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.

    1. 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

    1. 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.

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