Josh Payne, founder of Stack Commerce, shares his transformative journey after selling his company for nearly $100 million. He discusses the emotional aftermath, emphasizing how money didn’t solve everything. Family takes precedence now, and he reflects on the identity shifts entrepreneurs face post-exit. By training for an Ironman, Josh highlights lessons in overcoming mental barriers and the importance of finding purpose beyond mere profit. His focus is on creating sustainable businesses while prioritizing well-being and family values.
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question_answer ANECDOTE
Post-Exit Disappointment
Josh Payne felt shocked after selling StackCommerce, and the initial happiness wore off quickly.
His insecurities remained, highlighting that money didn't change his core beliefs.
volunteer_activism ADVICE
Post-Exit Recovery
Seek therapy to unpack emotional baggage and re-evaluate priorities after an exit.
Prioritize family, and consider a long trip together to strengthen bonds.
insights INSIGHT
Breaking Momentum
Long family trips can be healing for exited founders.
Such trips break the momentum of old habits and help decouple from the business.
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Welcome to Exit Paradox, where we explore what really happens after a successful business exit. I’m your host, Anastasia Koroleva.At some point post-exit, most of us ask the big question: How do I take care of my health, family, and wealth - without sacrificing my entrepreneurial ambitions? How do I build my next business without burnout?My guest today, Josh Payne, has developed fascinating insights and systems to do just that. Josh sold his company, Stack Commerce, for nearly $100 million 4 years ago. A huge milestone - but as all exited founders know, the real story starts after the deal is done.Today, he’s building again - but with a completely different approach.Josh isn’t optimizing for another massive exit. He’s after something bigger. So let’s see what we can learn from this fascinating man._____________________________________________________00:00:00 Introduction 00:00:45 Selling StackCommerce: Was It a Happy Moment?00:02:00 The Emotional Impact of Selling a Company00:03:30 Why Money Didn’t Solve Everything00:05:15 Prioritizing Family After the Exit00:06:30 Leaving the Company: A Tough Identity Shift00:07:45 Taking a Healing Family Trip00:09:00 Training for an Ironman & Overcoming Mental Barriers00:12:30 Decoupling Identity from Business00:14:00 Leadership & Purpose Beyond Business00:16:00 Sacrifice vs. Suffering in Entrepreneurship00:18:45 Ironman Training: Lessons in Overcoming Fear00:22:00 The Challenge of Finding a New Purpose00:23:45 Why Start Another Business After an Exit?00:27:00 Learning to Build a Company Without Fear00:30:00 The Difference Between First and Second Businesses00:33:00 Finding a Sustainable Way to Build Again00:35:00 Balancing Business & Personal Life After Exit00:38:15 Why Many Second Businesses Fail00:42:00 The Importance of Motivation in a New Startup00:45:30 Avoiding the Trap of Losing Interest Midway00:48:00 The Role of Peer Groups Like Tiger 2100:50:30 How Long Does It Take to Truly Adjust After Exit?00:53:00 Raising Kids With Wealth: Teaching Responsibility00:54:00 Closing Thoughts & Future Plans
Exit Paradox