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Episode 36: Why Builders Are Not Gamblers with Oliver Libby (Venture Capitalist, Founder, and Author of Strong Floor and No Ceiling)

2026-09-1540:51

Oliver Libby is a venture capitalist, founder, author, and cross-sector builder. He co-founded HL Ventures, helped build The Resolution Project, and recently published Strong Floor and No Ceiling, a vision for how America can rebuild opportunity without limiting ambition. In this episode, we talk about: - Oliver’s family history, legacy, and Nobel Prize lineage - Why every generation has to earn what it inherits - How venture capital can be more builder than gambler - Why founders need Sherpa...

Episode 35: Why You Should Never Bet Against New York with Kevin Appleby (Managing Partner at RUHL)

2026-09-0333:36

Kevin Appleby is the managing partner at RUHL, a New York City-based MEP design and engineering consulting firm focused on building electrification, energy efficiency, HVAC, and high-rise commercial and residential buildings. In this episode, we talk about: - How Kevin helped bring a 70-year German family business to New York - Why New York City is one of the hardest markets to break into - Why networking matters more in closed industries - How handwritten letters can still beat automated out...

Episode 34: Why Freedom Is the Real Goal with Joshua Lindsey (Founder and CEO of American Business Brokers and PHX Private Equity)

2026-08-1946:03

Joshua Lindsey is the founder and CEO of American Business Brokers and PHX Private Equity. He has bought and sold his own companies, taken a company public, represented hundreds of small business owners, and now uses his brokerage as both a business and a feeder for private equity deals. In this episode, we talk about: - Why selling a small business is nothing like selling a house - Why most business owners should not try to sell their own company - How Josh separates serious buyers from tire...

Episode 33: Why Buying Should Feel Personal, Not Pressured (with Urszula Bosco, Co-Founder of Amor 27)

2026-08-0443:13

Urszula Bosco was born and raised in Milan, moved to the U.S. for school, built a career in packaging, production, and development for beauty brands, and eventually co-founded Amor 27 with her husband in New York City. In this episode, we talk about: - Why starting a company means getting comfortable with uncertainty - How corporate skills can become the foundation for entrepreneurship - Why buying an engagement ring can feel so overwhelming - The difference between a transaction and a true c...

Episode 32: Why Growth Is Everyone’s Job with David Kidder and Grace Keenan, Building AI-Native Companies with Human-First Sales

2026-07-2141:45

David Kidder has built and exited multiple companies. Grace has worked alongside him for six years, from Bionic through its acquisition by Accenture and now into David’s newest companies, Board of Life and Primordium. In this episode, we talk about: - Why there’s a difference between being nice and being kind - How founders build trust without creating dependency - Why growth cannot just belong to the sales team - How AI changes the expectations for every person in a company - Why human-fir...

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