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Navigating the World of Liquidity Events: A Deep Dive Into Retired Founder’s Three Liquidity Events And Post-Exit Journey (#345)
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“It’s going to be OK.” -Retired Founder
In this episode of the Deep Wealth Podcast, post-exit entrepreneur and host Jeffrey Feldberg converses with Retired Founder, an anonymous guest who shares his journey from a middle-class Midwest upbringing to successfully selling his bootstrap SaaS business through three transactions between 2017 and 2022. He retired in 2018 and has since been building a community for post-exit founders. Retired Founder discusses the unexpected challenges of post-exit life, including grappling with identity and purpose. Key lessons include choosing the right investor, understanding company metrics, and managing life after an exit. The episode also highlights the transformative Deep Wealth Mastery Program and its benefits for business owners.
00:50 Sponsor Message: Deep Wealth Mastery Program
02:43 Welcome Back, Retired Founder
03:53 Jeff's Early Life and Entrepreneurial Journey
05:08 The Importance of Anonymity
08:57 Building and Growing the Business
19:46 The First Liquidity Event
21:57 Choosing the Right Investor
33:48 Understanding the Importance of People in Business Deals
35:37 The Difference Between Venture Capital and Private Equity
41:58 Emotional and Financial Outcomes Post-Liquidity Event
51:58 Life After Selling a Business: Challenges and Reflections
57:35 The Value of Bootstrapping and Deferred Gratification
59:40 Final Thoughts and Advice for Entrepreneurs
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