Gregory Shepard — 12 Startups, 12 Exits, and the Science of Startup Success

Welcome to another riveting episode of The Proven Entrepreneur Show, hosted by the ever-curious and seasoned entrepreneur Don Williams. With nearly four decades of entrepreneurial grit under his belt, Don brings listeners into the minds of those who’ve not only dared to dream but dared to do — and do it exceptionally well.

In this episode, Don sits down with a guest whose resume reads like a startup fairy tale — but with all the grit, grind, and gut-wrenching moments that make it real. Meet Gregory Shepard: Fulbright Scholar, TEDx speaker, author of The Startup Lifecycle, and the rare entrepreneur who’s built and sold 12 companies — each one a success story in its own right.

But this isn’t just a highlight reel. Gregory opens up about the soul-crushing detour into politics, the sleepless nights wondering how to make payroll, and the raw truth behind why most startups fail — even when they have a great product. He shares how a five-year, $500,000 research project led to the creation of Startup Science, a platform designed to fix the fragmented startup ecosystem and help founders avoid the very pitfalls he once faced.

As the conversation unfolds, listeners are taken on a journey through the startup lifecycle — not the one you read in textbooks, but the one forged in the trenches. Gregory challenges conventional wisdom, especially the advice founders often receive from investors. He introduces the concept of the Ideal Acquirer Profile (IAP), a game-changing strategy that flips the traditional startup model on its head: build your company with the buyer in mind from day one.

From the dangers of overvaluation to the hidden costs of premature scaling, Gregory breaks down the anatomy of failure — and more importantly, how to avoid it. He speaks candidly about being neurodivergent, growing up in poverty, and how those experiences shaped his resilience and perspective as a founder.

This episode isn’t just for entrepreneurs — it’s for anyone who’s ever faced a mountain and wondered if they had what it takes to climb it. Gregory Shepard doesn’t just offer advice; he offers a roadmap, forged in fire, for how to build something that lasts — and how to walk away from it with your head held high.

So grab your headphones, settle in, and prepare to rethink everything you thought you knew about startups. Because this isn’t just another business podcast — it’s a masterclass in entrepreneurial survival.