Rick Eigenbrod is a deeply respected thinker in the post-exit world. 

A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach. 

In this conversation, we get into why Rick believes a “death of who we used to be” and a subsequent "re-birth" are inevitable post-exit, and how resisting these changes only adds to the struggle. 

Rick generously shares the tools and exercises he’s found most effective in navigating this transformative process. We also explore the grip of dopamine addiction, the healing power of legitimizing post-success frustration, simple ways to reconnect with our natural curiosity and playfulness, and the bittersweet reality of leaving some people behind as we experience exponential personal growth.

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00:00:00 : Introduction 
00:00:21 : The paradox of success 
00:00:43 : Rick's background and contributions 
00:01:04 : Discussion on post-exit rebirth and struggles 
00:01:12 : Exploring dopamine addiction and post-success frustrations 
00:02:30 : Exploring the post-exit maze 
00:02:45 : Rick's background and experience with exited founders 
00:04:47 : Rick's critical event with Vistage group 
00:06:09 : The price and prize of money and freedom 
00:07:52 : Reflections on the dual meaning of success 
00:08:53 : Grappling with post-exit paradox 
00:09:41 : The "focusing illusion" and the arrival fallacy 
00:11:12 : The societal pressure to be happy post-exit 
00:12:01 : Support groups and legitimating experiences 
00:13:08 : Initial reactions and reflections on the post-exit reality 
00:14:31 : The societal issue of ignoring exited founders 
00:15:33 : The lack of support and self-blame post-exit 
00:18:00 : Escaping the blank sheet of paper 
00:19:07 : Dealing with loss of motivation 
00:20:38 : The challenge of striving without a company 
00:22:21 : Stories of loss of identity and success paradox 
00:23:02 : The impact on identity and structure post-exit 
00:24:29 : Avoiding the inclination to fill the void with the same elements 
00:25:32 : Closing the first business 
00:26:18 : Question of true desires and freedom paradox 
00:27:19 : Attempt to create a model from experiences 
00:29:06 : Journey from identity to meaning and structure 
00:30:02 : Revisiting personal development opportunities 
00:33:16 : Financial dangers post-exit 
00:35:30 : Paradox of money and its role 
00:36:09 : Evolution of the meaning of wealth 
00:41:03 : Refusal of the call and negative transfer of learning 
00:44:10 : Dopamine addiction as an obstacle 
00:47:00 : Fear of losing entrepreneurial identity 
00:49:00 : Navigating the journey of death and rebirth in personal growth 
00:51:13 : Leaving people behind during personal growth 
00:52:29 : Real journeys begin where fairy tales end 
00:54:08 : Redefining retirement and societal expectations 
00:56:03 : Advising young successful entrepreneurs 
00:57:23 : Identifying and addressing emotional struggles post-sale 
00:58:46 : Embracing a Mosaic Life 
01:00:00 : Communicating personal transitions to others 
01:03:07 : Returning to business after personal growth 
01:05:00 : Listening for truth, vitality, and fear in decisions 
01:07:32 : Distinguishing between legitimate fears and psychological barriers 
01:09:08 : Discernment of skill-related fears in new ventures 
01:10:14 : Transitioning from entrepreneur to investor 
01:13:20 : Rediscovering a sense of purpose post-exit 
01:14:00 : The search for meaning and what matters now 
01:16:22 : Two ways of knowing and going: Destination vs Direction 
01:17:57 : Understanding fulfillment and satisfaction 
01:19:20 : The importance of savoring moments 
01:21:00 : Stories about finding fulfillment 
01:23:26 : Legacy question 
01:24:00 : Discussion about dynamics of arrival 
01:27:00 : The role of intention in satisfaction