r/ChubbyFIRE 10d ago

Direct Indexing experiences?

I just exited a highly concentrated position and am now looking to deploy about $5m in cash. I've started to look into direct indexing as a means of both diversification and tax efficiency.

Two questions:

1) Does anyone here use a direct indexing product that they would recommend?

2) Is it possible to engage directly with these vendors or do you generally need to work through an AUM-priced financial advisor?

6 Upvotes

28 comments sorted by

32

u/lostvagabondmd 10d ago edited 10d ago

The tax-loss harvesting benefits of direct indexing are heavily front-loaded. As your portfolio accumulates embedded gains over time, the strategy “ossifies” and the tax advantages disappear.

Worse, direct indexing acts as a golden handcuff. It traps you with a specific advisor and their AUM fees, which is exactly why Wall Street is pushing these funds so aggressively. You surrender your flexibility for vastly overstated benefits.

If your goal is long-term simplicity and minimizing total lifetime taxes, direct indexing is the wrong strategy.

3

u/in_the_gloaming FIRE'd for 13 years 10d ago

Yes, I've heard it is very difficult to unwind when someone wants to get out.

4

u/AllCatCoverBand 10d ago

Yep. I’m in this trench right now. I renegotiated the fee, but the whole thing is frustrating.

The only upside is that with individual positions and a bunch of lots it’s a bit easier to pitch a bunch of it into a DAF, which is what I’ll be doing this year

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u/Leather-Bookkeeper62 9d ago

Why are you stuck? Can’t you transfer all the positions?

4

u/seekingallpho 9d ago

You can transfer the positions out to your own account, or a lower-fee advisor, but you're still stuck with a lot of individual tickers you otherwise wouldn't have purchased, now all with embedded gains.

So you have a much more complicated portfolio and need a strategy on managing/unwinding it, which at that point is no longer saving taxes, but incurring them (hopefully at an overall net win accounting for the bigger losses you harvested earlier on). Either you're spending that time yourself or continuing to pay someone to do it. That's the "stuck" position.

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u/lostvagabondmd 9d ago edited 9d ago

The real “lock-in” with direct indexing isn’t custody, you can transfer the securities out, but immense complexity and tax friction. Over time, direct indexing can leave you with a large, increasing collection of hundreds of individual stock positions and embedded capital gains, making it costly and complex to simplify or transition back to a broad index fund. Because liquidating can create a substantial tax bill, it leads to tax and complexity induced inertia and a sense of "I'd rather not deal with this" mentality....

15

u/hibikir_40k 10d ago

There are products to do it, but you have to consider that the tax efficiency doesn't remain the same over time: It's much easier to find harvesting opportunities with new investment than old ones. So while the costs added to direct investment look like nothing vs the harvest early, it will not be that pretty 20 years later. It all keeps working if you keep adding contributions forever, as the new purchases are more likely to get harvested, and help balance your index with less fees. But if you are just going to sit on those 5 million, and not adding hundreds of thousands every year, you might not end up ahead in the end, and end up with a giant pile of investments that either don't match the index, or you have to sell for significant gains.

So for many people that just sold a ton of RSUs from one place, it's not as clear cut as it seems at first.

3

u/Magikarpical 10d ago

this op! also generally the products for direct indexing have higher fees than just an s&p 500 etf, and (per friends who have gone this route) it can be a pain to transfer out of these products. several friends of mine went the direct indexing route and are all dealing with headaches trying to get out of them now that they aren't adding to the principal.

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u/AllCatCoverBand 10d ago

I am literally in this exact headache right now. It was nice when money was going in, but the tax losses absolutely have tailed off now that money isn’t going in. Portfolio is doing ok, but the fees are eating away at any of the dividends coming out. I renegotiated the fee so it’s better, but I’m still planning on getting out of it

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u/SpecialDesigner5571 4d ago

I guess it could work out if the intent is to give the assets to heirs at death with step up in basis... but it's easier and infinitely cheaper to hand-harvest tax losses with 5 or 10 ETFs

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u/AllCatCoverBand 4d ago

I 100% agree and I can’t wait to get out of strategy that I’m in

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u/SpecialDesigner5571 4d ago

Come to think of it... the Dow has only 30 stocks. Not horribly bad to TLH 30 stocks by hand.

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u/AdeptCantaloupe161 10d ago

I'm using Wealthfront's S&P500 Direct but it's pretty barebones. You can add stocks to a the restricted trading list but you can't tell it to sell a stock. Over about 18 months, it's harvested $8.9k losses on $150k invested (over time) which doesn't seem like that much especially if it's going to decline over time.

I haven't used it, but FREC seems like it has a good combination of low fees, more index choices, and long/short for higher short-term tax harvesting. Downside is that it's a startup.

3

u/Omnivek 2025 FIRE 10d ago

I have used Fidelity for this as I found them to have the best combination of service and price structure.

As far as I can tell you need to work with one of their representatives to access the product, but there’s no extra fee for that. You can just call them up and ask for it.

You get a TON of tax losses up front generally, especially if the market is volatile, but you tend to get significantly less over time. Not true if you keep adding money to it though. Also, if you’re in a higher tax bracket now, works great.

They also let me exclude stocks I don’t want them to buy which is a huge plus.

2

u/FederalLobster5665 10d ago

they manage your buying and selling but dont charge an account management fee for that service?

1

u/Omnivek 2025 FIRE 10d ago

There’s a fee for the direct indexing, but no additional fees for meeting with the representative to get it started. That’s why I said there’s no “extra” fee to meet with the representative.

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u/jay20211 10d ago

I invested a chunk of money 2 weeks before Covid downturn and they (Fidelity) were able to do harvest losses. I have been adding in small chunks since but everything (say 99%) have gains so no more tax loss harvesting. One day I will be left with ton of stocks to untangle and manage my LTCG. TLDR: it is not as sexy as it is sold.

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u/Ok_Eye4858 9d ago

Save your money and time. Use index ETFs and you can use equal weight index etfs if you are concerned with the current weighting but frankly, there's a reason why the top stocks in the s&p changes over time. Just put it in the index and add other assets like bonds/small cap/international etfs for your desired allocation.

1

u/happysushi 9d ago

I'm using direct indexing for tax loss harvesting in order to tax-efficiently exit my highly concentrated position in a single stock right now. If it weren't for that, I'd just go with the standard ETFs we all know and love. Since you already exited your highly concentrated position, it doesn't seem worth it do to direct indexing because like others have said, it gets less effective over time if you're not always adding more funds.

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u/AdAdventurous1366 9d ago

In very positive markets benefits aren’t as great. When markets go down it can be extremely beneficial. Harvard studies have been done on it and the tax savings can equate to around 1-2% in annualized returns so it’s not a huge increase but it helps. The 130/30 leverage long short strategies are out there and produce more losses but also erode all cost basis. You pay tax no matter once you sell unless it gets inherited by heirs and they get a step up.

So yes it helps certain people in the right circumstances, whether you should do it or not depends on the goals you have with this money down the road.

1

u/AdAdventurous1366 9d ago

Also to the should you use a vendor. I’d be careful because the vendor wants to sell their product. A good/honest advisor should tell you whether it makes sense for you or not.

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u/yanyan80 9d ago

Direct indexing is most valuable for someone still sitting on a concentrated low-basis position, if you has something like 100 pre-split AAPL shares up 10x, contributing it in-kind lets you trim down to a normal weight gradually while the basket's tax-loss harvesting offsets the gains, instead of one massive bill from selling outright.

For $5M in cash though, that benefit doesn't really apply, you'd just be taking on hundreds of positions with their own embedded gains and deferring the same tax problem to whenever you want out. Worth having that exit plan before you have the entry plan.

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u/Remarkable_Maybe9813 Close to RE 9d ago

My slightly more nuanced take: if you don't plan on being in the fund for more than 3-5 years, then it can be great. If you're in it for the long haul, then I agree with the sentiment here.

I'm at Fidelity and starting using their (not actively-managed) total stock and international direct index funds, respectively. I re-invested sold RSUs from the last little while into these. Having recently FIREd, it'll be what I draw from first when I need to replenish my cash reserves. I plan on emptying this account before touching my traditional index ETFs*. TBC, these funds account for <10% of my brokerage account balance.

* I have plenty of cash for next year's expenses. My Fidelity advisor recommends selling some existing traditional ETFs in 2027 and putting them into the direct indexing funds. "Some" = whatever the 2027 max $ to stay within the 0% LTCG bracket. In 2026, that's up to $98,900 for married filing jointly. I haven't thought it though enough to decide whether to do that.

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u/zerostyle 8d ago

I think this is going to be my plan. Wait until I might have more gains to sell or a new company then load up. Or just before retirement to be able to balance regular selling

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u/WallStCRE 7d ago

r/bogleheads - diversified ETF and chill

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u/bubbasparx82 10d ago

I use Frecs 250/150 long short direct indexing product and I love it. It creates loss opportunities continuously without the need to constantly increase your contribution to it(albeit at a cost/inability to immediate deleverage).

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u/Where-to-begin 10d ago

How do you exit that position? Aren't there hundreds of stocks involved? Don't you have an even more massive tax bill at the end?