Episode 41: "You Didn't Serve Alone, Don't Search Alone" | Owners in Honor Founder Patrick Flood on Why ETA Differs from Startup Investing, Post-WWII Entrepreneurship Patterns, and Risk Mitigation in Small Business Acquisition

The Diligent Observer Podcast

Today's episode explores three ideas that caught my attention:

1. "If these companies roll to zero, it's a big problem" – Understanding this fundamental difference between ETA and venture startup investing is critical for angel investor portfolio construction and risk management.
2. The "peace dividend" creating veteran entrepreneurs - Patrick's observation about post-combat veterans seeking meaningful civilian engagement revealed how macro geopolitical shifts can create unexpected entrepreneurial waves.
3. Military handoffs - Patrick's description of asking previous commanders about unfulfilled goals mirrors exactly what successful business buyers should ask sellers, which is one of the things that make veterans so successful in the ETA world.

I explore these ideas and more with Patrick Flood who is the Founder and CEO of Owners in Honor, a nonprofit organization that has guided over 190 veterans toward business ownership through acquisition. A decorated Special Forces veteran who served for 26 years, Patrick brings a unique perspective on how military leadership skills translate to business operations. After earning his MBA from Duke's Fuqua School of Business, he identified the gap between veteran capabilities and traditional entrepreneurship paths, leading him to create a structured approach to business acquisition that leverages the collaborative, mission-driven mindset inherent in military culture.

During our conversation, Patrick shares:

• The historical context of veteran entrepreneurship from WWII to today - explaining why current geopolitical conditions are creating a new wave of military-to-business transitions with unprecedented opportunity.
• Why the "smallest unit is two" principle creates natural advantages for veterans in business acquisition scenarios - contrasting this with the isolation challenges that traditional startup entrepreneurs face.
• A framework for understanding why ETA investments require different risk profiles than traditional startup investing - and how family offices and angel investors can benefit from this emerging asset class.

Connect with Patrick

LinkedIn | Website

Stuff We Reference

• Texas A&M
• Duke University
• Post-9/11 GI Bill

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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Chapters

1. Introduction (00:00:00)

2. Challenges and Rewards of Veteran Entrepreneurship (00:03:03)

3. The Unique Value of Veteran Entrepreneurs (00:04:26)

4. Financing ETA for Veterans  (00:27:03)

5. Capital Reserve and Outside Capital (00:29:48)

6. Key Questions for Potential Investors  (00:31:26)

7. Investment Strategies and Returns (00:35:30)

8. Family Offices and Veteran Investments (00:37:03)

9. Patrick's Journey and Military Service (00:40:26)

10. Building a Self-Sustaining Nonprofit (00:44:07)

11. Engaging with Owners and Honor (00:49:33)