Any Cool Stories on PM's Side Hustles / PA's?

Let's say you are passionate about stocks/investing, have a little luck, and have a very successful career at either a MM or a top SM HF. During your time as PM/Partner/MD, it is safe to say you have the ability to make 7-8 figures on excellent years, which unlike most other careers, puts millions in cash in your bank account. 

Most of the wealthiest people I know from my hometown (none of them were in finance) earned significant income/wealth from their personal investments, whether those investments may be in public equities, private equities, real estate, startups, etc.

So, I am curious to hear about what a successful PM does with the millions he can earn in a year. My thinking is that since most of them just love the game, they probably trade their PA heavily or even set up their own family office if they are successful enough. 

Does anyone have any cool stories on dudes investing heavily in real estate, startups, or anything else like that? And if so, I would imagine these side investments ultimately end up earning them similar money to what their actual job does, if not more. Also, are there any restrictions that prohibit them from investing in certain things on the side, maybe due to conflict of interest or something like that?
I know this is a pretty dumb thing to post on here so feel free to ignore but I'd love to hear any cool stories if anyone has some. 

8 Comments
 

That's so badass. Wonder what his biggest win was. 

"If you don't have any enemies in life you have never stood up for anything" - Winston Churchill | "It's a testament to the sheer belligerence of the profession that people would rather argue about the 'risk-adjusted returns' of using inferior tooth cleaning methods." - kellycriterion
 

Not a PM but a super senior analyst that survived the MM model for 15+ years. His son loved buying, fixing/restoring, and flipping vintage cars and they both were doing that on weekends. He got enough demand that he ended up quitting the HF life and doing that full time as a family business. 

 

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