Founder Curious Breakfast New York
Last Friday, BBG Ventures kicked off the first Founder Curious breakfast of 2026 in NYC. We teamed up with Katie Shea (Divergent Capital) and Jillian Williams (Field Ventures) and, despite freezing temps, had a packed room of impressive operators (thanks Silicon Valley Bank for supporting!). Brennan Pothetes (Infinity Constellation), Rachel O'Driscoll (Simbie AI), and Eleanor Morgan (Liftoff) shared how they made the jump from operator to founder. Here’s what stuck with me:
💡 1. You can “try before you buy” the founder path
Eleanor didn’t quit on day one. She sketched the idea over a weekend, built a scrappy prototype while consulting, and validated for ~six months before going full-time. Founding is one of the few career moves you can test with real users before committing. A good filter: follow the problem you can’t stop thinking about.
🧪 2. Validation requires lots of conversations and real willingness to pay
Think dozens to hundreds of user calls (Rachel even shadowed doctors). Everyone priced early. Problems people complain about aren’t always problems they’ll pay for. One sharp qualifier: “What would get you promoted this year?” If it’s not tied to budget, it’s not urgent. “Free pilots” can also mislead as real priorities move fast and find budget. Ask what they already pay for and how approvals work.
🧩 3. Start with the wedge, not the grand vision
Especially in regulated industries, you earn trust with one painful, must-fix workflow first. Simbie focused on a narrow, high-value use case, then expanded once embedded. Solve the “hair on fire” problem to start.
🤝 4. Co-founder trust (and the right advisors) are critical
The liveliest debate of the morning: 50/50 or not with your-cofounders? Different answers, same focus on building trust with someone who will have significant equity. The same theme showed up with advisors — the best founders focus on pulling in specific operators who’d already solved the exact problem they were facing as advisors.
🚀 5. The bar is higher now — obsession can be the edge
AI makes building faster, which means features get copied fast and true moats are hard to find. Brennan said it best: “love is leverage.” If you don’t genuinely care about the problem, someone better funded will outlast you. The only durable advantage is obsession — caring enough to talk to the 300th customer, ship the messy version, and keep going when it’s hard.
If you’re feeling that mix of frustration, clarity, and “maybe this is the year,” Founder Curious is for you. DM me if you want to join the next one — we’ll be in SF in Feb!
