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!

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?