January 1st, 2022. I sold 13 years worth of Song A Day NFTs. 4,000 songs. 1,600 collectors. ONE HOUR. THREE. MILLION. DOLLARS. My wife and I sat in her childhood bedroom, staring at the screen. We couldn't speak. It felt like winning the lottery. (Spoiler: It wasn't)

Here's what's painfully obvious now:   WE SHOULD HAVE SOLD THE ETH IMMEDIATELY. We didn't. One week later, ETH dropped below $3k for the first time in 5 months.  We watched our $3 million start melting away. We were paralyzed.  Couldn't bring ourselves to sell. Clinging to ETH for dear life. This was mistake #1.

Quick crypto tax lesson that might save your life: BUY ETH → Goes up → Sell = Capital gains tax  (on the profit) **EARN** ETH → It's income tax on the FULL VALUE when you got it Doesn't matter if ETH crashes after. You still owe on the original price.  I earned at $3,754. I owed tax on $3,754. Even when it hit $1,000.

Plot twist: 2021 had already been insane. Between @thefuckintrolls and airdrops (I'm looking at you @ensdomains, @ConstitutionDAO, @SuperRare, Adventure Loot, etc), we: - paid $600k in taxes - STILL OWED $400k more! ETH was crashing Bills were due   So we made  mistake #2...

We took out an AAVE loan. Put up 518 ETH as collateral (worth $1.5M at the time) Borrowed $400k to pay taxes About a week later Terra Luna imploded. I paid off the loan at the last second but... Our 518 ETH became 163 ETH. Worth ~$200k. $1.3 MILLION.  GONE.

Then came 3 years of hell. 2022, 2023, 2024: Endless Google Meets with my degen accountant. Line by line spreadsheets. Every extension filed. Every option explored. Final damage: $1,095,171.79 owed to the IRS. We didn't have it.

We hired a tax attorney.  We stalled.  We tried EVERYTHING. But time ran out. "You have 60 days or we take everything:  - Your house  - Your retirement  - Your NFTs  - Everything." I had one option left. One I'd been DREADING...

My Autoglyph 😭 Minted April 8th, 2019.  (Day before my birthday)  It cost $36. And this wasn't just an NFT. Matt Hall and John Watkinson (of Cryptopunks fame) had made something special. The day after the mint, I turned mine into music. John built a custom "glyph to midi" tool because of it. It was a piece of my soul from when 50 people knew what NFTs were.  By 2024, it was worth over $1 million. https://x.com/digitallyrare/st...

After turning down offers that would've been insane in any other context... The buyer offered exactly what we needed: $1,100,000 Because of our capital losses from the AAVE disaster, we could offset the gains. $36 → $1,100,000   Capital gain wiped out by capital loss. We were free.

The moral for every NFT creator: SELL. THE. ETH. IMMEDIATELY. Now I use 0xSplits to auto-convert 50% to USDC. If you learned something from this thread, share it. Someone you know may need to hear it!

Anwyay, that's my crypto tax nightmare. $3M → $0 → -$1.1M → Selling my soul → Freedom Tomorrow: Day 3 of the Road to Song A Day 6000. I'll reveal how I've channeled my trauma and shame into a brand new medium.