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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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My friend Jonathan has chosen to remain anonymous in exchange for stepping outside his comfort zone — and that he did! Eight years ago, he began a gradual exit from his incredibly successful, bootstrapped company. This strategic approach had an unexpected benefit: it smoothed his post-exit transition, making it more manageable both emotionally and financially. His search for a new purpose—a lengthy and confusing path for most—became clear and compelling after his family was hit by a mental health issue. In this interview, Jonathan shares raw, unconventional wisdom about the advantages of bootstrapping and exiting in stages, and how painful personal challenges gave him a new purpose and source of fulfillment.
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00:00: Introduction
01:00 Transition after selling the company
01:20: Jonathan's unconventional wisdom
02:08: Jonathan's previous careers
03:06: Motivation for starting a new business
03:53: Challenges faced in hierarchical systems
04:44: Importance of money in decisions
05:47: Founding a data business
06:44: Challenges in raising money
08:24: Misconceptions about data
10:03: Advantages of bootstrapping
11:14: Financial challenges and salaries
14:53: Impact of minority exit in 2016
17:02: Reasons for full business exit
18:12: Dividend checks and responsibility
19:04: Working with private equity firms
21:04: Importance of choosing the right partner
22:10: Reflections on Exiting During COVID
23:00: Health Issues and Impact on Business
24:03: Regrets and Decisions on Exiting
25:10: Continuing Involvement Post-Exit
26:14: Merging with a US Company
27:02: Adjusting to Life After Business
28:32: Personal and Family Focus Post-Retirement
30:26: Supporting Academic Research and Mental Health
31:29: Motivation of Wealth Training for Children
35:17: Disinterest in Material Possessions
38:13: Sources of Fulfillment and Life Satisfaction
41:47: Outdoor Activities and Personal Well-being
42:00: Processing Life's Experiences into Wisdom
45:36: Small experiences of delight
46:12: Caring for employees through share options
46:50: Satisfaction from contributing to others' happiness
47:08: Reflection on being remembered
48:04: Conclusion and gratitude
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