Dirty Deeds

What Happens When Your Real Estate Model Breaks?

Dec 15, 2025
Tim, a seasoned real estate investor transitioning into distressed property acquisition, and Emily, an acquisitions manager with a sales background, share their journey of adapting to market changes. They discuss the challenges of shrinking margins and canceled deals in land investing. A gripping story unfolds about their first distressed deal involving legal hurdles and jail records, resulting in over $100,000 in equity. They emphasize the importance of honesty with sellers and the need for operational systems to navigate the complexities of real estate.
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ANECDOTE

Jail Visit Turned Into Six-Figure Win

  • Tim found an heir in jail and personally visited to secure her signature through the visiting room process.
  • That in-person step began a chain that turned into a $100k+ equity outcome within weeks.
INSIGHT

Why Land Model Broke Down

  • Land spreads shrank and cancellation rates rose as buyer demand cooled, exposing fragility in their land model.
  • Tim realized market expansion alone couldn't fix structural margin and conversion-cycle problems.
ADVICE

Tell Sellers The Truth About Your Role

  • Be transparent with sellers about being a double-close intermediary and how you will market the property.
  • Honesty builds trust and often keeps deals from collapsing during disposition.
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