Free Tax Tips & Strategies

In this episode of Tax Tuesday, tax attorney Toby Mathis, Esq. brings tax knowledge to the masses and answers your tax questions LIVE!

Updated January 26, 2021


Featured Questions

  • 28:30 – Should I file bankruptcy for my business if I owe the IRS $1M in back payroll taxes, or should I try an offer-and-comprise and continue operating the business to pay back what is agreed upon?
  • 35:26 – If I own a commercial building in the name of my LLC and engage in a 1031 exchange, can my replacement property be purchased in a tenant-in-common (TIC) arrangement?
  • 38:48 – Does placing real estate in a solo 401(k) allow for the full use of real estate tax benefits?
  • 44:10 – In order to have losses from an active business be counted as active losses, do you have to work 500 hours a year in the business? I just formed my active business in September.
  • 49:18 – Can you describe the best strategy for selling ESPP shares obtained at a discounted rate? Do you always wait for it to be considered a qualifying disposition, or only when the stock has gone up in value during the purchasing term?
  • 56:41 – I’ve made some good money trading cryptocurrency. This puts me in the highest tax bracket. Is there a way to reduce my tax liability?
  • 1:04:57 – I am a limited partner investor in a hedge fund through a Wyoming holding company. How can I deduct the management fees?
  • 1:09:34 – My wife and I have W-2 jobs and are also renting out 3 rental properties. Those 3 properties are owned by our 3 LLCs: one property per LLC. What tax benefits are there if we form a C-Corp. on top of those 3 LLCs to act as a property management company? What if my wife quits her W-2 job and becomes a RE professional?
  • 1:16:48 – Would the capital gains exclusion apply to a 2-unit property where 1 unit is rented and the other unit we lived in? For purposes of this question, say the property was purchased in 1999 for $500K, and now it’s valued at around $2.5M. Can we sell the property without paying capital gains and, if so, how?

As always, take advantage of our free educational content and every other Tuesday we have Toby’s Tax Tuesday, another great educational series. Our Structure Implementation Series answers your questions about how to structure your business entities to protect you and your assets. One of my favorites as well is our Infinity Investing Workshop.

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