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Tax Tuesdays
Tax Benefits: A Nonprofit vs. A Foundation

In this episode of Tax Tuesday, tax experts Toby Mathis, Esq., and returning guest Jeff Webb, CPA, CFO of Anderson Business Advisors discuss various tax strategies for real estate, stocks, and nonprofits. Online we have Ander, Dutch, Sergei, Ross, Jared, Elliot, Troy and all kinds of staff to help answer all your Tax Tuesday questions.

Toby and Jeff cover topics such as 1031 and 721 exchanges, the Section 121 Exclusion, employee stock options, and the tax implications of short-term rentals and Health Savings Accounts (HSAs). They also discuss best practices for reimbursing personal contributions to a business. Submit your tax question to taxtuesday@andersonadvisors.


  • “Section 721 and 1031 differences” – It has the same effect as 1031 but you don’t pay tax on the sale, But you’re not exchanging one property for another…it’s a tax-free exchange, but it’s a one and done.
  • “Tax benefits of a foundation versus a nonprofit organization?” – The easiest way is – a nonprofit (public charity) DOES stuff, a foundation funds stuff…
  • “I have two houses I’m selling this year and or at the same time, both were residences for two years at the last five years consecutive. I have just lived in the latest house for the last two years and I’ve been preparing both to sell. Will I have a problem claiming both of them as residences two of the last five years and I’m selling them at the same time.” – So of the last 60 months, 24 of them you had to have lived in it as your primary residence. That met, then you can exclude, if you’re single, $250,000 of capital gain. If you’re married, you could exclude up to $500,000 of capital gain. DO NOT SELL AT THE SAME TIME.
  • “How are stock options taxed?” – Tax treatment varies depending on the type of stock option (ISO, NSO, RSU), time held, and exercise/sale timing.
  • “LLC taxed as S-Corp with brokerage account….anything similar to trader status?” – I have not seen anything that says any entity can make a mark to market section 475 election. If you’re making a mark to market election because you’re losing so much money in the market, get out of the market and go do something else.
  • “Does California’s 571L form business property tax apply to short-term rentals? – Yes, as short-term rentals are considered active trader businesses and subject to the tax.
  • “Who can qualify for an HSA?” – Eligible individuals must have a high deductible health plan (HDHP) and not be covered by another non-HDHP plan. Can I open an additional HSA with my LLC business? – No, you can only have one HSA per individual, but your LLC can contribute to your existing HSA.
  • “Anderson made me a C-Corp, I put money in from my personal account to pay expenses. I have to take out the initial $7K … How do I legally and ‘tax-friendly’ take the $7,000 back that I need for my personal reimbursement? – If the initial $7,000 was a loan, you can withdraw it tax-free as repayment; if a capital contribution, the process is different.
  • Send us your questions, and we do about 50 events a year – check out the event schedule listed in the notes.


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Full Episode Transcript: 

Toby: All right, welcome to Tax Tuesday. My name is Toby Mathis. I got Jeff Webb here.

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