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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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.
insights INSIGHT
Sacrifice vs. Suffering
Sacrifice is necessary for entrepreneurial success, but suffering is not essential.
Find a balance between dedication and personal well-being.
question_answer ANECDOTE
Ironman and Self-Belief
Josh Payne overcame his fear of drowning by training for and completing an Ironman triathlon.
This built his self-confidence and instilled a belief that he could achieve anything.
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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 Company 00:03:30 Why Money Didn’t Solve Everything 00:05:15 Prioritizing Family After the Exit 00:06:30 Leaving the Company: A Tough Identity Shift 00:07:45 Taking a Healing Family Trip 00:09:00 Training for an Ironman & Overcoming Mental Barriers 00:12:30 Decoupling Identity from Business 00:14:00 Leadership & Purpose Beyond Business 00:16:00 Sacrifice vs. Suffering in Entrepreneurship 00:18:45 Ironman Training: Lessons in Overcoming Fear 00:22:00 The Challenge of Finding a New Purpose 00:23:45 Why Start Another Business After an Exit? 00:27:00 Learning to Build a Company Without Fear 00:30:00 The Difference Between First and Second Businesses 00:33:00 Finding a Sustainable Way to Build Again 00:35:00 Balancing Business & Personal Life After Exit 00:38:15 Why Many Second Businesses Fail 00:42:00 The Importance of Motivation in a New Startup 00:45:30 Avoiding the Trap of Losing Interest Midway 00:48:00 The Role of Peer Groups Like Tiger 21 00:50:30 How Long Does It Take to Truly Adjust After Exit? 00:53:00 Raising Kids With Wealth: Teaching Responsibility 00:54:00 Closing Thoughts & Future Plans
Exit Paradox