I think a lot of what you said is true, but I have one overriding philosophy that I live by regarding money.
I own my money, my money doesn't own me. I'm not afraid to risk it all to get more, and sometimes I will loose. Mind you I come from a gambling family..... LOL
To me, and this is just my opinion, it all depends on if you spent the money on yourself or on a business. On yourself is stupid.
I lost a lot on a failed business. I don't regret it. Yes I spent a lot of money in the industry on what looked frivolous; tons of trips, parties, etc... but all were business related. None of those expenses really contributed to the losses I had in another business. I never threw any parties for people outside of my work, and in adult every penny I spent on that all came back to me 100X over.
I blew money on a car, sure it was over $1200 a month lease, but I could have afforded $8,000 or more on that at the time. didn't need it. I blew money on my house, but in the end I could have had a house 5X or more in value, didn't need it. My mortgage was only $1100/month. I always put money away.
I massively overextended myself on a business venture...and it failed for a number of reasons outside of my control. I kept trying cause it had potential and I believed it would turn around, it got worse. I lost all.
sometimes (if you have balls) you have to over extend yourself to go for something, and sometimes it fails. I knew the risks going in. I also had certain assets protected as well. No regrets.
I'll be bluntly honest here, most of the hugely successful people I know have gone broke or lost it all before, or at min had a failed businesses that cost them a lot and really set them back. In my experience it's usually the relatively successful ones, not the HUGELY successful ones, that haven't' ever gone under that wave their finger but won't ever experience 10,000% growth or more in a year cause they didn't have the guts to risk all.
And honestly, and this is just me, but I fucking HATE total security. I like having a rush. and to truly experience a rush you HAVE to loose once in a while to appreciate the wins... I never got into casino gambling huge, I do it with my real life.
just my opinion on money.....