In this episode of Tax Tuesday, Toby Mathis 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 March 30, 2021

Featured Questions

  • 00:06:14.08 – I recently retired from my job and had a direct rollover into a traditional IRA to self-direct the account in buying real estate properties. Is it better to convert the account now to a Roth IRA for tax purposes since I’m anticipating expanding my real estate venture in the future? Which will benefit me more in terms of taxes when I sell the properties?
  • 00:12:29.01 – I have my personal home and rural land in my personal name and want to be able to isolate it from future ventures as well as be able to pass it over to my sons when the time comes. I have an LLC that was established a year ago without any holdings. It is registered here in Colorado. Do I use this existing LLC on the ranch or go with a trust and use the LLC for a future real estate move?
  • 00:18:53.07 – Does anyone know what would happen if I quitclaim or transfer title of my personal real property that’s a rental into my LLC? How does it affect the existing mortgage on it? The mortgage is under my personal name. Will the lender force a due-on clause or disallow?
  • 00:24:23.01 – I have a property in a Wyoming LLC. I am preparing to sell the property; this is my first time selling a property in an LLC. Suggestions on how to do this for my best tax advantage? Any other advice you can provide will be much appreciated.
  • 00:30:19.07 – Can you ever do a 1031 exchange for tax lien certificates?
  • 00:32:19.04 – Are free and clear properties taxed more heavily?
  • 00:35:43.02 – I’m closing one business and starting another. The company I’m closing owns two vehicles. What is the best way to deal with these: have one company buy them from the other, or buy them personally? We will use them in the new business. Is it more advantageous for the company to own them or for us to own them and take the miles deduction? The company is an S corp. We used bonus depreciation two years ago and there are loan balances on both vehicles.
  • 00:43:12.01 – I recently tried to open a new account in a Delaware LLC. Was told the state of California passed new law in July 2019 requiring that an LLC from Delaware, Wyoming, or Nevada be registered in California, as well. This would remove the benefit of filing in one of these three states, thereby removing the veil of anonymity.
  • 00:50:29.01 – What are the tax consequences of borrowing money from a private lender and agreeing to pay a fixed percentage over time?
  • 00:53:54.00 – What itemized deductions will be allowed for 2019 returns?
  • 00:58:59.01 – The best vehicle to use for retirement without paying taxes?
  • 01:04:35.02 – I’ve just started trading weekly stock options as my sole source of income. How hard will taxes hit? What can I do to minimize them?


Watch now as Toby Mathis, Esq., and Jeff Webb, CPA, break down complicated tax laws to make them easier to understand, helping you save your hard-earned money.

Click here to register for the next Tax Tuesday. Then, send your tax questions in advance to for answers from the experts.