In the inaugural episode of The Cap Table, I sat down with Steve Hagenbuckle, founder and managing partner of TerraCap Management — a leading real estate private equity firm managing roughly $2 billion in assets.

However TerraCap is just the most recent chapter. Over nearly three decades, Steve has founded and sold a remarkable string of companies: TechWare, launched during the dot-com boom; ORUS Information Services; Collegiate Images; and Landmark Bank, later acquired by Nasdaq-listed Centennial Bank.

He started TerraCap in the depths of the 2008 financial crisis, and in 2019 founded Live Fest, now the biggest music festival in Southwest Florida.

We dive deep on his full journey — from putting himself through college with three jobs to becoming a self-made millionaire by 31. Steve shares why integrity became the foundation of every company he built, how he reverse-engineered his career toward his long-term goals, and how getting fired became the turning point of his career. We also get into how he raises institutional capital, builds great teams, navigates cyclical markets, and protects his reputation, relationships, and wealth as success grows.

I thoroughly enjoyed my conversation with Mr. Hagenbuckle, and I hope you do as well.

Steve H. https://www.linkedin.com/in/steve-hagenbuckle-5a58a6b/
Toby K. https://www.linkedin.com/in/tobykopec

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Timestamps

00:00:00 Intro
00:03:04 Childhood & College
00:11:35 Early Career
00:22:00 First Venture - Techware
00:40:00 Building Great Teams
00:43:30 Starting TerraCap
00:45:52 Dealing with Banks
00:49:00 Institutional Capital
00:56:50 Communication Skills
01:00:00 Real Estate Cycles
01:08:00 Balance
01:14:00 Dealing w/ Bad People
01:17:25 Greatest Challenge
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