Episode #9
Trevor Thompson- From Indoor Skydiving to Syndications
Trevor's LinkedIn https://www.linkedin.com/in/ktrevorthompson/ Trevor's Email KTTProperties@gmail.com Massive Capital https://massive.capital/ From iFLY VP to CRE Syndications: Trevor Thompson on Due Diligence, Sponsors & Buying in Today’s Market In this CRE Deep Dive episode, Trevor Thompson shares his path from attraction and indoor skydiving operations to commercial real estate investing, including helping open 90 iFLY locations and completing 48 syndications as both a limited and general partner. He explains what syndications are, how he overcame fears of single-family “toilets, tenants, and trash,” and lessons from his first passive deal, including the importance of property-level due diligence and COVID-era rent challenges. Trevor outlines how LPs can evaluate sponsors, spot unrealistic underwriting and return promises, and why education, transparency, and accessibility matter. He discusses recent acquisitions, including a Texas multifamily deal and a 32-bed assisted living project, plus how underwriting has shifted toward stable, fixed-rate debt and stronger risk controls. He emphasizes compounding, avoiding “get rich quick” expectations, and taking action to overcome analysis paralysis. 00:00 Meet Trevor Thompson 01:32 Real Estate Leap 02:15 Syndications Explained 03:19 Creative Deal Lessons 04:32 First Investment Mistakes 06:34 Choosing Great Sponsors 08:39 Property Tours Value Add 11:31 Deal Deck Red Flags 13:35 When To Walk Away 15:10 Buying In Todays Market 16:18 Assisted Living Expansion 17:05 Passion-Driven Operators 17:40 Underwriting in High Rates 19:04 Walking Away From Risk 20:06 Honesty Builds Trust 21:31 Setting Return Expectations 23:33 Investor Community in Action 25:11 Real Estate Is Rich Slow 27:07 Impacting 100000 Lives 29:39 Beating Analysis Paralysis 30:58 First Steps With 50000 32:01 How to Reach Trevor
