Most portfolios don’t fail from bad ideas.

They fail from bad structure.
@nntaleb's Barbell Strategy hits in the uncertainties:
- 90% in survival assets (cash flow, stable yield, long runway)
- 10% split across many tiny asymmetric bets (AI, crypto, early experiments)
If a small bet dies, I lose little. If one hits, upside is nonlinear.
I learned this after sharp drawdowns in 2018 and 2022. Not because my thesis was wrong — because my sizing was fragile.
My biggest shift:
- I stopped optimizing for being right.
- I started optimizing for survival + optionality.
Rules I follow now:
- No single position can kill the system
- Core capital compounds quietly
- Aggressive bets stay small enough to lose, big enough to matter
Most people chase certainty. I design for asymmetry.
Survive first. Then give yourself enough shots to catch convex upside.
Stay Invested in the Game🐍