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.
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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 🎙️
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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
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