Exploring Acquisition Entrepreneurship with Jordan Fliegel: From Sports Tech to Shareholder Ventures In this episode of The Next Next, host Jason Jacobs interviews Jordan Fliegel, co-founder and CEO of Shareholder Ventures. The conversation chronicles Jordan's diverse journey from a professional basketball player to a successful entrepreneur and investor in the sports tech industry. Highlights include the founding of Coach Up and successful ventures like Draft, which was acquired for $48 million. The discussion delves into Jordan's recent focus on acquisition entrepreneurship through Shareholder Ventures, a holding company aimed at helping entrepreneurs acquire small- to medium-sized businesses. The episode covers various topics such as the current state of youth sports, the nuances of sports tech investments, and the unique opportunities arising from the impending retirement of baby boomer business owners. Listeners will gain insights into different entrepreneurial models, the strategic building of a HoldCo, and how emerging tools can assist founders in building and sustaining profitable businesses. 

00:00 Introduction to Jordan Fliegel 

00:09 Jordan's Early Life and Career 

00:17 Founding Coach Up and Draft 

00:39 Transition to Techstars and Shareholder Ventures 

01:13 Discussion on Youth Sports 

03:05 Jason and Jordan's Personal Reflections 

04:13 Challenges and Realities of Entrepreneurship 

16:01 Jordan's Journey with Techstars 

31:53 The Concept of Shareholder Ventures 

45:46 The Challenges of Running a Business Solo 

46:10 Tim and I Bought Businesses 

47:53 Joining the Center for American Entrepreneurship 

48:55 Structuring Shareholder Ventures 

49:28 The HoldCo Model and Its Benefits 

51:04 Supporting Acquisition Entrepreneurs 

01:02:49 The Role of Search Funds 

01:06:53 Financial Structure and Cash Flow Management 

01:25:35 Final Thoughts and Encouragement for Entrepreneurs