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Tax Tuesdays
Tax Tuesday with Toby Mathis 10-02-18

Toby Mathis and Jeff Webb of Anderson Advisors are here again to bring tax knowledge to the masses by answering your questions about company vehicles, expenses, capital gains tax, payroll tax, and much more. Do you have a tax question for them? Submit it to


  • Should I buy a car in my business? Pros and cons of purchasing a car with business name, including depreciation write-off and taxable costs for personal use of vehicle
  • How to avoid/minimize capital gains tax on sales of stocks/mutual funds held for many years? Do it via appreciated stock; depends on losses and how much is made/sold
  • I’m selling a commercial property and doing a 1031 exchange. Can I withdraw the original down payment, tax free from the sale? Never take cash out of a like-kind exchange
  • If LLC is used only for trading, can it be a single-member LLC? Or, do you recommend a multi-member LLC? Usually a multi one, unless a day trader who trades a lot
  • What’s the difference between Section 179 and 100% bonus depreciation? 179 is for deductions on any piece of equipment, depreciation requires 100% percent on all assets
  • What’s a cash balance plan? Defined benefit plan that makes assumptions on how much money to deduct to eliminate entire income
  • Should I have my main family home in my real estate business? No. Don’t give up 121 exclusion; homestead exclusion can’t take equity; and need to recognize taxable wages
  • Can corporation reimburse us for our medical premiums and HSA contributions? Corporation can’t reimburse contributions for HSA because they’re pre-taxed
  • Can you have a leasing company and lease a vehicle from it? Yes. But you’re paying a lease payment, sales tax, etc.
  • What do you suggest for a single-member S corp for healthcare expenses? You can only write off personal insurance premiums; need a reasonable C corp
  • We invested $35,000 with an education company. How would startup expenses work? Write off, if increases skill; don’t write off, if qualifies for new trade
  • What happens if your business doesn’t make any money its first year? Can you write off expenses the next year? Depends on business type; may carry forward business losses
  • Trader vs. Investor Status: Does trader status need to be declared? Trader status doesn’t exist in internal revenue code; make an election and write it on your tax return
  • Should I run an assisted living/memory care center as a non-profit or for-profit? Such a health facility qualifies as a 501c3 and gets a tax break, but you don’t own it
  • Can real estate losses offset stock capital gains? If flipping houses, no – considered inventory, not capital gain/loss property; yes, if selling rental property or real estate pro
  • Which is better: Pre-nup or putting all assets in a trust? Avoid pre-nups because judges find other ways to make decisions; Nevada only state that protects alimony trust


Section 179 Deduction

Security Backed Line of Credit

Social Security Tax


1031 Exchange

Schedule A

121 Exclusion


Affordable Care Act

Electric Car Credit

Lease Income Inclusion


Section 195

Startup Expenses

Mar-a-Lago Club


Mortgage/Cash Boot

Klabacka v. Nelson: Nevada Supreme Court Makes Historically Significant DAPT Ruling

Employee Health Benefits Allowance – What Options Do I Have?

Homestead Tax Break

Anderson Advisors Tax and Asset Protection Event

Toby Mathis

Anderson Advisors

Full Episode Transcript:

Toby:Hey, guys. This is Toby Mathis and I’m joined with Jeff Webb, CPA. Hey, Jeff.

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