The Exit Strategy Most Founders Miss

What if the key to scaling and exiting your startup wasn’t hustle—but reverse engineering your success from day one? In this powerhouse episode, I sit down with Gregory Shepard—multi-exit entrepreneur, neurodivergent founder, TEDx speaker, and author of The Startup Lifecycle (Penguin Random House). With 12 exits, a $925M deal, and four Private Equity awards. I had a raw, deep-dive conversation with Gregory Shepard, a founder who’s mastered the startup lifecycle through grit, loss, reinvention, and an obsession with doing things smarter. We unpack why most startups fail (and how to avoid that fate), the mindset shifts that separate first-time founders from serial sellers, and his unconventional frameworks for scaling with purpose. Gregory doesn’t just talk exits—he builds companies designed to be acquired. If you're serious about scaling, this episode is a blueprint. JOIN the waitlist to get early access to our community for CEO's and founders that want to scale fast and exit fast.  Top 5 Takeaways Build to Exit: Design your business with specific acquirers in mind from day one. Bad Advice Destroys Startups: Most failures stem from well-meaning but poorly timed advice. Fix Mistakes with Reflection: Use Gregory’s whiteboard method to reverse-engineer decisions. Purpose Drives Performance: Aligning profit with purpose creates scalable, motivated teams. Exit Timing Matters: Spot industry shifts early—before it’s too late to sell. Chapters 00:00 Introduction to Gregory Sheppard 02:54 Reflections on Early Entrepreneurship 07:17 Learning from Mistakes 12:15 The Importance of Documentation 14:06 Pivotal Realizations in Business 20:47 The Impact of Hardship on Resilience 21:37 Balancing Multiple Startups 24:26 Motivation Behind the Hustle 26:30 Evolving Definitions of Wealth 27:43 Mindset Shifts in Exiting Businesses 31:34 Understanding Startup Failures 36:25 Navigating Bad Advice in Entrepreneurship 38:47 Navigating Startup Challenges 40:09 Defining a Startup 42:02 Lessons from High-Stakes Professions 44:56 Handling Business Fires 46:06 Moments of Brutal Honesty 48:39 The Importance of Altruistic Capitalism 49:08 Convincing Investors of Purpose 54:00 Understanding Exit Strategies 55:43 Selling to Competitors 57:25 Life After Exiting a Business 58:45 Future Aspirations and Legacy 01:02:05 Identifying Opportunities in Disruption 01:06:15 Timing Your Exit 🙏 How To Support The Business Strategist 🎙️ If this is the first time you’re listening congrats, if you like today’s episode please subscribe, listen and leave a review on 👉 Apple, Spotify ABOUT THE GUEST Website: https://www.gregoryshepard.com/ LinkedIn: https://www.linkedin.com/in/gregshepard ABOUT THE HOST LinkedIn: https://www.linkedin.com/in/adamistrong Learn how to scale fast by taking the business growth quiz: https://howtogrowabusiness.scoreapp.com YouTube: https://www.youtube.com/adamstrong Learn more about your ad choices. Visit megaphone.fm/adchoices