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Tax Tuesdays
What Is The Best Business Structure For Real Estate Agents?

In today’s Tax Tuesday episode, tax experts Toby Mathis, Esq., and returning guest Jeff Webb, Esq., CFO of Anderson Business Advisors discuss a number of common tax topics including IRA to Roth conversions, real estate depreciation deductions, LLC’s, S-Corps and Sole Proprietorships, gifting vs. inheriting property, and the title question about structuring your real estate business. Submit your tax question to taxtuesday@andersonadvisors.


  • “If I move money from my SDIRA, which stands for self-directed IRA, to a Roth self-directed IRA, can I use bonus depreciation from real estate owned outside of my IRAs to offset the taxes I owe from the Roth conversion?” – It’s really going to depend on where that depreciation is coming from.
  • “I’m new to real estate investing and haven’t purchased the property yet. Do I need to have an LLC to claim deductions this year on real estate–related expenses already incurred?” – An LLC really has nothing to do with taxes. It is strictly for liability protection, and asset protection.
  • “I’m a small business owner with three other employees working for me. I’m trying to open a solo 401(k) or some other retirement plan for myself as an owner. I believe I need to offer the same to my employees as well, which I can but am not interested in offering any matching contributions to other employees. How does it work? What is the best way to set this up?” – yes, you can open up a 401(k) and have your employees participate assuming they’re eligible to participate. However, you can’t pay yourself a match and not pay them a match. You have to treat everybody equally.
  • “I won $10,000 worth of furniture from a raffle or gaming event. How do I report this on my income tax?” – Whoever you won it from should be issuing you a 1099 miscellaneous with $10,000 of other income on it. You’ll record it on your tax return as other income.
  • “I’m a realtor operating as a sole proprietor. Should I be operating under a different entity to minimize taxes and liability? Over the years, I’ve received conflicting information and just don’t know.” – the math is 14.1% in addition to your state income taxes, in addition to your federal income taxes. The way you nix that is you run it through an S-corp or an LLC taxed as an S-corp.
  • “At what point in my real estate operation should I move from a single-owner LLC to S-corp for tax purposes?” – If we’re talking about investment real estate and rental properties, you don’t ever want to put them in an S-corporation. It’s a bad idea.
  • “If I transfer my rental property into an LLC for the purposes of depreciation, will the LLC get a step up and basis to the current market value of the property? Or will the LLC inherit my lower basis? – If you contribute property to any kind of entity that you own, it gets your basis.
  • “Do unrelated businesses have to have separate schedule Cs or LLCs, or can I rebrand myself on my Schedule C, DBA, JL Enterprises, and put everything together? What are the advantages or disadvantages?” -…most times I don’t see a whole lot of advantage to grouping unless it’s a real estate activity with an operation or something like that.
  • “In my father’s will, he’s leaving me a house.” Yes. “I’ve been living in it for nine years.” “If he puts my name on the title now along with his name, will I have to pay more taxes? I prefer to do that now. What would the difference be? He does have a living will.” – He would have to file a gift tax return for his basis in that half, or actually its fair market value on that half. I’m not a big fan of mixing things up under these circumstances…
  • “We are fixing the downstairs area of our home to rent out as a short-term rental. Are there any expenses that can be used in tax deductions? Should we run it under an entity?” – The repairs that you’re doing down there would be deductible. If you’re doing improvements to the property, it would be depreciable.
  • Send us your questions, and check out the event schedule listed in the resources section.


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Full Episode Transcript: 

Toby: Welcome to Tax Tuesday. My name is Toby Mathis.

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