My 3 biggest investing mistakes ever (learn from my mistakes):

1. Missing the Anthropic round at $67.5b in May 2025 ($100k would = $1.2m now - and that was just the minimum sizing) - I didn't even explicitly turn it down, it just got lost in my DMs (from a reputable source), and I ignored it. I wouldn't care if it was some random DM, but this person was trusted and even followed up twice. That blind spot is on me.
2. Not allocating more to equities or gold in 2024 (I played it too safe, keeping profits in stables instead of re-allocating) - cost me millions in opportunity cost.
3. Not taking enough profits on my shitcoins in November 2024! I thought I was taking profits, but I wasn't ruthless enough - I lost respect for money and learned a hard lesson (this alone cost me $3-5m).
All 3 happened for different (and some overlapping) reasons.
1 = lack of organization, systems fault (fixed this since with PersonalOS/AI CRM tracking).
2 = mix of fear (scared of losing what I made, complacency (I didn't execute on my plan), and judgment (I over-weighted the crypto/equities correlation).
3 = complacency (there's some crossover with the prior 2 points) - I wasn't organized/desperate enough to lock in gains - partly due to overconfidence but also due to systems
I think it's crucial that we all reflect on our losses and dive deep into WHY they happened. Or they will keep happening again. Something happening once is bad enough, but twice (if it's within your control) is idiotic. The great thing about AI is that it can fix a lot of this stuff (automated reporting alone would've solved a lot of this).