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

"Nightmare Alley"