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Tax Tuesdays
Tax Tuesday Episode 140: Holding Entity

From entity formation, income, and inheritance to losses, proceeds, and profits, Toby Mathis and Jeff Webb of Anderson Advisors answer your tax questions. Submit your tax question to taxtuesday@andersonadvisors.


  • How does a single, high W-2 earning individual take advantage of passive losses? It’s difficult because passive losses for a high earner are going to be subject to limitations
  • How are inherited stock shares treated when sold? If you inherit stocks, they are valued at fair market value now, not when they were bought due to the step-up in basis
  • Should an S Corp pay profits as dividends? An S Corp does not pay dividends; it passes on profits and losses to shareholders
  • Is it preferable to have a C Corp or an LLC as your holding entity? It’s better to have an LLC as your holding entity; there’s no tax treatment for an LLC
  • Are proceeds received from winning a court case ($20 million) taxable? It depends on the source of the claim, as a matter of rule, and attorney fees are no longer deductible

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

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Anderson Advisors’ Infinity Investing Through Stocks and Real Estate – Free event!

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

Capital Gains and Losses

Charitable Organizations

Wills and Trusts

Entity Formation

Retirement Plans

Real Estate Professional Requirements

Home Office Deduction

Kiddie Tax

1031 Exchange

Step-Up in Basis

Bonus Depreciation

Depreciation Recapture

California Proposition 19

Self-Employment Tax

Old-Age, Survivors, and Disability Insurance (OASDI) Program

121 Capital Gains Exclusion


Schedule A

Schedule E

Section 162 – Trade or Business Expenses

Form 1040

Form 1099

Tax Cuts and Jobs Act (TCJA)

Rich Dad Poor Dad by Robert Kiyosaki


Payroll City

Paycheck Protection Program (PPP)

Toby Mathis

Anderson Advisors

Anderson Advisors Events

Anderson Advisors Tax-Wise Workshop

Anderson Advisors Tax and Asset Protection Workshop

Anderson Advisors Infinity Investing

Anderson Advisors on YouTube

Anderson Advisors on Facebook

Anderson Advisors Podcast

Full Episode Transcript:

Welcome to the ‎Anderson Business Advisors Podcast, the nationally recognized preferred provider for asset protection and tax planning in the nation. This show is for investors and business owners looking to save on taxes and build long term wealth with Toby Mathis, an attorney, author, business owner, and a featured instructor at Anderson’s Tax and Asset Protection event held throughout the country. Enjoy the show.

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