I've been a founder in five companies. None of them have made me rich.
I could have stayed in corporate. By my early 30s, I was a VP at UnitedHealth Group, in the top 150 executives of a Fortune 25 company, managing teams of 40+ people with significant budgets. The trajectory was clear: keep climbing, keep collecting titles, retire comfortably.
Instead, I built an agency. That turned into a social platform. That created a TV show. Thanks to COVID in 2020 and some founder disagreements, The Jump led to two more focused ventures—Creator Space, connecting agencies and brands to creators and influencers, and Team Scout, a comprehensive platform for youth sports programs with group communications, websites, merch stores, registrations, and everything else a team needs to run well.
Each one taught me something. Each one led to the next. None of them became the billion-dollar exit that makes founders famous.
So why keep doing it? The honest answer is that I can't stop seeing problems that should be solved.
I watch high school football coaches struggle with websites that look like they were built in 2008 and I think: this should be better. I watch brands waste money on ads that annoy people and I think: there's a better model. I watch social platforms optimize for addiction instead of value and I think: someone should build the alternative.
The corporate world taught me how big systems work. Complexity, stakeholders, politics, scale. I appreciate the compounding power of large organizations—there's a reason UHG went from Fortune 50 to Fortune 3. That knowledge is useful.
But it's not where I want to spend my time. I'd rather be building the thing than managing the process. I'd rather have direct influence on culture and outcomes than navigate layers of approval.
Team Scout is the current bet. Maybe this is the billion-dollar venture. Maybe it's not. Either way, I'll learn something. And whatever comes next will be better because of it.