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Hey I'm Skylor 👋

I previously led growth for several venture backed startups. I now coach 200+ high school students to outlier outcomes (Y Combinator, Stanford, Oxford, Waterloo, NEO etc.) at TKS. I'm a proud learning machine. Check out my reading list for the 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. Start a company? Create content? Join a startup? Train my son, have more kids, and buy a house? Move to a new country where I want to raise my family, idk.

Predictions + things I believe:

• We need to be reminded more than we need to be taught
• Small teams > big teams; most companies are 3-5x overstaffed and will use AI for mass layoffs
• 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
• If you are an entrepreneur reading books is not productive, get the 80/20 from a 1 hour podcast
• 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
• 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
• The biggest unlocks in life come from compounding (skills, reputation, relationships, capital)
• By 2030, Bitcoin will hit $1M, Tesla will hit a $10T market cap, Nvidia will hit $5T, and expected lifespan for a newborn will hit 100 (Oct 19, 2026 update: looks like Nvidia will hit $10T by 2030 and I now believe Tesla will merge with SpaceX and that the combined entity will hit $100T by 2040.)

Predictions made as of July 2023

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