DiscoverResults DrivenEpisode 089: The Messy Deals Everyone Avoids Are Where You Make a Fortune
Episode 089: The Messy Deals Everyone Avoids Are Where You Make a Fortune

Episode 089: The Messy Deals Everyone Avoids Are Where You Make a Fortune

Update: 2025-11-24
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Most investors chase the clean, easy deals: vacant houses, quick closings, and situations with zero drama. But those deals are rare, and everyone is competing for them. The truth is that real profit usually comes from the messy ones.

In this episode, Tiffany breaks down how they safely and profitably close the tough deals. She walks through real examples, the tools they use, and the contract language that protects them.

You’ll Learn How To:

  • Handle sellers who need time after closing
  • Use escrow holdbacks the right way
  • Support sellers who need relocation help
  • Safely buy properties with tenants in place

What You’ll Learn in This Episode:

  • (00:59 ) Real money in real estate often comes from the messy deals
  • (02:06 ) How seller holdbacks work
  • (03:37 ) The contract language that protects your funds
  • (05:00 ) Why do you need a lease when a seller stays after closing
  • (06:13 ) What to do when a seller has no idea where they’re going next
  • (06:33 ) Building a relocation support
  • (07:22 ) Handling hoarder houses without losing time or money
  • (09:02 ) How to underwrite deals with eviction timelines
  • (10:03 ) Cash-for-keys done the right way
  • (11:13 ) The checklist you should review before closing any “messy” deal

Who This Episode Is For:

  • Wholesalers and flippers who are avoiding complicated deals
  • Investors who want bigger spreads without bigger competition
  • Newer buyers who need simple, clear tools for tough situations
  • Anyone wanting to level up their deal-making skills

Why You Should Listen:

Messy deals are where the real money is if you know how to protect yourself. This episode provides you with the exact tools, language, and steps that Tiffany and her team use to close deals that other investors won’t touch. 

Follow Tiffany and Josh here:

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Episode 089: The Messy Deals Everyone Avoids Are Where You Make a Fortune

Episode 089: The Messy Deals Everyone Avoids Are Where You Make a Fortune

Tiffany and Josh High