Who We Serve
The sale of a business. The sale of a property. The last day of a career.
Those are the three moments that end up on my calendar. Each one comes with a tax window, and each window has its own clock. Inside it, the tax strategy matters as much as the portfolio decision, and usually more.
The best time to plan is before the moment arrives, while every option is still open. If one of these is your year, keep reading. Each section ends with a question to take back to the advisor you already have.
Three moments. Three questions.
The Sale of a Business
The Offer Is Real. So Is the Deadline.
You haven't sold the company yet. There's an offer on the table, or a date on a calendar, and a version of your life that starts the day the wire lands. That's the day you become a full-time investor, often for the first time, with a tax bill nobody has walked you through.
A lot of it gets decided in the letter of intent. How the deal is structured, and how the price is split across what you're selling, gets negotiated there, and both shape the tax you'll owe. The earlier your own tax situation is part of that conversation, the more options you have.
If the sale already closed, don't assume the door is shut. Under current rules, some options for the capital gain portion stay open for up to 180 days after a sale. What matters is that somebody is looking at the deal and the tax together, alongside your CPA and your attorney.
The deadline
The letter of intent.
The question to take to your advisor
"Before I sign, has my own tax situation been a variable in this deal, or just something we report in April?"
Jones Fiduciary Wealth Management
The Sale of a Property
You'd Sell It. The Gain Is What Stops You.
You're done with the building. The calls, the tenants, the sense that too much of what you're worth is sitting in one place you can't easily leave. You'd sell tomorrow, and you've already run the numbers on what leaving it costs.
So it sits, and the gain that was supposed to be freedom becomes the reason you can't move. That's the tax tail wagging the investment dog. There's usually more than one way through a gain like yours, and each one has its own clock.
If you roll the proceeds into another property, you have 45 days after closing to name it, a window set by statute. Missing it closes one of your options, not all of them. Under current rules, other routes for the capital gain portion can stay open for up to 180 days, and not every one of them requires you to keep being a landlord.
The deadline
45 days, for one route.
The question to take to your advisor
"If there's a way to sell without the gain stopping me, when would I have needed to start?"
Jones Fiduciary Wealth Management
The Last Day of a Career
The Paycheck Stops. The Tax Bill Doesn't.
Your career is ending, or it just did. Almost everything you saved is in accounts that have never been taxed, and that's the real worry: the day you start taking it out, the tax comes due. How much depends on choices you still control.
The years between your last paycheck and required minimum distributions are when you have the most say over your own tax bracket. That's usually where Roth conversions happen, spread over several years instead of crammed into one. Medicare looks back two years at your income, so each year's choices show up later too.
There are a couple of one-time decisions on the way out as well. If you have a pension, the way you take it is usually permanent. And if your retirement plan holds your employer's stock, rolling everything into an IRA by default can cost you a special tax election on that stock.
The deadline
The years before RMDs.
The question to take to your advisor
"In the years before I'm forced to take that money, what's my taxable income actually going to be, and who's planning for it?"
Jones Fiduciary Wealth Management
An Honest Filter
This Is Not for Everyone.
If you want somebody picking hot stocks and calling it a strategy, that's not me. If you're comfortable keeping 40% of your money in bonds because that's what the standard chart says, we're going to disagree. And if you want a quarterly hot idea and the feeling that somebody is always doing something, we'll frustrate each other.
If you want somebody to look at your current plan and tell you it's great, I'm not the person to say it unless it's true. I'd rather lose you on this page than mislead you in a meeting.
How Fit Works Here
Boutique on Purpose
This is a boutique firm on purpose, so every client works with the owner. Your planning meetings are with me, the person whose name is on the door. Boutique also means honest about fit. If we're not the right firm for you, I'll say so plainly, and I'll point you toward somebody good.
That promise isn't a courtesy. It's the whole point of working with a fiduciary: the advice has to be right for you even when it costs me the client.
Start With a Score, Not a Sales Call
See What the Advice You Have Is Actually Doing
You don't have to move a dollar to learn something today. Take the assessment and keep the results either way. Or bring the question from your section above to a short call, and I'll tell you what I'd look at first.
No charge. No pitch. No obligation to move anything.
