EPISODE · May 27, 2025 · 51 MIN
Structuring Triple Net Sale-Leasebacks: Real Estate Financing with Tim Crowley, President, Crowley Financial Corp.
from T.U.T — The Unwritten Teachings · host Raj Tut
Tim Crowley is a St. Louis-based real estate investor and entrepreneur who built a decades-long career in triple net sale-leasebacks, conservative underwriting, and long-term investing. With no formal real estate background, Tim entered the industry after careers in manufacturing and oil & gas, eventually becoming a respected figure across 21 states. He’s also known for his role in golf course development, having helped build Gateway National, widely considered the best public golf course in the St. Louis region.In this episode, Tim shares the story of how he transitioned from commission sales into oil and gas and ultimately found his calling in real estate. He explains the mechanics behind triple net leasebacks, how to evaluate private credit risk, and why treating real estate as inventory changed the game. He opens up about failures, market shifts, and his conservative investment principles. Whether it’s raising a family, navigating recessions, or turning buildings into cash flow, Tim reveals timeless principles that guided his success.Connect with the HostTwitter: twitter.com/ItsRajTutLinkedIn: https://www.linkedin.com/in/rajtut/Instagram: instagram.com/ItsRajTutTikTok: https://www.tiktok.com/@itsrajtutConnect with the Guesthttps://www.linkedin.com/in/timothy-crowley-10881015/Timestamps00:0001:50 Lessons from his mentor Stanley Grossman03:00 Growing up in a working-class immigrant family 05:45 Why oil and gas investing didn’t work out 08:19 Tim’s first real estate deal: a bank leaseback 10:44 Risk-taking and getting married without a deal closed 12:00 Early bank sale-leaseback transactions 13:05 Why he avoided value-add outside St. Louis 14:10 What is a triple net leaseback? 15:13 How they underwrote tenant credit 17:03 Real estate as paying inventory 18:24 Creating favorable loan terms with banks20:35 Operating through rising interest rates 22:50 Navigating bankruptcies and receiverships 25:16 The golden years: a 10-year run of opportunity 27:18 How they structured 101% financing 28:09 What counts as value-add in net lease deals 30:01 Lease terms that protect investors 31:27 Why he avoided inflated rent deals 33:10 Golf course investing and Gateway National 35:27 The downtown St. Louis real estate opportunity 37:03 Challenges facing St. Louis today 39:18 Safety then vs. now40:00 Building Gateway National Golf Links 42:43 Buying Stonewolf Golf Club44:51 Legacy, parenting, and moral grounding46:16 Why he chose to walk away from upside on Gateway 48:28 Why the fundamentals always mattered more than flash 49:30 Tim’s hole-in-one advice: “Do what you say you’re going to do”If you're looking to sell us a 40+ unit multifamily property in the St. Louis region, or another part of MO/IL, please email [email protected] with us at our Website: https://storyboardliving.com/ LinkedIn profile: https://www.linkedin.com/company/storyboard-living/
What this episode covers
Tim Crowley is a St. Louis-based real estate investor and entrepreneur who built a decades-long career in triple net sale-leasebacks, conservative underwriting, and long-term investing. With no formal real estate background, Tim entered the industry after careers in manufacturing and oil & gas, eventually becoming a respected figure across 21 states. He’s also known for his role in golf course development, having helped build Gateway National, widely considered the best public golf course in the St. Louis region.In this episode, Tim shares the story of how he transitioned from commission sales into oil and gas and ultimately found his calling in real estate. He explains the mechanics behind triple net leasebacks, how to evaluate private credit risk, and why treating real estate as inventory changed the game. He opens up about failures, market shifts, and his conservative investment principles. Whether it’s raising a family, navigating recessions, or turning buildings into cash flow, Tim reveals timeless principles that guided his success.Connect with the HostTwitter: twitter.com/ItsRajTutLinkedIn: https://www.linkedin.com/in/rajtut/Instagram: instagram.com/ItsRajTutTikTok: https://www.tiktok.com/@itsrajtutConnect with the Guesthttps://www.linkedin.com/in/timothy-crowley-10881015/Timestamps00:0001:50 Lessons from his mentor Stanley Grossman03:00 Growing up in a working-class immigrant family 05:45 Why oil and gas investing didn’t work out 08:19 Tim’s first real estate deal: a bank leaseback 10:44 Risk-taking and getting married without a deal closed 12:00 Early bank sale-leaseback transactions 13:05 Why he avoided value-add outside St. Louis 14:10 What is a triple net leaseback? 15:13 How they underwrote tenant credit 17:03 Real estate as paying inventory 18:24 Creating favorable loan terms with banks20:35 Operating through rising interest rates 22:50 Navigating bankruptcies and receiverships 25:16 The golden years: a 10-year run of opportunity 27:18 How they structured 101% financing 28:09 What counts as value-add in net lease deals 30:01 Lease terms that protect investors 31:27 Why he avoided inflated rent deals 33:10 Golf course investing and Gateway National 35:27 The downtown St. Louis real estate opportunity 37:03 Challenges facing St. Louis today 39:18 Safety then vs. now40:00 Building Gateway National Golf Links 42:43 Buying Stonewolf Golf Club44:51 Legacy, parenting, and moral grounding46:16 Why he chose to walk away from upside on Gateway 48:28 Why the fundamentals always mattered more than flash 49:30 Tim’s hole-in-one advice: “Do what you say you’re going to do”If you're looking to sell us a 40+ unit multifamily property in the St. Louis region, or another part of MO/IL, please email [email protected] with us at our Website: https://storyboardliving.com/ LinkedIn profile: https://www.linkedin.com/company/storyboard-living/
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Structuring Triple Net Sale-Leasebacks: Real Estate Financing with Tim Crowley, President, Crowley Financial Corp.
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