Taxes by Jess

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08/18/2026

Your books are three months behind and it’s costing you more than your bookkeeper’s fee ever would. At $50K a month in revenue, messy books aren’t a paperwork problem, they’re a strategy blocker. Wrong categories mean missed deductions. Untracked basis becomes a real bill the year you take losses. And every strategy in this series, comp analysis, retirement design, the PTET election, all of it starts with numbers you can trust. You can’t make six figure decisions on financials you don’t believe. Clean books aren’t an expense. They’re the foundation the entire plan sits on. Comment PLAN if yours need to catch up to your revenue.

Tax Strategy From Europe, video 12 of 20.

08/13/2026

There’s a 20% deduction sitting on your business income, and it starts vanishing right at the income level where it matters most. Most owners have no idea whether they kept it, lost it, or left half of it on the table last year, because QBI at high income isn’t automatic, it’s engineered. Your salary, your retirement contributions, your entity, all of it interacts, and the right combination before December can revive a five figure deduction the wrong combination kills. This is chess your preparer plays in April, after the board is already set. Comment PLAN if you want it played in October, while the moves still count.

Tax Strategy From Europe, video 11 of 20.

08/03/2026

Your state is quietly taking a deduction from you that Congress already handed back. It’s called the PTET election, the workaround almost every high tax state built after the SALT cap, and it turns state taxes you’re already paying into a full federal business deduction. For an owner with $300K+ flowing through an S corp or partnership in a state like New York or California, that’s routinely $10K to $30K a year recovered. The catch: it’s an election with a deadline, and if nobody’s watching your calendar, the window closes and that money stays gone. This is the exact difference between someone who files your return and someone who runs your strategy.
Comment PLAN before your state’s window does.

Tax Strategy From Europe, video 10 of 20. Halfway through the series.

07/27/2026

The video every caption has been teasing. Here it is: no, your vacation is not a write off, and anyone selling you that is selling you an audit. But the rules are better than the myth. Primary purpose, documented business days, proper allocation on international trips. That’s why part of this trip is deductible for me: 20 videos, scheduled and produced for my firm, papered before I ever boarded. Not because I answered emails near a beach. The wealthy don’t write off vacations. They document business that happens to travel well. Comment PLAN if your strategy needs that level of clean.

Tax Strategy From Europe, video 9 of 20. The one you’ve been waiting for.

07/25/2026

The most expensive sentence in business: “I thought my accountant was handling that.” I hear it from six figure earners all the time, usually right after a bill they didn’t see coming. Here’s the truth. You send documents in February, a return comes back in March, and you call that a tax relationship. That’s compliance. Nobody asked if your entity still fits your revenue, whether your salary is defensible, or why you’re funding a SEP when better structures exist at your income. Those unasked questions cost more than any fee you’ve ever paid. Your preparer isn’t failing you. You just outgrew the service you’re buying. Comment PLAN when you’re ready for the upgrade.

Tax Strategy From Europe, video 8 of 20. Deductible trip rules drop in episode 9.

07/19/2026

I’m in Monaco, where the entry price for escaping taxes is about 500K in a local bank and an apartment that costs more per meter than anywhere on earth. The Augusta Rule costs a rental comp and meeting minutes. Fourteen days of tax free rent from your own business, sitting in the US code since the 70s, and most owners have either never heard of it or are running it so sloppy it won’t survive one IRS letter. The strategy isn’t the flex. The documentation is. Comment PLAN and I’ll show you the difference.

Tax Strategy From Europe, video 7 of 20. Deductible trip rules drop in episode 9.

07/13/2026

The Roth IRA part is what everyone misses. Your kid’s wages don’t just cut your tax bill, they unlock decades of tax free compounding most people can’t start until 22. A 10 year old with earned income and a Roth is playing a different game. Real work, real payroll, real records, that’s the whole price of admission. Comment PLAN if you want it set up so it survives a second look.

Tax Strategy From Europe, video 6 of 20. Deductible trip rules drop in episode 9.

07/12/2026

Most business owners think a SEP IRA is the ceiling. It’s the basement. There’s a structure that lets the right owner put away $150K or more in a single year, deducted now, growing tax deferred, funding your own pension. It’s called a cash balance plan and if you’re netting $500K+ and writing six figure checks to the IRS, the only question is why nobody’s shown you the math. Your accountant files what happened. A strategist designs what happens next.

Comment PLAN if you want to see your numbers.

Tax Strategy From Europe, video 5 of 20. The deductible trip rules drop in episode 9.

07/12/2026

Your tax bill should never be a surprise. If April shocked you, the problem wasn’t taxes, it was silence. At $50K a month in revenue your income moves all year, but your estimates were set in January and nobody touched them again. Then the balance due shows up with penalties on top. There’s a number called the safe harbor that makes the surprise impossible, and if you’ve never heard your accountant say it, that tells you everything. You should know your April number by October. If you don’t, comment PLAN.

Tax Strategy From Europe, video 4 of 20. The deductible trip rules are still coming in episode 9.

07/10/2026

Your accountant told you to buy a truck. A truck. You needed a tax strategy and you got a car payment. Spending a dollar to save thirty cents is not planning, it’s the most expensive advice in America. What actually moves a $50K+ tax bill: structure, retirement design, compensation, timing. None of it requires buying anything. If December is the only month your accountant calls you, comment PLAN.

Tax Strategy From Europe, Filmed on a canal because strategy travels. Deductibility rules drop in episode 9.

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