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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What really happens after you sell your business? In this episode, Mark O'Dwyer, former CEO of Big Red Cloud, shares the emotional, financial, and psychological reality of exiting after 33 years of building a company from scratch.
We talk about:
- The unexpected emptiness after the deal is done
- Why he refused earnouts—and why that was the smartest move of his life
- His experience using visualization and the Jack Black MindStore method to manifest his ideal exit
- What freedom really looks like after decades of being responsible for a team
- The surprising parallels between Ironman training and entrepreneurship
This is a rare behind-the-scenes look at what comes *after* the entrepreneurial dream is realized—when your identity, drive, and purpose need to evolve.
- 00:00 Intro and Welcome
- 02:10 What It’s Like After Selling Your Business
- 08:30 Why Most Earnouts Fail
- 14:45 Real Freedom vs Entrepreneurial Illusion
- 27:00 Using MindStore to Manifest the Exit
- 33:10 Saying No to the Wrong Deals
- 45:00 The Hidden Cost of Entrepreneurship
- 51:00 Ironman Training and Reinventing Purpose
- 01:05:00 Final Reflections
Key Topics
- Business exits and emotional fallout
- Negotiation strategies and earnout traps
- Visualization and manifestation (MindStore method)
- Entrepreneurial freedom vs responsibility
- Ironman mindset and high-performance habits
- Finding purpose after success
https://www.linkedin.com/in/marcodwyer/
About the host:
Paul Ryan is an entrepreneur, 8 figure business owner, mentor, podcaster and creator of the 1-Hour CEO Mastermind. As a CEO, Paul has a depth of 'real life' experience of what it takes to be successful in business and life.
Connect with the host:
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