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”

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 deals@storyboardliving.com

Connect with us at our Website: https://storyboardliving.com/ LinkedIn profile: https://www.linkedin.com/company/storyboard-living/