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Tax Tuesdays
How To Claim Capital Losses From The Stock Market

In this episode of Anderson Business Advisors, Toby Mathis speaks with Eliot Thomas, Managing Tax Advisor at Anderson Business Advisors. There are lots of people helping to answer questions online – Patti, Ander, Matthew, Troy, Jared, Piao, Ian, Dutch, and Dana are on. There are so many people here. You have a whole bunch of tax professionals that are here to answer your questions. You can just go into the Q&A and put in a question.

You’ll hear Toby and Eliot discuss several listener questions around how to report capital losses in the stock market, a few questions on real estate and business LLCs vs. S-Corps, C-Corps, and Sole Proprietorships, disregarded entities, entertainment meals vs. business meal write-offs, and an in-depth discussion about a real estate contractor not filling out a W-9 and all the difficulties that might present. Submit your tax question to taxtuesday@andersonadvisors.


  • “Hey, I’m looking to start a new business. I need to choose a correct business entity in order to maximize my tax benefits, so I need to know if starting the business as an LLC and potentially working the business out of my home would be the best option for me.” – by all means, you want the LLC for that asset protection, but the S-corp or the C-corporation—have those great reimbursements.
  • “Can I write off my stock holding loss at the end of the year to reduce my W-2 earnings?” Yes, but we’re limited potentially just to $3000 of capital loss that will offset against ordinary income, that being your W-2.
  • “What are the rules for HSAs for people over 62?” – For 2023, the amount is going to be $3850 if you’re single, and I guess it’d be $7750 for a family plan. If you are on Medicare, you can not contribute tax-free to an HSA.
  • “I became a real estate professional in 2021 and have a significant net operating loss due to depreciation. What are the limitations of carrying the NOL backward in 2020 and 2019 to use that to lower taxes in the previous year?”– As of right now, we don’t get to carry back NOLs. We just carry them forward.
  • “If my partnership LLC did not conduct any business this year, do I still need to file a Form 1065? — You don’t have to file 1065 for that first year.
  • I’m in the process of setting up my real estate business. I already have a Wyoming LLC as a holding company. It’s treated as a disregarded entity, but I have no investment in real estate yet. If I file my taxes this year before I acquire an investment property, what is the process for changing the filing election of the LLC from disregarded to a partnership for the new property?” – You don’t have to do anything but file that return, or you could file the Form 8832 and declare it as a partnership.
  • “I am new to real estate flipping and started my first flip last year. Construction was completed this year, and it closed this year. I asked my contractor if I need to complete a W-9 last year, and he told me not until the project was complete. Now, I’m realizing that I should have had him complete the form in 2021 for the amount I paid him and again this year. Can I now ask him to complete the W-9 and file the form for 2021 and 2022? The other issue is I had issues with this contractor for faulty workmanship he did on the flip and in the process of filing suit. What if he refuses to complete the W-9?” If you’re dealing with a contractor who’s organized as a business, chances are you still want that W-9 to prove that they’re a business.
  • “What forms do I need to fill out for my accountant to show capital loss in the stock market?” – Usually, you’re going to get a 1099-B from your brokerage house. They can just use that, and that’s really all you need.
  • “As an owner-operator trucking company designated as an LLC, can you write off 100% of the operating fuel costs?” – If the truck that was burning that fuel was used 100% for business, absolutely.
  • “I am a lender on a note to an LLC. What are the best practices for collecting payments and tracking interest payments for reporting purposes; separate bank account for the payments or create an end-of-the-year interest statement for myself?” – I like the separate bank account. Keep it separate from your personal obviously.
  • “I attended your Las Vegas event. Please confirm if we are to refrain from listing items as entertainment when filing taxes.” – They’re probably referring to the Tax Cuts and Jobs Act getting rid of entertainment. There is no deduction for entertainment. If you are getting a meal that is for entertainment purposes, you cannot write it off. Business meals only for 2022.
  • “I’m looking to convert from an LLC-S to a C-corp in 2023. Should I stay on a calendar or fiscal year schedule? What are the pros and cons?” – I like the fiscal year for C-corp because it tends to give you more flexibility, especially when it comes to payroll items or contributing to, say, Solo 401(k)s or something like that.
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Full Episode Transcript:

Toby: Good afternoon, and welcome to Tax Tuesday. My name is Toby Mathis, joined by…

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