This could turn out to be an epic thread. Sub'd.
No specific questions, but for one just now: You say you've lost everything numerous times over, so I'm interested to know - what was the biggest mistake that you made that cost you everything, what lessons did you learn, and what methods did you employ to get over that? Can you describe your hardest lesson & biggest turnaround.
The biggest mistake, over and over again, is money and time management.
A few years ago I had been working with a (legit) natural supplement company to bring a successful product to market in the US. Well money was flowing, I was only consulting for a couple hours of week and it was great. But I spent the money like it'd last forever. I'd take vacations. I wouldn't reinvest into other projects. Then it dried up overnight for legal reasons, and I wasn't expecting or prepared for that.
I wasn't flat broke but I was irresponsible. But within a week or two I found a new project to hop on and turned it around pretty quick.
I've had merchant accounts shut me down on launches and freeze huge amounts of money for months. I've gone all in on buying a business or on a marketing campaign and flopped.
It's easy for me to grow complacent/lazy, instead of continuing to hustle when I have the time. For me though it's always been more about freedom than money.
It's not a great excuse but I'm still young (30), I've never been married or had kids, so I've always been willing to put everything on the line when I believed in something. And there's been a lot of times that's backfired for me.
There are a few big lessons for me. One is to always look for opportunities to leverage. You can't do everything by yourself. You can work 100x faster and more effectively with a team, with existing assets, etc.
Another big lesson is to make and keep connections. I still work with guys I worked with 7 years ago, and I've learned a ton from clients/partners over the years.
Another is to always put your money to work for you. I've chronically sucked at this but I'm actively getting better at it.
Always have a plan b, c, d, e, etc. Have things to fall back on. Hope for the best, plan for the worst.
I'm kind of weird. I enjoy growing broke, at least in hindsight. It reminds me just how hard I can hustle when pushed, and for me I always know it's temporary, that I'll be okay because I have skills/assets that I can fall back on.
Partying/bars where a big problem for me when I was younger, not so much anymore. I'd go out every night and party like a rock-star, and not accomplish anything the next day.
The biggest lesson I think is actively working harder to better manage and leverage my time, assets, money and resources.