01 Sep They almost cost me everything. Then they wanted more of it.
The reality versus what you were sold as a founder.
Dealing with a certain kind of VC is a lot like playing chess with a pigeon. You study the game, calculate risk and execute your next move. You play the long game while they knock pieces around and panic over every move you make. And somehow, no matter how the game ends, the pigeon still acts like it was the winner.
I’ve lived this more than once. Multiple investors, same pattern. I bring a plan with real, calculated risk in it, the kind that actually moves a company instead of just keeping the lights on. And the same partner who talked big during the pitch turns into someone who wants to model out every downside on a spreadsheet before they’ll even look at the upside.
You invested in me. Then you started questioning me?
You picked me. You looked at what I built and decided I knew how to run this. That’s the deal.
Then I make a real call, and suddenly I’m getting questioned by someone who’s never run a company. Never made payroll. Never had to sit alone with a decision that could sink the business or save it. But there they are, telling me how to run mine. Not to mention, I have a solid track record of building winners and getting acquired.
That’s not oversight. That’s a guy with a board seat and zero scar tissue trying to coach a fight he’s never been in.
Every time, the bet paid off
I’m not saying this to brag. I’m saying it because it’s the whole point.
Most fights I had was over a call that worked. Sometimes even beating my own projections, even by a wide margin at times. This isn’t one lucky swing. It’s a pattern, across years, across multiple investors. When I trusted my gut on something big and pushed through the resistance, the return was great. My average on those calls is well above average and I have the record to prove it.
And the fight itself cost real money. Every “I don’t understand, I don’t think we should do this,” every extra round of convincing people who show up once a quarter to feel comfortable with a decision they’ll never fully understand, that’s weeks gone. Sometimes months. A call that should’ve taken a week takes two months because someone outside the business needs to feel safe about something that was never theirs to feel safe about.
Then, after I was right, this is what really pisses me off
You’d think being wrong, and being wrong big, would buy a little humility. Maybe some trust for next time.
Instead, some of them came back after the win and tried to hijack the deal. Not a friendly conversation about a bigger check. A retrade. Trying to unwind terms we’d already agreed on and already signed. Suddenly there were requests, meetings, “clarifications,” one thing after another, all designed to eat my time and wear me down until I’d just give in and hand over more equity to make it stop.
They fight you not to take the risk. You take it anyway. It pays off huge. Then they come back and try to take a bigger piece of the exact thing they told you not to do, using your own exhaustion as leverage.
That’s not a partner. That’s not even a rival negotiating hard. That’s greed wearing a Patagonia vest. They don’t care about you or the company you built. They care about the number on their stake, and they’ll burn your time and your patience trying to grow it after the fact so they look good to their partners.
It’s not all VCs, but it is far too common
I used to think this was bad luck, a couple of bad investors on my cap table. It’s not. I’ve heard the same story from founder after founder. Different industries, different rounds, same exact playbook. Founder pushes for something big. Money panics and fights it. Founder wins anyway. Instead of earning trust, that win becomes leverage the investor uses against you later.
That’s not a personality problem. That’s how a lot of these guys are built. Wired to protect a spreadsheet, not to back a real bet. And when the bet works despite them, they don’t see a lesson. They see an opening to grab more.
Founders know their business. Full stop.
I’m not saying founders are always right. Nobody is. Some founders need real pushback and a good board should give it to them.
But the gut instinct a founder builds from living inside the business every day is not a guess. It’s earned. It comes from a thousand things no board member sitting in one meeting a quarter will ever see. When that instinct says go, and the track record backs it up, the right move is to trust it. Or at least get out of the way.
Stay in your lane
A board seat gets you visibility. It gets you a voice. It does not get you the right to run the company from the sidelines, fight every bold call because it makes you nervous, and then try to retrade the deal after it wins because you didn’t like how it made you feel along the way.
If you fought a call and you were wrong, say it. That’s the whole ask. Own it, and let it earn the founder more trust next time. Do not come back with your hand out.
What you don’t get to do is doubt someone the entire climb, get proven wrong, and then try to plant your flag at the summit anyway.
The pigeon always struts
That’s the image I can’t shake. You out-think them. You take the real risk. You play the long game while they’re panicked and knocking pieces off the board out of nerves. You win, clean, no debate.
And the pigeon still struts around like it won the game… it was the mastermind. Doesn’t matter that it never had a real move the entire match. Doesn’t matter that the board is a mess because of it, not you. It struts anyway, because that’s what pigeons do, and then it comes back around looking for more crumbs off your board.
Let it strut. Just don’t hand over another piece to make it stop.