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The Taxman vs Traders – How To Minimize His Cut Of Your Profits – Chris Vermeulen

While the reality is hopefully not quite that bad, as Traders and Investors, we need to consider our silent partner, the “Taxman,” and how to minimize his cut of our profits. Having a “tax problem” can be a good “problem” to have. But we’re not obligated to pay any more in taxes than tax laws and regulations in our jurisdiction require.

As George Harrison of the Beatles famously penned…

“Let me tell you how it will be
There’s one for you, nineteen for me
‘Cause I’m the taxman
Yeah, I’m the taxman”

Are there strategies we can use to significantly reduce our tax bill, even to as low as $0? You bet!

Before we dive in, here are a few caveats…

We’re not tax advisors. You absolutely should review any taxation questions, strategies, or issues with a tax professional that is well-versed in your tax jurisdiction and familiar with your circumstances.

Much of the following pertains to those in the USA. But there’s some information here that may be useful to those outside the USA as well.

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Tax strategies can range from simple to complex. Some have rock-solid legal standing, while some of the more aggressive strategies may invite unwelcome scrutiny from tax authorities. Personally, I prefer simple strategies that are easy to maintain and not subject to “debate” with the IRS.

Lastly, laws and tax codes are subject to change. You need to continually educate yourself and have a good tax advisor to stay on top of any changes.

Traders Tax-Free Accounts

PayPal Founder Peter Thiel famously used the Roth IRA to turn a small investment in Founder’s shares into more than $5 billion tax-free. Google it. It’s a fantastic testimony to the power of the Roth IRA.

Hands-down, the Roth IRA (first created in 1997) is a simple and powerful tool for legally avoiding taxes. Why? Because any gains in the account are not taxed. Not now, not ever!

Reporting individual trades on your tax return in a Roth IRA is super simple. Why? Because none is required! Maintenance and reporting for a Roth IRA couldn’t be easier.

The tradeoff is that – like a Regular IRA – you generally cannot withdraw funds tax-free until age 59 ½. (There are ways around that with a 72t Plan, for example.) And contributions to a Roth IRA are not tax-deductible like they are with a Regular IRA.

If you have Earned Income in the United States, you should seriously consider maximizing contributions to a Roth IRA. Even if you currently don’t have Earned Income, but you have a regular IRA, there are ways to convert all or part of those funds into a Roth IRA should you choose to do so. Typically, you’d have to pay taxes on the converted funds. But once that’s done, the taxes are paid in full. This is commonly known as the “Backdoor Roth IRA,” which is also a way around the income-based annual contribution limits for a Roth.

Tax-Deferred Accounts

Second-best to the Roth IRA is a Regular IRA. Contributions are tax-deductible in the year made. Capital gains in the account are not taxed until funds are withdrawn. Distributions after age 59 ½ are taxed as regular income when they are made.

It used to be that the investment vehicles and strategies that could be used in both Regular and Roth IRAs were somewhat limited. Now there is an extensive range of asset classes and strategies permitted. For example, as an options trader, almost any defined risk strategy is permissible in either a Regular or Roth IRA at most options brokers.

Special Tax Treatment

Section 1256 contracts were created to eliminate a tax avoidance where contracts were sold near year-end to show a loss, and like-kind were repurchased in the following tax year. Section 1256 contract rules were created to require “marked-to-market” at year-end whether the contracts are sold or not.

The big side benefit of Section 1256 contracts is the 60/40 tax treatment, where 60% of gains are treated as long-term capital gains and taxed at a lower rate. The other 40% are treated as short-term capital gains and taxed as ordinary income. If you’re trading in a taxable account, it can be very beneficial to choose Section 1256 contracts where those happen to fit into your strategy. Section 1256 contracts include futures, options on futures, and certain indexes like SPX and VIX and options on those indexes. Be sure to verify Section 1256 treatment and report with your broker and tax advisor.

State Taxes

An additional layer of the tax burden is at the state level. One way to avoid that is to live in one of the states with no income tax for individuals. These are Alaska, Florida, Nevada, South Dakota, Tennessee, Texas, Washington, and Wyoming. You generally must file a federal tax return in those states.

Keep in mind that the “tax-free” states tend to have higher excise, sales, and property taxes. You should consider your overall tax burden and affordability ranking if you’re thinking about moving to one of those states.

Some traders live in multiple states and claim their “residency” in a tax-free state. That can get a little tricky as rules and enforcement will vary. You’ll need to keep good records of your time spent in the tax-free state and be sure to comply with all regulations for both states.

Tax Splitting

Regardless of where you live, it can be possible, legal, and common to create a separate entity, such as a C Corporation, that is domiciled in a tax-free state such as Nevada. Instead of capital gains bumping you into a higher marginal tax bracket as an individual, you could “tax split” and have the entity pay taxes on its gains at a lower Federal level and with no state taxes due. Typically, there are tax implications in your home state if you take income out of the entity for your use as an individual. But be aware that you can create and control a separate entity from yourself that has its own P/L for taxation purposes and that can reduce the overall tax burden.


Roth IRA.  If it’s available to you, think about maximizing it.  Outside of that, consider tax-deferred accounts, Section 1256, income splitting, and tax-free residency strategies as may be advantageous to your situation.

Now That You Know About Lessening Your Tax Burden, Read On To Learn More About Options Trading

Every day on Options Trading Signals, we do defined risk trades that protect us from black swan events 24/7. Many may think that is what stop losses are for. Well, remember the markets are only open about 1/3 of the hours in a day. Therefore, a stop loss only protects you for 1/3 of each day. Stocks can gap up or down. With options, you are always protected because we do defined risk in a spread. We cover with multiple legs, which are always on once you own.   

If you are new to trading or have been trading stock but are interested in options, you can find more information at The Technical Traders – Options Trading Signals Service. The head Options Trading Specialist Brian Benson, who has been trading options for almost 20 years, sends out real live trade alerts on actual trades, such as TSLA and NVDA, with real money. Ready to subscribe, click here:  TheTechnicalTraders.com.

Enjoy your day!

Chris Vermeulen
Founder & Chief Market Strategist