How One Musician’s $3M NFT Success Turned Into a Costly Tax Lesson

Jonathan Mann, the creator behind the long-running “Song A Day” project, has turned his crypto misfortune into a musical cautionary tale.

After earning $3 million by selling thousands of his songs as NFTs in early 2022, Mann found himself facing a massive tax bill and a portfolio in freefall.

Hoping for further gains, Mann and his wife chose to hold onto their earnings in Ethereum. But when the market turned and ETH began to slide, they were unprepared. Despite the shrinking value of their assets, U.S. tax law still treated the income at its original value—leaving them owing over $1 million to the IRS.

In an attempt to delay selling at a loss, the couple used ETH as collateral for a loan on Aave. But when the Terra ecosystem collapsed, it triggered a wave of liquidations, including Mann’s. In an instant, 300 ETH vanished—effectively erasing years of creative work.

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Faced with the threat of losing their home and retirement savings, Mann dug into his digital vault and sold a rare Autoglyph NFT for $1.1 million—just enough to settle the tax debt. Fortunately, the previous losses meant he didn’t owe capital gains on the sale.

Despite the ordeal, Mann continues his daily song project, still minting NFTs and hoping for a second act—this time with a clearer financial strategy.

Alexander Stefanov

With over 8 years of experience in the cryptocurrency and blockchain industry, Alexander is a seasoned content creator and market analyst dedicated to making digital assets more accessible and understandable. He specializes in breaking down complex crypto trends, analyzing market movements, and producing insightful content aimed at educating both newcomers and seasoned investors. Alexander has built a reputation for delivering timely and accurate analysis, while keeping a close eye on regulatory developments, emerging technologies, and macroeconomic trends that shape the future of digital finance. His work is rooted in a passion for innovation and a firm belief that widespread education is key to accelerating global crypto adoption.