In this episode of Tax Tuesday, Toby Mathis, Esq. brings tax knowledge to the masses and breaks down your tax questions LIVE! He’s joined by Jeff Webb, CPA and Tax Director at Anderson Business Advisors.


Updated October 6, 2020

Featured Questions

  • 22:38 – I made a backdoor Roth IRA contribution two years ago. If we need cash now and pull it out, since we already paid taxes, is it just a 10% penalty?
  • 34:09 – If I have a loss in my S-corp in 2019 and 2020 and from a 1244 stock, can I carry it back to recoup taxes paid on my personal 1040s of 2014-2018?
  • 43:06 – Can you tell me a couple of really good strategies to quickly recover the tax benefits from capital losses?
  • 52:10 – My wife is 60. In 2019, she had $13,200 of Social Security income and $0 earned income from work. Can she contribute to her health savings account for 2019?
  • 56:29 – I still have not received the $1200 check from the government, plus I have not filed my 2019 taxes. What options do I have? I am sinking here without earning any income.
  • 1:01:45 – What is the best way to set up a real estate LLC if you are an investor that does both buy and hold and fix & flips?
  • 1:04:31 – If I pull equity from a house, does the money need to go back into the house, or can I use it on another property or for other things?
  • 1:10:46 – Can we write off donations to our nonprofit even though we still have not been approved for that 501(c)3 status yet?
  • 1:15:29 – I am purchasing a new commercial building through a new LLC to add a new location and then rent it back to the business, which operates as an S-corp. With the new CARES Act changes, etc., what are the best tax benefits to this situation?
  • 1:21:38 – Will there be a penalty (forgiveness/tax) for paying an employee more than the average 2019 salary calculated (PPP) because of overtime or to catch up with pension plan payments, etc.?
  • 1:26:34 – If you purchase vacant unimproved land with the intent to build/develop homes for sale or rent within one to three years, what tax advantages can be taken?
  • 1:32:47 – My LLC owns mortgage notes. Can the LLC file for EIDL to recoup nonpayment (loss)?
  • 1:38:09 – Is there a way to withdraw all of my 457(b) funds? I do not want the 457(b) amount to count to the $100k CARES Act withdrawal because I want to take out a separate $100k from a 403(b) using the CARES Act.
  • 1:41:39 – If I pay my home personal internet bill with a personal credit card, and then pay the personal credit card transaction with my business checking account, is this considered piercing the corporate veil?
  • 1:42:18 – If my C-corp reimburses me for vehicle mileage, how do I then do my personal and C-corp taxes?
  • 1:43:18 – I use a series LLC. I am a passive investor in apartments, so Series “A” has apartment #1, “B” has apartment #2, etc. Each series has its own EIN number. It is a single-member LLC, so when I do my taxes, it flows through to my personal taxes. This year, my K-1s had to have my personal Social Security number instead of the EIN. I also have rental houses in the series LLC with separate EINs. My question is: if a renter tries to sue me, could a good lawyer reach into these other LLCs because the government associated my SSN with these LLCs?
  • 1:44:12 – Can we write off a passive loss against any taxable income (W-2 income, stock gains, active income, income reported on a K-1) under the CARES Act?
  • 1:48:23 – Even before this whole virus situation hit, we had a few tenants who skipped town early on their lease while also owing us back rent. What do we have to do in order to be able to claim this as a loss on our taxes?
  • 1:50:13 – My mom is 83 and, when she dies, she wants to leave her house to me and my three siblings. My mother currently has about $100k in equity, so each of us will receive around $20K after we sell the house. Should we transfer the house into a revocable trust with my brother and her as trustees to avoid probate and reduce our tax liabilities?
  • 1:53:09 – I purchased a rental property. The property appreciated greatly. I did a 1031 exchange after 10 years. Wouldn’t the FMV of the Section 1045 property have to separate out and the gain would be recaptured as ordinary income? Section 1031 does not apply to Section 1045 property.

As always, take advantage of our free educational content and every other Tuesday we have Toby’s Tax Tuesday, a great educational series. Our Structure Implementation Series answers your questions about how to structure your business entities to protect you and your assets.

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