Boris Berenberg. He thought he hit the jackpot selling his bootstrapped cash-rich software business. Two years later, he's filled with bitter regret. In this candid episode, Boris gets real about his exit—what he wishes he knew then and what we can all learn now.

LinkedIn Boris: https://www.linkedin.com/in/borisberenberg/

Blog Boris: https://www.nothingeasyaboutthis.com/i-regret-selling-my-startup/

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TIME STAMPS: 00:00:00 Intro 00:01:00: Beginning and Introduction 00:03:36: Discussing the Financial Side of Selling a Company 00:04:55: Talking About Financial Expectations and Reality After Selling a Company 00:07:33: Concept of "Dragon Mode" After Selling a Company 00:10:08: Discussing Reaction and Regrets After Selling the Company 00:13:25: Lessons Learnt and What Would Be Done Differently 00:16:03: Understanding Personal Values in the Context of Selling the Company 00:19:58: Mental Health Consequences for Founders Post-Sale 00:20:46: Looking Back - Starting the Business. 00:22:10: Effective team dynamics 00:22:54: Reaching a career apex at a young age 00:23:37: Starting on their own and consulting 00:24:24: Balancing job security with business growth 00:25:20: Shift in customer support ideologies 00:26:45: The motivations behind founding a company 00:27:21: The struggle with job autonomy 00:28:09: Working in an environment with almost complete autonomy 00:29:14: Perspectives on work-life balance and defining 'work' 00:31:26: Losing identity after selling the business 00:31:44: Contemplating next steps 00:34:01: Challenges of life as a digital nomad 00:36:33: Considerations on personal satisfaction vs financial security 00:41:11: Finding a happy place in specific environments. 00:42:15: The importance of networking and exploring future plans 00:44:21: Personal relationships and their effects post-exit 00:46:06: The benefits of the sale and finding a community 00:47:35: The loneliness pre-sale and finding community 00:48:24: Building acquaintanceships and friendships in new communities 00:49:47: Channeling dissatisfaction into motivation 00:50:46: Rating personal fulfillment 00:51:24: Searching for a sense of purpose 00:54:13: Discussing the difference in post-exit crisis for parents and non-parents 00:56:03: Desiring simple remembrance as a good family member 00:56:33: Aspiring to create a 'work playground' 00:57:37: Looking forward to future businesses and potential failures.