Founding Moments

Shensi Ding co-founded Merge after watching her own company lose deals it should have won — not on product, but on integrations. In this episode, she traces the path from teaching herself to code at 12 (building emo band fan sites in Boston) to building the unified API powering integrations for thousands of companies. She and Nate dig into why integrations went from "nice to have" to table stakes,...

Clark Peterson has been in the right place at the right time five times — and it was never an accident. From selling cell phones before most people had ever seen one, to building the nation's first nationwide cellular network, to pioneering cloud communications before anyone trusted the cloud, Clark has spent 35 years identifying windows of opportunity and moving fast before they close. In this co...

David Leeds spent nearly two decades building Tango Card from his basement in West Seattle — literally fulfilling gift card orders at midnight — into a company processing over $1.5 billion in rewards annually before being acquired by Blackhawk Network. But before Tango, he co-founded Fiber Tower, pitched 45 venture capital firms, got 45 rejections, and took it public anyway. What comes through in...

Renato Villanueva went from struggling to land a job out of UVU to helping build Divvy into a billion-dollar exit — then quit his job on a whim to start Parallel, an AI-powered financial modeling tool for founders. In this episode, Renato gets brutally honest about pre-selling a product that didn't exist, pricing mistakes that cost them 30% of their customers, and why he ultimately stepped down as...

What happens when your startup fails — and why that might be the best thing that ever happens to you? Chris Chumley has spent his career building, breaking, and betting on software companies. From nearly getting expelled for sneaking into school to play Oregon Trail, to leading product at a venture-backed startup that cratered, to helping build CampusLogic from a handful of customers to a $50M ARR...