The Next Next The Next Chapter: Redefining Entrepreneurship with Shareholder Ventures
Jun 4, 2025
In this conversation, Jordan Fliegel, co-founder and CEO of Shareholder Ventures, shares his journey from professional basketball to entrepreneurship. He discusses his ventures, including the creation of CoachUp and Draft, acquired for $48 million. The focus shifts to acquisition entrepreneurship, exploring how aspiring business owners can buy existing companies, especially amidst the aging baby boomer population. Fliegel also touches on the evolving youth sports landscape and innovative investment strategies, emphasizing the importance of mentorship and community support in fostering entrepreneurial success.
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Youth Sports Competitive Shift
- Youth sports have become more competitive and lucrative, especially with NIL opportunities.
- Most kids should just play for fun, but serious competition requires intense training and specialization.
Draft Startup Stress Anecdote
- Jordan Fliegel shares the intense startup stress of Draft, including sleeping in the office and risking payroll.
- They nearly lost employees to competitors but secured funding with a last-minute trip to California.
Boomer Retirement Opportunity
- A huge wealth transfer is occurring as baby boomers retire, creating opportunities to acquire profitable SMBs.
- Many owners lack successors, making acquisition entrepreneurship a timely and valuable path.
