I spent six years co-founding two startups. One was a sports technology platform. The other was a landscaping marketplace. Neither of those sentences captures what actually happened.
What actually happened was: I raised half a million dollars, flew across the country to sit in gyms and onboard coaches one by one, taught myself no-code development and UX design during a master's program, replaced HubSpot with a custom platform I built from scratch, managed field operations for a service business with no trucks and no W-2 employees, and got fired via my Google account being shut off.
Here's what I learned.
You will wear every hat, and nobody will notice
At CrewLAB, I was technically the data scientist. In practice, I built the self-serve team creation module, ran the first ad campaigns (learning as I went), managed the Instagram content, flew around the country for hands-on onboarding, and sat in every investor meeting showing financial models while our CEO pitched the vision.
Nobody sat me down and said "you're going to do all of this." It just happened. The work needed doing, and I was the person willing to do it. That's both the gift and the trap of being an operator at a startup — you become indispensable by being everywhere, but your contribution becomes invisible because it's spread across everything.
The equity conversation you avoid will cost you the most
At CrewLAB, both co-founders had roughly three times my equity stake. I knew this. I felt it was unfair given the work I was doing. And I never said anything.
Not once.
I'm conflict-avoidant by nature. Hard conversations about money, about fairness, about what I deserve — those are the conversations I'd rather build something than have. So I buried it. I focused on the work. And when a $2 million seed round closed and I still had the same stake I started with, I left.
That pattern repeated at Breeasy. I took on more and more responsibility — product, operations, fulfillment management, team onboarding — and eventually earned an equity stake. But the hard conversations about what that stake meant, about the company's debt situation, about what would happen if things went south — I avoided those too.
And then one morning my Google account stopped working. That's how I found out I was done.
Cash matters more than equity (until it doesn't)
One of the reasons I left CrewLAB for Breeasy was the promise of actual cash generation. CrewLAB was paying me four thousand dollars a month — less than I made at Deloitte. Breeasy was a real business moving real money.
But "the company makes money" and "you personally make money" are not the same thing. Breeasy took on debt to buy out an early investor, never refinanced it, and ran into a cash crisis. Having equity in a company that's running out of cash is worth exactly nothing.
What I learned: revenue solves almost everything, but only if the business is structured so the people doing the work actually benefit from it. And that goes back to the conversations you need to have early.
Building the thing is the easy part
I can build a platform in weeks. I built Breeasy's entire operational system on Bubble — order management, workflow tracking, field team dispatching. Then I built a mobile app on top of it. Then I started building a customer portal.
The building was never the problem. The problem was always the stuff around it: the co-founder dynamics, the equity conversations, the cash management, the customer expectations, the tension between what the product could do and what the business needed it to do right now.
If you're a builder, you'll always be tempted to solve people problems with more building. That instinct is wrong about half the time.
The best onboarding is showing up in person
Some of my best work at CrewLAB happened when I stopped sending emails and started buying plane tickets. I'd fly to wherever a coach was interested, sit with them and their team, and walk everyone through the platform in person. It was expensive and inefficient and it worked better than anything else we tried.
People trust people. They don't trust onboarding flows. They don't trust documentation. They trust the person who showed up and sat with them.
I think about that all the time now with ohdavid. The best version of what I do probably involves sitting across from someone, understanding their business, and building something together — not sending them a link.
What I'm doing differently now
I'm building ohdavid as the company I wish I'd worked for. Custom tech platforms for businesses that need them, consulting for people who are stuck. I own the business, I set the terms, and I have the hard conversations early — about pricing, about scope, about what happens when things change.
The six years taught me what I'm good at: seeing systems, building things, and moving fast across disciplines. They also taught me what I'm bad at: having the uncomfortable conversation in the moment instead of six months later.
I'm working on both.
