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 Introduction00:00:45 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

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