tax blogs and articles
Tax Tip of the Day
Upstream Gifting
10/14/2025
To understand the benefits of this tax strategy, you’d first have to understand Stepped-Up Basis. Stepped-Up Basis is a valuable tax strategies many use to pass their assets down to their heirs.
For example
Person A has an apartment building they have had for 30 years. The property has appreciated over the years and depreciation has taken the property’s basis down to $0. If Person A sells the property he/she will have a pretty large tax bill.
However, if Person A passes away and leaves the property to Child B, then Child B will get the Stepped-Up Basis (the FMV of the property upon Person A’s death) of the inherited asset. This could potentially greatly reduce the tax bill of a future sale of the property by Child B.
Upstream Gifting takes the Stepped-Up Basis tax strategy and adds a wrinkle. Person C bought Nvidia stock when it was a dollar. It has appreciated over the years and Person C knows if they sell the stock it could result in a hefty tax bill.
Instead, Person C places/gifts the Nvidia stock to an Irrevocable trust and Person C grants Parent D the testamentary general power of appointment over the asset.
When Parent D passes, Person C’s heirs may be able to receive the assets at the Stepped-Up Basis. Because Person C is expected to live longer the Parent D, Person C’s heirs will be able to potentially receive the property, at FMV, much sooner.
Like any tax strategy, there are lots of things to consider such as gifting limits, organization structures and etc. But overall, this could be an effective way to transfer appreciated assets, such as real estate, to their heirs at FMV at an accelerated rate.
This Weeks Tax Tip:
Legal Marijuana Is there anything more interesting than the tax treatment of a controlled substance such as marijuana? What makes the tax treatment of marijuana so interesting is that while some states have legalized it, the federal government has not. MJ is on Schedule One of the Controlled Substance List. So what does any of this have to do with taxes?
Well drug dealers (whether illegal or not) and legal marijuana facilities/sellers are required to file tax returns. Because MJ is considered illegal on the federal level, they are only allowed to deduct their Cost of Goods Sold (COGS) on their tax return. Nothing else. Just the cost of their MJ inventory. This means that MJ facilities/sellers are only allowed to deduct the costs of the product they sell itself.
They are not allowed to deduct any other Overhead (OH) or general and administrative (G&A) costs. They CAN’T deduct other expenses such as salaries, rent, electricity, fringe benefits, mileage, cell phones, advertising, marketing, depreciation and etc. This results in potentially huge tax bills. Way bigger tax bills than what is usually representative of the revenue they receive. There is no other business that face theses restrictions.
What makes it more interesting is that in 2019 the Feds were taken to the US tax court by a taxpayer. The taxpayer stated that the fact that they are unable to deduct any OH and/or G&A costs is cruel and unusual punishment and excessive fines and/or penalties and that violates their 8th Amendment rights. The taxpayer also claimed that their 16th Amendment rights were also violated.
The 16th Amendment basically gives congress the right to tax income. The taxpayer claimed that by having to add back all of their non-COGS expenses, that they really weren’t getting their income taxed. It was much more. The US Tax Court shot down all of their arguments and sustained the Fed’s position. However, there was one dissenting opinion by Judge Gustafson.
He stated if you force a MJ facility/seller to add back in all of their expenses, other than COGS, is the IRS still taxing income? And if it’s not, is it not violating their 16th Amendment rights? He also stated that the IRS might also be violating their 8th amendment rights because if you make a MJ facilities/seller add back all of their expenses, other than COGS, is that not a penalty?
All that being said, it is my belief that one day a MJ facility/seller is going to win in tax court. And when that happens the values of these MJ companies are going to skyrocket because they will be paying WAY WAY less taxes.
Tax Tip
Safe Harbor for Small Taxpayers
10/10/25
Conservation Easements
Sep 29, 2025
When I worked for the IRS we’d get these emails that summarized tax court rulings. A recurring subject would show up over and over again; Conservation Easements. The IRS would go after these deductions and would win Every. Single. Time. Over and Over the IRS would crush taxpayers who couldn’t support the dollar amount of the Conservation Easement deduction they took.
The lesson here is simple. If you are ever tempted to go to a seminar that discusses the tax benefits of a Conservation Easement. I’d probably do myself a favor and skip that one.
Nov 13, 2024
– For 2024 the Annual Gift Tax Limitation is $18K
