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NFT troubadour Jonathan Mann loses fortune to taxes after crypto boom

NFT troubadour Jonathan Mann loses fortune to taxes after crypto boom

Jonathan Mann, best known for his “Song A Day” project that has run uninterrupted since 2009, rose to unexpected fame during the NFT craze when he began selling his daily songs as digital collectibles. At the peak of the market in 2021, Mann earned over $1 million from NFT sales, transforming his quirky online music diary into a lucrative crypto venture. But just a few years later, the singer-songwriter finds himself virtually penniless, forced to sell off assets and start over after a crippling tax bill wiped out his earnings.

The downfall came not from a failed investment or market crash, but from an underestimation of how aggressively the United States Internal Revenue Service (IRS) would treat digital gains. Mann, like many NFT creators during the boom, treated his newfound wealth as fast-moving income. Yet as the value of crypto tokens such as Ethereum soared and fell, Mann held onto much of it—only to watch its value nosedive as his tax obligations solidified in dollars.

“I made about a million dollars, and I owe about half of that to the government,” Mann admitted in a candid video earlier this year. “But now I don’t have it. I didn’t sell it. I didn’t convert it to dollars. It’s gone.”

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Mann’s story echoes a wider problem that befell many early NFT artists and crypto traders: taxes were due in fiat, while assets collapsed in value. The result has been a wave of losses where the wealth, though once real on paper, vanished faster than it could be cashed out.

What makes Mann’s case particularly symbolic is how public and personal it has been. Through his daily YouTube songs—many humorous, many self-reflective—he chronicled the highs of the NFT market in real time. “I made $36,000 today” sang one viral video after an early successful drop. Others tracked his growing anxieties over taxes, plummeting ETH prices, and the mounting fear of insolvency.

Despite the financial collapse, Mann insists he does not regret his experimentation with NFTs. He views the technology as a powerful new medium for artists and believes its core potential remains intact, even if the speculative bubble has burst.

“I was part of something big,” he told fans. “It wasn’t sustainable, but it was a moment—and I learned a lot.”

He’s now pivoting back to his roots, focusing on audience-funded content, Patreon subscriptions, and the core creative mission that drove him from the start: a new song, every single day. While the NFT era might be behind him, Mann’s resilience and transparency have earned him a cult following among those who admire his honesty as much as his melodies.

Still, the fallout is a cautionary tale for creators lured into fast profits without considering the legal and financial complexities. In an industry that moves at the speed of the internet but settles debts in real-world currency, Mann’s story serves as a melody of both triumph and warning. The music plays on—but the taxman always gets his share.

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