people in person and they’re totally “off the apps” and so are all their friends. 🤔

It prompted me to dig further. Was this true? Because, I know we’re all kind of sick of the online slop, but I thought GenZ was still stuck on their devices!? 🔍

Turns out, there’s a surprising twist unfolding in how this next generation approaches connection. ⚡️ And I found proof.

Despite growing up with smartphones in hand, GenZ is quietly pushing back against the swipe. A growing body of data shows that — even though digital tools are part of how they socialize — younger adults are less enthusiastic about dating apps as the primary way to meet someone. In fact, fewer than one-quarter of GenZ adults reported meeting their partner through an app, social media, or an online community — meaning the vast majority still meet in person first.

• Across multiple surveys and trend reports:

  • 🥵 Many GenZers report dating-app burnout, citing superficiality, endless swiping, and emotional exhaustion as reasons to log off. Over half of them say they feel burned out by app-based dating.
    

  • 👋 One recent study found that only about a fifth of GenZs say apps are their primary way of connecting, and a majority are focused on meeting people face-to-face.
    

  • ⚽️ Event and social platforms are seeing a renewed role—as places where people bump into each other doing things they actually enjoy. Shared experiences like hobby groups, classes, and community events are becoming settings for “meet-cutes” again. (I brought this up last year in my Future Cast)

It makes sense when you think about it: dating apps reduce human connection to curated profiles and filtered photos — and then reward rejection with a flick of a thumb (I feel so fortunate to have missed this era 😮‍💨). For a generation that places a premium on authenticity and shared values, that can feel quite hollow.

What’s emerging isn’t a wholesale rejection of technology — it’s a hybrid approach:

Use tech to discover, but use real life to connect. 🤝 Rather than letting algorithms dictate who enters your orbit, GenZ prefers actual presence, shared moments, and spontaneous chemistry — the kinds of interactions that can’t be reduced to a profile pic and a prompt. 🦋

In other words, the meet cute — that accidental spark in the real world (that rom-coms have been taking my money to see for decades) — may be making a genuine comeback. (I’m really happy for them) ☺️

And as builders and communicators, this shift has a lesson pressed into it:

Connection still happens best where people show up as themselves, not as curated version stuffed into an endless scroll of filtered headshots (even better if you have no preface). 😉

Why This Matters for Builders 🧱

This isn’t just about dating. It’s about how humans want to communicate and connect (and I’ve been banging this drum for a while):

• GenZ values presence over profiles, depth over scrolls

• The fatigue with swiping reflects a craving for authentic, embodied interaction

• Real-world connection naturally generates richer emotional data — the kind that informs purpose, not just passion

So whether you’re building communities, products, or relationships — the future isn’t just digital. It’s digital + real world, where meaningful communication happens face-to-face, unfiltered, and in the messy magic of actual human presence. Keep that in mind as you build what’s next. 😚

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♥️ If you love…

… ‘something’ else pouring your wine 🍷

… ketchup with your fries 🍟

… a good long sturdy hug 🫂

… shady vibes 🕶️

… coffee with a reminder of where you came from 👶

… smelling your best 💨

… a date you don’t have to get up for (don’t not click this one) 🚍

…some sax with your TLC 🎵

…staying in on Valentine’s Day 🍝

…romanticizing your walls🪟

…faux pearls ⚪️

🔥 Your Burning Questions: “My business partner isn’t doing his part. I’m frustrated, and I’m starting to resent him, but I’m scared that bringing it up will blow up the relationship. How do I actually have the conversation?”

— Sarah, Experiential Marketing | Sacramento, CA

Oh Sarah… I’ve been here. And you’re right: this is never a fun bomb to defuse. 💣

Business partnerships are some of the most intense relationships out there. It’s a hot pot of interpersonal emotions, sacrifice, personal reputation, and the thing you’re both trying to build — like a marriage, but without the warm-and-fuzzy stuff to offset the hard days. (And if your partner is also your man-friend… whew. Been there too. That’s “hard mode” on top of hard mode.) 🎮

All that typed: disagreements and misalignment are normal. Expected, even. The strength of the two of you together may bend and break several times over the course of the partnership, but the hope is it gets stronger (and doesn’t blow). 💥

But if your partner is consistently not pulling their weight, you have to address it while it’s still fixable — before resentment calcifies and every conversation becomes a landmine.

Here’s how I’d approach it:

1. R.Y.E. — Remove Your Emotion (Keep the Receipts) 🧾

When there’s an imbalance, it feels like injustice… and injustice makes us run hot. 🥵

1. Before you say a word, cool it down. 🚿 Strip the story out and keep only facts.

   • What exactly isn’t getting done?

   • How often?

   • What was agreed to?

   • What impact is it having? (missed deadlines, lost revenue, team confusion, you working nights, etc.)
     

   Write it out. Bullet points. Undeniable receipts.
   

   You’re not building a case to “win” — you’re building clarity (and solid proof).

   ---

2. Get Clear on the Outcome You Want 👓

Ask yourself:

• If I bring up X, what do I want to be different afterward?

• What would “better” look like in concrete terms?
  

Because if you don’t know what you want, the conversation turns into a vent session — and vents don’t fix businesses. 🗣️ And could in essence do more harm than good. Writing this out can help you truly see if you’re just upset, or if there is a solution to work toward.

Because most ‘problems’ are really just decisions we don’t want to make yet.

3. Set the Conversation Like a Professional 💼

Do it intentionally.

• Ideally in person (or video if you must)

• Somewhere neutral (not in the office if the office is emotionally charged)

• Calendar it as a real meeting, not a hallway ambush

Frame it simply:

“I want to talk about how we’re working together. I care about this business and our partnership, and I don’t want things to quietly break.”

That line alone should help lower any weapons and defuse defensiveness.

4. Lead With Curiosity (Give Benefit of Doubt… at First) 🧐

Run everything through this filter:

“My partner might not be acting in malice.”

Not because you’re naive — but because curiosity gets you information. Assumptions don’t.

Speak from observation, not interpretation:

• “I’ve noticed X happening…”
  - not -

• “You don’t care / you’re being lazy / you’re checked out…”

Instead, ask him:

• “What’s going on?”

• “Is something blocking you?”

• “Do you still want to be in this?” ← This is the important one!

• “What needs to change for you to show up fully?”

Every time I’ve asked these questions, I’ve learned something I didn’t know. (And sometimes it has been wildly different from anything I’d dreamt up). 🤯

5. Be Ready for the Truth 💯

These conversations usually end one of three ways:

• It goes sideways → you probably have your answer about long-term viability. 😬

• It’s a reset → breath of fresh air, realignment, accountability. 😮‍💨

• It’s unresolved → then don’t let it simmer. Set a follow-up meeting before you leave the table. 😑

Either way, clarity is kindness.

If you’re able to prevent it from being hot and heavy, but rather a cool collected conversation between partners uncrossing their wires…

6. Put Guardrails in Place So This Doesn’t Happen Again 🔒

If the conversation goes well, don’t just “feel better” and move on. Lock in structure.

This is where operating agreements and expectations matter:

• How and when will you communicate? (I love a “grievance corner” — a designated space to bring hard stuff up before it boils over, maybe bi-weekly? Everyone gets 10 minutes to directly spill it). ✏️

• Who owns what? Who has final say where? raise ✋

• What happens if someone drops the ball? 👎

• How do you resolve conflict? Who breaks ties? (🔥 Hot tip: someone should always have the final say. In equity agreements, even if the two of you are equal partners, you shouldn’t be 50/50 — determine who has 51% vs. 49% and ultimately the final say. This will save you a lot of heartache).

Even though these convos are hard. Keep in mind that temporary discomfort is often the cost of long-term trust.

💌 A Final Note

Remember, your partner is half of the whole equation.

You can’t control how they react — but you can control how you show up.

Go into it calm, prepared, and clear. Have a mini decision tree in your head for:

• If they’re accountable → what’s the plan? ❤️‍🩹

• If they’re defensive → what boundary do you set? 🖤

• If they admit they’re out → what’s the next step? 💔

And Sarah — don’t let this simmer one more week. 🙅

Send the text today. Set the meeting.

Good luck and godspeed. 🫡

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🌹 Roses Are Red. Calendar is Full.

Winter & Spring things to catch me at…

👼 Feb. 18 | Online | Investing from your IRA Webinar presented by Cherub x Alto | I’m moderating. Register Free

👩‍⚖️ Mar. 11 | Austin, TX | Startup Mania & Pitch Competition presented by Startup Grind | I’m judging the pitch competition + speaking on a panel. More info & Tickets

☁️ Mar. 12 | Austin, TX | ‘Founder Heaven’ presented by Cherub | I’m moderating our investor panel | Free for Founders & Funders - RSVP

🥾 Apr. 3 | Temecula, CA | ‘Find Profit & Sustainability’ my 6-Week Small Business Bootcamp begins 4/3 | Free to SMBs in Riverside County - Waitlist open

🪽Apr. 15 | CSUSB, CA | Defining the Future of Angel Investing | I’m speaking - RSVP link coming soon!

🍽️ May 7 | Newport Beach, CA | Coterie’s Angel Investing Private Dinner | I’m speaking. RSVP link coming soon!

📫 NEXT LETTER: 🍀 Luck 🍀 & 🤑 Money 🤑

The Hollywood Hills Halloween party gave me a little extra push in the direction of my purpose. About three months after the party, I started piecing together the dusty plans I had in a drawer for RAW Artists.

I had no grand plan for profit. No investors to pitch. No obsession with optics. No idea how I’d make it all “worth it.”

But I knew — deeply — that I was following both my passion ❤️‍🔥 and my purpose🫀.

At the first-ever RAW showcase in downtown Los Angeles, my web developer acquaintance, Matthew, showed up (a mutual friend had introduced us). He was originally trying to sell me a website, but instead we got to talking about the concept of merging an online arts community into the offline one I was building.

And since that night in 2009, we never really stopped talking.

Hours on the phone.
In-person strategy sessions.
Facetimes.

We once had a brunch meeting that lasted 14 hours. (I swear it was not a date). We were just colleagues — who also genuinely enjoyed each other’s company.

I wouldn’t classify our initial connection as fireworks 🎆 — it was more like a slow, steady burn. 🕯️ A comfortable one. Almost too easy to categorize it as chemistry. 🧪

Six months later, we officially became business partners on paper.

I tried to ignore the fact that we would finish each other’s sentences.
That we had the same sense of humor.
Or how our ideas individually became stronger when combined.

Our personalities meshed well. I pushed him toward bigger ideas. He grounded me in reality.
Nothing felt forced, or coerced, or uneven. We could talk endlessly about anything and never really get bored.

It was equilibrium…and effortless compatibility.

Friends and even strangers clocked our flow. (I ignored them too).

I knew this was bad for business. And I wasn’t about to cross that line.
We had something good going.

So I chose my head over my heart 💗 — like a good businesswoman would. 💪

One night, after a charity event I’d produced (that Matt attended in support), we took a late-night walk by the Belmont Pier in Long Beach. (Totally normal for friends and business partners, right?) 🤷‍♀️

We sat in a lifeguard tower and finally said it out loud. We admitted we were more than collaborators — we liked each other. 😱

We talked it through. Thoroughly.
On all accounts, it was a terrible idea 🫣.

And still…we knew we’d regret it if we didn’t at least give it a whirl.

I don’t remember if there was some big dramatic kiss — but I do remember that we shook on it. 🤝 Ha!

What followed were 11 straight years of building together.
Hard days.
Boring days.
Days that felt like nothing could stop us.
Days where I can confidently say I did not like him. (Positive he felt the same)
Days where one (or both) of us wanted to throw in the towel.
Big wins and giant crisis.

But something always brought us back to center. Usually, it was more talking.

RAW Artists grew bigger than both of us — and for a long time, it was my sole passion and the reason I was excited to get to work each morning. It was a mission worth fighting another day in the arena for.

Woven into all of that building: a proposal 💍, a marriage 👰🤵‍♂️, and more recently, two whip-smart, wildly lovable kids — who now represent the most profound version of purpose I’ve ever known.🫀

There’s something real about following your heart — even when it’s messy, inconvenient, and makes zero sense on paper. When you choose the harder road. The one with more obstacles, not fewer. The warmth of a log in the fireplace over the crackle of a firework.

Sometimes, the universe conspires to help you endure. And it provides you just the right balance between passion and purpose to drive longevity. 💫

This year, Matt and I will celebrate 17 years together, 9 years married (and 6 years not working together 🙌 ). 😆

Choose carefully.
Choose boldly.
Confirm with yourself (and others).
And don’t ignore what keeps showing up. 😉

Happy Groundhog Day,

XOXO

✌️ - H

Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (2.5 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
💸 Fundraising? Shoot me your deck or check out Cherub
🔨 Building something? I wanna hear about it. Hit reply
📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
💼 LinkedIn
📕 Buy my Book

• 🧹 I Give You Chores (kinda, by accident)

• 🙊 Some Tough Love on Leadership

• 🎭 Leadership Styles You’ll Definitely Recognize

• 🧬 I’m Coining “Nexus Leadership” (my biggest leadership unlock)

• 🎶 Dusting off a (very old) Oldie

• 🎨 A Squeegee as the Finishing Touch

• 🔮 An Organized List of Predictions for 2026

• 🔥 Your Burning Questions About Building an Effective Startup OS

• + Some Internet Inspo: organizing people, places & things; a meme for your return to work post–holiday grog; a Frenchman’s bold business idea & more

There’s an ancient tradition that originated in China that goes something like this:

Before the Lunar New Year (this year it’s February 17th), 🌙 you clean your house from top to bottom.
You sweep out bad luck and old misfortune to make room for the best of what’s coming next. 🧹
Important caveat: you must clean before the new year arrives — not on the new year itself — or else you risk inviting the opposite kind of luck.

When a friend first told me about this (somewhat superstitious) tradition, I latched on immediately. Because once you know something like that… you can’t unknow it. And you certainly can’t sit in your dusty house as the lunar cycle turns with this information rattling around in your brain.

You’re basically asking for bad luck, right? 🤷‍♀️
(Sorry if I just gave you chores.)

The funny thing is — I was already doing a version of this.

Every year, sometime between Christmas and the stroke of midnight on January 1st, I’d feel an almost physical urge to reset my environment for the year ahead. I’d reevaluate and rethink everything. Every drawer. Every cupboard. Every closet. Windows washed, baseboards wiped, fixtures dusted. All in time for the new year. My space was pristine before the ball drop. 🪩

This timeline is a bit unrealistic in my current season of life.

Adopting this new cut-off date has given me a much-appreciated deadline extension. I get some rest after the holidays and some breathing room to wrangle 3,000 square feet, two little humans, and two large doodles hell-bent on undoing my work (entropy is undefeated). 😮‍💨

So for the past twelve-ish years — even though it’s not my cultural burden to bear — I’ve fully adopted this pre-Lunar New Year tradition. I clean my house top to bottom, reset and wash everything.

It feels nice to start fresh.

And it doesn’t hurt that it feels like I’m setting my family — and maybe our odds for good fortune 🤞 — up for success.

(You have 6-ish weeks if you start now). 😉

Cleanliness really does feel close to godliness to me

📐 I like order.
⚙️ I like systems.
🧽 Cleaning has always been cathartic for me. (You?)

One of my former clients once called me the “Marie Kondo of Small Business.”
I took that as a very serious compliment.

I like organizing and operating in clean environments, at a (generally) clean desk and having everything mise en place. I find it’s calming; I prefer preparation over panic. It’s the most efficient and effective way I know to get things done. ✨

I’ve always been this way.

My family used to call me “Monica” — as in, Monica Gellar from Friends. Intense, hyper-organized, meticulous. Always organizing people, places and things. 🧑‍🍳

As the eldest of four, organizing came naturally to me. Leadership was baked into the family org chart. I lined my siblings up. I assigned them chores, or roles in my latest playbill, or outfits in my living room fashion shows. (They have stories.)

My leadership experience started long before I ever had a CEO title. 😉

On those grade school questionnaires that asked What’s your favorite hobby? I wrote: cleaning. Not kidding. (Decorating my room and writing were a close second).

Maybe that’s weird. But it’s served me well — in life and in business.

Because what’s messier than business? 💩

People. Personalities. Wants. Cash flow. Comms. Customers. Expectations.
Trying to get all of those moving parts into the right places — operating efficiently, sustainably — is no small feat.

It requires someone with vision to roll up their sleeves and get organized.

Organizing a home is one thing. 🏡
Organizing younger siblings is a rite of passage. 🪆
Organizing people and leading them well is a whole other ball of wax. ⚪️

Because vision without structure is just vibes (and vibes don’t always spark the joy of profit effectively).

Today, I want to talk about leadership and organization (inspired by your burning questions) — and why the two are absolutely inseparable.

Let’s get started…

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🙊 The Quiet Part Out Loud: A Business Will Only Ever Be as Great as Its Leadership.

You are the problem and the solution.

If you’re in charge of a business, you already know the deal: you get all the credit and all the blame. You own what goes right and what goes wrong. Every time. No exceptions.
Sorry not sorry — that’s the gig.

But it runs deeper than that.

Here’s the uncomfortable truth:
your business will only ever run as well as you lead it.

A business is a reflection of its leadership — the leader’s strengths and weaknesses, their priorities, and what they deem important versus unimportant. Even if you have seven layers of management between you and your most junior employee, the nature of your leadership will all come out in the wash. 🧼🙊

As the owner of your business, your example and focus determine your culture:

💼 How people show up
🧠 How decisions get made
🤝 How conflict is handled
🌳 How big you grow — or how small you stay

If there is order 👔, that will compound. Disorder does too.
Mistakes left unattended become stains, 🫟 and stains require a much harsher scrub.

And eventually, all of it bubbles back to the top.

🫧 You Set the Culture

Culture is either designed — or neglected. 🦠

When culture suffers, dysfunction typically follows. And so begins the cycle of a business propagating a poor experience for everyone— slow or rushed decisions, employee and/or customer churn, poor sales, late bills, strapped cash flow, unhappy vendors, broken trust, silent resentment.

It’s not fun (I’ve been here).

Great leaders don’t succeed because they have all the answers. They succeed because they’re thoughtful about the environments they create — who they bring onto the team, how they are set up for success, and are incentivized, how customers experience value, and how problems are handled when things inevitably break. 🧨

This is why they say heavy is the head. 👑 It’s a lot to be responsible for.
🫶 Tough love: you signed up for it!

Your job as a leader is to provide clear vision — what you’re building, why it matters, and how people can succeed within your vision.

If this is a dirty part of your business right now — you’re the only one that holds the power to clean up your act. 🚿

I’ve worked with hundreds of startups and small businesses over the years, and the same pattern shows up again and again: the mindset, leadership style, and thoughtfulness (or lack thereof) of the leader in charge determines the ceiling and the floor of their success.

🎭 Leadership Styles (And When They Help — Or Hurt)

No one leads the same way all the time. Different moments call for different approaches. The problem isn’t using the “wrong” style — it’s using one unconsciously.

Here are the most common leadership styles I see, when they work, and where they break down.

🔭 Visionary Leadership — “Here’s where we’re going.”
Great for direction, change, and building something new.
Dangerous when inspiration replaces execution.

🤝 Servant Leadership — “My job is to help you succeed.”
Builds trust and loyalty.
Falls apart when empathy replaces accountability.

🗳️ Democratic Leadership — “Let’s decide together.”
Powerful for complex problems and buy-in.
Risky when consensus replaces decisiveness.

🚦 Autocratic Leadership — “This is the call. Move.”
Necessary in crises. When speed is imperative.
Toxic when used as a default.

🌴 Laissez-Faire Leadership — “I trust you — run with it.”
Fantastic with senior talent and strong systems.
Disastrous when confusion masquerades as freedom.

🔢 Transactional Leadership — “Do this, get that.”
Efficient for execution and short-term goals.
Soulless if it’s the only motivator.

Q: Which Leadership Style do you resonate most with? Did you recognize yourself in any of these? Tell me.

🧽 The Most Effective Styles (in my experience)

I’ve personally been all of the above styles at one point or another. And the truth is we all probably rotate through these leadership types for different circumstances in our business.

I was more visionary when I was starting (mostly because I was creating something from nothing).
More transactional when I had a working system that I had perfected myself.
More Laissez- faire when I had talented management that earned my trust.

But the two leadership styles that have served me well, most often:

1. 🗳️ Democratic - This style was effective when managing change, or solving a big hairy problem. Especially when I needed everyone in the boat rowing in the same direction. Employees who are in the trenches have a lot of information, and sometimes, most of the answers. Crowdsourcing solutions helped tremendously and made sure I wasn’t making decisions for the whole company blind in a silo.
   

2. 🤝 Servant - Because helping people help themselves compounds faster than control ever will. People mirror the investment you make in them. Asking them what tools, resources, people or knowledge they need to succeed and then delivering those things can lead to sparkling results. Every opportunity you give someone else to succeed, strengthens your team further.

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👑 And Still… Heavy Is the Head

All that said, as a CEO — and the leader of a 65-person team — I was also the only one with a true 360-degree view of the business.

I knew what every department needed, where they were struggling, and how those challenges were impacting the company as a whole. I knew where our money was — and where it wasn’t. I knew our next move. I kept a pulse on where I thought things were going in the macro. I saw people’s strengths, and also where they needed to be pushed… and polished.

I understand that you can’t always share all of the information, all of the time. You can’t always fully explain yourself. And as a bootstrapper, there are often constraints on giving your people exactly what they need, exactly when they need it.

This is where your talent, creativity, and communication — come in as a leader.

Again… heavy is the head. 🫡

There is one more style of leadership that unlocked a lot for me.

It doesn’t have a name to my knowledge (maybe I’ll coin one myself). It’s perhaps a blend of a few of the above, but with the employee at the center. It took me over a decade to unlock this and put it into practice. And it is truly the best and most effective leadership style I can share with you…

🔓 My Biggest Leadership Unlock

For many of my early years as a CEO, I was baffled by one thing:
Why didn’t people care as much as I did? 🤷‍♀️

Why wouldn’t they go the extra mile? 🏃‍♀️
Why didn’t they treat decisions like everything was on the line? 💣

And then it clicked — because for them, it wasn’t.

This was my business, not theirs.
They were employees, not owners.

I was expecting people to think like me, sacrifice like me, work like me, and care like me — and that expectation led to frustration, resentment, and years of unnecessary stress. 😣

Once I accepted that most people care primarily about what’s in it for them (not sometimes — most of the time — because that’s human), everything changed.

💎 NOTE: I have encountered a few rare, more evolved gems who genuinely see the bigger picture. They are uncommon. When you find them — hold on tight.

Instead of trying to change people, or mold them into their job title, I started asking better questions:

• What do you care about? — Like, in life in general?

• Where do you want to go in your career? (Long-term. I know you won’t retire here.)

• What gets you out of bed to do this work? (Is it just rent money — or something more?)

• What does success actually look like for you? (Growth here? A stepping stone? A three-year plan?)

When you understand what your people truly want, you can almost always find a nexus between what the business needs, your vision, and where someone wants to go.

⏱️🪙 (💡That’s it! ☝️ — The Nexus Leadership style!) 🪙⏱️

Nexus Leadership is the practice of aligning what your business needs with what your people want — without pretending those two things are always the same.

Never assume people want what you want.
Never assume you already know what they want.
Ask.

I’ve never had anyone not tell me.

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One of my favorite anonymous quotes sums it up perfectly:

People generally all want the same couple of things for themselves; to make a good living, to make a name for themselves and to make a positive impact on others. The difference between us is how we prioritize those things.

— An anonymous woman on NPR, about ten years ago
(If this was you: thank you.)

Leadership isn’t about changing people — it’s about organizing incentives, expectations, and paths forward.

🧬A Real-Life Example of Nexus Leadership

In the beginning of building RAW Artists, we had a helluva time finding great web developers. They were either skilled but unreliable, communicative but underqualified, or truly unaffordable. 😩 It was a painful revolving door. (Oh the analog digital days before AI — it was a different life).

Then a friend of a friend mentioned he knew how to code. My ears perked up. As I dug into his experience (which was extensive), I learned he was on a visa from France — and it was expiring soon.

He wanted to stay in the U.S.
I needed a developer.

We ran a trial. He was highly skilled, fast, knowledgeable, and communicative — albeit with some hilarious French-to-English translations that still make me laugh.

He was a fit. But he was also expensive.

As a bootstrapped company, we couldn’t pay top dollar. But in talking further, we learned he desperately wanted a green card and permanent residency. He also had passions beyond web development that he hoped to pursue one day.

So we struck a deal.

He gave us three great years of development work.
We paid a semi-competitive (but not top-tier) salary — and sponsored his green card.

The revolving door stopped.
The stop-and-go tech build stabilized.

Win-win. 🏆

Today, he lives in Florida and runs a go-kart racing team — as a U.S. citizen. 🇺🇸

🚿 The Maintenance of Leadership

Being a “boss” doesn’t automatically make you a good leader.

Leadership is a skill — and like any skill, it requires practice, reflection, and ongoing maintenance. ✏️

And here’s the real-real: even if you’ve been leading for decades (maybe even since childhood 😉), most of us start out… not great. You don’t bypass being a bad leader on the way to becoming a good one. You learn through experience — usually the hard kind. Mostly the failed kind.

I’ve been a bad leader before. I’ve said and done things I cringe at now. It’s not pretty, but it’s honest — and it’s part of the process.

Becoming a great leader takes time, repetition, and a genuine willingness to learn. 🤓

I encourage you to treat leadership more like a practice than a personality trait.

I have spent heaps of time reading management and business books, studying leaders I admired, watching documentaries, reading memoirs, and swapping notes with founder friends about what actually works when running teams. 📚 I still have more to learn.

No one is perfect (I’m no exception — and neither are you). Everyone is human. Even the boss.

But you can get better if you want to.

Whether you’re just stepping into leadership or you’ve been doing this a while, don’t forget: leadership is a muscle. If you don’t use it with intention, it weakens. If you work it consistently, it gets stronger.

Maintenance matters.

The best leaders don’t wait for a crisis to clean things up — they maintain early, often, and with intention.

Wax on. Wax off. 🧽

✨A few characteristics I’ve noticed in great leaders…

• 🛡️ They build trust.
  They never miss a payroll. They remember key dates. They keep their promises.

• 🗣️ They communicate early and often.
  Even when the message is uncomfortable. Especially then. They’re direct and don’t let things get swept under the rug.

• 👂 They ask for feedback — and actually listen.
  Not performatively. Not defensively. Curiously.

• ⚖️ They balance the needs of the business, the culture, and the customer.
  Gracefully. Intentionally. Not perfectly — but thoughtfully.

• 🏆 They celebrate wins.
  Big ones, small ones, and the quiet progress in between.

• 🪞They reflect when things go wrong.
  Losses aren’t buried. They’re examined.

• 🌱 They don’t blame.

  They get to the root of problems. Untangle them. And present a solution.

• 📑 They’re organized.

  They have a plan. Direction. Lists. They know where they are headed. They label things so others can find them.

Less experienced leaders do the opposite of all of the above. They deflect, they avoid, they delay, they delegate mess downward.

As a leader you must own and organize your “mess” 💩 or it will spread. 🪰

Leadership isn’t about control — it’s about stewardship.
And organization, whether in a home or a company, always starts with ownership.

You don’t have to take my word for it, take it from Simon Sinek

You’re the Boss.

You get to decide the type of leader you want to be, how you want to show up for your team and fulfill your mission. And how great (or not great) the business you’re building will ultimately be. 🏆

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🐱 Memes on Work-Life Leadership

🎵 A Fresh Take on a Throwback to Cleanliness

Willie Watson is a musician (and actor) based in Los Angeles. On his second act, fully solo (he was part of the Grammy-award winning folk band, Old Crow Medicine Show) he’s released this cover of “Keep it Clean”, originally written by Charley Jordan in 1930. You can listen to the grainy pops of that original record here if you want to hear what time passed sounds like.

If you like the clean pick of a banjo, with some whiffs of Bob Dylan, and a classic bouquet of Blues metaphors this one’s for you. 🪕

The double entendres might seem nonsensical but they’re fun and a reminder to keep your yas-yas-yas clean (look it up). 😉

🎨 The Satisfaction of a Squeegee

Visual artist and painter, Sharece has one of the most satisfying creation processes to watch (that might explain her almost 2M followers on the ‘gram).

Starting with lines, dots, and blots of paint on paper, she uses items found around the house to create layers and texture in her work. Once the colors are set she finishes her paintings off with a squeegee to blend it all together and create a bold abstract look.

Her videos are addicting. I bet you can’t watch just one. 🪟

🔮 Future Cast: My Predictions for 2026+

This month, I decided to do a round-up of a handful of predictions from previous Building Bold issues — pulling them together to show where I believe we’re headed in 2026 and beyond.

I don’t have a crystal ball. But I do pay close attention.
Here’s a neatly wrapped look at what I see coming next in the cycle. 👔

🫂 Being Human will become a Competitive Advantage

As markets saturate, how something feels will matter as much as what it does.

Politeness, responsiveness, emotional intelligence, and aesthetic coherence will quietly outperform sharper elbows. Brands — and leaders — that feel human will earn trust and win.

Knowing how to do things will matter less than knowing what to do, why it matters, and when to act. Human judgment, taste, discernment, and values will become more important — not less.

What this looks like in practice:

• Community leaders become the new celebrities 💐

• Brands hire storytellers as an actual job, not a side task 📖

• Businesses move offline again — brick-and-mortar becomes a differentiator 🏬

• Younger Gen Z and Alpha ditch the current social media model, for being more social IRL 🤝

• Personal brand becomes paramount 🪪

• Distribution becoming the moat, not product alone 📣

• Marketing will go full guerrilla: creative, scrappy, distribution-first, IRL campaigns & events explode 🎉

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🌱 Growth for Growth’s Sake Will Fall Out of Favor

Bigger businesses mean more complexity, more to maintain, and more to break.

More founders will intentionally choose smaller, saner outcomes — not because they lack ambition, but because they’ve redefined it. Restraint will start to look like wisdom.

Signals already forming:

• “Seedstrapping” officially enters the lexicon 💵

• More cottage industries and “vibe coding” — building for fun that turns into income (purposely or accidentally) 💻

• Founders raise smaller rounds — or none at all 🥾

• Valuations shrink 📉

• More VC funds fold, former fund managers turn into angels 👼

• Profitability and sustainability come back into fashion 🤑

• Neo-banks win small business trust by being faster, clearer, and more transparent💳

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💸 Alternative Investing Will Go Mainstream

Millennials and Gen Z will continue to diversify away from traditional public markets and into private companies, early-stage ownership, and alternative assets.

Angel-style investing won’t stay niche — it will become cultural.

What follows:

• Education for a new generation of angels becomes essential 👩‍🏫

• Founders seek angels with a name, a network, and a point of view 😉

• A new ecosystem spins up around early-stage access and community 🔄

Predictions are only useful if they inform how we act. 🔮

If these shifts are even partially true, then the question isn’t what’s coming — it’s how we prepare for it.

How do we lead, organize, and maintain what we’re building inside all this change?

I share my Startup Operating System with you below, (thanks to Dylan for the Burning Question of the month that inspired this entire issue).👇

🪆 Internet Inspo for Organizing People, Places & Things

🍹 The ultimate “Servant Leader”

🦇 When you feel drunk with power

🥤 What drinking chaos looks like

🍣 When you want to eat sushi like a boss

🏆 What it looks like to be rewarded for everything you do

🍽️ The perfect disorder of a meal

👕 Another way to organize your closet

🛋️ If you like your couch unscathed

🥖 A Frenchman wants to make America crispy again

📄 Paper thin walls you might want

🔥 Your Burning Questions: How do I organize my business operations?

- Dylan, Stealth Startup, first-time CEO

Dylan, I’m sure there are a million ways, and mostly I say to each their own. But here is what’s worked best for me. I figured this out after a lot of time and energy NOT doing these things (and not liking the results).

Here is my fully optimized Startup Operating System:

🧠 The Core OS: Planning & Cadence

📆 Host Two Dedicated Planning Meetings Per Year

(Six months apart, with your executive team)

In each of these sessions, the goal is to decide on the following:

• Review stats, facts, and figures from the last two quarters

  • Highlight what went well

  • Identify what you want to improve (based on actual data, not vibes)

• Define two major quarterly initiatives for the next two quarters

• Select a handful of smaller projects, improvements, or growth benchmarks
  (Again, informed by last quarter’s actuals)

• Lay everything out on the calendar

  • Assign an owner to each project

  • Define a target goal (and optional stretch goal)

  • Establish a clear success metric for each initiative

• Break quarterly benchmarks into:

  • Monthly targets

  • Weekly milestones

  • Daily goals

I highly recommend a daily dashboard that everyone can access. Shared visibility drives alignment — and momentum.

🍸 A Note on Format (Highly Recommended)

I structured these as in-person off-sites:

• ~7 hours

• Fully catered

• Agenda distributed a week in advance

• Whiteboard + timer to keep things moving

Afterward, we’d do dinner and drinks together. Some of the best ideas and solutions surfaced over cocktails.

I always scheduled these on Fridays so everyone could take the weekend to decompress. It’s a long day — but a powerful one.

🧹 The Rest of the System: What to Maintain & When

Because there are many other moving parts that need regular organization too.

♻️ Annually

• Revisit compensation plans

• Update your Brand Bible

• Purge your cloud drive (aka the digital junk drawer) and paper files

• Update your employee handbook

• Review vendors, tech stack, and subscriptions (cut ruthlessly, revise thoughtfully)
  

✌️Semiannually

• Conduct performance reviews

• Update SOPs
  

4️⃣ Quarterly

• Update your website and client-facing materials

• Review and refresh marketing assets

• Track employee birthdays and anniversaries (put key dates on the calendar)
  

🗓️ Monthly

• Host an All-Hands meeting to review the previous month’s progress, wins, and opportunities
  

7️⃣ Weekly

• Host a weekly team meeting

  • Same time, same day, every week

  • Maintain a running agenda

• Track:

  • Action items

  • Ownership

  • Decisions

• Start each new meeting by closing the loop on last week’s actions
  

🌞 Daily

• Track progress in a shared dashboard

• No closed doors. Full transparency.

• Healthy accountability — maybe even a little friendly competition

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If this feels overwhelming — that makes sense. It is a lot.

My encouragement: carve out the time and intentionally design your own operating system — whether you use this framework wholesale or adapt it to fit your business more precisely.

Mark all of the above on a calendar, so you can put this on auto-pilot as much as possible.

Getting organized won’t just make you a better operator or leader.
It will help your business run cleaner, faster — and thrive.

🔥 Do you have a burning question? I’d love to answer it for you. Anonymous or not. Hit reply.

I read and respond every one.

📫 NEXT LETTER: ♥️ Passion vs. Purpose🫀 + ☎️ Communication ☎️

January is the leader of the year.

It gives us an opportunity to look up from our work and rethink.
It gives us permission to reset with intention. To pause. To take stock. To notice the dust bunnies that accumulated quietly while we were busy building, surviving, and shipping.

I encourage you to take some time to declutter your thinking.
To clean up the decisions you’ve left half-made.
To untangle the systems that have been running on duct tape and good intentions.
To name the messes you’ve been stepping around — and finally deal with them.

Evaluate what needs a spit shine or a full-on pressure wash (and put that load of clean laundry piled up on the chair away finally, yeah?) 🧺

I hope you’re making room for what’s next. Poised for prosperity and good fortune in 2026.

Here’s to a lemon-fresh new beginning and a Happy Year of the Horse to come! 🐎 ✨

Out with the old, 🧹🍋 🥂

✌️ - H

P.S - If Jan 1 was a bust, Feb 17 is right around the corner, and if that isn’t a suitable deadline — don’t forget your birthday is your true new year 😉

Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (2.5 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
💸 Fundraising? Shoot me your deck or check out Cherub
🔨 Building something? I wanna hear about it. Hit reply
📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
💼 LinkedIn
📕 Buy my Book

• 🪞A Year-End Reflection

• 🔑 How Most Small Businesses End in America

• 🚪 Oh, the Ways You Can Exit

• 💋 How to be Irresistible to Potential Buyers

• 🎶 A Song for Many Seasons

• 🎨 Some Fleeting Fashion

• 🔮 The Rewrite on Wealth Creation

• 🔥 Your Burning Questions About Goal Setting

• + A Holiday Gift Guide for all the people that make your world go round, and some timely memes to balance the weight of it all.

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It’s officially December — the final 31 pages in the book of 2025.

This has been a wonderful year for me personally. A very lucky year. So I’m kinda sad to see it come to a close. Here’s to hoping my great fortune doesn’t run out with the clock. 🤞

Endings always make me a little tender, and sometimes emotional. I fully own my sentimentality (and maybe a bit of superstition). I don’t feel this way about every year (and certainly not about 2023), but I see endings (of any kind) as an opportunity to reflect.

What did I learn? What would I do differently? What went beautifully? What could be better next time? How can I improve?

And what’s most exciting…what’s next?

This year, I checked nearly every goal off my 2025 list 🎉 — and even received a few surprise gifts I couldn’t have scripted myself.

I usually accomplish most of the goals I set, but this year was a record! I hit 99% of them! 🥳 And I’m almost certain it has something to do with the fact that I turned 40 this past January.

🎁 The Gift of Now

Say what you will about this milestone birthday (I know, I know — I’ve heard it’s the ‘new 30’, the best years are yet to come, yadda, yadda), but I was personally full of existential dread about it. I felt a lot of turmoil about the transition. As I was rounding the date, time felt more like a texture than a construct.

I was really feeling it, coping with the fact that I was officially crossing over into middle age. 😩 Noticing that the news anchors on TV looked about my age all of a sudden. Seeing the icons I grew up with soften, silver, and age like real-life people. Seeing this in my friends and my family as well. It all felt so heavy.

And I topped off all the tumult with the pressure of this likely being the last big milestone birthday bash where I could get everyone I loved in one room. 😭 (My guess is life will change a lot between now and 50). 🎈

BTW: Did it! (Minus a few). 👇

In the days leading up to 40, I spent a lot of time combing back over the past twenty years. I thought about the friendships, the experiences, the romances, all the things I’d built, the things that ended, the mistakes, the decisions I’d made that forked into the beautiful life I have today. 🥲

I wrote down 40-ish Theories & Thoughts on Life at 40 too.

It was a bittersweet exercise.

I swear that after I blew out the candles on my birthday cake — something in that nostalgic waxy smoke filled me with: I’m done waiting for the perfect conditions. I’m doing the things I want to do. I’m 40 now, goddammit!

My initial existential spiral of dread evaporated and was replaced with some type of bold IDGAF energy. 😎 (Also could have been the wine). 🍷

If aging does anything well, it has a way of making you truly appreciate time.

So I didn’t waste any.

📝 Made a List (and Checked it Twice)

Around this time last year, I listed my goals for 2025.

Post-birthday, I looked again and decided to make them bigger.

The core themes were centered around finding more community with like-minded builders, 💪 achieving a mommy-makeover (after spending the past 5-ish years pregnant or breastfeeding), 🚲 writing more 👀 and being more “out there” — meaning speaking and sharing my thoughts publicly. 🎤 I was also ready to shed some old skin and re-envision the next chapter of my career. 📖

So I got to work:

🤝 In February, I hired a new CEO for RAW Artists.

🫂 In March, I said farewell to the RAW Artists community I built (and that also built me) over the past 16 years, to make way for new things.

I took some new headshots (including the one my daughter has deemed “mama going potty”) and overhauled my website. 📸

🍾 In April, I decided to launch this newsletter! And, I had a surprise (modest) exit from a company I helped start a few years prior. I also started getting serious about my health goals and I welcomed a Peleton to my bedroom.

📫 In May, I put the first Building Bold letter out into the world. I also helped start a monthly Working Mom’s Supper Club in my community.

I went to Camp Hustle in Silicon Valley to be in rooms (and pine trees) with my Angel investor friends (who I had only met over screens for the past few years). So many hugs! So much trail mix! 🌲

🏓 Through summer, I joined a founders’ league of pickleball players (and subsequently learned to play pickleball). We got second place in the beginners’ tournament — not bad for knowing nothing about the sport six weeks prior. Plus, I made awesome new founder friends.

I helped my clients achieve some record successes! 🙌

I traveled to Tulsa, OK to consult with over 50 small businesses that came from all over the U.S. as a judge and mentor in a week-long startup competition. 👩‍⚖️

I spent some time at the beach and Los Olivos wineries with my nearest and dearest friends and family. 🍷

👼 In September, I joined the team at Cherub an unexpected but aligned new adventure that is scratching my builder itch.

🎤 In October, I travelled to Omaha and Santa Clarita, to speak on multiple stages on the topics of entrepreneurship, scaling, event marketing and building a creative business from scratch.

🏆 Last month, I spoke to emerging founders online and a powerful group of women in Newport Beach via the Coterie on the topic of investing and fundraising. I also reached some exciting goals at Cherub!

Also stoked that this newsletter hit over 1,100 subscribers this month 🙏

And somewhere in between all of that I also…

✅ Lost 30 pounds
✅ Got back into a first-thing-in-the-morning meditation routine
✅ Taught three, 6-week small business bootcamps
✅ Showed up for the people I love as they turned 40, had babies, celebrated milestones, and mourned losses
✅ Hosted several holidays and celebrations at our home
✅ I added some new companies to my Angel portfolio
✅ Started advising some promising new ventures

Oh — and chased two small humans around my house as they morphed into four- and two-year-olds. ♥️

(typing that made me kinda tired). 😮‍💨

But somehow, I’m totally content. Grounded in my flow. Poised for a fresh flip of the calendar and full of gratitude for 11 months bursting at the seams with things I love to do.

I once heard a quote that said:

Happiness is defined as having something to do, someone to love, and something to look forward to.

I feel grateful to have all of that. 🙏

I hope your year was as good as mine (and if not, you’re so close to a refresh. Hang in there). 📆

📦 The Unchecked Box

All this productivity and yet — there’s still one goal I haven’t checked off. It’s big. It’s been on the list for three-ish years. And yes… I’ll absolutely share it once it’s done.

I really wanted to get it done this year. I worked on it. I spent the time. I got close a couple of times. It would have been so perfect to tie a nice bow on the year. But it doesn’t look like it’s happening in 2025. 👎

Having that stubborn unchecked box as we slide into the final month the year has forced me to reckon with some facts:

⏳ Not everything can be achieved on a tidy timeline.
⏰ You can’t brute-force outcomes that depend on others.
🕰️ Some goals have seasons of waiting (even years).

All you can do is practice patience and wait for the seasons to change. ❄️🌱☀️🍁

So for now, I’m keeping that one big unchecked goal on ice as I keep chipping away at the prospect of accomplishing it.

🤞 for 2026.

🏆 How’d you do this year? What did you accomplish? What do you wish you would have done more or less of?

Did you also turn 40? Hit Reply. I want to know. Seriously.

Today, I’m writing to you about goal setting, what it takes to achieve your desired outcome and how to move toward the things you want (even if that means letting go of something else).

Psst…it starts with considering how you’ll wrap it all up one day. 🎀

Let’s get started…

🙊 The Quiet Part Out Loud: Every Business will have an ending.

How you plan (or don’t) often decides whether it’s intentional… or accidental.

Most people start businesses with excitement, optimism, and copious amounts of caffeine — not necessarily with a plan for how they’ll one day walk away. 🚪

This was definitely me.

But after two decades in the arena, I urge you: Before you set goals for today, you have to start at where you want to be at the end of tomorrow.

❎ Where are you trying to land?
🎯 What outcome are you actually building toward?
🎉 What’s the big, juicy, pie-in-the-sky finale?

In other words — what’s your exit plan?

Some founders want to run their companies forever and pass them down as the ultimate family heirloom. 📜 (save the gift receipt)

Some want to build, scale, and sell for a multiple that reflects their time, risk, and contribution. 🥂

And some (🙋‍♀️ hi) start building because they can’t not build — and figure they’ll deal with the ending later.

For years, thinking about “how I would one day leave” my business felt almost blasphemous. When more seasoned founders told me to think about my exit at that point, it felt like signing a prenup with myself. Like I wasn’t fully committed or that I wouldn’t see it through. But truthfully, I didn’t know how I wanted it to end. 🤷‍♀️ Seemed like a waste of time to think about.

But now I can say to you with certainty: Plan for the exit. Chart the path. It’s imperative.

Because…

🌟 You need a North Star if you expect to arrive anywhere on purpose. 🌟

If you haven’t already thought through the ending of your business here’s your homework:

🛖 Start thinking about your end goal.
🥁 Maybe it’s a magic number.
🐑 Maybe it’s a feeling.
👑 Maybe it’s the point at which you’ve built something of notoriety.
🐴 Maybe it’s when your desired impact has been achieved.
🤱Maybe it’s simply the moment you feel you’ve “done it” and you’re done.

Examine it from all angles. Decide what’s true for you. Then run every decision in your business through that filter:

Does this decision, person, sales goal, or daily practice align with my exit strategy?

You can make much wiser decisions when you know the direction you’re heading. ✨

🏔️ Cold, Hard Facts

Now let’s bring this back down to earth — and into some cold, hard facts (and numbers). ❄️

According to BizBuySell, the median small business has annual revenues around $674K and sells for about 1.5×–3× net profit.

Lots of nuance here: assets, debt, cashflow, IP.

Meaning:
The average small business is doing roughly $100K in net profit per year. (How do you measure up?)

The median small business sale price in the U.S. is currently $352,000. The data is imperfect — it doesn’t account for age, sector, EBITDA, or region — but it’s directionally helpful.

And here’s the super duper chilly fact: 🥶 70–80% of listed small businesses NEVER sell.🥶

Bootstrappers typically pour and average of 7–10 years of sweat equity into something… and many walk away with $0 (and sometimes still owe money). Not because they aren’t brilliant, hardworking, or worthy — but mainly perhaps because they never did the math.

🎿 Work it Back

So how do you make sure your company is attractive enough to sell for more than $300K?

You start with your number — and reverse-engineer the path.

Let’s be ambitious. Say you want a $3M post-tax exit. 💰
You’ll likely need to be generating $1.5M+ in revenue with healthy margins.

Don’t forget the time it will take you to achieve that (there is no such thing as an overnight success).

💋 Want to be irresistible to buyers? You’ll need:

⭐ Best-in-class profit margins for your industry (compare apples to apples, not the 1% mega corps)
⭐ Low debt + consistent, reliable cashflow
⭐ Organized proprietary data & IP
⭐ Clean systems (SOPs, playbooks, handoff docs)
⭐ A strong brand, reviews, and social proof
⭐ Repeatable revenue — not “hope and hustle” revenue
⭐ A team member (or a few) willing to stay on with the new owner

Easy, right? (I kid. This is hard.👆)

You have to be an absolute animal to accomplish this! You’ve got it in you! 🐆

Take a look at competitors in your space that have been acquired. How long did they take to arrive at that moment? How many users or customers did they have at what stage in the business? If you have somewhat of a blueprint — use it!

Achieving a meaningful exit becomes infinitely easier when you’re aiming, not wandering. 🫏

What do you need to firm up in your operation to achieve the above?

🚪 Where There’s an Ending, There’s an Exit

Most people associate an “exit” with a big wire transfer and champagne. But there are many ways to leave a company.

I’ve had 2.5 modest exits, and they were all completely different — proof that no two endings look the same.

Some are more exciting than others…

🤝 The Strategic Acquisition
A competitor, platform, or complementary brand buys you for your customers, IP, product, tech, brand, or market advantage.

💰 The Financial Acquisition
A buyer purchases your business based on earnings, cashflow, valuation multiples, or ROI — less emotional, more math.

💼 The Acquihire
A buyer acquires your team, talent, or founder — sometimes the product is secondary.

👔 The Management Buyout
Your internal leaders, employees, or partners purchase the company.

♥️ The Family Succession
Passing it to kids… or nieces… or the cousin who thinks he’s ready.

🌴 The Lifestyle Exit / Passive Runoff
You keep the business, reduce involvement, and let it operate for income.

💵 The Licensing or Royalty Exit
Your brand, IP, curriculum, tech, or systems get licensed — you keep ownership, income continues.

📈 The IPO (rare for small businesses, but fun to say)
Going public — twinkly, mythical, unlikely for 99.9%.

❄️ Less-Fun Exits

🔥 The Fire Sale
Sell fast, cheap, distressed.

💀 The Fizzle
It slowly winds down until one day… it isn’t.

🏚 Bankruptcy / Dissolution
Legal, expensive, sometimes necessary.

🫥 The Quiet Walk-Away
Close the doors, turn off the lights, and leave with lessons instead of liquidity.

💰 And What About Venture Exits?

Venture-backed startups have bigger potential outcomes — and far lower survival rates.
Roughly 75% never see a meaningful exit, and 98% go to zero.

But when they do sell, it’s big.
Huge-wire-hits-your-account big. 📈 Champagne-flowing big. 🍾

But outcomes for the founder still depends on the same simple math: Did the founder own enough equity? Did the cap-table get to top heavy? How much debt did it take to build the company?

After several rounds of funding the founder could own very little of their company and investors get paid out first. If there is a cool mil+ in debt and other IOUs this can literally mean that huge wire could amount to $0 for a founder and their team no matter how much they raised. 😬

In fact, some venture-backed founders (even ones you might admire 👀), might have walked away with less than life-changing money, (and perhaps a bruised ego and a dent to their reputation). 🤕

The founders who do win big are the ones who keep ownership in tact, manage dilution strategically, and build something buyers actually need.

Small business or big money raised, the stakes are high in every direction, because either way, you’re betting years of your life on a future you can’t fully predict. ⛰️

Choose your path wisely. ⬅️ ➡️

🪷 The Art of Letting Go

One of the most inspiring examples of an intentional ending is the sacred practice of Tibetan monks creating a sand mandala. I think of this practice everytime I fear I’ve wasted time on something.

Have you seen this? It’s stunning.

Mandalas are a visual diagram, usually displaying some type of concentric circular design represent the macro and micro interactivity of a theme. Each mandala is different and tells a story. They typically pay homage to deities and/or represent a cosmic palace. ☸️

Mandala creation is an important meditative practice for the creators. In fact, they train for many years to learn the skill of creating these sand mandalas. I don’t know if I could ever do this (it certainly takes so ironclad patience).

Sand Mandalas require the painstaking, precise work of placing each grain of sand into a grand template. It often takes days or even weeks to complete by a handful of monks collaborating day and night. All the while, they’re meditating on the intention behind the piece — the purpose of creating it at all. 📿

Once it’s completed (and shown publicly), they engage in a ritual dismantling. They wipe their work clean and return the sands to nature, most often back to a body of water.

It’s a profound lesson in impermanence — for both the makers and the onlookers.

Sometimes the blessing is in the work itself, and not how it ends.

Whether you’re celebrating a multimillion-dollar wire… or cashing a $300K check… whether you’re sunsetting after a great decade-long run… or passing the keys to your cousin…

Not every exit comes with confetti. (Most don’t.) And honestly? Maybe they don’t need to. 🧘

If you built something you’re proud of, learned lessons no one can take from you, made an impact, formed real relationships in the process, and earned some money along the way — that’s success, dude. Be proud. An exit of any kind means you accomplished something. You built something with your bare hands. 🙌

Everything ends — (sometimes, even when we don’t want it to). And every ending creates space for a new beginning. 🌱

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🎵 A Song that Changes Seasons

The Ruen Brothers self-produced record Sitting at the Station feels like the first sip of a whiskey on rocks on a damp December night. The song (and the whole album — which I recommend) is a melancholic, eerie ode to the art of waiting.

The brothers’ twangy folk Americana vocals are a juxtaposition to their English roots. They struck a chord in me nonetheless.

I hope you enjoy this month’s more emotive selection.

🐱 Timely Memes

🎨 How to Walk in a Winter Wonderland

Artist, Katerina Shukshina better known by her insta handle Shu Katerina creates fashion pieces and accessories made from the natural world, like brussels sprouts, snap peas, and other seasonal plants. From fleeting cabbage handbags to coats made of clover, Katerina’s designs regenerate with the seasons

Her work is alive for only a moment and captured for us to appreciate. Take a gander.

🔮 Future Cast: Wealth Creation gets a Rewrite

The majority of millionaires in the United States (currently made up of Baby Boomers) generated their wealth in three main ways:

🏡 owning real estate
🧑‍💼 owning businesses
💸 and mostly… owning equities (investing).

As our parents and grandparents age, they’ll eventually transfer that wealth (if they’re nice 😅) to us — the younger generations.

The real question is: what will we do with it?

I have a hunch…

Millennials and Gen Z aren’t following the same financial playbook our grandparents used (and many of us have been priced out of homeownership entirely).

According to Charles Schwab’s Modern Wealth Survey, 📊 younger investors are allocating a higher percentage of disposable income into equities than Boomers did at the same age.

✍️ Fidelity’s annual analysis shows Gen Z opened brokerage accounts at a record pace in the last two years, with a double-digit increase in first-time investors. 📈

And the Federal Reserve’s Distribution of Financial Accounts reports that Millennials have quadrupled their share of total U.S. stock ownership in the past decade — and that number is accelerating.📈📈

But, it doesn’t stop at public markets.

The same Fidelity report (mentioned above) notes:

“Wealthy next-generation investors are more attracted to new investment products than Boomer+, with significantly higher interest in replacing passive ETFs with active ETFs and gaining exposure to alternative investments.”

Alternative investing — once reserved for the ultra-wealthy — is becoming mainstream. As an angel investor who works at Cherub… I guess I’m part of that “new mainstream.” 🐠

Meanwhile, the SEC’s expansion of Regulation Crowdfunding (Reg CF) has made angel-style investing accessible to everyday accredited and non-accredited investors. Platforms like Republic, Wefunder, and AngelList have seen year-over-year growth driven by Millennials and Gen Z — many of whom want to invest in the founders and products they believe in, not just the tickers scrolling across CNBC.

I know I feel this way.
The public markets have my money (but not all of it)— it’s a bit too boring for this elder Millennial. 🥱 I want to see my money move and make an impact. 🎯

And now, the really exciting part: 🤩 pending legislation and regulatory momentum are pointing to an even bigger shift: allowing retirement vehicles like 401(k)s and IRAs to allocate into private companies, venture funds, and alternatives.

Can you imagine, if almost everyone could invest in what they want to?! 🤯

Bipartisan proposals would expand private-market access so younger generations can put a portion of their tax-advantaged savings into early-stage companies — the very engine of innovation (and sometimes those outsized returns we talked about 👆🥂 ).

This opportunity excites me! So if Boomers built their wealth through equities…
Millennials and Gen Z may build theirs through equities 📊 + entrepreneurship 💪 + early-stage ownership. 🏦

I’m a fan of this future. I’m giddy about what this means for innovation, entrepreneurship, and generational wealth.

(pssst)… if you’re curious about angel investing, I can help. Hit reply.
97% of people that are accredited to invest aren’t investing (or don’t even know that they can).

So here’s my future cast (finally! Sorry! I have so much to say on this):

When the largest wealth transfer in recorded history collides with a generation that prefers investing over saving, ownership over employment, and impact over tradition?

Let’s just say that’s a bottle ready to pop! 🍾

💸 Hit reply if you have comments, questions, or thoughts — I’d love to hear them.
I read and respond to every one.

👧 Q: Is there a Latin word for when you’re almost 41, but you feel 24?

🎁 Holiday Gift Guide

They say you only ever keep what you give away, so here are some cool experiences and gift ideas you might consider giving the many types of loved ones in your world.

For your friends or family who…

🧀 …love Cheese Pulls

🍭 …want to increase the property value of their Gingerbread House

🌙 …want to see a ‘bowl full of mush’ IRL

🧩 …are hard to put together

📻 …love conspiracies

🍝 …are Gen Z and also loves pasta

😢 …are sad sometimes

☄️ …are wondering what to wear post 3I/ATLAS

🦆 …who likes to stand out

🪑 …who can’t sit still

🔥 Your Burning Questions

Q:“How do you personally set your goals and get stuff done?” - Audra, Savannah, GA (no business yet, just building curious)

Audra, I have to start by saying I’m kind of an anomalous person. I have more energy than the average bear (or so I’ve been told). But, I also have a process I’ve built up over the years. Here’s works for me!

Before I get started…
I give myself time to figure out what I want. That part matters.

Every year, I start thinking about my next moves typically around October or November. I spend time in solitude (no devices), I think, I reflect. I ask myself what I truly want.

Here’s my process. I hope it helps you build yours:

✍️ 1. I make Multiple Lists (that make up one big Annual Goals List)

I start by shooting from the hip — everything I want, big or tiny, goes on the page (I write it out old school first). 🖊️ Then I categorize.

And yes… this eventually lives in a spreadsheet (shocking, I know).

My categories are broad but consistent each year:

• Health - e.g, Drink water before I have my coffee

• Home & Family -e.g, Get a new pool pump installed

• Relationships - e.g, Take a girls trip this year

• Business - e.g, Take care of that final unchecked box! 😉

• Travel - e.g, Plan a trip to Greece with the fam

• Legacy - e.g, Volunteer at a Youth Entrepreneurs Organization

• and a “Small Things” list e.g, put up that hat rack (I bought it two years ago 🤦‍♀️).

Once it’s organized, that’s when I get deeper.

🏆 Let’s use, I want my business to earn $500k in revenue this year as an example.

🧠 2. I Get Crystal Clear on the “Why?”

Clarity is everything.

I ask myself why I want some of the bigger more substantial goals I set for myself. I try to look for other angles of arriving at the same outcome to ensure I’m being resourceful enough. Or the path I have in mind is the only way. Or, I ask myself whether this is truly necessary.

I always ask the question “why?” a few times so my goal isn’t driven by ego or pressure… but purpose.

🏆 Why do I want $500k? Is this arbitrary? Or does it help me reach my other goals? Does this help inch my closer to my exit plan? Are there multiple ways I can arrive at this goal? Which one suits my values?

🧱 3. Once I Commit, I Break It All the Way Down

If I’ve decided “Yes — this is the goal, and I’ve found the route,” I break it into pieces.

I give myself an artificial deadline.

🏆 By December 31, 2026, I want to have earned $500k.

I do this because I need a frame to wrap my systems in.

Then I reverse engineer it:

🏆 $500k /Year = $125k/Quarter = $31,250/Month = ~$7,812/Week = $1,116/Day

• What does month one need to look like?

• Do I start slow and ramp up?

• Do I divide the goal evenly through my expected timeline?

• How many clients, customers or contracts is that equal to?

• What’s realistic based on my life season, responsibilities, and bandwidth?

If the numbers feel impossible, I adjust the goal or the approach, or the timeline, until it feels doable —even if it’s a bit challenging.

🛠️ 4. I List What I’ll Need to Succeed

This is the part most people skip — but it’s the key to making things happen.

I list out:

• tools

• education

• support

• childcare

• systems

• time blocks

• money

• software

• accountability

• rest periods

I source and organize those things. I start getting these in place first. To match what needs to happen.

🏆 For my example $500k/year goal: I might need a sales team. Or to sharpen my own sales skills or to squeeze another 1.5 hours out of the work day. Figure out what’s needed and get those pieces in place.

⏰ 5. I Time-Block My Reality

I look at my weekly and monthly rhythms and carve out space to run at my goals.
This ensures the daily work ladders up to the weekly progress that ladders up to the monthly milestones.

This is discipline meets realism.

I also build in soft seasons — vacations, travel, life chaos.
I know I won’t hit peak productivity everywhere, and I don’t pretend I will.

🏆 So maybe my monthly revenue goal needs to be lower some months and higher others to balance out?

🚀 6. I Give Myself a “Start Date”

It’s almost never January 1st.

I give myself a week or two after the holidays to mentally prepare and marinate on what’s coming.
This way, when I officially begin, I’m aligned — not rushed, or groggy from the holiday blur.

Set yourself up for success 😉

🔄 7. I Revisit My Goals Quarterly

I refresh, revise, celebrate wins, and adjust based on what I’ve learned.

Sometimes the goalpost moves.
Sometimes I move faster than I expected.
Sometimes life shifts and I pivot.
Or, I decide meh — I don’t really want this anymore.

The important part to note, is to stay in conversation with yourself about your goals.

💰 After Q1 if I haven’t made much progress on that first milestone, I might adjust my expectations, or double down on my intensity to meet my goal.

📊 8. I Keep Everything in a Living Document

I recommend finding a location you see often — preferably daily.

Mine is a Google Sheet called Productivity & To-Do List.

It has three tabs:

1️⃣ Weekly To-Do List

• broken up by Work, Family, Personal, Admin

• viewed daily

• checked off daily

• rebuilt every Friday afternoon for the next week

2️⃣ Beast Mode Schedule

• this is my life template and pace I try my best to follow (I broke it down here)

3️⃣ Annual Goals

• there to remind myself what I’m working toward

• and always, a click away from daily life

Because if I’m touching it daily, I’m moving toward it daily.

🖼️ Overall

We can make a list of things to do until we’re blue in the face, but it’s truly your internal operating system that checks the boxes at the end of the day (or year).

Note: When I’m feeling like my goals aren’t getting checked off quickly enough, or I’m not being as productive as I could I visit the small things list (and put up my hat rack for some momentum). 😉

Would love to hear if this process for works for you! Keep me posted!

📫 NEXT LETTER: 🪆Organization 🪆 + 🦁 Leadership 🦁

As we say farewell to this year’s version of ourselves, I keep coming back to one of my favorite mantras: everything is temporary — and that’s what makes it precious.

Our businesses will end. Our babies will grow. Our faces will wrinkle. Generations will emerge and fall away.

The society we live in will continue to transform until it’s unrecognizable to the one we grew up in (and we become grumpy about it). 👵

Resistance to change is futile. We don’t get to keep any of it forever.

We’re all just grains of sand that will one day return to the ocean.

But we do get to choose how intentionally we build, how bravely we let go, and how present we are in the middle.

My hope for you as we wrap up 2025 is simple: that you celebrate what you created this year, honor what’s ending, and step into 2026 with a clear vision, a rested soul, and at least one wild, unreasonable goal that makes you feel unmistakably alive. 😎

Happy Holidays, ya filthy animals. 🤶
✌️ – H

P.S- This is out a day early — I didn’t want to be one of many emails on Cyber Monday, or wait another week to publish. (I know December starts tomorrow don’t @me) 😜

Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (2.5 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
💼 Linked In
📕 Buy my Book
🔨 Building something? I wanna hear.
💸 Fundraising? Shoot me your Deck or Check out www.InvestwithCherub.com

• 🎣 The Fisherman & The Banker

• 🐘 The Growth Trap You Must be Careful Of

• 🍔 A List of Private Scalers

• 🎶 A Song to Help You Slip Into Gratitude

• 🔮 The Future = Smaller Teams

• 🎨 Printed Fish

• 🔥 Your Burning Questions About Scaling Without Breaking

  + some seasonal memes + some big and small things (for good measure). 😉

There’s this story that floats around the startup ecosystem. It’s a parable really. It’s used so often that I debated not paraphrasing it here, but I haven’t found a better illustration of the scaling paradox. So here it is…

The Fisherman & The Banker

An American investment banker was on vacation in a small coastal Mexican village when he observed a modest little boat coming into the pier. A local fisherman had returned with a small catch of large yellowfin tuna. 🐠

The banker complimented the fisherman on the quality of his fish and asked how long it took to catch them.
The fisherman replied: “Only a little while.”
The banker then asked: “Why didn’t you stay out longer and catch more fish?”
The fisherman said that he had enough to support his family’s immediate needs.

The banker then asked: “What do you do with the rest of your time?”
The fisherman replied:

“I sleep late, fish a little, play with my children, take siestas with my wife, and stroll into the village each evening where I sip wine and play guitar with my amigos. I have a full and busy life. 🍷

The banker scoffed gently and said:

“I have an MBA from Harvard, and I could help you. You should spend more time fishing; with the proceeds you could buy a bigger boat. 🛶 With that you could buy several boats and eventually you might have a fleet of fishing boats.🛥️ Instead of selling your catch to a middleman you could sell directly to the processor, and eventually open your own cannery. You’d control the product, the processing, and the distribution.”

He continued:

“Of course you’d first leave this small village and move to Mexico City or Los Angeles 🌴 and eventually New York City 🗽where you’d run your expanding enterprise.”

The fisherman asked: “But señor, how long will this all take?”

The banker said: “Fifteen to twenty years, or so.” 📆

The fisherman then asked: “And then what?”

The banker said (with a laugh): “That’s the best part. When the time is right you’ll announce an IPO, sell your company’s stock to the public and become very rich. Millions!”💰💰💰

The fisherman asked: “Millions…then what?”

The banker replied: “Then you’d retire. Move to a small coastal village again where you could sleep late, fish a little, spend time with your kids, take siestas with your wife, stroll to the village in the evenings and sip wine and play guitar with your friends.” 🍷

The fisherman smiled and said: “But señor, I’m doing that now.”

This story is a mirror — reflecting how easily we trade contentment for ambition disguised as progress. Even if you’ve heard this story before (like I have, at least 20 times), it never ceases to punch me in the gut.

It begs the question: When is enough truly enough?

And maybe more importantly — what is it all for? What’s the endgame? What’s the prize at the end of the journey?

I can’t help but wonder if I’ve been the banker a few too many times.

In my early founder years, I bought into the narrative that bigger was always better.
More revenue. More customers. More locations. A larger team. A fancier office (or three, or five).

That was the goal — be the biggest, the best, the boldest. 💪

The scaling paradox is that we chase more to eventually earn the right to live with less.

Big Builder Energy

Don’t get me wrong — there’s nothing wrong with thinking and building big.

Personally, going big is part of my DNA. If I commit to something, I’m all in. 🔥

No matter how big or small.

If there’s a celebration to be had, I pull out all the stops. 🎉 If you’re coming to dinner at my house, it will be planned from napkin to dessert. 🍰 If I enter a costume contest, I go full throttle. 😉 🏆 🏆 🏆 🏆 🏆

I’m asked regularly where I find the energy. This isn’t a humble brag. I simply don’t know how to be any other way.

My husband probably wishes I’d phone it in every now and then. 🤷‍♀️

I’m not the type to keep the couch wrapped in plastic or save the “good” bottle for someday. I like living life now — fully and with urgency. I embrace going big. Life’s too short, tomorrow is too unknown not to.

That same energy fuels how I work. I don’t know how to do anything less than 💯.

Scaling Success

But as I get older (and as I raise two small humans) I find myself defining success differently.

What used to feel like success — headlines, headcount — now feels different. Today, it looks more like peace and presence. The same drive is there, but it’s paired with intention (and less ego). I’m still in the fast lane, but I’m looking around at the foliage at little more. Enjoying the color. Thankful for the ability to be driving at all.

This month we’re exploring scaling — and the trade-offs that come with growth.

Is more always necessary? Is the financial payoff at scale worth the personal cost?

I’ve decided: that’s a deeply personal question. It’s one only you, the builder, can ask and answer. There’s no universal right or wrong, but there are certainly a few notes you should consider (from someone who has scaled for two decades). 😜

Before you grow anything I think it’s important to ask “why?”.

Because sometimes, the very life we’re chasing is the one we already have.

Let’s go 🚀

Hey Founders, wanna learn more about Cherub ?!

ICYMI: I’m the brand spankin’ new VP of Community & Partnerships at Cherub. We help fundraising founders co-pilot their raise and match with our community of Angel Investors. Over $5M has flowed to founders on our platform since launch 18-months ago. 🤯 We’re just getting started!

I’m hosting a Virtual Tour & Open House over Zoom to show you around the platform on November 11, 2025 @ 11AM PST

Register Here

🙊 The Quiet Part Out Loud: Growth can be a Trap

Every time you expand what you’re building, something else must contract.

Usually, it’s your time. Your presence. Your freedom. (Sometimes your health 🙋‍♀️) at least for a period of time.

One of the world’s largest companies right now — both in growth and in revenue — is Nvidia (they just hit a $5T valuation 🤯). In case you’re not familiar, they make the semiconductors (chips, etc.) and computing infrastructure powering much of today’s AI capabilities.

Their CEO, Jensen Huang has become a bit of celebrity in recent years. Partly because of Nvidia’s dominant market position, but also because he tends to say the quiet part out loud —which I love (and he also wears cool leather jackets). 😎

You should check out this video about his take on happiness while building something great.

Earlier this year, Jensen shared this:

“I work from the moment I wake up to the moment I go to sleep. I work seven days a week. When I’m not working, I’m thinking about working. I sit through movies, but I don’t remember them because I’m thinking about work.”

When I heard this, I could instantly relate.

I’ve been there several times — building RAW, writing my book, partnering on new ventures, turning around client’s businesses.

It’s fun; it’s intense.

When you’re in hyper-focus mode, the real world fades and your to-do list becomes your dopamine hit.

The feeling that nothing else is as interesting, urgent, or exciting as what you’re molding. A movie, gossip, the latest celebrity trend, politics — all distractions from the mission breathing down your neck. 🌬️

🌀 I call it Builder Psychosis. 🌀

In the builder’s quest to be better, bigger, greater, there usually has to be a level of focus and devotion that drowns out anything else (we talked about this sacrifice last month). That gravitational pull toward the next milestone sometimes comes with tunnel-vision, or a short memory about how far you’ve already come.

It even tricks you into thinking that once you hit the next milestone, growth will get even easier. 😉

Subscribe now

Here are some considerations for your journey to Scale:

⛓️‍💥 More to Break

The bigger a company grows, the more moving parts it has — and the higher the probability that something will break.

Like moving from an apartment to a house with triple the square footage, there tends to be more fixtures, appliances, more knobs (more to clean). More things means more possibility of more things to do. It certainly feels grander to be bigger, but it comes at the cost of having more to monitor and maintain.

🌱 Growing means: You’ll have more responsibility.

🏔️ More to Learn

When I scaled RAW — first statewide, then nationwide, then international — each level of success brought new layers of complexity (and skills I had to sharpen).

My job as Founder and CEO morphed with each new level. My day-to-day went from training our showcase directors, to soon vetting CPAs in Canada, or untangling the convoluted entertainment tax laws in Las Vegas. 😣

My later stage CEO role wasn’t exactly as fun as it was in the early days, but that’s what was required of me. You’ll likely be less creative and more engaged in mitigating risk.

Such is the CEO life for a business that’s growing.

🌱Growing means: You’ll need different skill sets for different levels.

⛈️ More Cause & Effect

RAW operated in 70 communities worldwide. So there was always an issue somewhere. If everything was generally fine at our Los Angeles HQ, there was surely a venue issue in Austin, or DC was bracing for a storm on showcase day, and surprise, an insurance claim popped up in Philly. 😩

Non-stop fires. All the time. At least somewhere in our ecosystem. 🧑‍🚒

🌱Growing means: Having to compartmentalize and prioritize the things you can control, and knowing that on even the best day, there will likely be a problem somewhere that needs your attention.

🥬 Mo’ Money, Mo’ Problems

As revenue increased, we needed more people — on top of sustaining the team we already had. More investment in people. More upfront costs (training, benefits, onboarding) before seeing ROI (60-90 days usually).

And adding people meant systems built for a smaller team broke (or needed expansion). Now we needed a bigger coffee maker, more desks, more parking stipends — a bigger office, which meant higher utility bills, more office cleaning services, etc.

(If you give a growing business a cookie, amiright?)

The list never shortened — it evolved into costlier versions of itself. 🧾

And if you’re not too careful, (and you don’t run the numbers in advance), it could be that the growth you’re experiencing isn’t growth at all. It could be more like astro turf than an alpine forest. 🌲

🌱Growing means: Mo’ money, mo’ problems. (RIP Biggie.) 🙏

🪤 Sometimes Growth Feels More Like a Trap!

You’ve got to be careful not to get stuck in the vicious growth cycle: you grow to be bigger → you need more of everything to sustain and maintain → then you feel you must grow even bigger to add more margin so you grow to be bigger…(See what I’m saying?) 🐁 🐈 🐕 🐘

The bigger beast you build, 👹 the more you have to feed it, comb its hair, tell it it’s pretty. And it’s not easy to slow down or step back, or stop. Even if you want to! Even if you’re living in some type of no-man’s land that exists far past burnout, and you’re desperate for a breather. 😮‍💨

When you have employees relying on you to feed their families, customers expecting your product or service, vendors tied to your success — you can’t just halt and take a break. Not for long at least (especially in the early days).

You’re the boss. You’re in charge. And this is all your responsibility. At some point it might not feel like much of a choice. Hence, the trap.

Share Building Bold: A No-Nonsense Newsletter for Bootstrappers

🫸 Outside Forces, or —Yourself

It’s usually outside pressures like stakeholders, investors or board members that press for acceleration.

As a bootstrapper, 🥾 you might not have this outside pressure — instead you might be putting it on yourself (I did). Which is valid as someone who wants to be great!

I get it.

On our office wall we had a decal: “What would the Greatest Arts Organization in the World do?”

My goals weren’t small.

I would be lying if I said I found it easy to be satisfied with wherever we were at any given stage in the growth of the company. I might take a moment to celebrate and be grateful, but the next day? It was back to the grind to meet the next goal post.📍

I wanted to keep building, I wanted to keep getting bigger. I wanted to be better.

Being the greatest meant I couldn’t relent. And being relentless comes at a cost.

Usually, the founder foots that bill. ✍️ You should know this before you scale.

🌴 We Thought This Would Be Easy

When I talk to entrepreneurs who’ve built big — really big — they almost always reminisce about the early days.
When things were scrappy and simpler. When the path forward was foggy, but full of hope and possibility. 🤩
When they were tired, yes, sleeping under their desk, maybe, but still - creative and free.

When you could almost taste the success around the corner. 👅

Those were the years filled with possibility — fewer headaches, more heart. 💚

(If you’re here right now, know that so many are envious).

Another anonymous quote I love:

“We don’t do this because it is easy, we do this because we thought it would be easy”

🤷‍♂️ What to ask yourself before you scale…

As a stubborn, tough-as-nails builder, you will likely need to trek the journey to “big” for yourself to fully appreciate its complexity (and understand why second and third time founders sometimes opt for Lifestyle business models, or early retirement). 😜

You will likely not heed my warnings — (that is ok. We’re still friends). 😉

Promise me this… before you scale, at least ask yourself these questions:

⚖️ Is scaling worth it? Weigh the trade-offs. Run the numbers (add a 20% buffer on the top of what you think it will cost). Is there an ROI after everything you need to invest in to grow?

☝️What does the business truly need? And for what reason? Do you need another location? Will more customers actually make your life better — or just busier?

🪓 What will it take to get there? What might you need to hack through? Who needs to be on your team? What weak points do you have in your organization now that need to firm up?

🧍‍♂️Who do you want to be when you arrive at your destination? How do you want to maintain your personal code of conduct? How do you want to treat others in the process? What are you willing to sacrifice?

The price of anything is the amount of life you exchange for it.

— Henry David Thoreau

💜 Purposeful Growth

My two-decades of battle scars might be showing above 👆 (sorry, not sorry). 🤕

But let’s balance this with some optimism. 🪄

Of course, not all growth is treacherous.

Not all growth is bad idea.

Some ideas, products, missions need to be BIG — because they serve a purpose, affect change, maybe even break generational curses. If you’re curing disease, shaping education, building the next super-app to impact millions of lives, or just rewriting your family’s narrative — go big! The world needs you. It’s waiting. 🙌

And just maybe your sacrifice to scale will echo for centuries 🔊 and inspire the masses. ✨

Just make sure your growth serves your purpose — not the other way around.

✅ Don’t be Afraid to Keep it Simple

Because scaling for the sake of scaling is just another form of scarcity mindset— the belief that what you have built isn’t enough. Or that you need to be bigger to be better.

This is a fallacy.

🏃‍♂️You can be ambitious and content.
💜 You can stay small and be fulfilled.
🧘‍♀️ You can chase what’s next while staying grounded in gratitude for what you already have.

Be mindful of the “why?” to your “big”.
Be cognizant of what “big” will require of you (and your team).

If your version of success looks a lot like the fisherman’s — simple, meaningful, full — don’t let anyone convince you it’s too small.

Sometimes the most impressive thing you can build isn’t a large company — it’s a life you actually have time to live. One that you’re proud of. 🎣

🙋‍♀️ Quick Question: What are your growth goals & why?

Hit reply.

📝 Scaling Slow

There’s a common assumption that staying small, or growing slow means staying stuck. But some of the most enduring, profitable, and respected companies in the world prove that restraint is actually a strategy.

You don’t need a billion dollar valuation or to be publicly traded to win big (or be big)!

Let’s stop comparing ourselves to the 1% of entrpre-rockstars (ahem- Jensen) and also turn our attention toward a different route.

There’s a difference between not scaling and scaling on your own terms.

Here are a few giants that chose depth over speed, culture over quarterly gains, and control over chaos:

🍫 The Mars Company
Founded in 1911, Mars is one of the largest privately held companies in the U.S., generating tens of billions in annual revenue. The Mars family has kept the business fully private for over a century — trading public market pressure for long-term thinking, legacy, and autonomy.

🧾 Ernst & Young (EY)
One of the “Big Four” accounting and consulting networks, EY employs hundreds of thousands across more than 150 countries — yet it’s still privately held. The company’s structure has allowed it to maintain independence, cultural continuity, and the ability to reinvest earnings without answering to shareholders.

🛒 Publix
This beloved grocery chain generates roughly $60 billion annually and employs over 260,000 people. Publix is not publicly traded — it’s employee-owned. By sharing ownership internally, they’ve created a company culture built on shared stewardship rather than shareholder demands.

🍔 In-N-Out Burger
Founded in 1948, In-N-Out has grown steadily into a multi-billion-dollar brand with a cult following. The Snyder family has resisted franchising and refused to go public, prioritizing quality, culture, and operational simplicity over fast expansion. Their belief: grow right, not fast.

💪 Restraint as a Form of Power

What I love most about these companies is their self-control through scale.
They are great reminders that growth doesn’t have to come at the expense of your values, quality, or joy.

They also challenge a dangerous modern belief — that bigger is always better.

Because sometimes, the strongest move isn’t expansion.
It’s the discipline to hold the line.

🌲 To grow when it makes sense.
✋ To pause when it doesn’t.
🤗 To protect what made you good in the first place.

To take your time on your own path without giving into the pressures of outside people.

That, to me, is the ultimate kind of power — and the kind of growth worth being grateful for. 🙏

🎵 Slip into Something more Gracious

This month’s music highlight comes from emerging Nigerian artist, Majeeed

His vibe-y Afrobeat jaunt, “Cheers to Life” is like a thanksgiving toast. 🥂 This song is simple, soft, and short with a through-line that both relaxes and sways in gratitude. I hope it reminds you to pause and be grateful for all you’ve built in life thus far. 🙏

🐱 Seasonal Memes

🎨 Master of Scales

Artist Dwight Hwang is a master of the classical Japanese technique known as gyotaku— the art of applying ink to a fish (or other sea creature) and stamping its impression onto paper or fabric. Fun fact: he is also a RAW Artist!

Originating in the mid-1800s as a way for fishermen to record their catches, (and measure them against each other for competitions) 🏆 the method has evolved into a fine art form.

I met Dwight years ago (a delightful dude), and I’m thrilled to see how his art and career have grown — from epic murals to custom work on the siding of a sailboat.

Check out his work both large and small scale. 😉

🔮 Future Cast: The Small(er) C-Suite

All this talk about big stuff. I think it’s time to (re)address the elephant in the room 🐘

AI is shrinking teams (we went over this), and the trend in smaller size is already showing in the data.

According to ADP Research in January 2019 the average team had about 6.6 people. By May 2025 it’s around 5.3. 📉

Firms are thinning middle management, reshaping the manager role, and asking themselves if the old org chart still makes sense. Deloitte has more.

🧙‍♀️Here’s my prediction: Companies will be made up of small but mighty C-Suites, running armies of agents.

Teams will actually become leaner and sharper than ever before, in which case — scale can be achieved much cheaper than the days of ol’. 👆

If I look deeper into the crystal ball 🔮 I see teams looking like so:

• 🔭 A founder / CEO who sets mission, tone and direction.

• 🎯A COO or integrator who handles road map execution, systems, and process development.

• 💻 A head of AI/data or innovation who integrates technology into workflows from R&D to sales and marketing.

And maybe one more role — depending on your business — but the point is: fewer seats at the table with broader scopes.

🌟Bonus: If someone on the team has built-in distribution. A large following, a hefy subscriber list, etc. This is gold in the new world. (pssst…It might be the last defensible moat).

As AInvest article put it: “About 50–100 AI agents can be managed by just two or three humans.” 🤯

What does this mean for you? — the founder, the builder, the one who wants to scale, win and also not break yourself in the process?

1. You’re in a VERY lucky era of business building! It will be cheaper than ever to grow. This will be really great for founders with big ideas and small budgets. Five person companies can scale large in format with less pressure and more lifestyle business hours. Seriously, lucky you! 🦴
   

2. Like the meat off of a turkey drumstick, 🍗 scrappy generalist talent is going to get picked off quickly by every company in the world. You’ll want to start shaking hands, and taking names, and testing projects with these folks now.
   

   What roles will matter most?
   
   Who are the people you want at your (much smaller) table? 🪑🪑🪑

   ☝️ Remember: Almost no one is technically an “expert” in AI or agentic deployment (it hasn’t even been five years) so “scrappy” is imperative to your job description now and in the future.

   
   Start talking to the people you want to snatch up now. If you wait too long, it might be slim pickins’.
   

🤖 PS — I’m patiently waiting for the right natural-language model accessible enough for laymen (that’s me) to build and deploy agents. Know of one? Hit reply!

🐘 Big & Small Things from the Internet 🐭

🎤 Big Voice

🦠 Small View

🚴 Big Feat

🦋 Small Wonder

🏃‍♀️ Big Pain

📆 Small Question

🕶️ Big Following

🪰 Small Distraction

😂 Big LOLs

🌞 Small Scale

🎸 Big Bass

🔥 Your Burning Questions: Scaling without Breaking 📈

Q:“How do I scale without losing myself in the process”
- Mike B., Florida, Crypto space

Mike, the truth is you will shed some layers of skin in the process. There is no way you’ll come out unscathed. 🩼

If you’ve decided on the path of BIG growth, you’ve weighed the trade-offs, built something worth expanding, and you’re ready to grow — but not at the expense of your sanity, your team’s culture, or your purpose…

Here’s where I suggest you start:

1️⃣ Lay the Foundation First

Scaling doesn’t fix chaos — it multiplies it. 🐟 🐠 🐡
Before you pour fuel on the fire, shore up your footing: cash flow clarity, clean data, a product with a solid and secure foundation and a simple strategic plan you can actually follow.

This isn’t about a perfect business plan — it’s about creating stability so that growth feels like acceleration, not whiplash. (See: my Magic Cashflow Formula).

Ask yourself: If I doubled tomorrow, could my current systems and team handle it?
If the answer’s “not yet,” that’s your work. Make the list and knock it out.

2️⃣ SOPs & Systems

You can’t scale what only lives in your head.
Every repeatable task — from onboarding to invoicing — needs a home outside your brain. 🧠

Start small: Loom videos, step-by-step checklists, shared folders in Google Drive.
Documenting now saves you later. ✍️

Systems give you freedom.
They’re what allow you to take a vacation and have your business keep humming while you enjoy that fishing trip. 🎣

3️⃣ Talented Operators You Trust

A vision is only as scalable as the people carrying it with you. 🪨

Hire operators who are not just skilled, but aligned — people who understand the mission and can make decisions that reflect your values when you’re not in the room.

Your first hires set the culture. ♥️
Your best hires protect it. ☂️

When you trust your operators, you can finally step out of the weeds and into the role of visionary — which is where you belong.

4️⃣ Document What You Learn (in Real Time)

The founder’s brain is an evolving playbook. Write it down.

Create a simple “Builder’s Bible” — a living doc where lessons, wins, and warnings get captured as you go. 📖 — I did this and later it became a book (and this Substack)
It keeps “future you” aligned with your North Star (and is a good reminder of why you made certain decisions along the way). ⭐️

Reflection is a great growth strategy.

5️⃣ Get your Head Around it

Right before RAW went national, I went to Sedona. 🏜️ I sat in a vortex. 🌀 I visualized my life-to-be. 🧘‍♀️

I tried to feel the busyness, the work, the marathon I was about to embark on. I found my version of peace before I took my first step.

🐜 (I also remember that I accidentally sat in a pile of ants, but that’s beside the point).

Mentally and emotionally preparing for a long road that will be hard and will surely dare you to throw in the towel at some point or another is a good practice.

It doesn’t need to be a Sedona vortex, but find a place where you can center and really think about it. Visualize what life might look like and ask yourself if you’re willing to pay the cost.

And remember the secret to scaling might not be how far you go, but how closely you stay connected to what made you start.

Stay hydrated. 🫡

📫 NEXT LETTER: 🏆 Goal Setting 🏆 + 🚪Exiting🚪

As we set the table with our loved ones this month. 🍽️ I hope you have a moment to reflect on your year and all the things you’ve done and built. I hope you’re proud of what you accomplished, lessons you learned, and the lives you’ve impacted for the better!

Even if you’re far from where you want or plan to go, take a moment to feel gratitude for how far you’ve come. 🙏

Don’t forget how very lucky you are to be building something you love, or building something at all. 💪

Here’s to counting our many blessings and measuring ourselves by the impact we create. 🥂

I’m thankful for you and your readership, and that you’ve embraced the long form alongside me. I tried to be all 6-7 about it, but again, couldn’t do less than what was in my heart. 🤎 (Kids, did I use it right?) 🙊

Happy Thanksgiving to you and yours! 🦃

✌️ – H

P.S - My daughter saw the picture of me below as she was sitting on lap and I was getting ready to publish. I kid you not she said “Mama going potty” — when I change my picture, you know why.

Enjoy that laugh for the road. 😘

Hi, I’m Heidi. 👋

I’m a two-decade bootstrapping serial business builder (2.5 exits), author, strategist, and non-technical tech founder turned angel investor & advisor. I’m also mom to two doodles and two small humans, a wife, and a classic eldest daughter — no hobbies (unless building equity counts).

I believe entrepreneurship makes the world go round, and creativity is our greatest asset. I help founders and business owners start, scale, and streamline profitably and sustainably. More recently, I’m the VP of Community & Partnerships at Cherub, where we help fundraising founders co-pilot their fundraise and match them with Angel Investors.

I write small angel checks — but I’m still bullish on bootstrapping. 🥾

💻 Visit my Website
📱 Follow my Insta (if you like cute kids), or my X account (if you like radio silence followed by the occasional re-tweet).
💼 Linked In
📕 Buy my Book
🔨 Building something? I’d love to help!
🌈 Is your business struggling? Let’s turn it around!
💸 Fundraising? Shoot me your Deck

• 👩‍🍳 How to Start from Scratch

• 💪 I implore you to get Lean

• 🎶 A song that changes flavors as you listen

• 🍳 Building Utensils

• 🔮 MY Future Cast - (psst...it’s personal)

• 🔥 Your burning questions about GTM without rushing

  + a meme for the married, some pants for your Cheeto fingers and more!

  ---

In late 2008, I was laid off from my first (and only) corporate job at CBS Radio, where I sold on-air advertising (back when radio was a thing). I’d taken the job after walking away from my first company, Project Ethos.

PE was a glossy fashion, music and art show in Hollywood. Red carpet. Celebrities. 2k+ attendees. We gave independent artists a platform (sound familiar?).

Project Ethos ended for me due to messy partner breakup (a story for another letter). And right after walking away from that situation I stumbled straight into a financial disaster. I took some bad advice and attempted an experimental event series. I’d poured all my time and money into it and it failed, big time! (Also, another letter).

🥊 🥊

My ad rep at CBS — the very one I had bought air time from for that ill-fated event — noticed my lineup of big-name sponsors and asked how I managed to land them.

“I cold called them,” I shrugged. 🤷‍♀️

Impressed, she marched me in to meet her boss a few weeks after my big flop. (Fast forward: that same man would later sit on my advisory board for RAW Artists.)

My CBS stint was short-lived — less than a year, if memory serves. But I learned a lot. As one of the youngest reps on the team, my managers were shocked that I sold any spots during my tenure (statistically, it takes most reps more than a year to land their first client).

I even got to go on-air with infamous food critic, Merrill Shindler 🎙️ and talk restaurants and food culture around Southern California as his dedicated salesperson. That was super fun!

I very much enjoyed helping small businesses strategize their marketing campaigns. Still, radio wasn’t my passion. The longer I showed up at my desk, the hungrier I was to build again. My creative fire was still very much burning between my cubicle walls.

And then the Great Financial Crisis hit. 📉🗑️🔥

About 80 of us were handed pink slips as the station flipped formats — from talk radio’s Adam Carolla, Frosty, Heidi & Frank (and my beloved Merrill Shindler) to the cheaper-to-fund Top 40 AMP Radio. It’s still playing “all the hits” today!

Shit Sundae 💩

I was 23. Broke. Still paying down the debts from my failed event. And now… unemployed.

With no safety net and no appetite for climbing back into the corporate ranks (who was hiring, anyway?), I went back to my former college hustle: slinging cocktails and seafood at a beachfront restaurant just down the street from my Long Beach apartment. 🍹🌴

Walking distance was key — because my car had just been repossessed by the bank after I missed two payments. 🤦‍♀️ Yep — humiliating, but true.

After a painful exit 💔, an epic flop 💸, and the quiet weight of what felt like owing everyone money 🪨, the layoff sealed the deal on my shit sundae. Losing my car was the cherry on top. 🍒

This was my rock bottom. 💔💸🪨💩🍒

Have you ever had one of these periods? Where everything just slid down the slope of shitty mountain until you had nothing left to lose?

Hit reply. Tell me about it. 🙏 I’d be happy to commiserate!