From Filmmaker to Al Founder: Jason Sherman on Reinvention and Resilience

Most entrepreneurs do not fail because they lack ideas. They fail because they fall in love with the idea before they prove there’s a market, a customer, and a path to revenue.My guest today is Jason Sherman, and he has spent much of his career helping founders avoid exactly that trap.Jason is a technology entrepreneur, author, filmmaker, startup advisor, and AI founder. He is the author of Strap on Your Boots, a practical startup guide built around the lessons founders need most: validating ideas, understanding target markets, building MVPs, making data-driven decisions, and turning a concept into a real business.But Jason’s story is not just about startups. It is about reinvention. He has worked as a filmmaker, journalist, author, podcaster, teacher, software developer, and entrepreneur. Today, he is also connected to the world of artificial intelligence through Vengo AI as their co-founder & CEO, where the focus is helping businesses use AI to engage customers, search company knowledge, and create more effective sales conversations.In this episode, we will talk about Jason’s own entrepreneurial journey, the mistakes he sees founders make again and again, how storytelling shapes business success, and how entrepreneurs can use AI without losing sight of the human problem they are trying to solve.VENGO AIhttps://vengoai.comSPINNRhttps://spinnr.appStrap on Your Bootshttps://tinyurl.com/bdh3s79zJASON SHERMAN's Websitehttps://jasonsherman.org