This week on Generating Alpha, I sat down with Larry Connor, founder and managing partner of The Connor Group and one of the most successful real estate investors of the past three decades.

Larry's path was unconventional. After graduating summa cum laude from Ohio University with degrees in English and history, he started a painting business in high school, built and sold a tavern with a 300% return, then spent nine years running Orlando Computer Corporation before it failed. That failure became his "PhD in the Hard Knocks of business" and the foundation for an extraordinary career.

In 1991, Larry founded what would become The Connor Group with just $400,000 and one investor to buy three apartment communities in Dayton, Ohio. He built the firm on a contrarian thesis: treat apartments not as passive real estate investments, but as operating businesses with dramatic margin improvement potential. Over 32 years, The Connor Group has delivered over 30% average annual IRR to investors—outpacing firms like Brookfield and Blackstone. Out of 241 acquisitions, they've lost money on only eight. Today, the firm manages $5 billion in assets across 18 markets.

Beyond business, Larry is one of the world's most accomplished adventurers. In 2021-2022, he became the first person in history to dive to the deepest part of the ocean—the Mariana Trench—and travel to the International Space Station in the same year. He's won national racing championships, competed at Le Mans, flies F-5 fighter jets, and is planning to dive to the Titanic wreckage to prove deep-sea exploration can be done safely.

In our conversation, we explored how Larry thinks about counter-cyclical investing and building a culture of extreme accountability. We also discussed his philosophy on hiring people with no industry experience, why failure is the greatest teacher, and what connects exceptional entrepreneurship with pushing the limits of human exploration.

It's a rare look at one of America's most distinctive investors and a masterclass in contrarian thinking, operational excellence, and living without limits.

Presented by: rho.co/generatingalpha