EPISODE · Feb 9, 2026 · 38 MIN
495: 45 Deals Last Year—And Why He’s Playing the Long Game
from The DealMachine Real Estate Investing Podcast · host Thomas DeMoss, David Lecko
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 - Intro 0:36 - An Overview Of Thomas Demoss’s Business 1:42 - His First Deal 4:05 - His Second Deal & Their Marketing 6:18 - Average Assignment Fees & Having His License 9:04 - Why He Started Doing The ADU Strategy 13:21 - DealMachine’s Corner Lots 15:07 - The Impact Of ADUs & Flipping Numbers 20:08 - Why Thomas Loves Buy And Hold Investing 21:13 - How To Find ADU Deals And Builders 24:18 - Using Lending For ADUs 27:16 - What He Wants His Kids To Learn 28:28 - Retaining Tenants 31:44 - Hard To Get Data 32:40 - Previewing Postcard.ai 34:20 - Investing In Gold 38:42 - Outro LINKS: Instagram: Thomas DeMoss https://www.instagram.com/thomasmdemoss/ Website: Chattanooga Property Solutions https://www.chattanoogapropertysolutions.com/ Instagram: David Lecko https://www.instagram.com/dlecko Website: DealMachine https://www.dealmachine.com/pod Instagram: Ryan Haywood https://www.instagram.com/heritage_home_investments Website: Heritage Home Investments https://www.heritagehomeinvestments.com/
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A 20-year investor explains how he closed 45 deals in a year while shifting his focus toward long-term equity through buy-and-hold and ADU strategies.
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495: 45 Deals Last Year—And Why He’s Playing the Long Game
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