Our family rented a newly-built apartment a few years back. We bought a bunch of new furniture / appliances.

The apartment had a terrible smell (I bought a machine to measure formaldehyde and was off the roof).

With a newborn son and everything going on we decided not to stay there and lost quite a bit of money staying in hotels, selling the stuff for cheap and the down payments (it wasn't worth to fight it).

Terrible experience, but that year my professional life went very well. I always think everything happens for a reason.

That and the time my friend convinced me many years back to split 1 BTC into five other coins that I don't even remember the names -- Cardano, Iota, and some other fancy pants names. After two weeks of stress and gambling I turned everything back into bitcoin. Phew.

Honestly the worst part of it all was the wait time sending it to the exchange. My friend is now a maximalist and we often laugh about this incident.

Lol shitcoins, I bought TNT - Terion and and RCN - Ripo and they went to zero and got delisted before I knew what I was even doing

FOMO buying BTC at >60k feels pretty silly now in retrospect 😂 I remember wishing I could have gotten in under 30k! Will have to slowly work on lowering that average...

Shitcoins... lots of shit coins...

Never again!

I'll start.

My biggest financial failure is being a founder rather than just taking a job. I last had a fiat job 5 years ago and the income that I've lost is impressive. In one way, it's kind of high time preference behavior: I wanted to build things that I wanted and didn't want to wait to be rich to do it. In another way, it's low time preference: I was willing to sacrifice income for experience and at-bats.

I'll continue making this mistake probably forever, because I still don't think of it net-net as a mistake, but it's probably the single biggest "purchase" that I could've otherwise spent on Bitcoin.

2nd biggest miss: up until 2020 I still had a relatively diversified portfolio which was also a missed opportunity given my conviction levels.

Bought my first mechanical keyboard using BTC earned from mining in 2014. It was done to prove liquidity. Now my $12,000 keyboard is broken but I still keep it as a reminder.

I do this every once in a while. Some thing i buy that i end up never using, latest thing was a large set of speakers. And it builds up over time. So i have stuff that i barely use. Then i give it away to charity and the cycle repeats.

I bought and tried to mine Storj-coin. A total waste of time. (https://www.storj.io/)

A Coinmine. I am sure I bought stupid things but I was duped into getting one of those

Ive spent a crazy amount on bicycle equipment and racing. It was a passion that cost me a lot of money. It did make me very happy, but I could have bought bitcoin over expensive lightweight equipment that kept breaking.

Nerd Merit Badge 1.0 BTC

"Bought This Bitcoin Badge With A Bitcoin" Badge https://www.nerdmeritbadges.com/products/bitcoin?variant=95488652

Spent “invested” a whole BTC on the Bittunes project because I was emotionally sympathetic to the idea of linking musicians, fans, and curators. Good idea but they didn’t get it done.

Rekt