Month: November 2025

2025 has been an excellent year for investors in cryptocurrency, with Bitcoin reaching all-time highs.

With high profits, however, can come high taxes. Fortunately, there are several strategies you can employ before year-end to reduce your 2025 crypto taxes.

If you invested only in Bitcoin, you may not have any crypto losses. But you could have losses if you invested in other forms of crypto. 

If so, you should consider selling your losers before the end of the year. You may fully deduct your losses from any capital gains you realize during the year, such as gains from selling other crypto or stocks at a profit. 

If your losses exceed your capital gains for the year, you can use your remaining losses to offset up to $3,000 in personal income. You can carry over any unused losses to future years to offset future gains or income.

Donating appreciated crypto to charity is a great tax strategy if you’re charitably inclined. You’ll not only help a charity but also get two terrific tax benefits:

• You avoid long-term capital gains taxes on your appreciated crypto.
• You can get a charitable contribution deduction equal to the appreciated value.

To obtain these two benefits, you must itemize your deductions on Schedule A, and you must have held the crypto for more than a year.

You should also consider giving crypto to a child, a grandchild, or another loved one. For 2025, you may gift up to $19,000 each to an unlimited number of people without triggering any tax or reporting obligation for you or the recipients. If you’re married, you and your spouse may gift $38,000 per recipient.

Another strategy is establishing a self-directed IRA or a self-directed solo 401(k) to purchase crypto. You can use a self-directed regular or Roth IRA or 401(k).

If you want to discuss your crypto holdings, please call me on my direct line at 408-778-9651  

• By Leon Clinton
• November 28, 2025

Wow, how time flies! Yes, December 31 is just around the corner. 

That’s your last day to find tax deductions available from your existing business and personal (yes, personal) vehicles that you can use to cut your 2025 taxes. But don’t wait. Get on this now!

Take Back Your Child’s or Spouse’s Car, and Sell It

We know—this sounds horrible. But stay with us.

What did you do with your old business car? Do you still have it? Is your child driving it? Or is your spouse using it as a personal car?

We ask because that old business vehicle could have a big tax loss embedded in it. If so, your strategy is easy: sell the vehicle to a third party before December 31 so you have a tax-deductible loss this year.

Your loss deduction depends on your percentage of business use. That’s one reason to sell this vehicle now: the longer you let your spouse or teenager use it, the smaller your business percentage becomes and the less tax benefit you receive.

Cash In on Past Vehicle Trade-ins

In the past when you traded vehicles in, you pushed your old business basis to the replacement vehicle under the old Section 1031 tax-deferred exchange rules. (But remember, these rules no longer apply to Section 1031 exchanges of vehicles or other personal property occurring after December 31, 2017.)

Whether you used IRS mileage rates or the actual-expense method for deducting your business vehicles, you could still find a significant deduction here.

Example. Check out how Sam finds a $27,000 tax-loss deduction on his existing business car. Sam has been in business for 15 years, during which he

• converted his original personal car (Car One) to business use;
• then traded in Car One for a new business car (Car Two);
• then traded in Car Two for a replacement business car (Car Three); and
• then traded in Car Three for another replacement business car (Car Four), which he is driving today.

During the 15 years Sam has been in business, he has owned four cars. Further, he deducted each of his cars using IRS standard mileage rates.

If Sam sells his mileage-rate car today, he will realize a tax loss of $27,000. The loss is the accumulation of 15 years of car activity, during which Sam never cashed out because he always traded in for his next car. (This was before he knew anything about gain or loss.) 

Sam thought his use of IRS mileage rates was the end of it—nothing more to think about (wrong thinking here, too).

Because the trades occurred before 2018, they were Section 1031 exchanges and thus deferred the tax results to the next vehicle. IRS mileage rates contain a depreciation component. That’s one possible reason Sam unknowingly accumulated his significant deduction.

To get a mental picture of how this one sale produces a cash cow, consider this: when Sam sells Car Four, he is really selling four cars—because the old Section 1031 exchange rules added the old basis of each vehicle to the replacement vehicle’s basis.

Examine your vehicle for this possible loss deduction. Did you procure the business vehicle you are driving today in 2017 or earlier? Did you acquire this vehicle with a trade-in? If so, your tax loss deduction could be big! 

Put Your Personal Vehicle in Business Service

Lawmakers reinstated 100 percent bonus depreciation for 2025, creating an effective strategy that costs you nothing but can produce substantial deductions.

Are you (or is your spouse) driving a personal SUV, crossover vehicle, or pickup truck with a gross vehicle weight rating greater than 6,000 pounds? Would you like to increase your tax deductions for this year?

If you answered yes to both questions, place that personal vehicle in business service before December 31.

Check Your Current Vehicle for a Big Deduction

Your current business vehicle, regardless of when it was purchased, could have a big deduction waiting for you.

Example. Jim purchased a $60,000 vehicle in 2022 and used it 85 percent for business. During the four years he used it (2022, 2023, 2024, and 2025), Jim depreciated the vehicle $10,000. If he sells the vehicle today for $25,000, he has a $19,750 tax loss. 

If you see opportunities for deductions that you would like to discuss with me, please call me on my direct line at 408-778-9651  

• By Leon Clinton
• November 25, 2025

When you take advantage of the tax code’s offset game, your stock market portfolio can represent a little gold mine of opportunities to reduce your 2025 income taxes. 

The tax code contains the basic rules for this game, and once you know the rules, you can apply the correct strategies. 

Here’s the gist:

• Avoid the high taxes (up to 40.8 percent) on short-term capital gains and ordinary income.
• Lower the taxes to zero—or if you can’t do that, lower them to 23.8 percent or less by making the profits subject to long-term capital gains taxes.

Think of this: you are paying taxes at a 71.4 percent higher rate when you pay at 40.8 percent rather than the tax-favored 23.8 percent. 

To avoid higher rates, here are seven possible tax planning strategies.

Strategy 1

Examine your portfolio for stocks you want to unload, and make sales where you offset short-term gains subject to a high tax rate, such as 40.8 percent, with long-term losses (up to 23.8 percent). 

In other words, make the high taxes disappear by offsetting them with low-taxed losses, and pocket the difference.

Strategy 2

Use long-term losses to create the $3,000 deduction allowed against ordinary income. 

Again, you are trying to use the 23.8 percent loss to kill a 40.8 percent rate of tax (or a 0 percent loss to kill a 12 percent tax, if you are in an income tax bracket of 12 percent or lower).

Strategy 3

As an individual investor, avoid the wash-sale loss rule. 

Under that rule, if you sell a stock or some other security and then purchase substantially identical stock or securities within 30 days before or after the date of sale, you don’t recognize your loss on that sale. Instead, the tax code makes you add the loss amount to the basis of your new stock.

If you want to use the loss in 2025, you’ll have to sell the stock and sit on your hands for more than 30 days before repurchasing that stock.

Strategy 4

If you have lots of capital losses or capital loss carryovers and the $3,000 allowance is looking extra tiny, sell additional stocks, rental properties, and other assets to create offsetting capital gains.

If you sell stocks to purge the capital losses, you can immediately repurchase the stock after you sell it—there’s no wash-sale “gain” rule.

Strategy 5

If you give money to your parents to assist them with their retirement or living expenses, or to your children (specifically, children not subject to the kiddie tax), consider giving them appreciated stock instead.

Why? If the parents or children are in lower tax brackets than you are, you get a bigger bang for your buck by 

• gifting them stock, 
• having them sell the stock, and then
• having them pay taxes on the stock sale at their lower tax rates.

Strategy 6

If you are going to donate to a charity and you itemize your deductions, consider using appreciated stock rather than cash, because a donation of appreciated stock gives you more tax benefit.

It works like this: 

• Benefit 1. You deduct the fair market value of the stock as a charitable donation.
• Benefit 2. You don’t pay any of the taxes you would have had to pay if you sold the stock.

Example. You bought a publicly traded stock for $1,000, and it’s now worth $11,000. If you give it to a 501(c)(3) charity, the following happens:

• You get a tax deduction for $11,000. 
• You pay no taxes on the $10,000 profit.

Three rules to know:

1. You must itemize your deductions to benefit from this strategy.
2. Your deductions for donating appreciated stocks to your church and other 501(c)(3) organizations may not exceed 30 percent of your adjusted gross income.
3. If your publicly traded stock donation exceeds the 30 percent, no problem. Tax law allows you to carry forward the excess until used, for up to five years.

Strategy 7

If you could sell a publicly traded stock at a loss, do not give that loss-deduction stock to a 501(c)(3) charity.

Why? If you sell the stock, you have a tax loss that you can deduct. If you give the stock to a charity, you get no deduction for the loss—in other words, you can just kiss that tax-reducing loss goodbye.

These seven stock strategies have a long history of effectiveness in tax planning. If you need my help with any of them, please call me on my direct line at 408-778-9651  

• By Leon Clinton
• November 21, 2025