50 Chairs

50 Chairs
Podcast Description
Welcome to 50 chairs, where Gary Hensley — a 3x founder, investor whisperer, and storyteller at heart — sits down with world-changers, educators, and entrepreneurs to uncover how bold ideas become real movements. Whether it’s startups, school funding, or life’s curveballs — Gary’s been there, built that, and has the receipts.
Podcast Insights
Content Themes
The podcast focuses on entrepreneurship, technology, and personal growth, with episodes designed to highlight transformative ideas and leadership lessons. For example, the first episode features Tucker Hamilton discussing AI initiatives and the importance of teamwork in high-stakes environments, emphasizing themes such as resilience and adaptability.

Welcome to 50 chairs, where Gary Hensley — a 3x founder, investor whisperer, and storyteller at heart — sits down with world-changers, educators, and entrepreneurs to uncover how bold ideas become real movements. Whether it’s startups, school funding, or life’s curveballs — Gary’s been there, built that, and has the receipts.
Summary
In this episode of 50 Chairs, host Gary Hensley engages with Ryan Micheletti and Mike Sherbakov from the Veteran Fund, exploring the journey of building a community for veterans through entrepreneurship. They discuss the importance of integrity, conviction, and relationship-building in the investment process, as well as memorable pitches and the future of innovation. The conversation emphasizes the significance of supporting veteran-led startups and the unique qualities that veterans bring to the entrepreneurial landscape.
Takeaways
The Veteran Fund is a culmination of decades of work.
Building a community of veterans is essential for success.
Investing is a people business, focusing on relationships.
Integrity is crucial when pitching to investors.
Conviction and passion are key to inspiring others.
Memorable pitches often come from founders with deep conviction.
The future of innovation relies on supporting veteran-led startups.
Clear and simple communication is vital in pitches.
Building a tribe of like-minded individuals enhances success.
The journey of entrepreneurship is often non-linear and requires resilience.
Sound bites
”It's important to build a relationship.”
”It's a people business.”
”You have to be very clear and simple.”
Chapters
00:00 The Genesis of the Veteran Fund
02:58 Building a Community and Ecosystem
06:00 The Journey of Entrepreneurship
08:52 Connecting the Dots: Military to Business
11:57 The Unique Value of Veteran Leadership
15:00 The Investor's Mindset
17:54 Evaluating Founders and Startups
20:56 The Role of Veterans in Innovation
24:03 Navigating Challenges in the Tech Space
27:04 Red Flags in Pitching
29:49 The Long-Term Relationship Between Founders and Investors
33:51 Navigating Rejection and Building Relationships
36:10 The Importance of Consistency in Communication
38:23 Identifying Key Traits in Founders
40:06 The Intangible Qualities of Successful Founders
42:20 The Role of Conviction in Entrepreneurship
45:08 Inspiring the Next Generation of Innovators
48:05 Memorable Pitches and Their Impact
50:58 The Power of Conviction in Founders
54:20 Inspiring Future Generations Through Innovation
56:34 Crafting the Perfect Pitch for Investors
@50chairs
For the 50chairs Playbook from every episode go to 50chairs.com

Disclaimer
This podcast’s information is provided for general reference and was obtained from publicly accessible sources. The Podcast Collaborative neither produces nor verifies the content, accuracy, or suitability of this podcast. Views and opinions belong solely to the podcast creators and guests.
For a complete disclaimer, please see our Full Disclaimer on the archive page. The Podcast Collaborative bears no responsibility for the podcast’s themes, language, or overall content. Listener discretion is advised. Read our Terms of Use and Privacy Policy for more details.