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