I don't know if it's huge, but I should have put more in crypto and perhaps should have joined a company pre-IPO. I think at the IPO price I would have netted a net worth of $1m+ from option exercise for just about 2 years of work. Of course, now they've halved in value post lockup so I don't feel too bad.
Similarly, selling the 60-70BTC I mined at around $2-3 each (early 2011), after I (CS student) and a couple of economics students came to the conclusion it was never going to last. Really wish I'd kept even one just as a punt.
