Harvested $2,100. Waited 31 Days.
I sold two ETH lots on Jul 16 for a realized loss of $2,100 to neutralize February's gains, then waited the full 31 days before rebuying on Aug 16 at $308 more. A manila folder and a stubborn tax preparer kept every step on paper.
4:22 p.m. on Thursday, Jul 16, my kitchen table held a manila folder with a rubber band around it, nine printed confirmations fanned out like a bad poker hand, and my phone on speaker with Rune, my tax preparer, who was telling me to sell the second lot while he literally watched his clock. I had a pen in my hand. The pen did the real work.
The numbers on the table were two ETH lots underwater by a combined $2,100, snagged in March at $2,260 and $2,340 and worth $1,860 and $1,840 by mid-July, and across the ledger sat $2,100 of gains I had grasped in February selling 0.09 BTC. Offset one with the other and February's bill mostly evaporates. Simple, on his terms.
Rune had exactly one condition, and he repeated it three times on that call: 31 days minimum before I buy anything back, written on the calendar in ink, because the way I understand it, the wash-sale rules around crypto are murkier than either of us likes, and he builds his clients' files for the version of the world where the rules arrive late and apply retroactively. The folder is what that caution looks like.
the folder with a rubber band
Rune is 71, refuses email attachments on principle, and wants printed trade confirmations with handwritten dates beside them, hand-delivered to his October appointment. Everythin gets printed at the public library at 10 cents a page, which came to $1.40 for this file, and every page gets initialed by me the day it happens. His phrase, spoken on the speakerphone that Thursday: paper first, app second. No man has ever owned less cryptocurrency and understood more about keeping it.
lot 2, sold at 4:37 p.m.
Rune stayed on the line while I executed, his rule, timestamps written as they happen. Lot 1, 3.35 ETH snagged Mar 9, sold at 4:37 p.m. for a grasped loss of $1,340. Lot 2, 1.52 ETH snagged Mar 21, sold at 4:52 p.m. for another $760. I wrote both numbers on the folder's cover while he repeated them back to me. $2,100 of red. In ink.
$9,028 into the untouchable account
The proceeds, $9,028 all told, went into a savings account I do not touch, and a paper calendar on the fridge got one enormous X chain counting down 31 days from Jul 16, cuz the buyback date, Aug 16, needed to be visible from the coffee maker every single morning. Rune's voice lived in my head the whole month. Nothing about the market made the wait easy. More on that in a moment.
his one condition
The condition itself deserves its own paragraph, cuz I argued with it for fifteen minutes on the first call. Crypto, the way I understand it today, sits outside the wash-sale rules that govern stocks, so on paper I could have snagged back the same afternoon and kept the entire loss. Rune's answer never changed: today's paper is not October's paper, lawmakers have been circling this exact loophole since 2024, and a 31-day wait costs some price drift while a retroactive rule costs the whole tax deduction. We talked through the retroactive scenario twice. I pay him $180 an appointment to be that stubborn.
31 days of watching, not buying
The month had a sense of humor. ETH slid to $1,790 on Jul 29, seventy dollars below my sale prices, and every fiber of my acquiring self wanted to pounce, calendar be damned. I jotted down the price on the back of the folder instead, weekly, like rainfall. The back page now reads like a weather log: Jul 19, $1,912. Jul 23, $1,864. Jul 29, $1,790. Aug 2, $1,821. Aug 9, $1,866.
The capital gains tax logic held steady the entire time, which is what the folder was for: February's $2,100 of grasped gains, July's $2,100 of grasped losses, one neutralizing entry, one printed trail with initials and dates showing the two events were 31 days apart and the repurchase was deliberate, documented, and dull. Boring is the entire product here. Excitement is what auditors refund.
the Aug 16 buyback, $308 late
Sunday, Aug 16, I snagged back 4.87 ETH at $1,917, spending $9,336 against the $9,028 the July sale had fetched, so the clean paper cost me $308 of drift, which I sat with for a full evening before writing it in the ledger. The way I understand it, the deduction shelters $2,100 of gains worth approximately $500 at my bracket, minus $180 for Rune, minus that $308. The folder says what it says. Twelve dollars, plus 4.87 ETH still mine.
twelve dollars, all in
Twelve dollars of net cash benefit, then, for a month of discipline, two phone calls, and a library printout, and I want to defend the number. The $2,100 of losses also reset my cost basis higher, so any future sale starts from $1,917 instead of $2,260 and $2,340, which is worth real money the next time ETH hands me a good exit. Harvesting this way is a habit with receipts. The receipts are the habit, honestly.
back to the rubber band
The folder is fat now, nine pages grown to fourteen, the original rubber band replaced after it snapped, and it lives in the drawer where the property tax bills wait til Rune's October appointment. Last Thursday I pulled it out at 4:22 p.m. without planning to, the exact hour of the first call, and reread the cover: two lots, two timestamps, his initials, mine. The pen is still in the kitchen. The app is where money happens. Paper is where money survives.