If I could sit down with the version of myself who started this nine years ago, I wouldn’t hand her a pitch deck template (which took months of refinement by the way, and still didn’t land right). I wouldn’t give her a fundraising book (which I read all of them) or walk her through how to build a sales pipeline. She’d figure those out.

I’d give her this list.

Every lesson below was learned the hard way. Some cost money. Some cost time. Some cost relationships. A few nearly cost me the company. If you’re building something right now, my hope is that reading these saves you a few of the years they took me.

Lesson #1: Revenue solves more problems than funding

For a long stretch, I treated capital as the answer to everything. Short on runway? Raise another round. Stalled? Find another investor. Whatever the problem was, more money felt like the solution. It almost never was, and one stretch taught me that the hard way.

We bootstrapped for three full years, 2017 through 2019, and I mean truly bootstrapping. We lived off our savings, didn’t pay ourselves, and took a paycheck only when a contract closed. You’d be surprised how far $20 could go at Chick Fil A for a family of four. By the time we’d rebranded, we had several hundred thousand dollars in revenue, real Fortune 100 and Fortune 500 names on our customer list, and one of the largest oil-and-gas majors in the world about to close. On paper, we were doing everything right.

By early 2020, we had two term sheets in front of us. The first firm we genuinely liked the energy was right, they liked us, it was the kind of partnership you actually want. But their charter required a minimum revenue threshold, and we were a few hundred thousand dollars short of it. The second firm understood our market well, but it was a smaller round, and if I’m honest, the energy was off. They were the kind of partner you can already feel the friction with before you’ve signed a thing.

Then, the week of Christmas 2019, one of our largest customers three years in told us they weren’t renewing. It dropped our ARR by close to $300,000 overnight. And that single non-renewal did something a pitch deck could never undo: it knocked us below the revenue floor in the first firm’s charter. The investor we wanted was suddenly out of reach, not because they stopped believing in us, but because our numbers no longer cleared their bar. We were forced into the second choice.

Sit with that for a second. We didn’t lose our preferred investor over vision, or team, or market. We lost them over a single line of revenue that walked out the door right before the deadline. That’s the whole lesson: revenue isn’t just fuel, it’s leverage. It’s the thing that decides which doors stay open to you. When it’s there, you have choices. When it drops, your options disappear, often at the worst possible moment, with no time to win them back.

And what ultimately carried us through the months that followed wasn’t any investor’s check. It was that oil-and-gas major’s contract closing, and the customers who kept paying. Funding buys you time. Revenue buys you freedom, and sometimes it buys you survival. The strongest negotiating position a founder can hold isn’t a beautiful deck or a hot narrative; it’s a bank account filling up from people who already decided you’re worth paying for.

Lesson #2: Not all money is good money

Which brings me to the other half of that story, and the more expensive lesson buried inside it. We took the second-choice money. The firm whose energy was off, the one I told you I could already feel the friction with before we’d signed a thing. We took it anyway, because we were short of the first firm’s revenue floor and we wanted the round done. When you’re running low on cash and options, every dollar looks like a lifeline ( especially when your’s and your team’s family depend on it). That’s exactly when founders make their most expensive mistake.

We closed in February 2020, and going in second choice or not we were genuinely optimistic. We had our round, we’d told ourselves the friction was something we could manage, and we were ready to put the money to work and scale. That optimism lasted about three weeks. COVID was being announced by the end of February and declared a global pandemic in March, and the partner I’d had a bad feeling about showed me exactly who they were under pressure. Their LPs got skittish and held funds back. The capital we’d signed for didn’t fully arrive until June, and when it did, it came in tranches, a trickle, at the exact moment we needed a lifeline. A committed partner might have leaned in when the world got scary. Ours pulled back.

And the timing could not have been worse. COVID froze our entire market overnight. Everyone stopped spending. Demand vanished. The oil-and-gas major launch we’d fought for paused indefinitely. So there we were in a double bind: the investor capital was late and rationed, and the customer revenue we’d been counting on vanished at the same time. We stayed alive on PPP loans and the one major contract that had closed at the top of the year barely until the rest of the money finally trickled in.

And this is where the relationship I’d had doubts about began to come apart. Because the money was late, we missed our go-to-market window not just with existing customers, but with the pipeline contracts we’d been days from closing. That window doesn’t reopen; once it’s gone, it’s gone. So we missed our targets. And then came the part that still gets me: the same partner whose late capital had helped cause the miss now held us to the very targets we’d missed. We were falling short of expectations that their own delays had made impossible to hit and from that point forward, the relationship turned tumultuous. Every quarter became a negotiation about why we weren’t where we’d promised to be.

Here’s the part that still stings. Had I known COVID was coming, I would never have taken that partner’s money. But that isn’t really the lesson, because you can’t predict a pandemic. The lesson is that I ignored what I already knew. The friction was there before we signed. The energy was wrong before we signed. I read a smaller round and a partner I didn’t click with as the safe, available option when in truth, the wrong partner is the one most likely to disappear in the exact moment you need them. Adversity didn’t create that relationship’s problems. It revealed them.

The wrong investor can cost you far more than no investor at all not just in dollars, but in everything downstream: board meetings for years, signaling to the next round, pressure in the moments you most need room to breathe. So diligence your investors the way they diligence you. Call the other founders in their portfolio, especially the ones whose companies struggled, because that’s where you learn who someone actually is when things go sideways. And take the soft signals seriously the friction, the energy, the feeling you keep talking yourself out of. The check clears in a week. The relationship lasts the life of the company.

Everything to this point is the part I’ll give to anyone. What comes next is for the people building something serious enough to want it starting with the lesson that cost me the most: how power actually works, how a strategic investor can wait you out and take control for pennies, and the terms I signed that I’d give almost anything to take back. The remaining eight lessons are below, for subscribers.

Lesson #3: You have to understand power before you need it

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Nine years ago, I emptied my savings and pulled the money out of my 401(k) not to fund the company, but to live off while I built it. At this time I was married, had a mortgage and two kids under 2. For three years I took no outside capital. No venture firm. No bank loans. Just conviction I was willing to risk it all on the line, for a hundred percent ownership of what I was building.

That matters more than most founders realize. I built something real before I asked anyone else to bet on it.

(My co-founder, by the way, was my husband. That’s a whole series of its own and I’ll tell it. Later.)

I wasn’t a Silicon Valley founder. I wasn’t backed by an elite venture firm. I wasn’t part of the “right” network. I was a woman who’d chosen cybersecurity at thirteen studied it through pre-freshman engineering programs and computer science scholarships, coded since I was sixteen, fell in love with hacking somewhere in the middle. By the time I built a company in industrial cybersecurity, one of the most complex, highest-stakes, and male-dominated industries there is, I’d already spent twenty years getting there. It was never accidental. It was chosen. It choose me.

Since I finally took that first round of capital, I’ve raised millions, won and lost deals that could have ended us, sat through boardroom battles most people never see, and learned what it actually costs to keep the thing you built when other people’s money gets a vote. I started with a hundred percent of my company. After multiple rounds, I sit with less than a quarter percent .That number teaches you something about dilution that no business school ever will.

I started this publication because I finally understood something:

Most founders are being sold a fantasy. And the systems that are promoted best practices when forming/building your company for “scale and value” are not built to protect Founders and their inventions from corruption and greed.

The real thing is messy, lonely, expensive, and emotional. It’s also the hardest and most worthwhile thing I’ve ever done. And almost nobody tells you the truth about it because the truth usually stays behind closed doors, under NDAs, and in the room where the real decisions actually get made.

That’s what this is. The room behind the door.

Not theory. Not recycled advice. Not motivational quotes. Real stories, real mistakes, real numbers, real lessons, including the ones that cost me millions to learn. I won’t name the companies or the people across the table; I can’t, and I wouldn’t anyway. The mechanics are the lesson, and the mechanics are universal.What you’ll find here

I write about what actually decides whether a company and a founder survives.

The boardroom. Power, governance, control, influence; how founders gain or lose the ability to shape their own companies. This is the stuff almost nobody writes about honestly, and it’s where I go deepest.

Capital and investors. What raising money is really like, how investors actually think, and the terms I wish I’d understood before I signed them.

Founder survival. The emotional load no one warns you about leading through fear, deciding in the dark, and protecting yourself while you protect the company.

Building in critical infrastructure. Cybersecurity, OT, energy, industrial systems — the realities of selling enterprise software when the stakes are this high.

Leading while underestimated. What it takes to hold a room that wasn’t built for you, and why the hardest moments taught me the most.

Why this is paid

Because it isn’t written for an algorithm. It’s written for people who want substance and paying subscribers are what let me write openly, name the things most people won’t, and share lessons that took years and millions of dollars to earn.

My goal is simple: to hand you the playbooks, perspective, and hard truths I wish someone had handed me when I started. And if you want live engagement all the more reason to join.

If you’re here

You’re building something, a company, a career, a vision, or rebuilding after it broke. Either way, you’re in the right room.

Subscribe to join me for monthly deep dives on fundraising, founder survival, boardroom strategy, leadership, and the reality of building a company when the odds are stacked against you.

My first subscriber-only post drops this week: “The 10 Founder Lessons That Cost Me Millions of Dollars to Learn.”

I held the line in rooms designed to make me stop, rooms that tried to break me. I’m still standing and I’m done waiting for permission to build tables of my own.

Let’s get to work.

— Cherise Founder. Operator. Builder.

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