How do you define success? Money, position, freedom, happiness, etc. I know guys with a mid 9 figure net worth and I don't know that they're any happier than those with far less. I do think, at a certain level, money allows for (not provides - it's just the piece of mind it allows for) happiness. Once you have enough, the lines blur. From what I observe, the business owners tend to be "happiest" as they do what they want without a lot of accountability.

 
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richest person - billionaire heiress (a beverage company you've heard of), no clue if she's happy, most conversations are just surface level

how I define success (independence and capitalizing on it) - a couple that worked in executive roles in big pharma for a while, saved enough to retire early and live very well in my city. they've traveled all over the world, live a stress free life (mostly), have a great network of relationships, and on and on. few people I know are as genuinely happy as they are, even those with many multiples of their wealth ($5-10mm liquid in my T3 city)

an example of monetary success but maybe not life success (true story) - guy I know personally retired with $20mm in a low CoL city (to give you an idea, you can get a luxury home for $600k), passed his business onto partners, got a nice buyout, and had dreams of travel since he'd only taken 2 weeks off once in a 40 year career. everything looked great. kids were happy and healthy, no elderly parents left to take care of, and more money than they'd ever need by orders of magnitude. and then covid hit.

unlike yours truly who said "OK, can't go to europe, let me do the most possible given the restrictions (went to Miami and Mexico)," he got scared. to. death. mind you, this is someone who's in his 60s but with the heart of a guy in his 40s, lifts weights and does cardio 5-6x a week, eats as healthy as a boring blogger for men's health likes to make you believe, and on and on. zero comorbidities. now, I don't "know" if covid could kill him, so I understand hesitation. but now he's moved from "I'll get back out there once I get the shot" to "I'm not comfortable eating anywhere without a vaccine mandate and I'm not comfortable travelling or being around anyone who's travelled until______" and that ______ changes day to day. this is not a covid comment, this is a comment about life. you have no clue what life is going to throw at you, so don't wait. that idea of "I'll retire and then I'll _____ is idiotic. you could die tomorrow, so be damn sure that you're conducting your life in such a way that you can look back at your life and be pleased with what's happened so far. maybe you haven't accomplished all of your life goals and there's a few more things left on the bucket list, but you can at least say you were marching in the right direction, rather than 100% putting off what you really want for whatever reason. and no, I don't mean "live every day like it's your last" because otherwise we'd all just be skydiving and doing mountains of psilocybin in the Cote d'Azur, but it means living with intentionality, and not waiting to do things you can do today.

 

My uncle founded a hedge fund.  On one hand, his competitive nature definitely leaks into other parts of life such as his kids sports, school and all.  On the other hand, it feels weird calling a middle aged guy “chill” but he is one of the most easygoing guys I know.

I also know a really rich guy who is the heir to an old manufacturing company.  He is one of the biggest douches ever.

 

Was this supposed to be in response to my answer?

Well, he loved coke, women and fast vehicles, and he used to flaunt it to the guys just trying to make a living.  For example he used to race his motorcycle up and down the factory floor while other people were working.

 

The wealthiest person I know (not super well but I know him) made his money in the restaurant business. He's one of the largest franchisees in the country and at this point a billionaire. He also helped my uncle set up his businesses. The other two wealthy people made their money in owning pharmacies + gas stations + a handful of large apartment buildings which they bought after the crash.

I don't know the billionaire franchisee super well, but he seemed like a decent down-to-earth guy and so did the kids. The other two people are happy, even after facing some tragic family events (child committed suicide) they really stuck together as a family and also support a lot of the less fortunate members of our community any way they can. They're actually really good people.

 

My aunt - she was on the board of directors of a company and owned a bunch of its stock and the company was acquired for billions and she made good money. 

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Hey man I appreciate the support, but an autobiographical memoir is not really my goal for a book. I do plan on writing a book, but my goal for the book is more of a guide for people suffering manic depression. I feel I have conquered it in my life and just want to share a reaction based system where I describe what to do in certain circumstances. I also feel I have perfected recovery from a severe manic depression diagnosis and my psychiatrist would probably agree and he views me as his star patient. 

I feel an outright autobiography would be boring. I’m just a well traveled military vet who likes the beach, 420, boardsports, Muay Thai and triathlon. I’m not really exceptional in anything. I thought at snowboarding boardercross nationals that I’d have a shot of the X-games or Olympics, but did terribly. Now I just like chilling out and playing poker.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Self made, net worth $1bn+. Joined a top hedge fund before it got really big. Worked there for 20 years before calling it quits and retired because he got 'bored'. Basically retired by early 50s.

Completely down to earth, normal looking and acting guy. Happily married with two kids and several homes, main one being in the UES. Nothing extraordinarily lavish. His life now consists of angel investing, going to his kids' sports games, Classpass workout sessions and going fishing.

 

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