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 Host

Twitter: twitter.com/ItsRajTut

LinkedIn: https://www.linkedin.com/in/rajtut/

Instagram: instagram.com/ItsRajTut

TikTok: https://www.tiktok.com/@itsrajtut

Connect with the Guest

https://www.linkedin.com/in/timothy-crowley-10881015/

Timestamps

00:00
01:50 Lessons from his mentor Stanley Grossman
03:00 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 banks

20:35 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. now

40:00 Building Gateway National Golf Links 

42:43 Buying Stonewolf Golf Club
44:51 Legacy, parenting, and moral grounding
46:16 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”

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