Key insights
- An individual is seeking strategies to offset a large capital gain in the current tax year due to a layoff and stock issuance. The strategies considered include tax-loss harvesting funds, prediction markets, exchange funds, and tax alpha accounts. Given the limited time and capital, the feasibility of generating substantial losses is questioned. The individual's $2M brokerage account could potentially be used for margin to facilitate these strategies, but the overall impact on the US equity market is slightly negative due to potential selling pressure.
I’ve been laid off recently and at the same time will have a large capital gains moment this year, say 500k+ in capital gains. I’m going to be getting some shares and it’s not yet known if we’ll be taxed at the moment the shares are issued or if it will be until we sell the shares. It’s probably going be a taxable event when we get the shares.
So this calendar year I’m going to be in a high tax bracket probably 35 or 37% and next year I’ll probably have no ordinary income and will be living off of long term capital gains and might be doing some Roth conversions.
Ideally I would like to defer the 500k LTCG till next year but timing is out of my control.
I know there are some 140/40 type funds that try to use tax loss harvesting, but I don’t think I have enough time to generate meaningful losses unless I was able to find more like a 400/400 type neutral fund.
But even then, I’d have to realize LTCG to create capital to fund these account which would defeat the purpose. I could possible transfer my brokerage account and use it as collateral for margin but not sure.
I was trying to think of other ways to achieve something like this such as some binary prediction market bets, or something where I could have offsetting positions and exercise the loser at the end of Dec and the winner in the start of Jan.
I also know about Exchange funds which might be an option depending on how this all goes down but then I’m locked in for 7 years.
I’m assuming the real way to do this is to use a tax alpha account and I don’t really have enough time and enough starting free capital to make it work.
I’ve got about 2M in brokerage accounts that I could use for margin fwiw.