Andrew Tobias is a New York City millionaire, and he will happily pay more taxes. Just make sure to send him a fruit basket.
The financial writer is part of the Patriotic Millionaires, an advocacy group of high-net-worth Americans who crusade for higher taxes on the wealthy. He said he would not mind paying them in New York City, which he said is a city “worth supporting.”
One of Mayor Zohran Mamdani’s key campaign promises was to raise taxes on the wealthy to help bridge the city’s budget gap and use that money for free buses and universal childcare. In May, state lawmakers passed a pied-à-terre tax, spearheaded by Mamdani, that more than doubled property taxes on second homes valued at over $5 million.
Many wealthy New Yorkers are not on board. Citadel CEO Ken Griffin denounced the new policy after Mamdani filmed a video announcing the tax in front of Griffin’s New York City penthouse.
“The tax itself is a tax that discriminates against a narrow group of people,” he said in an interview with CNBC.
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While Tobias agrees with Mamdani that the ultrawealthy should pay more taxes, he said that these wealthy taxpayers should be celebrated, not vilified.
“The Mayor should send the ultra-wealthy taxpayers a thank-you note and a fruit basket, so to speak,” he said. “People who are successful and pay a lot of taxes should, first of all, be celebrated, and respected, and probably thanked.”
Tobias is one of several New Yorkers Business Insider interviewed as part of our Cost of the City series, which looks to understand how people across the five boroughs get by in one of the most expensive cities in the world.
How a multimillionaire makes and spends his money in NYC
The 79-year-old writer, who winters in Miami, gained his fortune after publishing his book “The Only Investment Guide You’ll Ever Need” in 1978 and launching Managing Your Money, a personal finance software application, in 1984. He also benefited from property investments he bought in Miami in the mid-1980s and sold about 20 years later.
Tobias made a living by giving investment and financial advice to people through the written word. He wrote articles and columns for multiple magazines, including Esquire, Time, and Playboy, and published 12 books — three that became New York Times best-sellers. He is also well known for his memoir, “The Best Little Boy in the World,” originally published under a pseudonym in 1973, that recounts his experiences growing up gay in the 1950s, 60s and 70s.
Now, he splits his time in New York between his beach house on Fire Island and his Upper West Side apartment, which he bought in 1977 for $11,000 in cash plus a $30,000 mortgage. Today, he estimates the apartment is worth around $2.5 million. He also owns four apartments in Miami — one for him and the other three for guests.
“I’m one of the very fortunate people who can afford to live in New York,” he said. He receives a monthly $3,360 check from Social Security, $6,600 a month from a charitable gift annuity, an annual royalty check, and “takes a few hundred thousand dollars a year” from his IRA. Every other year, he also gets a check from reruns of his appearances on The Tonight Show with Johnny Carson: the last one he got was for 38 cents.
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He estimates his biggest expense, along with taxes, is charitable and political giving. He said his federal taxes vary a lot year to year, but he paid $350,000 in city and state taxes in 2025. Every year, he donates money to build a school through the international nonprofit buildOn, and donates both to the Success Academy, a network of free public charter schools in New York City, and the Amazon Conservation Team, a nonprofit focused on Amazon conservation and Indigenous rights.
“I like money,” he said. “I love being able to give it away.”
Paying taxes in NYC hasn’t always been smooth sailing
Tobias was born in Lenox Hill Hospital on the Upper East Side. He came from an upper-middle-class family, with a father who worked as an advertising executive and a mother from whom he inherited the “happy gene.”
“The one really smart thing I’ve done in my life is my choice in parents,” he said with a smile.
He briefly lived in Cambridge, Massachusetts, while completing his undergraduate degree in Slavic languages and literatures at Harvard University and later on his MBA at the Harvard Business School.
While Tobias today supports higher taxes on wealthy people like himself, he moved out of the city in the 1980s after a tax dispute with the New York City Department of Finance. The department wanted to charge him unincorporated business taxes for work he had been doing as a writer and speaker outside New York, which Tobias argued was absurd.
“I read all their definition of who’s a business — and I wasn’t a business,” he said.
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He said it didn’t make sense to pay the unincorporated business tax for “the privilege of doing business in the city of New York” when giving a speech in Utah, for example.
He threatened that if they made him pay the tax, he would permanently move to Miami, spending six months there a year and costing New York City all the taxes he was already paying. In the end, he paid the tax and changed his permanent residence to Miami.
“It was a matter of manhood. Having made that threat, I felt I had to follow through,” he said. “I didn’t leave because of the money, I left because they made me crazy.”
He said he used the extra money he saved from not paying New York City taxes to give away to charitable causes.
“Being able to take that same money and give it away instead to worthy causes that I chose was such a better feeling than having it taken,” Tobias said. “Every time I gave that money to whatever cause it was, I would get a wonderful thank you note — which wasn’t the reason I gave it — but it just makes you feel great,” he said, referring to his fruit basket analogy.
Hallway lined with art, comics and historical documents in Andrew Tobias’ apartment
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Corner of Andrew Tobias’ office in his apartment
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Yet, Miami was no New York. After 25 years, he decided to move back to New York to be close to his loved ones.
“I decided I didn’t want to worry about how many days I spent where, I wanted to be close to important people in my life who were dying,” he said. “I just started paying New York taxes again nearly 20 years ago. I don’t mind: it’s a great city.”
Although he still spends the winters in Miami, the rest of the year he splits his time between his Manhattan apartment and his beach house on Fire Island, a residence he said had “more happiness per square foot.” Although taxes are high, he said he can afford them and would not live anywhere else.
Frugal in some ways, extravagant in others
Tobias considers himself “frugal” in some aspects. He does not own a car, takes public transportation, and refuses to waste food.
“One of my hobbies is eating expired food,” he said. “I have some salad dressing that’s older than you.”
He also never had kids, a therapist, or any big medical bills to add to his regular expenses.
What he likes to spend his money on is unique pieces of documented history, eccentricities, and art. His apartment walls are lined with lithographs, New Yorker comics, and signed historical documents, like the Presidential Pride Proclamation signed by President Bill Clinton.
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“It’s a crazy person’s apartment, but I love it,” he said.
Tobias considers himself very lucky. He travels to Europe every May, splurges on dinners with friends, and was able to pay for the wedding of his two closest friends. Still a political activist, he served as the Treasurer of the Democratic National Committee from 1999 to 2017, remains involved with the party, and continues to write about politics on his personal website.
“Instead of the enormous expense of raising kids in New York, and hats off to the parents who do,” Tobias said. “I get to raise Democrats — and help things like Success Academy and BuildOn and the Amazon Conservation Team. I am a very lucky guy.”
