I got into crypto when Stellar (STR at the time) was giving away 1000 coins airdropped to email addresses. I was apart of a "grey hat" SEO team, which combined had hundreds, if not thousands of emails. We saw this as an opportunity and combined all of our emails into a pool and then split the airdropped coins appropriately (as someone had to have the tech knowledge to get past the checks and balances to run all of them through for the coins, to get them to a central wallet, and then to distribute them).
I ended up getting, I think, around 150,000 STR, which at the time was only maybe $100. Stellar is now Lumens (XLM) 10 cents each, so if I just kept it, it'd be $15,000 today.
However, what I ended up doing was getting into Bitcoin, the free forks, and Ethereum.
My worst decision ever was to not keep the ETH and BTC that I was able to trade into as that would be over half a million dollars today. Instead, I took 1 ETH and put it into shitcoins that are worthless. I did put a lot into Syscoin and have a $10,000 (like $100 to $10,000 gainer) wallet that I can't access because I forgot the password. If it ever blows up, I'll get someone to hack into it and give them a percentage.
But, I widdled down my holdings a lot and also spent it over the past 10 years, and yet still have thousands of dollars to play with... all from $0.
I'm now holding on to what I have left, and someone still owes me about $10k in crypto cause the exchange went bankrupt. So, that's still an asset on my books as I'm slowly getting that money back.
I'm hoping this follows the DOGE trend where it's 19 cents to 0.000019000 cents, or when DOGE pops off to $5, it would be 0.0005 cents and I'll have five figures that'll make up for my mistakes. I'm also in DOGE, so that'd be another 5 figures. And then, the remaining BTC/ETH would put me in the low 6-figure range.
But, the opportunity cost of not holding the coins I had... man. I don't even like to think about it.