Most Visceral investing miss this year for me is not Full porting to GOOGL this summer. I was deep down the rabbit hole on their AI prowess (Data, Infra, Multi-modal models) and really respected their leadership (Demis) and team - especially after reading The Maniac. This was at a time when it was contrarian (OpenAI would rule the world outright, Meta spending $100m per mercenary hire and Chinese models getting really competitive). I was also pretty distrustful of OpenAI's leadership and strategy. Anyway we all romanticize playing things perfectly and hindsight is 2020 but a few lessons that are imprinted onto my brain 1/ Bet sizing REALLY matters. If you under allocate to your best thesis you don't win big enough for it to matter. Druckenmiller, Soros, Ribbit and all the greats put all their eggs in one basket and watch the basket closely. 2/ Many small plays is pointless. Yes you need to have a huge research breadth and watch everything but trying to do a million trades or investments ends up as massive distractions. Even if you're right, you don't win financially in a big way. I feel these plays come along 1x a year, maybe twice if you're lucky. 3/ People forget they are long what they are sitting in. Sitting in cash, some random token you were bullish on, real estate or Apple stock? It's easy to forget you are long that asset (I.e. USD) in comparison. We assign some "safety" feeling to what we are already in when in reality what we are in must be compared to what we could buy. 4/ Always go max long the things YOU are convicted in. You can't borrow conviction or copy trade to greatness. I.e. you hold during downturns + on the way up since you know the play inside and out. This is also where you learn the absolute most. Next time I see a play I'm max bullish on, I'm betting the farm. Anyway, everyone shares their wins, this was one of my misses lately. I wont make this bet sizing mistake again.