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Anderson Business Advisors Podcast
How to Structure Your Real Estate Flipping

In this episode, Toby Mathis, Esq. chats with Jeffrey Cottle, Esq., Senior Attorney at Anderson Business Advisors, about the world of house flipping, with a focus on how to handle the tax implications. It emphasizes the importance of avoiding “dealer” status with the IRS and explores strategies like asset protection. Toby and Jeff discuss limitations placed on frequent flippers and analyze the pros and cons of different business structures like LLCs, C-Corps, and S-Corps. It concludes by examining the most common scenarios Jeff encounters at Anderson Advisors when working with house flippers.


  • Jeff Cottle intro
  • Flipping all comes down to ‘intent’ with the IRS
  • Avoid “dealer” status, and consider asset protection when flipping
  • 1031 exchanges, installment sales are not available to dealers
  • Flipping risks increase with each new property you purchase
  • Pros and cons to LLCs, C-Corps, S-Corps
  • What is the “typical” scenario Jeff sees for flippers?
  • Send us your questions and ideas for future show topics!


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Jeffrey Cottle LinkedIn

Anderson Advisors

Toby Mathis on YouTube

Full Episode Transcript:

Toby: Hey, guys. Toby Mathis here, and I’m joined by attorney Jeff Cottle. First off, welcome, Jeff.

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