I think back to when I first moved to SF in 1999.My friend Chris introduced me to his eldest brother, early 30-something, Larry was in management consulting at that time.I remember being very impressed by him.His big goal was to cut his cost structure and maintain a good basic lifestyle while he invested his savings in investments.A precursor to the FIRE (Financial Independent Retire Early) movement.
He also bought a multistory apartment building, living on the top floor while his tenants paid the mortgage.This was back in 1999 btw, before 2003 when everyone rushed to get into real riches before things imploded in 2008.
I should add this was when prices were reasonable and not so crazy.He did well.
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Subscribe Or another friend who I will anonymize for his privacy.A former American banker at Goldman who took off to Eastern Europe to do PE (Private equity) in the early 2000s.He traveled the world before he came back to San Francisco to start a niche CPG company at the start of the energy foods craze.
He was an early adopter of Tim Ferriss remote work, 4 Hour work week style of business.He ended up exiting the company and then using his earnings to do micro PE fund rolling up software businesses from a remote massive sized ranch while building several side businesses for multiple revenue streams.A remote work and portfolio entrepreneur before the term was coined.This was in the mid 2010s before it was cool.
Forward thinking is the term I’d use here.
People who you knew were sharp or ahead of the curve but then you realize a decade or two later just how far ahead they were.I’m surrounded by so many of these folks it’s quite exhilarating and depressing at the same time.
Alex Danco coined the term “Upside Regret” which is the missing out of something or underestimating someone that ended up being very successful.It’s like missing the chance to angel invest in Coinbase or Solana, or join PayPal or Facebook in their early days for example.I’ve definitely had a bunch of these which I highlighted previously here:
The Hard Fork by Marvin Liao Lessons, Not Regrets: Missing Life Changing Wealth Multiple times I was talking about the Crypto token Solana (SOL) with a friend a few weeks back.Solana’s value has literally exploded, pumping a full 24% in one day.I made a remark about the fact that I knew the Solana team back in 2017 and had the chance to buy some tokens.They actually went through the Accelerator program I ran and the 500 Mobile fund (now Race C… Read more a year ago · 11 likes · The Hard Fork by Marvin Liao But for me, the real “Upside Regret” is more about not realizing or understanding & internalizing key concepts or ideas earlier than I eventually did.
The crazy amount of upside that I missed to my quality of life and personal finances is “oh so” high.
This is why I read so much, take as many classes or courses as I do, and go to as many interesting conferences like Founders Summit, the Leveling Up Mastermind or Capital Camp.And of course, I try to talk to and invest in as many awesome founders and VCs (I also do small select LP cheques on occasion).
This is the only way to keep up.And for the most part, it’s damn fun, so I don’t always mind being the dumbest person in the room.I’ve come to accept that I may always be slightly behind the curve.
But just as the tortoise who loves the game, I will keep on going, slow and steady to win the race in the end.
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