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Anderson Business Advisors Podcast
Can I Contribute To My Health Savings Account After Leaving My Employer?

In this episode, Toby Mathis, Esq., and Eliot Thomas, Esq., bring more of their tax knowledge to the masses, answering questions on HSA contributions, employing your children in your business, and keeping your assets in a self-directed IRA. Be sure to check out our FREE virtual events happening this month. Submit your tax question to taxtuesday@andersonadvisors.


  • “For an LLC that opted to be taxed as an escort is it better to not just. the profits and let retained earnings grow on the balance sheet and invest retained earnings in stocks or other investments in the name of the LLC? – the profits are automatically going to come down to hit your return. You’re going to have to pay tax on those
  • “I am considering signing up with Anderson and contemplating having you amend the last three years as I don’t think my CPAs or TurboTax gave me all the write-offs that I was eligible for as a real estate investor.I think I may qualify for a greater return, but also don’t want to automatically trigger an audit. – the “triggering an audit” that’s, I think, a really common scare tactic that’s out there…amending is not going to create an audit.
  • “Can I continue funding an HSA account if I am no longer employed by the company that offered it but still have the account? Does it make sense to place it into a HSA investment account? – You certainly can continue with that HSA. Even if it’s an employer-sponsored HSA, it is the employee’s property, should they choose to leave.
  • “I have a K1 that will be late from the sale of an apartment complex in Georgia. I am a married filing separately tax payer. I will do an extension but still have to pay tax in April How do I know how much to pay without the K1? I Went through a similar sale last tax season and had to pay a late fee due to the late K -1. I’d like to avoid that again.- There is a safe harbor. If you’ve paid in at least 90 % of what will be due during your time period before April 15th,
  • “What are the benefits of having children as employees? Are there education expenses eligible for payment by the company? – if kids are paid underneath the standard deduction for that particular year, then there’s no federal income tax on it. There are many benefits to shifting income to your children.
  • “If we live in our rental house for two of the prior five years to avoid full taxation on capital gain, take advantage of the $500,000 exemption for married joint-filing, can the remaining amount that we, remaining amount we will pay in taxes be offset? Can the remaining amount we will pay in taxes be offset by losses in our other rental properties? Capital if we qualify as real estate professionals during the year for filing. For example, if we purchase another property, cost seg it can those potential deductions be used to offset the taxes paid on the primary residence sale? – As long as they’re in there for two of the last five years, they are eligible for ownership and use.
  • “How long do I need to have a property in service to rent to be able to deduct bonus depreciation from a cost segregation study? – you want to be reasonable, probably a reasonable amount of time, but if it was available for rent. That’s it!
  • “My asset is in a self-directed IRA, so when you see SDR at IRA, that means self-directed. I am assuming if I sell it, the money is considered income and I’m taxed on it like any other income. Also, if I use the money from the sale of that property for the purchase of a different property, not kept in the self-directed IRA, can I avoid taxes? What is your suggestion in this type of situation? – there’s a whole lot of misconception going on in this question. So no, we are not taxed on it like any other income. It’s quite the opposite.
  • “Just started an ink taxes as C Corp What is an accountable plan? Is it something I need to join before I can get the benefit of it? Can any reimbursement be an expense with my personal name and get reimbursement like health dental vision cell phone, etc Do I need to have my cell phone account in the business name? – an accountable plan just means reimbursement. It’s a fancy IRS term.
  • “Does the assignment of beneficial interest in a land trust count as an installment sale for tax purposes? Who’s responsible for the property taxes in such a transaction? – another one with some misunderstanding here.


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Full Episode Transcript:

Toby: Welcome to Tax Tuesday. We’re going to let everybody pile into the room because gosh knows there’s a line. There’s a virtual line. If you’re watching out there, first off, welcome. This is Tax Tuesday. If you can, just because it’s fun, there’s a way to make a reaction. You can do a thumbs up, a crying face, or all sorts of cool stuff.

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