495: 45 Deals Last Year—And Why He’s Playing the Long Game

Thomas DeMoss has been investing in Chattanooga for over 20 years and closed 45 deals last year. In this episode, he breaks down how he uses wholesaling as active income while building long-term wealth through buy-and-hold, new construction, and ADUs. We get into how zoning changes create opportunity, why certain lots matter more than others, and how experienced investors think beyond the assignment fee. KEY TALKING POINTS:0:00 - Intro0:36 - An Overview Of Thomas Demoss’s Business1:42 - His First Deal4:05 - His Second Deal & Their Marketing6:18 - Average Assignment Fees & Having His License9:04 - Why He Started Doing The ADU Strategy13:21 - DealMachine’s Corner Lots15:07 - The Impact Of ADUs & Flipping Numbers20:08 - Why Thomas Loves Buy And Hold Investing21:13 - How To Find ADU Deals And Builders24:18 - Using Lending For ADUs27:16 - What He Wants His Kids To Learn28:28 - Retaining Tenants31:44 - Hard To Get Data32:40 - Previewing Postcard.ai34:20 - Investing In Gold38:42 - Outro LINKS:Instagram: Thomas DeMosshttps://www.instagram.com/thomasmdemoss/ Website: Chattanooga Property Solutionshttps://www.chattanoogapropertysolutions.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/