SEPTEMBER 2025: How to Make $3 Million "Disappear" From Your Tax Return

I’ll be straight with you.

I’m not putting a lot of new money into the market right now.

To be clear, I’m not selling everything and running for the hills just yet—and I don’t recommend that you do either. It’s still too early for that. Our portfolio is firing on all cylinders, and I see no reason to rock that boat. I’ll be reviewing the portfolio and updating our stop losses, so please be sure to read through to the end.

But I’m also treading carefully. It seems reckless to go “all in” right in front of the most highly-anticipated Fed meeting in years… and right before the Supreme Court rules on the legality of the Liberation Day tariffs. Seasonally, this is also the time of year when volatility tends to explode.

So, let’s go bigger picture this month. Let’s set you free from taxes, Freeport Society style.

As Ben Franklin put it, a penny saved is a penny earned. A dollar you save in taxes is as good as a dollar you earn in the stock market. It spends just the same.

I chose the September issue for a reason. Many of the best tax-saving tricks have to be done before year end, so by covering them today we still have plenty of time to put them into practice.

It’s Like a 401(k) on Steroids

My recommendation this month won’t be appropriate for everyone. It’s only going to make sense if you’re in the prime of your career and are self employed or have significant income from a side business. It tends to be a great option for solo practitioner doctors, lawyers, accountants or consultants but could just as easily work for an entrepreneur or the owner of a car wash or laundromat under the right conditions.

If that sounds like you, then perk up and pay attention. Because, depending on your age and income level, you can potentially stuff a couple hundred thousand dollars per year into a super-sized retirement plan that most people have never heard of. It’s such a monster of a tax break, I’m actually shocked it’s still legal.