DiscoverThe Private Equity Podcast, by Raw SelectionOvercoming adversity to become a serial entrepreneur and successful investor, with Gregory Shepard.
Overcoming adversity to become a serial entrepreneur and successful investor, with Gregory Shepard.

Overcoming adversity to become a serial entrepreneur and successful investor, with Gregory Shepard.

Update: 2024-03-12
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Welcome to The Private Equity Podcast! In this insightful episode, host Alex Rawlings engages with Gregory Shepard, a distinguished entrepreneur, co-founder of BOSS Capital Partners, and a Forbes Books author. Shepard shares his remarkable journey from humble beginnings, growing up in a tent and facing challenges due to his neuro divergences, to becoming a serial entrepreneur with 14 liquidity events and multiple awards under his belt.

Breakdown:

[00:03 ] Gregory Shepard's Background: Gregory opens up about his challenging upbringing, living in a tent while building their house, and dealing with autism, dyslexia, synesthesia, and savant syndrome. Despite these obstacles, he went on to build and sell 12 companies, winning four Private Equity awards for transactions between $250 million and a billion.

[02:05 ] Entrepreneurial Journey and Achievements: Gregory discusses his role in significant transactions, including the consolidation of eBay enterprise companies, and his efforts to promote diversity in politics. He also highlights his work on Startup Science, a platform based on his research on why start-ups fail, and his upcoming book, "The Startup Lifecycle."

[03:32 ] Investment Philosophy and Private Equity Insights: Gregory shares his unique perspective on investment, emphasizing the importance of understanding both the founder's and the investor's viewpoints. He discusses common mistakes he sees in Private Equity, such as overvaluation and the failure to focus on real business fundamentals.

[09:47 ] BOSS Operating Support System: Shepard explains how his proprietary system and the StartupScience.io platform help educate founders and investors, improving the success rate of start-ups and investment returns.

[19:43 ] Dealing with Neurodivergence: Shepard speaks candidly about the challenges and advantages of his neurodivergence. He views his condition not as a hindrance but as a set of superpowers that have enabled him to see the world differently and achieve success.

[27:25 ] Altruistic Capitalism: Shepard introduces the concept of using capitalism for altruistic outcomes, such as environmental sustainability and inclusion, highlighting the potential for significant impact and profit.

[36:18 ] Closing: Contact information for Gregory and an invitation to engage further with the discussed topics.

To connect with Gregory Shepard, you can visit his LinkedIn Page: Gregory Shepard on LinkedIn.

Thank you for tuning in!

To get the newest Private Equity episodes, you can subscribe on iTunes or Spotify here.

Lastly, if you have any feedback on the podcast or want to reach out to Alex with any questions, send an email to alex.rawlings@raw-selection.com.

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Overcoming adversity to become a serial entrepreneur and successful investor, with Gregory Shepard.

Overcoming adversity to become a serial entrepreneur and successful investor, with Gregory Shepard.

Alex Rawlings