Three years ago, Scott Wolfe sold his company, Levelset, for half a billion dollars. 

Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized. 

Scott is a natural creative who sees building a business as an artistic endeavor. 

It was this intrinsic need to create that sustained him through the grueling journey of building his business. Post-exit, he misses being driven by that vision and working alongside his exceptional, organically built team—one he feels can never be re-created. 

In this conversation, we explore the pros and cons of starting a sequel, the paradox of purpose, being a true “hedgehog,” the need for authenticity, full-time parenting, and raising entrepreneurial children.

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00:00:00 : Introduction and welcome to Scott 
00:01:11 : Reflections on selling the company 
00:02:22 : Feelings post-sale and personal identity 
00:05:01 : Comparing business to art 
00:06:58 : Transition from attorney to entrepreneur 
00:08:57 : Founding and growing Levelset 
00:11:15 : Key roles and talents in the company 
00:13:21 : Starting a new business and family considerations 
00:19:00 : Debating the reasons to start another business 
00:21:02 : Seeking purpose and fulfillment 
00:23:21 : The necessity of creativity and purpose 
00:24:06 : The challenges of balancing personal and professional life 
00:25:01 : The paradox of purpose 
00:26:31 : Rebuilding life and purpose post-exit 
00:27:56 : Adjustments and surprises after exiting a company 
00:29:02 : Facing mortality and existential reflections post-exit 
00:31:36 : Managing personal expectations and regrets 
00:34:07 : Reflecting on unfinished business and the non-finality of accomplishments 
00:38:03 : The journey and appetite for creative endeavors 
00:40:44 : Exploring new experiments and hobbies post-exit 
00:42:28 : Writing and reflecting on vision after business exit 
00:43:32 : Building and helping companies after the exit 
00:45:08 : Structuring the company's vision 
00:45:48 : Financial exit and its impact 
00:47:25 : Managing newfound wealth 
00:54:58 : Becoming a cautious investor 
00:56:00 : The hedgehog concept 
00:58:53 : The influence of entrepreneurial family upbringing 
01:01:42 : Wishing entrepreneurial experiences for children 
01:05:32 : The importance of self-reliance and vision for entrepreneurs 
01:06:22 : Strategy Development and Investment Philosophy 
01:08:07 : Changes in Motivation Over Time 
01:10:40 : Current Motivation and Challenges 
01:13:36 : Inspiration and Choosing People to Surround Yourself With 
01:14:21 : Building a Network Organically 
01:16:33 : The Importance of Purpose and Motivation 
01:17:49 : Reflections on Authenticity and Meeting New People 
01:18:04 : Legacy and How to be Remembered