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Tax Tuesdays
Tax Tuesday Episode 144: Estate Planning

Do you want to be the next Elon Musk of Tesla Motors? Do you have stocks that you want to buy, sell, or borrow against? Find out first if they have tax benefits or consequences by asking Toby Mathis and Jeff Webb of Anderson Advisors your tax questions. Submit your tax question to taxtuesday@andersonadvisors.


  • Can we defer capital gains tax or spread it across multiple years? Use the 1031 exchange with real estate only to defer the capital gains; or the qualified opportunity fund/zone for any other capital gains installments over multiple years
  • Can I do a 1031 exchange from a single house rental into a percentage group rental? Or to a partial interest in multiple rentals? Only if you are a tenant in common (TIC), but not in a partnership
  • How does an LLC that’s a disregarded entity differ from a living trust in terms of estate planning? What if you have both? How do I use both in estate planning? An LLC is for liability protection, so the recommendation is to have both – LLC owned by the living trust
  • Are the gains in a traditional self-directed IRA taxed the same as the rest of the money in the SDIRA when doing a conversion to a Roth SDIRA? There is no such thing as capital gains in IRAs

For all questions/answers discussed, sign up to be a Platinum member to view the replay!

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Anderson Advisors Tax and Asset Protection Workshop (July 17)

Infinity Investing: How The Rich Get Richer And How You Can Do The Same by Toby Mathis

Entity Formation

Self-Employment Tax

Old-Age Survivors and Disability Insurance (OASDI) Tax

Real Estate Professional Requirements

Step-Up in Basis

Bonus Depreciation

Depreciation Recapture

Schedule K-1 (Form 1065)

Capital Gains and Losses

Section 121 – Capital Gains Exclusion

1031 Exchange

Schedule C

Schedule D

Schedule E


Retirement Plans

Wills and Trusts

Section 1244 Stock


Cost Segregation Authority

Qualified Opportunity Fund/Zone

Charitable Organizations

Paycheck Protection Program (PPP)

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Anderson Advisors Tax and Asset Protection Workshop

Anderson Advisors Tax-Wise Workshop

Anderson Advisors Infinity Investing Workshop

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Full Episode Transcript:

Toby: Welcome to Tax Tuesdays. Hopefully you can hear as well. Welcome to another fun day of bringing tax knowledge to the masses. My name is Toby Mathis.

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