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Skylor James picture

Hey I'm Skylor 👋

I'm a founder, investor, and creator of Learning Machines. I'm a proud learning machine and am trying to help others do the same. I highly recommend checking out my reading list for the "Internet Hall of Fame" content I've found most valuable.

My life story:

  • Age 1-18: Polar Bear Era. I grew up near the literal north pole in the Northwest Territories, Canada
  • Age 18-20: Struggle Era. I moved to the big city of Edmonton, AB and thought I wanted to be a cop. While training, I broke both my ankles and plugged into the internet for the first time. I decided I wanted to become a rich businessman & investor like Warren Buffett but no one would hire me.
  • Age 20-26: Startup Era. I started a semi-fictitious management consultancy, Swanson Carlyle, first running FB ads for blue collar businesses, and eventually doing growth for startups and research + due diligence for VC & PE firms. I learned that VC firms have a vice clause in their GP/LP agreements and started a 'Stripe for vice' payments startup.
  • Age 26-28: Health Era. I had a heart attack running my company as I was working literal 16-20 hour days only sleeping 3-4 hours a night for years. I travelled the world seeking tactics to give me back my health. This was the first time in my life I put something (my health) above money.
  • Age 29-31: J.O.B. Era. I took a white collar job in Toronto which was my dream city growing up. I thought I would only stay for a year but I actually love this job as I coach 200 teens to outlier outcomes (Stanford, Oxford, Y Combinator etc). I got married and became a dad for the first time.
  • Age 31-??: The Next Era. Coach adults? Create content? Train my son, have more kids, buy a house and establish roots? Maybe move to a new country where I want to raise my family, idk.


Things I believe:

  • We need to be reminded more than we need to be taught
  • Smaller teams are more productive; most companies are 2-5x overstaffed
  • Time is more important than money; few would trade lives with Buffett or Munger 1:1 today
  • What you work on is more important than how hard; janitors work hard but lack leverage
  • Deliver to the world what you would want on the other end
  • Ignore 'most people' arguments; most people end up divorced, obese, and broke
  • To retire is to expire. Build a life you don't need to 'retire' from
  • If you're an ambitious person you need to work, its almost like a medical condition
  • The average man is a '3/10' while the average woman is a '6/10'
  • By 2030, Bitcoin will hit $1M, Tesla will hit a $10T market cap, Nvidia will hit a $5T market cap, and expected lifespan for a newborn will hit 100
  • Our western diet is hijacking our biology and will be looked upon similarly to smoking
  • Incentives matter and are great fortune tellers; show me the incentive I'll show you the outcome
  • Sales and distribution is just as important as product
  • The biggest unlocks in life come from compounding i.e. skills, reputation, relationships & capital

Predictions made as of July 2023

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