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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TIME STAMPS:
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