The Leap to Founding: Insights from Our April NYC Founder Curious Series

Best way to kick off the week: BBG Ventures teamed up with Kristin McDonald (Eniac Ventures) and Susannah Shipton (AlleyCorp) for a Founder Curious breakfast in NYC, with support from Silicon Valley Bank. Rebecca Schwartz (Tabs) and Natan Wise (Conduit Health) joined us to share how they made the leap. Here are my favorite takeaways:

💡 1. There is risk to every career path, founding is just one of them. Rebecca worked at later-stage companies during business school and realized the chaos wasn't all that different from the earliest stages. If it was going to be chaotic either way, she'd rather own the decisions (and the mess!) than inherit someone else's. Once you internalize this, founding feels like a logical next move.

🔍 2. A hundred conversations beats jumping into code. Tabs didn't touch production code for nearly a year. Instead Rebecca did over 100 customer discovery calls - and the most valuable were with people she'd never met. Warm intros tell you what you want to hear but strangers won't. Some of those cold outreach contacts are now customers. Back into the technology from the pain point, not the other way around. This has never mattered more than now, when you can ship product in an afternoon.

🤝 3. Every co-founder story looks different. Natan and his co-founder had been close friends for years before starting Conduit. Rebecca met her co-founders after she'd already identified the opportunity. Long-time friends, professional acquaintances, strangers at a coffee shop - there's no "right" origin story. What matters is being intentional about understanding each other before the hard moments hit.

🧠 4. Lived experience opens doors, but going deep can too. Some industries demand credibility from the inside, but when you don't have that background, there's no excuse not to close the gap. Learn the language, know the players, understand how deals get done before you try to sell anything. The founders who win aren't just the ones who felt the pain, they're the ones who went deepest on understanding it.

💰 5. Lead with ROI, not features. It's easier than ever to build, and the conversation has shifted to defensibility, data flywheels, and AI-native advantages. But the founders who cut through are the ones who can clearly articulate what changes for a customer when they buy - in dollars, time, and outcomes. Know the ROI before you build it, and let that shape the product.

🎯 6. If founder curiosity has sat at 15% for a while, it's time to time-box it. Rebecca and Natan's advice: go for it. Decide what you need to know to really lean in, then go all in. The long-term downside of taking the swing is less than most people think.

If that 15% feeling resonates, our next Founder Curious might be the push you need. Reach out at hello@bbgventures.com.