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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TIME STAMPS:
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