Tax Chats

Latest Episodes:

An Audio Tour of the Tax Museum Dec 30, 2021

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Jeff talks with Scott about a few of The Tax Museum's thousands of items. Jeff shows Scott a stack of expired lotto tickets purchased on EBAY and describes what they have to do with tax fraud. They discuss some old revenue stamps, an actual stamp from Burkina Faso, and other items that have amazing connections with taxes.

Tax Tune - Tax Advice Dec 27, 2021

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Lyrics by Scott Dyreng
Sung by Scott Dyreng and Three of Dyreng's Deductions
Lyrics

Tax Advice, Tax Advice
So many options confuse me.
Roth I R A
401-K
Which is the one that best suits me?
Pay my tax now or pay when I am old
Maybe not pay forever
Tax Advice, Tax Advice
Help me choose which is better

Pay the Price, For the Advice
That will help me choose wisely.
L L P?
S-Corp or C?
Which is the one that best suits me?
Pay the tax twice or pay only one time?
Claim QBI deductions
Pay the Price, For the Advice
That will help me choose wisely!

Tax Short - Can You Reduce Your Tax Bill by Bundling Charitable Contributions? Dec 27, 2021

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Scott describes a year-end tax planning technique called bundling.

I'll Have One Large Offensive Lineman with a Tax Deduction on the Side, Please. (A Conversation with Brian Mittendorf.) Dec 22, 2021

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Scott and Jeff are joined by Brian Mittendorf from THE Ohio State University to discuss not-for-profit entities. We discuss the recent creation of Horns with Heart, a not-for-profit entity recently created to pursue charitable causes using the Name, Image, and Likeness (NIL) of offensive lineman for the University of Texas football team. If this arrangement proves to be legitimate, not-for-profit entities could proliferate as a way to facilitate NIL deals and pay college football players, while allowing donors to make tax deductible contributions to their favorite football players.

Tax Short - What do Taxes Have to Do with Christmas? Dec 21, 2021

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Jeff describes what taxes have to do with Christmas. Mary and Joseph went to Bethlehem to be taxed (or maybe to be counted, so they could be taxed).

Tax Tune - Away to Pay Taxes Dec 21, 2021

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Away to pay Taxes (to the tune of Away in the Manger)
Lyrics by Jeff Hoopes, Sung by Stacey Hoopes
Oh Joseph and Mary
They were there for a task
They came to the city
To pay their tax
But as they remitted
The tax on their worth
Oh Mary, a virgin
She had to give birth

They went to the city
By Caesar’s decree
As taxes touched Joseph
They affect you and me
When we give birth
and when we die
How much we work
And what car we buy

For every decision
We weigh how we act
By counting the cost
And we do it post-tax
The pros and the cons
In dollars and cents
We consider the taxes
Before we commence

Do You See OECD? A Discussion with Tom Neubig on the OECD's Global Minimum Tax Dec 15, 2021

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Scott and Jeff discuss the OECD's Base Erosion and Profit Shifting (BEPS) project with Tom Neubig, a former Economist with the OECD. We answer basic questions about the OECD, BEPS, Pillar One and Pillar Two, which includes the proposed global minimum tax. The project is designed to stop the "race to the bottom" and to prevent large multinational companies from shifting their income to low-tax jurisdictions like tax havens. We also briefly discuss how country by country reporting will help with analysis after implementation.

Tax Short - Why is it so Hard to Tax Giant Multinational Companies? Dec 13, 2021

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Scott describes why it is so difficult to tax giant multinational companies.

Tax Short - Don’t let Fear Of Missing Out (FOMO) get in the way of tax loss harvesting Dec 13, 2021

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In a recent episode of Tax Chats, Scott and Jeff had a little disagreement over a potential downside of tax loss harvesting. In this short, Jeff summarizes his argument that in tax loss harvesting, you should not delude yourself into thinking there is something special about the stock you hold. You should not decide not to tax loss harvest because you might miss out on a stock going up in value--don't have tax loss harvesting FOMO.

Capitalizing on Capital Gains Tax Breaks Dec 08, 2021

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Jeff and Scott discuss how to legally reduce or avoid paying capital gains taxes. We use Satya Nadella's recent sale of half his stake in Microsoft as an example. To reduce the capital gains tax burden, one can:

Change the timing of capital gain income
- sell before a new tax is imposed, or after an old tax is retired
- wait to sell until capital gain becomes "long term," currently after 1 year
- wait to sell to take advantage of the power of deferral
- Examples
  - https://www.journals.uchicago.edu/doi/abs/10.17310/ntj.2015.3.02
  - https://tax.unc.edu/index.php/news-media/should-you-sell-stock-before-president-biden-raises-the-capital-gains-tax-rate/
Change jurisdictions
- Move to Texas, Florida, Wyoming, etc.
Hold until death to take advantage of the "step-up" in basis.
- Inheritance, Estates and the Step-Up in Basis Rule - WSJ
Donate appreciated assets to charity
- Charity gets assets at their fair market value
- Donor does not pay capital gains tax
- Donor gets charitable contribution deduction for full market value if itemizes on personal tax return
Tax loss harvesting
- Sell assets that have losses to offset assets that have gains.
Invest in Opportunity zones

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