How the Wealthy Do Taxes With Mrs. Dow Jones

Plus: An update on Mr. Chow Tribeca from The Chows, a new Hermés leather goods production site in France, what Rory McIlroy really wanted at his Masters Club Dinner and more...

Apr 10, 2026

Big letter today to hold you over through the weekend. Haley Sacks joins RPS to talk through how the wealthy actually handle their money and her upcoming book, the Chow family weighs in on the future of Mr. Chow Tribeca, Rory McIlroy hosts at Augusta with a menu that may or may not reflect what he actually eats, Claridge’s proves there is effectively no limit to what a hotel will do if you ask, and Hermès continues to scale the one thing it insists is still scarce. What more could you ask for?

Ahead of everyone’s least favorite day of the year next week—U.S. tax day on April 15—Haley Sacks, better known as Mrs. Dow Jones and the voice behind the Financial Tea podcast, gave Rich People Shit some insight into how the wealthy actually handle their money—and a few useful takeaways for everyone else.

If you’re one of the 1.3 million people who follow the Upper East Side native on Instagram, you already know the tone: money, without all the austerity or the idea that everyone’s playing the same game.

And RPS is lucky to have snagged her. Sacks is a very busy lady these days. She is about to release her debut book, Future Rich Person: The New Rules for Building Wealth (Even if You’re Stuck, Broke, and That Billionaire Won’t Text You Back), out May 12, and available for pre-order now.

Rich People Shit: Before you became Mrs. Dow Jones, what was your own relationship with money and finance?

Haley Sacks, better known as Mrs. Dow Jones: Honestly, nonexistent. I grew up on the Upper East Side with a Wall Street father, which sounds like I should have had a head start — but I was like if LeBron James’s daughter couldn’t shoot a free throw. I loved spending money and talking about it, but I had no idea how to make it, keep it, or grow it.

RPS: Was this always an interest of yours, or did it come later?

MDJ: Definitely later. My “Aha Money Moment” came at 25 when I started a job working for Lorne Michaels and HR asked about my 401(k) contributions. I had no idea what they were talking about — and if I’m being honest, some part of me had always assumed my dad would handle it, or eventually a husband. That realization was more humiliating than the ignorance itself. I understood that not knowing was actively costing me and that no one was coming to fix it. So I became obsessed. And then I became Mrs. Dow Jones.

I understood that not knowing was actively costing me and that no one was coming to fix it. So I became obsessed. And then I became Mrs. Dow Jones.

RPS: Financial advice has traditionally been delivered in a very dry way. What did you feel was missing from the way money was being discussed when you first started posting?

MDJ: Two things: personality and permission. Every resource I found was either a bro in a T-shirt who never went through puberty explaining index funds in front of a whiteboard, or a woman telling me to wash and reuse my paper towels. Neither made me feel like financial success was actually available to me or chic. I wanted someone who could make understanding money feel as compelling as reading a gossip column: aspirational, not punishing. I couldn’t find her, so I became her.

RPS: You spend a lot of time around high earners. What are the biggest misconceptions people have about how wealthy Americans actually pay taxes?

MDJ: That because they earn a lot they pay a lot in income tax . Many don’t, because the truly wealthy aren’t living off income. They’re using a strategy informally known as “buy, borrow, die.” You buy appreciating assets (or are paid in company stock,) you borrow against them to fund your lifestyle (and these loans aren’t taxable) and when you die, your heirs inherit those appreciated assets at a stepped-up basis, wiping out the embedded gains entirely. No income recognized = no income tax paid!

RPS: Once someone moves into the seven or eight figure income range, what tax strategies become available that most people never encounter?

MDJ: Wealthy people structure things so that “income” is rarely recognized at all. You borrow instead of selling. You donate appreciated assets instead of cash. You shelter gains inside the right business structure before a sale. You pass wealth to your kids in ways that reset the tax clock. The tax code was written with a lot of input from people who had a lot to protect, and it shows.

The tax code was written with a lot of input from people who had a lot to protect, and it shows.

RPS: For founders, investors, and private equity partners, income often comes in very different forms than a salary. How much of the tax conversation at the top is really about how income is structured rather than how much someone earns?

MDJ: A PE partner can have a lower effective tax rate than their assistant, not because of anything shady, but because of how their compensation is structured. It’s not really about the number on the check. It’s about what kind of check it is, when it gets written, and what entity it flows through. That’s the game. Because salary is the worst way to receive money from a tax perspective: you earn it, it gets taxed immediately at ordinary income rates, done. But founders and investors are often receiving carried interest, equity, and long-term capital gains, which are taxed at significantly lower rates or deferred entirely.

It’s not really about the number on the check. It’s about what kind of check it is, when it gets written, and what entity it flows through. That’s the game.

RPS: There is constant debate about whether the wealthy pay too little tax. From a practical standpoint, where do you see the biggest gap between the tax code as written and how it is actually used?

MDJ: The code is theoretically the same for everyone. The gap is in execution: having advisors who plan proactively all year vs. scrambling in April. Depreciation, charitable vehicles, tax-loss harvesting, timing of income recognition; none of this is secret, but it requires someone in your corner who’s thinking about it before you need it. Most people don’t have that until they’re already wealthy, which is part of why the gap compounds.

Depreciation, charitable vehicles, tax-loss harvesting, timing of income recognition; none of this is secret, but it requires someone in your corner who’s thinking about it before you need it.

RPS: Among the affluent, which tax strategies are completely legal but would surprise people who assume the system treats everyone the same?

MDJ: Step-up in basis at death is the one that genuinely shocks people when they learn about it: the idea that unrealized gains can essentially disappear at inheritance. Donor-advised funds are another: you get the tax deduction now but can distribute the money to charity over years. These aren’t hidden. They’re in the tax code. But they’re only useful if you know they exist and have enough assets to make them worth structuring around.

RPS: When people talk about tax loopholes, which ones actually matter for high net worth families and which ones tend to be exaggerated?

MDJ: The ones that actually matter aren’t really loopholes- they’re just features of the tax code that most people don’t know exist because they’ve never had enough money to need them. Borrowing against your assets instead of selling them. Passing wealth to your kids in a way that erases the tax bill entirely. Writing off a building that’s actually going up in value. These have been sitting in the tax code forever because the people who benefit from them have the power to keep them there. The “loopholes” that tend to be overhyped are the sketchy one-off schemes that work until they get audited. The really wealthy aren’t doing anything that exotic. They’re just using a system that was written in their favor.

The really wealthy aren’t doing anything that exotic. They’re just using a system that was written in their favor.

RPS: For someone who suddenly becomes wealthy after selling a company or receiving a large equity payout, what are the most common tax mistakes you see in the first year?

MDJ: Not planning before the sale closes. The biggest tax decisions in a liquidity event happen before the money hits your account- entity structure, timing, installment sales, opportunity zone investments. Once the cash lands, a lot of options disappear. The people who get hurt most are first-time founders who didn’t know to bring in a tax advisor during the deal, not after.

RPS: Do you notice generational differences in how wealthy Americans approach taxes, particularly around philanthropy, trusts, and where they choose to live?

MDJ: Older wealth tends to think in terms of trusts, estates, and legacy planning- tools they’ve had decades to build. Younger wealth, especially tech and creator economy money, is often more transactional and less planned. The interesting shift I see is that younger high earners are also more mobile- they’ll actually move to a no-income-tax state like Miami or Puerto Rico in a way that previous generations were less likely to do.

Older wealth tends to think in terms of trusts, estates, and legacy planning- tools they’ve had decades to build. Younger wealth, especially tech and creator economy money, is often more transactional and less planned.

RPS: Your book is titled Future Rich Person. Who exactly did you have in mind when you were writing it?

MDJ: Honestly, more people than I originally expected. I started writing for the person I was at 25: ambitious, culturally switched-on, completely financially lost. But as I got deeper into it, I realized the audience was much wider. There are 40 somethings who make real money and still feel like they’re winging it. People who went through a divorce or a job loss and had to rebuild from scratch. Women who spent decades letting a partner handle the finances and suddenly found themselves needing to take control. The specifics are different but the feeling is the same, like you missed a class everyone else somehow took. This book is for anyone who’s ready to stop feeling behind and start actually building something.

RPS: Many personal finance books focus on saving more or spending less. What ideas in this book do you think will feel new to readers who believe they already know the basics?

MDJ: The concept of Action Money: reframing the money left over after your bills not as discretionary spending but as the only variable you actually control, and the thing that determines your entire financial future. And learned financial helplessness: the idea that a lot of financial inaction isn’t laziness, it’s a psychological response to repeated setbacks and a genuinely difficult economic environment. Naming it changes how you relate to it.

RPS: The subtitle mentions people who feel stuck or broke. What patterns do you see most often among people who want to build wealth but feel like they can’t get traction?

MDJ: They’re optimizing the wrong things. Clipping coupons, chasing slightly better savings rates, stressing over the $7 oat milk latte; meanwhile they haven’t negotiated their salary in three years and their Action Money is leaking out in a hundred small ways they’re not tracking. The other pattern is waiting for conditions to be perfect before starting. “The market’s too volatile.” “I’ll start investing when I have more saved.” “The debt is too overwhelming to even look at.” That’s learned financial helplessness, and it costs people years.

“The market’s too volatile.” “I’ll start investing when I have more saved.” “The debt is too overwhelming to even look at.” That’s learned financial helplessness, and it costs people years.

RPS: Your online voice about money is very direct and funny. How did you translate that tone into a book without losing what makes it work?

MDJ: I basically wrote it the way I talk — which meant my editor had a lot of notes. The instinct when you write a book is to get more formal, more credentialed-sounding. I had to keep pulling it back toward the voice that actually connects with people. The pop culture references, the personal stories, the direct “do this” instructions—because they’re how the information lands for an audience that has been talked down to or bored to death by financial content their whole lives.

RPS: When someone finishes Future Rich Person, what is the one shift in behavior or thinking that you hope actually sticks with them?

MDJ: That their financial situation is not permanent, not pervasive, and not personal. Those three words are the whole thesis. You are not bad with money. You were never taught. The system was not designed for you to win easily. But the people who get ahead are the ones who decide to play anyway—and Future Rich Person is how you learn how.

Future Rich Person: The New Rules for Building Wealth (Even if You're Stuck, Broke, and that Billionaire Won't Text You Back...) is out May 12th and available for pre-order now.

From the response, it seems many of you are as excited about RPS’s inaugural event as we are. The details are coming together quickly. As a reminder, to attend, you’ll need to be a paid subscriber—annual or monthly—by May 1. Questions? Email Carson@readrps.com.

In today’s letter: an update from The Chows about Mr. Chow Tribeca, California cracks down on the Ferrari loophole, the upper middle class expands without feeling it, a Claridge’s doc, Gabbana steps back, McIlroy hosts, Hermès scales Kelly production, L.A.’s mansion tax gets a light edit and more…

After RPS’ story on Wednesday about the Mr. Chow Tribeca space being on the market for rent, I spoke with Vanessa Chow on behalf of the Chow family. Despite brokers for the space maintaining that it is very much available and still on the market, Chow says that Mr. Chow Tribeca will not be going anywhere.
“Mr. Chow Tribeca is not closing and is operating as usual. The restaurant remains family-owned, and we continue to serve our guests while evaluating future options,” she said in an official statement. Chicken satay lovers (myself included) can relax. The lychee martinis may live to see another day downtown! For the annual lease price and more, paid subscribers can get the details here.
California is cracking down on the “Montana loophole,” where wealthy buyers register Ferraris and Porsches through Montana LLCs to avoid paying California taxes. Authorities have already charged multiple owners and identified thousands of suspect transactions. There goes that open secret!
More Americans are technically “upper middle class” now—about 31%, up from roughly 10% in 1979—but most of them still wouldn’t describe themselves that way.
A few subscribers weren’t as shocked as I was about the billionaire shipping his mattress to Claridge’s (from Wednesday’s newsletter for paid subscribers), but that’s because they had seen Inside Claridge’s and knew the hotel operates at that level. The 2012 docu-series, which followed a year behind the scenes at the Mayfair hotel, showed staff installing in-room gyms, replacing bathtubs with Jacuzzis, and even reconfiguring entire floors before guests had formally confirmed their stay.
Speaking of London, is anyone a member of Oswald’s? It’s the last box I want to tick for my visit.
Stefano Gabbana has stepped down as chairman of Dolce & Gabbana, a move that comes as the company navigates broader financial strain. He remains involved creatively.
At the Masters Club Dinner, the reigning champion sets the menu for a room full of past winners. Rory McIlroy made the selections ahead of the tournament, with chefs from Le Bernardin in Manhattan brought in to shape the menu and supervise the clubhouse kitchen. Word in the clubhouse is that he prefers corned beef on rye, though he seems to have gone a bit fancier for this meal.
Hermès announced today the opening of its 25th leather goods production site in France, located in Louviers (Gironde). The facility will notably be dedicated to the manufacturing of the house’s Kelly handbags and will eventually house 260 internally trained craftspeople. (For more Hermès, RPS will have a story on the best stores in the world to get a handbag for paid subscribers next week with a handful of experts).
L.A. officials are considering changes to the city’s “mansion tax,” but the revisions are relatively minor and don’t address the bigger complaint that the tax has slowed high-end real estate deals.