In this episode, Matt Watson and Sean Beckner discuss the journey of entrepreneurship, investment strategies, and the evolution of business growth. Sean shares his experiences transitioning from a startup founder to an investor, highlighting the importance of timing in business exits and the dynamics of customer engagement in the digital age.

They explore the challenges and rewards of acquiring businesses, the balance between equity and cash in exits, and the future of investing through a family office model. The conversation emphasizes the need for purpose and passion in entrepreneurship, as well as the potential for growth in existing businesses.

Takeaways
Entrepreneurship involves phases: founding, acquiring, and investing.
Transitioning from operator to investor can feel boring but offers freedom.
Building businesses profitably allows for better optionality in exits.
Customer engagement strategies have evolved with technology.
Timing the market is crucial for successful business exits.
Acquisitions can provide a win-win for founders and investors.
Balancing equity and cash in exits is a strategic decision.
Investing through a family office allows for more control and flexibility.
Purpose and passion are essential for long-term entrepreneurial success.
Growth in existing businesses can be more manageable than starting anew.

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This episode is sponsored by Full Scale:
https://fullscale.io/

Learn more about Sean Beckner here:
https://www.linkedin.com/in/sean-beckner-558a916/

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Sound Bites
"It's hard. It's hard."
"We all need some sense of purpose, right?"
"You can still get those types of returns."

Chapters
00:00 Introduction to Entrepreneurship and Investment
02:56 Transitioning from Operator to Investor
06:56 Early Ventures: From Startups to Exits
10:28 The Evolution of Customer Engagement
13:31 Viral Nova: Riding the Wave of Social Media
19:41 Timing the Market: Selling at the Right Moment
25:04 Acquisitions: Finding the Right Fit
31:02 The Balance of Equity and Cash in Exits
36:10 The Future of Investing: Family Office vs. Fund
40:32 Conclusion: The Importance of Purpose in Entrepreneurship

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