In the heart of New York City, a unique voice is advocating for higher taxes on the wealthy. Andrew Tobias, a millionaire financial writer is part of the Patriotic Millionaires a group of high-net-worth individuals who believe in increasing taxes for the affluent. Unlike many of his peers, Tobias is not opposed to the idea of paying more; in fact, he welcomes it.

Tobias’s stance on taxes aligns with Mayor Zohran Mamdani’s campaign promises to raise taxes on the wealthy to fund free buses and universal childcare. In May, state lawmakers passed a pied-à-terre tax spearheaded by Mamdani, which more than doubled property taxes on second homes valued at over $5 million. While many wealthy New Yorkers, like Citadel CEO Ken Griffin, have denounced the new policy, Tobias sees it differently.

Celebrating Wealthy Taxpayers

Tobias agrees with Mamdani that the ultra-wealthy should pay more taxes, but he believes these taxpayers should be celebrated rather than 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’s perspective is part of a broader discussion on how people across the five boroughs navigate life in one of the most expensive cities in the world. As part of Business Insider’s Cost of the City series Tobias shared insights into his financial journey and his views on wealth and taxation.

A Life of Financial Success and Philanthropy

The 79-year-old writer amassed his fortune through various ventures, including 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 in Miami, which he bought in the mid-1980s and sold about 20 years later.

Tobias made a living by providing investment and financial advice through his writings in magazines like Esquire, Time, and Playboy. He has published 12 books, three of which became New York Times best-sellers. His memoir, “The Best Little Boy in the World,” originally published under a pseudonym in 1973, recounts his experiences growing up gay in the 1950s, 60s, and 70s.

Today, Tobias splits his time 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. He estimates the apartment is now worth around $2.5 million. He also owns four apartments in Miami—one for himself and the other three for guests.

Charitable and Political Giving

Tobias’s biggest expenses, alongside taxes, are his charitable and political contributions. He paid $350,000 in city and state taxes in 2026 and donates annually to build schools through the international nonprofit buildOn. He also supports 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.”

Navigating Taxes in New York City

Born in Lenox Hill Hospital on the Upper East Side, Tobias comes from an upper-middle-class family. His father worked as an advertising executive, and his mother passed down what he calls the “happy gene.” Tobias briefly lived in Cambridge, Massachusetts, while completing his undergraduate degree in Slavic languages and literatures at Harvard University and later his MBA at the Harvard Business School.

While Tobias now supports higher taxes on the wealthy, he moved out of the city in the 1980s due to 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. Tobias threatened to move to Miami permanently if the tax was enforced, 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.” Tobias used the extra money he saved from not paying New York City taxes to give away to charitable causes.