Portfolio tax optimization strategies:
1. Tax loss harvesting
2. Sell winners in January
3. Use options to hedge winners to delay selling until January and/or eligible for long-term capital gains
4. Delay closing shorts for years after they're economically impacting your
My dad took career risks that I'd consider insane many times. Part of it was his genetics, but part of it was also growing up poor. The risk isn't nearly as scary when you feel you've already won life in the bad case.
One of the issues with fintwit is that many of the most successful investors can't or won't tweet about what actually differentiates them. So even high alpha investors can leak negative alpha on this platform.
I try not to judge statements as true or false, but through the lens of 'is there a reasonable world view where that's a correct thing to believe'. I think it's a more intellectually constructive approach and fosters empathy. It makes building conviction very difficult though.
John Hempton, a very talented investor, has an interesting take on my business partner David Orr, who I believe is one of the best discretionary investors active today. John sees David as a poker player-turned-trader, not an investor, and is uncertain his edge will scale.
I
I don't know David personally, but have followed him extremely closely on Twitter. In addition to learning a ton, I have put ~20% of my net worth in his ETF. In my opinion what differentiates him is how well rounded he is. He excels at all three of what I consider the main roles