A voice memo showed up on my phone the other day. Three minutes and twelve seconds long. I hadn’t even hit play yet and I already resented it a little.

Because here’s the thing about a voice memo — it’s a way of outsourcing the work you didn’t want to do onto whoever has to listen to it.

Write something down and you’ve already done the hard part. You’ve figured out what matters, thrown out what doesn’t, and put it in an order that makes sense. It might take you three minutes to write. It takes me fifteen seconds to read. That’s a fair trade.

Hit record instead, and none of that happens. You start with the backstory, wander toward the actual point somewhere around minute two, remember something you forgot, and tack on “oh, one more thing” right before you hang up. I’m stuck with no way to skim, no way to jump ahead, no way to do anything but sit there and wait for you to get to the point.

Your convenience just became my problem.

The Ninety-Second Lie

People tell me it’s just faster to talk than to type. And they’re right — for them. Talking is faster because they’ve moved the work downstream. They save ninety seconds recording. I lose three minutes decoding. Send that same memo to five people and you’ve saved yourself ninety seconds and burned fifteen collective minutes of other people’s lives.

Mark Cuban put his finger on the other half of this. He doesn’t do calls anymore, and his reason isn’t etiquette — it’s memory. “If we do it by phone, I’m going to forget half the stuff that we talked about,” he said. “If we do it via email, I can search for it, always.” Talk evaporates. What you write down stays put.

Communication was never supposed to make life easier for the sender — it’s supposed to make the message useful to the receiver. Optimize for your own speed instead of their clarity and you’re not communicating. You’re broadcasting.

Garbage-Bag Communication

A few months ago I launched a mentoring platform call Wisen that - for now - is built entirely around writing — no calls, no video, nothing but text, back and forth. I did that on purpose. Writing forces a kind of discipline talking never does. You can’t ramble your way through a memo the way you can through a phone call. You have to know what you’re trying to say before you say it.

Jeff Bezos figured this out at Amazon long before anyone was turning it into a framework. He banned PowerPoint from executive meetings and made everyone write six-page memos instead — real prose, no bullet points. Then he’d open the meeting by making the whole room sit in silence for the first thirty minutes and read the thing cover to cover before a single person spoke. He called it the smartest thing Amazon ever did. Writing one honestly is so much harder than talking about it — most bad ideas don’t survive the page.

Good communication works like good packaging. Ship something in a sturdy box with clear instructions and I can open it and use it in seconds. Stuff those same parts into a garbage bag and hand it to me, and now I’ve got a project instead of a product — even though, technically, everything’s in there.

Most “quick” memos are garbage-bag communication. And every time you send one, you’re quietly telling the person on the other end that your minutes are worth more than theirs. You probably don’t mean it that way. It lands that way anyway.

One Question Before You Hit Send

Are you making this easy for them, or just easy for you? Could that email be skimmed in ten seconds? Does that meeting really need thirty minutes, or would a tight paragraph do the job?

None of this means never use your voice. Tone matters sometimes. You’re driving sometimes. You’re brainstorming with someone who signed up for the ramble. I grant that there are lot of reasons you need to speak instead of write. Fine. Even then, you can respect the other person’s time — lead with a one-line summary, keep it structured, and close with the actual point instead of burying it. “Leaning toward option B, September launch, smaller scope” tells me everything I need to know before I’ve spent thirty seconds listening for it.

Good communication looks a lot like a good rewrite: say what you mean, cut what doesn’t matter, move the important part to the top, tell people exactly what you need from them. It feels slower than hitting record. It isn’t. You just moved the work to before you hit send — where it belongs.

A young founder called me last week with what she was sure was a dilemma.

Someone wanted to invest in her company. Good terms. No strings. Money in the bank by Friday.

So what’s the problem?

She wasn’t sure she needed it yet. She and her co-founder were still testing channels, still refining the product, still finding their footing. They had runway. They were making progress. And taking outside money felt like it would change something fundamental about how they operated.

She was right to hesitate. Just not for the reasons she thought.

The question underneath the question

Most founders treat fundraising as a yes-or-no question: do I need capital right now?

Wrong question.

The real question: what does taking this money commit me to?

Because money is never neutral. It arrives with expectations — spoken and unspoken. It creates a burn rate. It invites opinions. It quietly shifts your timeline from “whenever we figure this out” to “we’d better have something to show at the next board meeting.”

One of my CEOs is running head-on into that wall right now. For years she’d been perfectly content growing 15-20% annually — a healthy, manageable pace that let her build the company she wanted to build. Then came the capital. And suddenly her VCs are visibly unhappy, because 15-20% was certainly not what they signed up for. Nothing about her business changed. But the definition of success did — the moment the wire hit her account.

That’s the thing about taking money: you’re accepting someone else’s expectations of what your company is supposed to become. Remember, an investor’s job is to generate returns. That’s it.

When you should grab it

Sometimes, though, the answer is yes. Fast.

Just a few days ago I asked one of my founders what had happened to his category-creation product — the one that, last I’d heard, was growing by leaps and bounds. His answer: his board had advised him not to raise yet. So when all that new business brought his servers to their knees, he had no resources to fix it. And at that exact moment, a competitor — fresh off their own $20 million raise — entered the space.

He’s gone now. That other company defines the category.

If you’re in a market where the winner takes most of the pie, every month of delay can be fatal. The same goes if you’ve already found something that works — you’ve cracked an acquisition channel and just need fuel for the fire, or there’s a hire who could transform your output if you could afford them now instead of in six months.

In those situations, hesitation is expensive. Take the money.

When broke is better

But here’s the part nobody tells you: in the early days of Netflix, being perpetually short of cash made us better.

Every hire mattered. Every expense got scrutinized. Every experiment needed a clear hypothesis, because we couldn’t afford to waste a week on “let’s try this and see what happens.”

The minute there’s a cushion in the bank, that discipline starts to evaporate. You hire because you can, not because you must. You run ads because there’s budget — never mind that you haven’t proven the unit economics yet. And six months later you’ve burned through half a million dollars... and you’re no closer to product-market fit than the day you cashed the check.

How to actually decide

Start by writing down — specifically — what you’d do with the money. Not “hire some engineers.” Who would you hire? What would they build? What would success look like in six months? If you can’t answer with precision, you don’t need money yet. You need time.

Then look hard at the person attached to the check. Good investors open doors, help you recruit, and have seen your movie before. Bad ones send you random articles at midnight and want to “hop on a quick call” every week to share their latest brilliant idea for your business. Money always comes attached to a person.

And check your own motives. There’s a certain pride in bootstrapping — I’ve felt it. But if you genuinely need capital to compete and someone is offering it on reasonable terms, turning it down to prove you can go it alone is just ego. Don’t let your ego cost you the business.

So what did I tell the founder?

Nothing, really. She knows more about her business than I ever will. But by the end of the call, she’d stopped asking whether she needed the money — and started asking what it would cost her.

That’s the right question.

I was two hours into a board meeting that should have taken sixty minutes, and it was my own fault.

I had mentioned — casually, I thought — some pricing challenges we were working through. I already knew what I was going to do. I wasn’t asking for help.

But I hadn’t told them that.

What followed was an hour of well-intentioned chaos. Every board member had an opinion. Contradictory advice flew across the table. By the time we wrapped up, I was more confused than when I started, they felt unheard, and we’d burned an afternoon debating a decision that was never really up for debate.

The problem wasn’t my board. The problem was me. I never told them what I actually wanted from them.

Mind readers

Your board members genuinely want to help. So does your boss. So does your team. So does your spouse, for that matter. But none of them are mind readers. Raise a topic without signaling what kind of response you need, and every well-meaning person in the room jumps in with opinions.

I’ve mentored dozens of CEOs since my Netflix days, and this is one of the first things I share with all of them. Before you communicate anything important, decide which of three buckets it falls into.

Informing

“Here’s what I’m doing.” A pure update. No feedback required, no discussion necessary.

At Netflix, almost from day one, our most common customer service ticket was a lost or stolen disc. I didn’t ask the board how we should handle it. I told them: when a customer says a disc went missing, we ship them another one. No questions asked. Yes, some people will take advantage of us — but it’s still cheaper than treating every honest customer like a criminal.

Framing something as information prevents needless debate on a decision that doesn’t need to be debated. And believe me, this one was debatable. Framed as a question, it would have eaten an hour: What about fraud? What’s our exposure? But your board isn’t there to second-guess your execution — they’re there for governance and strategy. Help them respect that distinction.

Checking

“Unless you object, here’s what I’m doing.” Subtle, but powerful. You’re giving people a chance to wave a red flag if they see something you’ve missed — but the default is action. Again, you’re not asking permission. You’re doing a final sanity check.

At Looker the announcement was “enterprise contracts are closing faster than we expected. Unless you see a risk we’re missing, we’re accelerating our sales hiring.”

That sentence does a lot of work. It presented our decision as the default while leaving a narrow window for substantive objections. It respected oversight without killing momentum.

Asking

“What should I do?” Sometimes you genuinely need guidance. When you do, frame the question precisely... vague questions get vague answers.

Don’t walk in and say “we need to talk about fundraising.” Say: “We have two paths. We can raise big at a higher valuation and buy ourselves two years of runway — but risk a down round later. Or we can raise small, preserve our equity, and give ourselves ten months to prove the model. How should I be thinking about this?”

Now you’ve channeled a room full of expertise toward an actual decision instead of unlimited brainstorming.

Weekend plans

Being explicit about what you need frees everyone. When you signal you’re just informing, people don’t feel obligated to weigh in. When you’re checking, their attention goes to risks instead of preferences. When you’re genuinely asking, they know their input will actually shape the outcome.

Without those signals, people default to treating everything like it’s up for debate. Which is exhausting for everyone involved.

And this isn’t just for boardrooms. Try it with your team. Try it with your boss. Try it at home when you’re negotiating weekend plans... you might be surprised.

People want to help you. That’s never been the problem. The problem is that you haven’t told them how.

For years, I worried about the wrong thing.

Every time I sat down to write something about entrepreneurship, I’d ask myself the same question: Is this original? Has anyone said this before? I wanted my advice to stand out — some fresh insight nobody else had stumbled onto.

That was exactly backwards.

The internet is drowning in startup advice. And most of us assume the good stuff is the rare stuff — the secret nobody else has figured out, the contrarian take, the angle you haven’t heard yet. But the most valuable advice I know isn’t the advice that’s different. It’s the advice that keeps showing up, again and again, from people who have nothing to do with each other.

Because that’s the only proof it actually works.

You can’t trust a one-hit wonder

Here’s the problem with taking advice from someone who succeeded once — especially someone who knocked it out of the park on their first swing. They don’t actually know why it worked.

When you’ve only done something a single time, you can’t separate the signal from the noise. You can’t tell what worked because of what you did versus what worked in spite of it. You can’t tell skill from luck. You just know you won — and you assume everything you did along the way was the reason.

It usually wasn’t.

I waited sixteen years to write my book about Netflix. It took me that long to look back honestly and figure out which decisions actually mattered. Which ones were smart. Which ones were lucky. Which “failures” turned out to be the best things that ever happened to me.

Take Blockbuster. The day they laughed Reed and me out of their offices, I was crushed. I was certain I’d just failed to save the company — the biggest failure of my career.

Was it? Or was it the single luckiest break Netflix ever got?

I couldn’t have told you back then. It took years — and a lot more experience — before I could see it clearly. Time gives you that answer. One success never will.

Why I trust the stuff I keep hearing

This all snapped into focus recently when I read Kaz Najatian’s “blueprints” — his principles for how to work. And reading them was a strange experience, because I kept recognizing my own stuff.

His first one — trust your people, assume they’ve got your back — is Freedom and Responsibility by another name. Another is just radical honesty. And one of them captures the exact reason I’ve always loved writing: you can’t fool yourself on paper the way you can in conversation.

None of that overlap made his advice feel less original to me. It made it feel more true.

Think about what’s actually happening there. Two people who built different companies, in different industries, at different times, by completely different paths — and they land on the same lesson. Two people who never compared notes, coming back with the same scar.

When that happens, pay attention. That’s the advice that transcends one person’s luck.

So here’s my advice about advice

Stop hunting for the secret nobody else has discovered. The unique insight, the clever hack, the edge you’ll have because you alone know it — that’s mostly a fantasy. And chasing it is a great way to talk yourself out of the boring guidance that actually works.

Look for the patterns instead. When you hear the same thing from a founder, a mentor, and a book you read ten years ago — that’s not noise. That’s the signal you’ve been ignoring

There’s a business school hiding in plain sight. You probably walked past it last night on your way to dinner.

It’s called a restaurant. And if you’ve never worked in one, you’re missing one of the best educations money can’t buy.

In my 20s, I spent time waiting tables, and I learned more in those shifts than in any classroom I ever sat in. Not because the job is glamorous. Because it isn’t.

Real Stakes, No Syllabus

Think about what you actually have to do. You’re managing inventory in real time — what’s in the kitchen, what’s running low, what’s coming off the line slow. You’re reading customers before they say a word. You’re balancing six competing priorities that each feel urgent. And you’re doing all of it under conditions specifically designed to make you fail — a full house, a slammed kitchen, a table of twelve that just walked in at 8:45 on a Friday night without a reservation.

The Upsell

Every good waiter knows something most founders learn too late: a transaction is never just a transaction. The couple at table four aren’t just ordering dinner — they’re celebrating something, or they’re not talking to each other, or they’ve had a terrible week and just want someone to make it a little less terrible. You learn to read all of that before you open your mouth.

And the upselling — God, the upselling. The best upsell never feels like one. You’re not pushing the special because the kitchen needs to move the halibut. You’re recommending it because you genuinely think they’ll love it. You believe in the product, and that belief is contagious. Sound familiar?

The Customer Service Trick

When I moved into marketing at one of my early jobs, I made a point of spending a few days a month in customer service — just picking up the phone and taking calls. My colleagues thought I was nuts. But that’s where I found out who my customers actually were. Not who we thought they were. Not who the focus groups said they were. The real ones — confused, frustrated, delighted, specific. You can’t get that from a report.

Getting Stiffed

Nothing recalibrates your ego quite like getting stiffed on a tip after a three-hour table, or having someone wave you over like you’re invisible, or watching the kitchen lose the ticket for the birthday party that’s been waiting forty minutes. You don’t get to pout. You don’t get to explain yourself. You smile, you fix it, you move on.

A lot of people in corner offices never actually learn that one.

Thirty Seconds

In school, you get a grade weeks later. Waiting tables, you find out in thirty seconds whether your read on the table was right. That kind of feedback loop changes you in a way no case study ever will.

The best entrepreneurs I know can put themselves in almost anyone’s shoes — not just their customer’s, but their employee’s, their vendor’s, the guy-who’s-about-to-leave-a-terrible-Yelp-review’s. It’s empathy. It’s one of the most important skills you can have. And waiting tables builds it like nothing else.

Spend six months doing it. Really doing it, not coasting through it. Most founders are in such a hurry to get to the launch, the raise, the scale — they skip the part where you actually learn how humans work.

Don’t skip it.

A full-grown saltwater crocodile is a terrifying thing. They can grow to more than 20 feet long and weigh over 2,000 pounds. Their jaws bite down with a force of 3,700 pounds per square inch. And since they can swim about 15 miles per hour, there’s no out-swimming them. So it’s no surprise that at least half of all crocodile attacks on humans are fatal.

But you know what’s even more dangerous than a full-grown saltwater crocodile?

An adolescent one.

True, an adolescent croc isn’t as strong, and his bite is somewhat weaker. But even at 2,500 PSI, it’s still double the bite strength of a lion, a tiger, or a hyena — more than enough to kill you quickly.

So why is the smaller one more dangerous? It has nothing to do with that old story about rattlesnakes — the one that says young rattlers have the worst bites because they can’t control how much venom they inject. That’s a myth. An adult rattlesnake actually produces, stores, and injects 20 times more venom than a baby.

The real reason an adolescent croc is more dangerous is much simpler. It’s faster. It accelerates more quickly. It changes direction more suddenly. At some point, the additional size and weight of an adult crocodile stops delivering more killing power — and just starts slowing him down.

That’s exactly why startups are so dangerous.

You don’t see them coming.

When Reed and I started Netflix in 1998, Blockbuster had 9,000 stores, 60,000 employees, and $6 billion in revenue. We had a warehouse in Scotts Valley, a hundred thousand DVDs, and no idea what we were doing. On paper, it should have been the most lopsided fight in business history. And it was — just not in the direction anyone expected.

Blockbuster couldn’t move. They couldn’t change direction. Every late fee, every retail lease, every store manager’s bonus structure — all of it locked them into the way things had always been done. They were the 20-foot crocodile. We were the adolescent.

Here’s the thing about being big. The very things that made you successful — the scale, the systems, the playbook everyone else has to study — are the same things that make you slow. You can’t cannibalize your legacy product line. You can’t ship the new feature that breaks the old code base. You can’t tell the 70,000 people whose comp is tied to revenue that you’re going to give some of that revenue away to delight a customer.

If you’re running a mature business and you think your size and scale will protect you? Think again. They’re not protecting you. They’re slowing you down.

And if you’re an early-stage company going up against an entrenched competitor? Stop being intimidated by their size. That’s not their strength. That’s where they’re vulnerable. Take advantage of the one thing you have that they can never have again — the ability to turn on a dime.

Because whether it’s an African river delta or a competitive startup category, the rule is the same. It’s not survival of the fittest. It’s survival of the quickest.

And if you’re unwilling to disrupt yourself, I promise someone smaller, hungrier, and quicker is working hard to disrupt you.

There are four words no founder wants to hear from their co-founder.

“We need to talk.”

It was September of 1999. Reed Hastings stood in the doorway of my office at Netflix and said exactly that. Then he closed the door quietly behind him, sat down, and proceeded to tell me — kindly, but unmistakably — that I wasn’t doing my job.

His biggest complaint? I wasn’t hiring superstars.

I’d been hiring competent people. Reliable people. People who could do the job. But I’d been hiring for the company we had — sixty employees, a few million in revenue, mailing DVDs out of a strip mall in Scotts Valley. Reed was already thinking about the company we were going to become. And he could see what I couldn’t: the people I was bringing in weren’t going to get us there.

When he left, the sun had set but I didn’t have the strength to turn on the light. And as I sat there in the dark, the question I couldn’t shake wasn’t about the people I’d hired. It was about me. If the team I’d built wasn’t going to get us where we needed to go — was I?

A few weeks later, I had my answer. Reed took over as CEO. I’d been demoted from the company I’d started.

It took me a long time to make peace with that conversation. But Reed was right. About all of it.

The Generalist Trap

In the early days of a startup, everyone does everything. They have to. Reed and I were doing customer service in the morning, arguing about the website in the afternoon, and stuffing DVDs into envelopes at night. We knew just enough about everything to be dangerous — which is exactly what you need when you’re scrambling to keep the lights on.

But survive that stage and something changes. Fast. The business gets complicated. And complicated businesses need people who know exponentially more than you do about their corner of it.

A lot of founders get stuck right there. They’ve made every important decision since day one. The company is them and they are the company. Bringing in someone who actually knows more? Someone who might push back? That feels threatening.

What Reed understood — and what I didn’t yet — was that one of your most important jobs as a founder is to work yourself out of every job in the company. One by one.

Hire People Who Make You Look Dumb

When we needed someone to run our warehouse and shipping operations, we didn’t look for another generalist who could “figure it out.” We went and found Tom Dilllon, someone who’d forgotten more about logistics than I’d ever known.

Reed eventually took it further than I ever would have. A few years after I stepped aside, Netflix hired Bill Henderson as COO. Bill had just spent three years as Postmaster General, running the United States Postal Service. The guy responsible for 650 million pieces of mail a day looked at our million-DVDs-a-day operation and called it a trickle.

Read that again. The Postmaster General. Of the United States.

That’s the bar. Not “someone better than us.” Not “someone with relevant experience.” Someone so far beyond your current situation that they look at your hardest problem and call it a trickle.

Here’s the thing — Reed’s criticism in 1999 wasn’t really about hiring. It was about ambition. About aiming higher than you think you can actually land. The instinct is always to hire for the company you have. You should be hiring for the company you’re trying to build. And then aim higher than that.

Doing It Right the Second Time

By the time I agreed to help Lloyd Tabb start Looker, I’d absorbed the lesson.

My initial title at Looker was ABC. As in: Anything But Coding. That’s what I did. I was simultaneously the CFO, the head of sales, the chief counsel, and the head of marketing. None of those was a job I was actually qualified for. I muddled through. And in the process, I learned exactly what each of those roles required at our particular company at our particular stage.

Then, little by little, we recruited people who knew vastly more than I did. A real CFO. A real head of sales. A real general counsel. Each time, I handed off the job and watched the function get dramatically better than anything I could have built.

By the time we sold Looker to Google for $2.6 billion, my title was just “Board Member.” And I was completely fine with that.

That’s what success looks like at a startup. You work yourself out of every job, in order, until the company doesn’t need you anymore.

The Ceiling Is You

If you’re still the smartest person in the room at your company, you don’t have a hiring problem. You have an ego problem.

Brilliant people don’t want to work for someone who needs to be the expert on everything. They want to work for someone secure enough to hire people better than themselves — and smart enough to listen to them.

If you’re unwilling to make yourself the dumbest person in the room, I promise you’ve built a company with a very low ceiling.

And that ceiling is you.

A founder I’m mentoring sent me an email last week I haven’t stopped thinking about.

She’s running a real business. Paying customers, growing revenue, no death march. And she’s wrestling with something most founders never let themselves say out loud: what if the hyper-growth, VC-fueled, up-or-out playbook just… isn’t her?

Her question — and she was almost embarrassed to ask it — was whether choosing a slower, more sustainable path is a sign of lesser ambition. Whether she was talking herself into “lifestyle business” because she couldn’t hack the big leagues.

She also asked something more interesting: are some CEOs just wired for the chaos of hyper-growth? Or is it a muscle you build?

Here’s what I told her.

Some founders are chaos metabolizers. The ones who get strangely calm when everything is on fire. A competitor drops a surprise product, the burn rate looks like a countdown clock, the lead engineer quits on a Tuesday — and they don’t spiral. They get curious. To them it’s not a catastrophe. It’s data.

At Netflix, that wasn’t a personality quirk. It was a job requirement. We rewrote the operating plan every week. If you needed certainty before you could move, you wouldn’t have made it past month six.

Innate or learned? Bit of both. You can build the muscle. But some people are just born with a higher tolerance for randomness — energized by the same volatility that wipes everyone else out.

If you’re not one of them, that’s not a flaw. It just means you burn a different type of fuel.

Profitable Isn’t a Dirty Word

Somewhere we got it into our heads that “profitable” is a dirty word for an early-stage company. That if you aren’t constantly doubling down, chasing 2x growth year over year, you’re not really playing. That growing “within your means” is what people settle for when they fail to raise.

Nonsense.

Building something durable — funded by your customers instead of your bankers, hiring people you actually plan to keep — is a perfectly legitimate game. It’s just a different game. You know your employees. Your product doesn’t get hijacked by whatever will make the next board deck tingle.

I’ve watched plenty of founders force themselves into the hyper-growth mold because they thought they had to. They raised the money. They hired the people. They were crushing it on paper and miserable in their actual lives. Running a race they didn’t want to win.

The Fit Nobody Talks About

Everyone obsesses over product-market fit. Almost nobody talks about founder-model fit. But it’s the same idea. If the way your company is built to grow doesn’t match the way you’re built to operate, you’re going to spend every day fighting yourself. And you’ll lose.

The question isn’t whether you can handle the rocket ship. You probably can. The question is whether you want to.

Don’t talk yourself into running someone else’s race.

In That Will Never Work, I wrote about visiting Amazon in the early days. Every desk in the building was a repurposed door. The offices were ugly. Bezos was unapologetic about it — Amazon was focused on the customer, and a pretty office wasn’t going to help the customer.

This always sparks the same question: do you have to pick? Employees or customers? Can’t it be both?

Sure, it can be both. I’m not suggesting you treat your team like dirt. But the operative word in what Bezos was saying is focus. And focus, by definition, means an unequal allocation of time, money, and attention.

In a startup, you will always have more demands than resources. Always. You can spread everything evenly across every competing need — and end up doing nothing particularly well. Or you can pick the one thing that matters most and pour everything you have into making it great.

Pick the right thing, deliver on it, and it lifts all the other boats. The customer is almost always that thing.

The kombucha problem

Somewhere along the way, startups got it in their heads that the way to take care of employees is to throw amenities at them. Kombucha on tap. Nap pods. Fireman poles between floors. Cold brew, hot yoga, catered lunches Tuesday through Thursday.

It’s ridiculous. None of that is what your best people actually want.

What they want is agency — the freedom to make real decisions and own real outcomes. And they want to be surrounded by other people who are just as talented and just as committed as they are.

The free snacks aren’t retaining anyone worth retaining. The thing that keeps your best people around is the chance to do meaningful work alongside other people doing meaningful work. Everything else is decoration.

The Aeron chair tell

One of my reliable signs that an early-stage company is in trouble: I walk in a few weeks after their seed round closes, and every employee is sitting in a $1,000 Aeron chair behind an automatic standing desk.

Whatever they raised, they’re burning it on the wrong things. They’ve confused the trappings of a successful company with the actual work of becoming one. And worse — they’ve signaled to their team that the company’s priorities are inward, not outward.

Because culture is observational, not aspirational. Your team isn’t watching what you say. They’re watching what you spend money on. They’re watching where you spend your attention. When Bezos worked at a desk made of a door, he wasn’t being cheap — he was signaling, every single day, that this company existed for the customer.

The real way to take care of your team

Here’s the part that gets lost. Your ultimate job — the most important thing you can do for your employees — is to make the company successful.

A company that wins gives everyone in it something that no amount of free kombucha can. Equity that’s worth something. A track record they can build on. Stories they’ll tell for the next twenty years.

A company that rewards people lavishly at the beginning and then goes out of business has done nothing for anyone. Lavish in the early days is just a more comfortable way of losing.

There’s a story founders love to tell themselves: more hours equals more progress. Grind harder. Sleep less. Out-work everyone. The badge of honor isn’t the company you built — it’s how broken you got building it.

It’s nonsense. And it’s making you worse at your job.

I think a lot of this comes from a basic misunderstanding of what a “sprint” actually is. There are absolutely times when you need to put in crazy hours with intense focus — when you’re shipping a product, when you’re on either side of an M&A transaction, when you’re raising a round. Those moments call for everything you’ve got.

But a sprint, by definition, is a brief period of intense exertion. You don’t run a marathon by stringing together one sprint after another with no break in between. That’s not heroic. That’s just bad pacing.

The Diminishing Returns Nobody Talks About

Here’s what nobody warns you about: at a certain point, grinding harder just means you’re making slower, dumber decisions with more confidence.

You stop listening. You stop noticing patterns. You confuse motion with progress. The 16-hour day feels productive because you were busy — but the decisions you made in hour 14 were worse than the ones you made in hour 4, and you were too fried to notice.

Some of the worst calls I ever made at Netflix came in periods where I was genuinely exhausted. Not because I lacked information. Because I lacked the bandwidth to actually process it.

Why Tuesday Night Date Night Was an Operating Decision

People hear about my Tuesday night date night and assume it’s a marriage thing. It is. But it was also something else — a forcing function.

Every Tuesday at 5pm, I had to walk out the door. Which meant the company had to function without me for a few hours. Which meant I had to delegate. Build systems. Hire people I actually trusted. If the place fell apart because I left at 6, that wasn’t a sign of how essential I was. It was a sign that I’d built something fragile.

That’s an operating lesson disguised as a personal one.

The Elon Problem

I’ll admit — I’m impressed by what people like Elon Musk, Jenson Huang and Mr. Beast have managed to build by working continuously. Genuinely impressed. The output is staggering.

But I don’t admire what it’s done to their lives. Or their health. Or the people around them. The price they’ve paid isn’t a footnote. It’s the actual story.

And here’s the part founders don’t want to hear: if your business only works when you’re exhausted and omnipresent — and when you force everyone around you to be the same — you don’t have a company yet. You have a job. But it’s one with worse hours and less stability.

The Real Test

A real company runs without you sometimes. A real company makes decisions when you’re not in the room. A real company doesn’t collapse when its founder takes a Tuesday night off.

If yours can’t do those things, the problem isn’t that you need to work harder. The problem is that you’ve been working too hard on the wrong things — and using exhaustion as cover for not building the systems and the team that would actually let you step away.

Sprint when you have to. Then stop sprinting.

The marathon is the whole point.

In the early days of Netflix, I was a perfectionist.

Not the admirable kind — the paralyzing kind. The kind where you spend a month commissioning custom photography for a test that ultimately fails in the first hour. The kind where you labor over every word of copy and stress-test every link and hire a copy editor before a single real customer has even seen the page.

You know what all that careful preparation got us? Slower.

Every test took weeks. Every test failed. So we’d start over, and do it again. Weeks. Fail. Weeks. Fail.

Finally, out of desperation more than wisdom, we started cutting corners. We did a test in two weeks. Then one week. Then every other day. Then every day. And then — because we had no choice — three or four different tests a day.

Things got sloppy. Photos still had watermarks. There were typos, dead links. We crashed the site. It was a mess.

And here’s what we discovered: it didn’t matter.

Not only did our sloppiness not hurt us — our speed helped us enormously. The insights we gathered in a single sloppy week of testing were worth more than a month of perfect preparation. We stopped trying to get it right in advance and started letting reality tell us what “right” actually looked like.

That’s when we stopped being a company that made careful decisions and became something far more valuable: an idea machine.

The perfectionism trap

Here’s why perfectionism is so insidious. It doesn’t feel like fear. It feels like quality control. It whispers that you’re being thorough. Responsible. That you’re just waiting until things are truly ready.

But there’s a word for building something in your head and refusing to show it to the world until it’s perfect.

That word is stalling.

The sculptor analogy I always come back to: when you’re doing iterative testing, you have to get used to having your perfect sculptures squished. You spend two weeks crafting something beautiful — the right messaging, the right design, the right flow — and then you find out it doesn’t work. Squish. Start over.

If you can’t handle that, you’ll find yourself building bigger and bigger sculptures, taking more and more time, spending more and more money — all in service of delaying the moment when reality gets to weigh in.

Perfectionism assumes you know what “perfect” looks like in advance. You don’t. I didn’t. Nobody does.

No business plan ever survives a collision with a real customer.

What we actually shipped

When we launched Netflix in April 1998, the website was clunky. The fulfillment system was manual and error-prone. Genuinely rough.

But it worked well enough that customers could find a movie, order it, and receive it in the mail. That was the bar. Everything else was secondary.

And because we launched when we did — instead of six months later, polishing things that didn’t need polishing — we found out stuff we never could have learned in a conference room. That late fees were a bigger emotional trigger than we’d realized. That people were more willing to wait for a DVD than conventional wisdom suggested. That our packaging needed serious work.

None of that was available to us until something real was in front of real customers. Focus groups don’t tell you what people will actually do. Behavior does.

You’ll learn more in one day of doing than in a month of thinking about it.

The actual cost of waiting

What perfectionists never calculate: every day you don’t launch is a day you don’t learn. And in a startup, that’s not a small thing.

The subscription model at Netflix — probably the single most important decision we ever made — wasn’t the result of careful analysis. Reed and I were in the warehouse one day, looking at 100,000 DVDs just sitting on the shelf. We were almost out of money. We were joking that maybe we could save on rent if we could store the DVDs at customers’ houses.

And then we thought… what if we just mailed them and let people keep them as long as they want? No due dates. No late fees. Just a flat monthly subscription that let them exchange discs as often as they wanted.

It wasn’t a carefully researched strategic pivot. It was a half-baked idea we decided to try. And astoundingly enough — when we tried it, it worked.

Perfect information doesn’t exist. You’re always making a bet with incomplete data. The question is whether you make that bet early, when the stakes are small, or late, when you’ve burned months and money protecting an idea that’s never been tested.

What “good enough” actually means

It doesn’t mean everything works. It doesn’t mean you’re not embarrassed.

“Good enough” means one thing: it’s the version that lets you start learning. Not the version that covers every edge case or impresses your board or makes you feel confident at a dinner party. Just enough to find out if there’s a there there.

The test I always apply: what’s the quickest, cheapest, easiest way to try this? Not the best way. Not the right way. The fastest way to find out if the idea has legs.

If it does — great. Now you can invest more. If it doesn’t — you’ve lost a week, not a year.

Build the thing. Ship it. Let reality sort it out.

I get pitched a lot. And I mean a lot. After seven startups, a few hundred angel investments, and more mentoring conversations than I can count, I’ve developed a kind of pattern recognition that kicks in almost instantly.

One of the clearest patterns? The Obvious Idea.

You know the one. It’s the idea that sounds so sensible, so clearly needed, so obviously good — that the founder can’t imagine why it doesn’t already exist. And when they pitch it, they lead with the size of the opportunity. How big the market is. How nobody has cracked it yet.

That last part is where it gets dangerous. Because if you think nobody has cracked it yet — you’re most likely wrong. Yes, the field is empty. But that just means you haven’t found the wreckage yet.

I got a pitch recently for a gift-matching website. The founder was smart, enthusiastic, clearly had thought about it. And I had to tell him something I’ve had to tell a lot of people: the fact that an idea seems obvious to you is not a sign that nobody has tried it. It’s almost always a sign of the opposite.

Here’s the thing about obvious ideas. They attract obvious entrepreneurs. If you can look at a problem and immediately think “someone should build this,” so can the other ten thousand people who’ve encountered the same problem. And some of them already did. And most of them failed. And the question you should be obsessing over isn’t “why hasn’t this been built?” It’s “why did everyone who tried it fail?”

That’s not a rhetorical question. It’s the most important question you can ask.

Restaurants are a perfect example. Everyone thinks the restaurant business is about food. It’s not. It’s about inventory management, labor scheduling, lease negotiation, and razor-thin margins that punish the slightest miscalculation. The people who fail don’t fail because their food was bad. They fail because they didn’t understand what business they were actually in. The idea — “people need to eat, I love to cook” — was obvious. The traps were not.

So if you’re sitting on what feels like an obvious idea, here’s what I’d want you to do before you write one more line of your pitch deck. Search the category. Not a casual Google — a real search. Find everyone who has tried this. Find the ones who failed. Then ask yourself: what did they not understand that you do? What’s the non-obvious thing your approach gets right that theirs got wrong?

If you can answer that question with something specific and credible, you might actually have something. Not because the idea is good — remember, all ideas are bad ideas — but because you’ve done the work to understand why this particular minefield keeps blowing people up.

And if you can’t answer it? That’s your homework. Not the pitch deck. Not the financial model. Go figure out where the traps are.

One more thing worth saying. There are really only two reasons something obvious hasn’t been built: either nobody has truly thought of it — which is nearly impossible for anything genuinely obvious — or it has been tried, repeatedly, and it keeps failing for a reason you don’t yet understand. The second explanation is almost always the right one.

The founders who succeed with obvious ideas aren’t the ones who found the idea first. They’re the ones who understood the problem deeply enough to find the non-obvious solution hiding inside it. Netflix wasn’t “movies by mail.” That idea had been tried. What we figured out — eventually, after a year and a half of testing — was the subscription model. No late fees. No due dates. A completely different relationship with the customer. That was the non-obvious thing.

So the next time you’re convinced you’ve spotted an obvious opportunity, treat that conviction as a warning sign, not a green light. Do the homework. Find the traps. Figure out what everyone else missed.

Then come back and show me why you’re different.

A few months ago, my family flew to a remote island in Indonesia to start a sailing trip. Our boat captain was supposed to meet us at the airport. When we emerged from baggage claim, squinting in the tropical heat, nobody was there.

He showed up nearly 30 minutes later, full of excuses. He didn’t know we’d be traveling without checked bags. There was a dignitary in town and traffic had been a disaster. Elaborate stuff, all of it easily disproven.

He was lying to us. About something that didn’t matter at all.

We weren’t going to miss the boat. There was no real hurry. If he’d just said, “Sorry — I was getting the boat ready and lost track of time,” we would have forgotten about it before we reached the dock.

But instead of nothing, he gave us something we didn’t ask for: a reason not to trust him. If he’d lie so easily about something this small, what would he do when there was an inconvenient truth we actually needed to know?

———

I’ve worked with a compulsive liar. A genuine one — someone who could say things that were completely untrue with total conviction, about things that were easily disproven and offered no obvious benefit.

He told stories about his wedding. (He’d never been married.) He mentioned classes he’d taken and degrees he’d earned. (Neither.) And in his finest moment, he mentioned he’d been in the tunnel in Paris the night Princess Diana was killed.

I don’t know how he kept it all straight. And I know at some point it got expensive. He once offered me his fourth-row Lakers season tickets if I was ever in LA. A few weeks later, I called his bluff. He produced the tickets — which I found out later he’d gone out and bought. Another time he offered the use of his cabin on Lake Tahoe, which happened to be “undergoing renovations” just days before I was supposed to arrive, so he’d arranged for me to use a friend’s place instead. Rented. For the weekend.

All of this to maintain fictions that cost more to keep up than they’d ever been worth.

———

Honesty was never something I decided should be part of the Netflix culture. It’s just how I’ve always operated. And it’s what drew Reed Hastings and me together — we started carpooling before we started a company, and somewhere in those early morning commutes, we figured out that we could just… say what we thought. That turned out to matter a lot.

It’s what let Reed and me argue like cats and dogs about almost every aspect of Netflix without it ever getting personal. We were both just trying to build the best company we could. And when I was struggling as a leader, it’s what allowed Reed to tell me so — without me wondering if there was something else going on. I didn’t have to guess what he really thought. I already knew.

That kind of culture doesn’t get announced. People see it and they either match it or they don’t.

———

Think about how many companies announce someone’s departure by saying they’re “leaving to spend more time with family” or “pursuing other opportunities.” Everyone in that room knows it’s not true. You’ve just stood up in front of your team and lied to them. And somewhere in the back of their heads, they’ve filed that away.

Next time they see a problem, they’ll think twice before saying so.

———

On a weeklong sailing trip, a captain who lies about small things costs you a low-grade unease. On a years-long entrepreneurial journey, it costs you the ability to actually see what’s happening — which is just about everything.

There’s no safe place to draw the line between acceptable dishonesty and unacceptable. You can’t quarantine the small stuff. The small stuff is exactly where the pattern gets set.

My boat captain thought he was smoothing things over. What he was actually doing was teaching me, quietly, not to trust him.

Here’s the thing about trust: you can lose it in thirty seconds. Getting it back takes forever — if it comes back at all.

Tomorrow is the 28th anniversary of the day we launched Netflix. And every year around this time, I get the same kind of message from founders. Some version of: I love your story, but my company is a mess. Nothing works the way it should. I’m embarrassed by what we’ve built so far. How did you guys have it so figured out?

We didn’t.

On April 14th, 1998, we launched Netflix out of a converted bank building in Scotts Valley. By 10am we’d crashed the servers — turns out we’d dramatically underestimated demand, which sounds like a good problem until you’re the one frantically running to Fry’s to buy more servers. By 2pm we’d run out of mailing labels and somebody was making a run to Office Depot. By midnight we were sitting on the floor eating cold pizza, watching orders trickle in one at a time, wondering if any of these people were ever going to come back.

The website was ugly. The checkout flow was broken in three places we knew about and probably ten we didn’t. Our “fulfillment system” was a folding table and a stack of shipping envelopes. When a DVD got returned, somebody literally walked it back to the shelf by hand. We typed all the order acknowledgements by hand.

That was the company. That was the launch. That was the version of Netflix that, eventually, became Netflix.

Here’s what I want you to take from that.

The companies you admire were held together with duct tape on day one. All of them. Amazon was Bezos packing books in a garage. Airbnb was two guys renting out air mattresses because they couldn’t make rent. The polished, professional, inevitable-looking version of those companies didn’t exist yet. It got built later, slowly, by people who were embarrassed by what they had but shipped it anyway.

The reason this matters... founders today are comparing their messy, unfinished, embarrassing day-one company to other companies’ day-3,000 versions. And then wondering why they feel like frauds.

Stop doing that.

Your competitors aren’t the polished public companies. Your competitors are the other founders sitting in their own warehouses tonight, eating their own cold pizza, wondering if their thing is going to work. Most of them won’t ship. The ones who do — even with the duct tape, even with the broken checkout flow, even with the embarrassment — those are the ones who get to find out what their company actually wants to become.

Because here’s the part nobody tells you: Netflix didn’t become Netflix because we had a vision. We became Netflix because we shipped a deeply imperfect thing on April 14th, 1998, and then spent the next 28 years finding out what it was.

You don’t need a better idea. You don’t need more funding. You don’t need to wait until it’s ready.

You just need to be willing to ship something embarrassing.

Everyone says they want a culture of experimentation. They put it in the all-hands deck. They say the words out loud: “We need to take more risks.”

And then they go back to their offices and quietly punish the people who do.

These are well-meaning leaders, all genuinely convinced they want their organizations to experiment more — who then flinch the moment an experiment takes longer than planned or costs a dollar more than the safe route would have. They’re not hypocrites. They just don’t understand what experimentation actually requires.

Real tolerance for failure. Not the inspirational-poster kind.

The math nobody wants to talk about

Experimentation fails 99% of the time. That’s not pessimism — that’s the math. If you’re running genuine experiments, testing things you don’t already know the answer to, most of them aren’t going to work. That’s what makes them experiments rather than implementation.

The problem is that “99% failure rate” sounds terrible in a budget meeting. Time and money are easy to measure. The learning embedded in a failed test is not. So leaders who say they want innovation keep defaulting to the metrics they understand — and those metrics punish exactly the behavior they claim to want.

They’re not lying when they say they want more risk-taking. They just keep rewarding something else.

Culture is observational

You cannot install a culture of experimentation. You can only model it.

Culture isn’t what’s written in the employee handbook or posted on the lobby wall. Culture is what people observe — who gets celebrated, who gets promoted, who gets fired, and why. Everything else is decoration.

Geology works this way too. Ninety-nine percent of the change to a landscape happens in one percent of the time — earthquakes, floods, eruptions. The slow steady stuff barely moves anything. Culture is identical. Most of what you do day-to-day barely registers. But a handful of moments — specific, visible, impossible to misread — reshape the terrain completely.

Those moments are the three decisions every leader keeps making: who you reward, who you promote, and who you fire.

That’s the whole game.

The gap between saying and doing

If you say “fail fast” but spend forty minutes in a post-mortem grilling the team on why a test underperformed — you just taught everyone in that room that failure is dangerous. If you say “take risks” but give the bigger raise to the person who hit their number safely rather than the one who tried something ambitious and came up short — you’ve told your team exactly what you actually value.

You can’t talk your way to an experimentation culture. Ninety-five percent of the signal comes not from what you say, but from those three decisions. Reward. Promote. Fire.

At Netflix, we ran tests constantly — ten, twenty different things a day at our peak. The overwhelming majority failed. That wasn’t a bug in the system. It was the system. The subscription model that became Netflix’s core business came out of a year and a half of relentless testing. It wasn’t a brilliant idea someone had. It was what was left standing after everything else failed.

I had to genuinely stop caring whether any individual test succeeded. The only thing that mattered was whether we were learning.

Make sure your incentive system can tell the difference between the team that played it safe and hit their number, and the team that ran a fast cheap test and came up empty. Be loud about your own real failures — not the humble-brag kind. And when you make those three decisions, make sure people understand why. The story that circulates around them is the actual culture document of your organization. Not the one in the handbook.

Most leaders don’t actually want a culture of experimentation. They want the results of one — without tolerating the failure rate that makes those results possible.

You can’t have both. Pick one.

Someone asked me recently if testing sets direction early on, and then specialists take over once things are clear.

My answer? You never stop testing. But the type of testing changes — and more importantly, so does the ratio.

Early on, you’re doing almost exclusively breakthrough testing. Not nibbling at the edges — swinging at big questions. Different directions. Fundamentally different approaches. The steps are still small and cheap, but the ideas you’re testing are substantive. You’re looking for a there there.

Once you’ve found something that works, a second kind enters the mix: iterative testing. Optimization. Fracking — you’ve found the oil, now you’re figuring out how to get every last drop out of the ground. At Netflix, we never stopped tweaking the sign-up flow. Even a fraction of a percent improvement matters when the volume is that high.

But you never put down the first tool. You’re always scanning for the next breakthrough — the thing that doesn’t just improve what you have, but opens up a whole new category of results. The ratio shifts. Early on it’s mostly breakthrough, a little optimization. Later it flips. But both are always in play.

Here’s what neither kind of testing can do: make decisions for you.

Back in the 80s, I did a lot of direct mail. The data could tell me — after the fact, to four decimal places — that the red envelope had beaten the blue one. What it couldn’t tell me was which colors to test. Or that color was worth testing at all.

Data tells you what happened. It doesn’t tell you what to try next.

The best entrepreneurs I know use testing to validate direction — not to avoid choosing one. If you’re hiding behind “we’re still testing,” you haven’t had the courage to make a decision yet.

Never confuse the data with the insight. The data is just the answer. You still have to ask the right question.

Every December, the book lists start rolling in.

Barack’s reading the sweeping historical biography. Bill just finished three dense policy tomes and a novel shortlisted for the Booker. Oprah has discovered an obscure debut author who will now sell three million copies.

And everyone turns to me and asks: “So Marc, what are you reading?”

I dread this question.

Not because I don’t read. I do. But because my answer is never going to match what people expect. They imagine there’s a rigorous intellectual life behind whatever modest success I’ve managed — a bedside pile stocked with Drucker and Isaacson, maybe a dog-eared copy of something Buffett mentioned at the shareholder meeting.

That’s not me.

The question I dread almost as much is: “What’s your favorite book of all time?” It’s the second most common question I get, right after favorite movie. And here’s the thing — both questions have the same structure. There’s the public answer. And there’s the real one.

For movies, for years my answer was Pulp Fiction. Appropriately arty. Appropriately edgy. Just well-known enough to support my bona fides as a media company founder. But the real answer? Doc Hollywood. A somewhat corny fish-out-of-water story where Michael J. Fox plays a hotshot plastic surgeon forced to do community service in a small town. What can I say. It speaks to me.

Same thing with books. The public answer is The Endurance — the classic account of Shackleton’s extraordinary saga of survival, leadership, and Antarctic exploration. It’s genuinely great. I’m not embarrassed by that one. But if I’m being completely honest, the book that probably shaped me more than any other is The Fountainhead. Which is, along with Catcher in the Rye, the book that has produced more insufferable 17-year-olds than any other.

Here’s the truth: my mind is a sieve. I can barely remember the name of the book I just finished. The one before that? Genuinely can’t remember what it was about. If I didn’t keep a book journal, I’d have no idea what I’ve read. Which probably means that 90% of what’s actually shaped my thinking came from somewhere else entirely — newspaper articles, blog posts, long-form magazine pieces, Substacks I’ll never admit I subscribe to.

And when I do read books, it’s usually to decompress. Which means they’re, more often than not, kind of trashy.

My current read is Project Hail Mary by Andy Weir. Make of that what you will.

I also have a rule — applied without mercy — that if a book hasn’t grabbed me in the first twenty or thirty pages, I’m done. Too many books in the world to white-knuckle your way through one that isn’t working.

So, every January, when the celebrity reading lists drop, I’m conflicted. Partly embarrased, because I can’t compete. But partly there’s a slight bit of condescension, because I suspect that many of those lists are the literary equivalent of the celebrity living room — filled with impressive objects clearly purchased and arranged by someone else, placed just so for the Instagram shot.

Don’t get me wrong. I give Oprah and Bill genuine credit. I’m confident they actually read everything on their lists — and probably two or three books that didn’t make the cut for every one that did. I’m not casting shade. I’m not in that league. So I don’t pretend to be.

But if you’re curious, here are the last 10 books I actually read. In the order I read them. Because that’s the only order I have.

The Correspondent — Virginia Evans. A retired lawyer rediscovers herself through the lost art of letter writing. Quiet and surprisingly moving.

32 Yolks — Eric Ripert. The Le Bernardin chef’s memoir of a turbulent French childhood and a punishing culinary apprenticeship. Eric’s not Anthony Bourdain . . but he has his moments.

The Art of Spending Money — Morgan Housel. How aligning your spending with your actual values — not with status — leads to a better life. This book was meh. But Morgan is one of my favorite short-form writers. His blog posts are gold. No idea where he comes up with so much cleverness.

How to Build a Car — Adrian Newey. Formula One’s greatest designer on a career building championship car for Williams, McLaren, and Red Bull. Even if you don’t follow F1, the problem-solving is extraordinary.

Prodigal Summer — Barbara Kingsolver. Three interwoven stories in the Appalachian wilderness — predators, ecology, human desire. Reminded me that great fiction teaches things nonfiction can’t.

Million Dollar Weekend — Noah Kagan. How to validate a business in 48 hours. Supports - and instructs - everything I’ve always thought about validation hacking.

The Center Cannot Hold — Elyn R. Saks. A USC law professor’s memoir of living with schizophrenia while building an extraordinary career. Genuinely hard to read in all the right ways. (Last year I read the equally amazing The Best Minds, by Jonathan Rosen, also featuring a schizophrenic protagonist. The Center Cannot Hold is the counterweight to that heavy).

The Paper Palace — Miranda Cowley Heller. On a single summer day, a woman must choose between her husband and the love she never quite forgot. I struggled with this. Interesting but a little too arty for my taste.

Dogland — Tommy Tomlinson. A behind-the-scenes journey through the Westminster Dog Show. Awesome. I cried at one part. Trust me on this one.

Culpability — Bruce Holsinger. A family torn apart — legally and morally — after their self-driving car causes a fatal crash. Ripped right from the near future. Gripping.

That’s it. That’s the whole system. No Hemingway. No Clayton Christensen. No autobiography of a visionary founder I’m supposed to be learning from.

Look at that list and you won’t learn much about my professional life. You might learn something about me, though.

Because the books that stuck weren’t the ones I thought I should read. They were the ones that caught my eye at the right moment, and I was buying them on Kindle before I’d talked myself out of it.

And yes — I’m the person who genuinely enjoyed a book about dog shows. Completely fine with it.

A good friend of mine is absolutely obsessed with Disneyland. We’re talking full commitment — goofy hat and all. A few years ago he splurged on a room at the hotel right inside the park, specifically because guests get in an hour early. The plan was simple: the moment the gates opened, he’d sprint across the park and grab a fast pass for his favorite ride before they were gone.

He made it to the kiosk within fifteen minutes of opening. Already sold out.

He stood there stunned, probably looking as devastated as he felt, when a Disney employee noticed him and walked over. “Is everything okay?”

He explained what had happened. She listened, nodded sympathetically, then asked: “And how does that make you feel?”

“Well... I’m kind of bummed out.”

She smiled. “Anything else?”

“I mean, I’m a little upset.”

She smiled again, waiting. “Yes... anything else?”

“I’m...” He paused. “I’m really disappointed.”

Her whole face lit up — like he’d finally said the magic words. Because he had.

“Well, we can’t have that, can we?” she said. She walked over to the kiosk, punched in a code, and printed out three passes.

I’ve thought about that story a lot since my friend told me. Because what he stumbled onto — almost by accident — is one of the most powerful tools you have in any negotiation, any difficult conversation, any moment when you need someone to actually help you.

Two words. I’m disappointed.

Here’s why they work so well.

Every other approach puts someone on the defensive. You make an argument, they counter it. You explain why you deserve more, they explain why you don’t. You get frustrated, they get stubborn. The whole thing devolves into a tug of war where nobody wants to be the one who gives ground.

But “I’m disappointed” does something entirely different. It doesn’t accuse anyone. It doesn’t assign blame. It doesn’t make the other person wrong. It simply implies — quietly, powerfully — that you expected better. That you deserved better. And it puts the other person in a position where they genuinely want to make things right.

I saw this play out again with another friend who was preparing for a job offer. He’d done his homework — he had a pretty good read on the title they were going to offer and roughly what the salary range would be. And he was already pretty sure it was going to come in lower than he thought he was worth.

“So what do I do?” he asked me.

“Easy,” I said. “When they make the offer, pause. Take a breath. And then say, I’m disappointed. Then explain, calmly, what you were expecting and why.”

Two days later he called me back. It had worked like a charm.

The thing is, “I’m disappointed” is disarming in a way that almost nothing else is. It doesn’t start an argument. It starts a conversation. And it signals — without any hostility — that the gap between what was offered and what you expected is real, and meaningful, and worth closing.

Now. If you want to level up even further, there’s a technique that doesn’t require any words at all.

The wince.

In any negotiation, the single best response to an offer you don’t like isn’t a counter-argument. It’s not even “I’m disappointed.” It’s saying absolutely nothing — and letting your face do the work.

A slow, almost involuntary wince. A slight intake of breath. The expression of someone who was hoping for better and is genuinely trying to hide how much that number stung.

Then silence.

I cannot tell you how effective this is. The other person — almost reflexively — starts filling that silence. They explain. They justify. And often, they start improving the offer before you’ve said a single word. Because nobody wants to be the person who caused that wince.

Together, these two techniques — the words and the wince — work for the same fundamental reason. They appeal to something basic in people: the desire to be seen as fair, as generous, as someone who did right by you. Most people, given the chance to make you feel better without losing face themselves, will take it.

You’re not putting them in a corner. You’re giving them a door.

The next time someone makes you an offer that falls short — a salary, a contract term, a fast pass at Disneyland — resist the urge to argue your case. Skip the spreadsheet of reasons you deserve more.

Just pause. Let your face fall. And say the magic words.

I’m disappointed.

Then wait.

Early in my career, I was working at Borland International. It was the first place I’d ever worked where I had stock options — and I was clinging to every single one of them like they were sacred objects.

One night in Hong Kong — jet-lagged, sticky-shirt tired — I’m at a bar with our VP of Sales. He mentioned, casually, like he was ordering another round, that he’d just sold every one of his vested shares. He smiled, like this was the most obvious thing in the world.

I must have looked like I’d been slapped, because he laughed and explained his logic: “If the stock keeps going up, I’ll do fine with what I’ve got left. If it goes down, I’ll be thrilled I sold when I could. And if I keep doing a good job, they’ll always give me more.”

That conversation changed the way I think about equity. Forever.

There’s a myth in startup culture that the truest sign of belief in your company is holding every single share. That selling even one is a betrayal — a vote of no confidence.

That’s not conviction. That’s bad risk management.

I’ve started seven companies. I’ve invested in over a hundred more. And across all of them, I’ve followed the lesson I learned that night in Hong Kong: when you can take money off the table, take money off the table.

Every time stock vested, I sold some. Every time a secondary opportunity came along, I participated. Not once have I regretted it — even when my ego tried to talk me out of it.

Here’s the thing about startups: shit happens. Not “sometimes.” Constantly. Markets crash. Deals fall apart at the last second. The one person who knew where the bodies were buried quits without warning. A platform changes a rule. A regulator wakes up cranky. These aren’t edge cases — they’re just Tuesday.

If you’ve been selling 10% of your stake as it vests, you’ve still got 90% working for you. If the company hits, you’ll never miss that 10%. But if you’ve held everything and the company craters? You end up with nothing. Years of sweat, and you’re starting over from scratch.

And here’s the part that surprises people: a CEO who’s taken some chips off the table is often more aligned with investors, not less. If your entire net worth is riding on this one outcome, you’re not thinking about shooting the moon — you’re thinking about not ending up broke. That fear makes people conservative at exactly the moment you need them bold.

A founder who isn’t terrified of losing everything can take real risks. That’s the whole point.

The best entrepreneurs I know don’t bet everything on one outcome. They make the cost of failure manageable — and then they go after it

Last week I got another letter from an aspiring filmmaker. Same story I’ve heard a hundred times — passion for making films that “feel honest, human, and meaningful,” some mention of Netflix, the usual.

But then he said something that stopped me cold: “I don’t have many filmmaking opportunities where I live.”

And I realized he’d fallen into the same trap that catches so many creative people — waiting for someone to give them permission to start.

Start Being a Filmmaker

Here’s what I wrote back, and what I’d say to anyone who dreams of being a filmmaker, musician, writer, or any other kind of creative:

If you want to be a filmmaker, start being a filmmaker. Right now. Today. Where you live.

You don’t need a Hollywood studio. You don’t need a $100 million budget. You don’t even need fancy equipment. You have a phone? Then you have everything you need to write scripts, shoot video, edit, add effects, sync soundtracks. In short — to do actual filmmaking.

Every great filmmaker you’ve ever heard of started small. Scorsese. Tarantino. Nolan. They would have killed to have the production power you carry in your pocket every single day.

I Started Small Too

People see Netflix and assume I somehow jumped straight into building billion-dollar companies.

Not even close.

Netflix was my sixth startup. Before that, I’d already launched dozens of things — started clubs, launched student magazines, put on plays. Small stuff. Low stakes. Most of it went nowhere.

I didn’t need to ask permission or raise money. I just did them.

But here’s what those experiences gave me: how to raise money, how to get people to help me, how to figure out what actually matters and what’s just noise. The same skills I learned putting on a bad play at seventeen were the ones I leaned on when it came time to build something real. The scale changed. The stakes got higher. The fundamentals? Identical.

You learn by doing. There’s no other way.

Why Do You Actually Want This?

Here’s the uncomfortable part. Most people who say they want to be filmmakers don’t actually want to make films. They want to be rich. They want to be famous. They want to be recognized.

I get it. But the odds of achieving any of those things through creative work are vanishingly small. If that’s your primary motivation, you’re probably going to be disappointed.

If you love the craft, though — if you genuinely enjoy the process of creating, of telling stories, of making something that didn’t exist before — then nothing is stopping you from doing it right now.

Nothing.

Start Making Your Rookie Mistakes

I told him to make one complete film every week. Twenty-four hours to think about it. Twenty-four hours to film it. The rest of the week to edit and post it on YouTube.

Not finished by the end of the week? Doesn’t matter. Put it in the can and start the next one.

By this time next year, he could have fifty-two films under his belt. Will they all be good? Of course not. Most of them will probably be terrible.

But that’s exactly the point.

Make your rookie mistakes on your own time — don’t expect to make them on someone else’s dime. With each film, you get better. You learn what works. You find your voice. You build a portfolio that shows you actually know what you’re doing.

The only person holding you back is you.

One More Thing

Here’s something I’ve noticed — with this kind of creative, with first-time founders, with anyone who’s been sitting on an idea waiting for the right moment: the moment you just start doing the work, something changes. Not in your circumstances. In how you see yourself.

You’re not someone who wants to be a filmmaker someday. You’re someone who is already making films.

That’s a different person. Go be that person.