My situation is that I have large cap gains from selling AMD (cap gains alone of 450K+ in 2026) with a mix of long term and short term sales. I have sold a bit too much, because 1) I am moving to a higher tax state with much higher W2 income in the latter half of 2027, 2) I am hoping to buy a house within the next 2-3 years and 3) did feel that the market was running hot/euphoric.
I feel overwhelmed by the impending tax bill and was reading up on direct indexing offered by firms like PGIM and Natixis. This made me think about doing a DIY version of this by buying a wide range of indices in different sectors (in addition to a few individual stocks of interest) as well as materials, crypto etc. Every month, I would sell the losers and repurchase a similar ETF/stock (to avoid wash rule), keeping the winners until long term when I would sell to fund my house purchase.
The goal is to cancel out short term gains as much as possible this year while diversifying to minimize my risk. I have another window in the first half of 2027 to realize my gains in a relatively low tax environment, so some tax deferment this year could be beneficial.
1.Does this sound like a reasonable plan and theoretically beneficial for me in my situation? When I run rudimentary math, I see this strategy winning against putting all of my cash into treasuries/SGOV in choppy/neutral and bull markets. In a bear market, SGOV would win short-term but diversified TLH investing partially offsets losses through tax loss harvest while maintaining market participation with possible recovery in the future.
- If so, the big question is exactly what mix to buy? A balance of ETFs in various sectors (semis, healthcare, finance, insurance, consumer defensive, communications, consumer cyclical, industrial, energy etc) would be important obviously. And I plan on throwing in a few individual stocks like WMT and car repair stocks which would be resilient in case of sector rotation or a bear market. Anything else I should consider like materials (e.g. gold, plat), foreign markets, storage REITs etc?
The proportions would be something that I would need to figure out too. (Maybe I can just go by the sector's relative sizes in the sp500). For example, how much to put into something like SOXX where I already have good exposure with 25 percent of my portfolio remaining in AMD?
Overall, I would need to have some confidence in the mix to hold up even in case of a market downturn, so that I feel comfortable putting in a lot of cash in accordance with this strategy.
3) How much of my cash (~750k) should I keep in SGOV/cash? Obviously, I should have enough to pay off my taxes (I am planning to utilize the safe harbor rule to avoid penalties) next year, in addition to holding some reserve for re-entry of AMD if it experiences a significant dip. So I am thinking around 250K.
Thank you!
Large capital gains ($450k+) — considering DIY direct indexing / TLH
byu/shoenberg3 intax
Posted by shoenberg3
1 Comment
This is not immediately relevant to you, but in the future when you buy a house you should check out Box Spreads if you haven’t heard of them.
You can effectively borrow against your stock portfolio, at a rate of US treasury yields +.2%, and the interest is counts as a mix of short term and long term capital losses. It’s a pretty neat trick if you can pair it up with positions you want to exit. Great for a down payment.