Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished"

Oct 15, 2024

Scott Wolfe, founder of Levelset and author of a $500 million exit, shares his post-sale reflections on life, purpose, and creativity. He grapples with the emotional rollercoaster from pride to frustration after selling his business, highlighting the challenges of reclaiming identity. Wolfe compares entrepreneurship to art and discusses the bittersweetness of leaving behind a collaborative team. He also dives into the quest for fulfillment, the impact of entrepreneurial parenting, and the paradox of purpose in a new life chapter.

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Intro

00:00 • 2min

The Bittersweet Farewell of Entrepreneurship

01:32 • 4min

From Law to Innovation: The LevelSet Journey

05:45 • 5min

Navigating Growth and Identity After Success

10:25 • 16min

Navigating Life After Business Exit

26:12 • 18min

Navigating Wealth and Purpose Post-Exit

44:23 • 13min

Entrepreneurial Upbringing and Personal Growth

57:08 • 19min

Reflections on Legacy and Personal Fulfillment

01:16:03 • 4min

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. _____________________________________________________ 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