I've invested in some domains that if i don't one day build them into something substantial i'll lose a lot on since I overpaid for them. I wasted 10K on dotTV domain leases when it was brand new.
I blew 25K 'investing' in stock options - buying/selling puts and calls, learned my lesson. Another 10K in sports wagering, learned my lesson.
I've lent/invested in people and not sure I'll get my money out.
