#017 - Go-to-Market Lessons from a Repeat Founder (After a Successful Exit)
Building a company once is hard. Building one again comes with an entirely new set of challenges. In this episode, Ben Schmidt, Founder & CEO of HeyLoopy, shares what he's learned as a repeat founder returning to the startup world after a successful exit. Ben shares during this conversation: The realities of going to market with a product that can serve multiple industries Strategies he's using to find early customers Decisions behind a freemium model Mistakes he's made (so you don't have to) Whether you're a first-time founder or building your next venture, this conversation offers practical go-to-market lessons on finding traction, choosing your market, and turning early relationships into opportunities. Visit HeyLoopy.com Follow Ben on LinkedIn About Ben Ben Schmidt is a Pittsburgh founder building HeyLoopy: a learning platform where one person can orchestrate whether an entire organization actually knows how to do the work, instead of just tracking who completed the training. His frustration was watching companies confuse completion with competence. They hire great people, hand them a stack of docs and a "good luck," mark the course done, then act surprised when nobody can do the thing when it counts. HeyLoopy sits on top of the tools and content a team already has and turns them into daily practice, so one person can conduct the competence of a whole floor. The road to that idea starts further back than most founder stories. Before he built companies, Ben was a recovering brain scientist. He did a PhD studying how networks in the brain communicate, which is where he first got his hands on machine learning, years before it was the thing every startup claimed to do. That left him with a conviction that still runs everything he does: the real answers are almost always less magical than the headlines promise. From there he spent a decade turning AI into companies. He co-founded RoadBotics, which used computer vision to help cities decide which roads to fix, then as CEO sold it to Michelin in 2022. He stayed on as a CTO to land the integration, then left to build HeyLoopy. The throughline across all of it: technology should make people harder to replace, not easier, which is exactly what a knowing platform is for.
