Kyle O'Hehir, CTO of Constitution Lending - Real Estate Open Season - The Michael Girdley Show Episode 43

21 Jul 2022 · 66 min
Episode

21 Jul 2022 · 66 min

0:00

In this episode of The Michael Girdley Show, Kyle O'Hehir, CTO of Constitution Lending, walks through his unconventional career path—from a commodities desk on Wall Street to a hands‑on real‑estate investor and credit provider. He explains how he identified his first short‑term‑rental (STR) opportunity in Savannah, Georgia, using data‑driven screening and regulatory due‑diligence, and how that deal yielded a 40% cash‑on‑cash return. After leaving the hedge fund, Kyle built a portfolio of affordable‑housing multifamily assets in Connecticut, sourced distressed loans at judicial auctions, and launched a hard‑money lending operation that now originates $10 million a month for equity‑focused investors. He discusses operational challenges (self‑managing versus third‑party property management, in‑house general contracting, and the “hit‑or‑miss” nature of external GCs), capital‑stack strategies (partner capital, bank relationships, credit‑hedge‑fund facilities), and the decision‑making framework he uses to allocate time across multiple ventures. The conversation also delves into broader entrepreneurial philosophy—effectuation versus VC‑style big bets, the importance of a translation layer for blind spots, learning from mentors, and the role of gut instinct versus data. Kyle shares advice on saying no, focusing on high‑leverage activities, and how he balances domain‑specific expertise with transferable business skills. The episode ends with contact information for listeners interested in debt financing.

Chapters

More from Michael

PodcastNick Gray, founder of Museum Hack - Profiting from awesome in-person events - The Michael Girdley Show episode 51
Podcast

Nick Gray, founder of Museum Hack - Profiting from awesome in-person events - The Michael Girdley Show episode 51

4y ago
PodcastJames Camp, Founder of Nanoflips.com - Solopreneurs and Scale - The Michael Girdley Show Episode 50
Podcast

James Camp, Founder of Nanoflips.com - Solopreneurs and Scale - The Michael Girdley Show Episode 50

4y ago
PodcastDave Kline, Owner of SkillScouter - How to become a great manager? - The Michael Girdley Show Episode 49
Podcast

Dave Kline, Owner of SkillScouter - How to become a great manager? - The Michael Girdley Show Episode 49

4y ago
PodcastJoe Wilson, Managing Partner at Undeterred Capital - VC from the ground up - The Michael Girdley Show Episode 48
Podcast

Joe Wilson, Managing Partner at Undeterred Capital - VC from the ground up - The Michael Girdley Show Episode 48

4y ago
PodcastLinda Lebrun, Writer Recruitment at Substack - Online content masterclass - The Michael Girdley Show Episode 47
Podcast

Linda Lebrun, Writer Recruitment at Substack - Online content masterclass - The Michael Girdley Show Episode 47

4y ago
PodcastTai Rattigan, Global Head of Partnerships at Deel and Co-Founder at Partnership Leaders - The Magic of Partnering Well - The Michael Girdley Show Episode 46
Podcast

Tai Rattigan, Global Head of Partnerships at Deel and Co-Founder at Partnership Leaders - The Magic of Partnering Well - The Michael Girdley Show Episode 46

4y ago
PodcastRohun Jauhar, Co-founder of JT Capital - From W-2 into Real Estate - The Michael Girdley Show Episode 45
Podcast

Rohun Jauhar, Co-founder of JT Capital - From W-2 into Real Estate - The Michael Girdley Show Episode 45

4y ago
PodcastMoses Kagan, Founder of Adaptive Realty - Perspectives on Real Estate - The Michael Girdley Show Episode 44
Podcast

Moses Kagan, Founder of Adaptive Realty - Perspectives on Real Estate - The Michael Girdley Show Episode 44

4y ago
PodcastBarrett O'Neill, CEO of Bright Line Media - The competitive mindset - The Michael Girdley Show Episode 42
Podcast

Barrett O'Neill, CEO of Bright Line Media - The competitive mindset - The Michael Girdley Show Episode 42

4y ago
PodcastJustin Hill, Hill Law Firm - San Antonio Love Fest - The Michael Girdley Show Episode 41
Podcast

Justin Hill, Hill Law Firm - San Antonio Love Fest - The Michael Girdley Show Episode 41

4y ago
PodcastKevin Dahlstrom, CEO of Swell Money - The future of wealth building - The Michael Girdley Show Episode 40
Podcast

Kevin Dahlstrom, CEO of Swell Money - The future of wealth building - The Michael Girdley Show Episode 40

4y ago
See all content