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Tax Tuesdays
Tax Tuesday Episode 137: Gambling Taxes

Are you lucky to be alive and taking care of your taxes? Toby Mathis and Jeff Webb of Anderson Advisors answer your tax questions. Submit your tax question to taxtuesday@andersonadvisors.


  • If a non-profit (NP) organization opened a trading account and got options income less than $50,000, does the NP file an income tax return (besides a 990-N)? If you have gross receipts less than $50,000, you only need to file a 990-N (e-Postcard)
  • Are losses from gambling deductible? If you have gambling losses, they are deductible on Schedule A as long as you have gambling winnings on tax return
  • I have a rental property that is owned by my self-directed IRA. Does it need to be in an entity or is it safe in the IRA? Individual owner of an IRA is always personally reliable for the acts of the IRA, so put in an LLC or self-directed IRA
  • How do you claim the solar credit on your personal residence? Use Form 5695 – Residential Energy Credits; put in how much you paid for solar and multiply times percentage credit (26%)
  • Doing a cost segregation on a condo that was purchased out of my inherited trust to pay off other beneficiaries. Can I take bonus depreciation? Yes, and you can write-it off twice if you inherit it
  • Can I include my roof replacement for the solar tax credit? You can write-off roof if for dual usage; roof replacement is not part of the solar installation and labor
  • How is the in-home office deduction being treated since most of us have been working from home? Still a red flag for realtors? If you are an employee, there is no home-office deduction; the home office is only for sole proprietors and if you’re being taxed on Schedule C and receive a 1099, then you can deduct reasonable expenses

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

IRS – Coronavirus (COVID) Tax Relief

Bonus Depreciation

Depreciation Recapture

Charitable Organizations


26 U.S. Code Section 168K

Section 179

Retirement Plans

Self-Directed IRA (SDIRA)

Entity Formation

Cost Segregation

Wills and Trusts

Homeowner’s Guide to the Federal Tax Credit for Solar Photovoltaics

Real Estate Professional Requirements

Home Office Deduction

Section 1245

Section 1250

Capital Gains and Losses

Step-Up in Basis

Schedule A

Schedule C

Schedule K-1 Form 1065


72t – Substantially Equal Periodic Payments

Setting Every Community Up for Retirement Enhancement (SECURE) Act


Form 5695 – Residential Energy Credits

Section 48 – Business Assets

Form 8829

Toby Mathis

Anderson Advisors

Anderson Advisors Events

Anderson Advisors Tax and Asset Protection Workshop

Anderson Advisors Tax-Wise Workshop

Anderson Advisors Infinity Investing

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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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