otoh me giving someone 6 figures and having them lose it is much more meaningful to me because: 1. It's my money, not money someone has given to me to invest

otoh me giving someone 6 figures and having them lose it is much more meaningful to me because: 1. It's my money, not money someone has given to me to invest 2. It's a pretty significant part of my net worth. If I was worth $100 million and gave someone $100k and they spent it all without any return, I doubt I'd lose much sleep over it. If I do that now it would be very hard to get over. I'm not really disagreeing with you here, but the emotions at play are different I think.