Should You Participate in an Exchange Fund with Your Big Pile of Company Stock?

Block Woman peers over the edge of a clear blender, looking down on an ice cube and the stainless steel blender blade.

Do you have too much of your company stock? Today let’s talk about one specific solution to that “concentration risk”: the exchange fund. (Really, I talk, you listen. Juuuuust the way I like it.) 

Many people seem to think that exchange funds are another one of those “rich, sophisticated people who know how to work the system” tools. So much cool. So much smart. So much brag-worthy. In my opinion, however, in general, you’d be well served by staying away.

I recently went through this analysis with a client, who’d been invited to join an exchange fund and was wondering if she should. (Yes, you have to be invited to participate.) I hereby share the results of that analysis with you, in case you are tempted to join an exchange fund.

Much of what I know about exchange funds comes from my favorite book about equity compensation: Managing Concentrated Stock Wealth. The author, Tim Kochis, is kinda the godfather of equity-comp planning. The first time I ever heard him speak, I remember walking away with this single impression: Almost all the time, the best solution is to sell it, pay the taxes, and move on. So, be aware that that is the attitude I bring with me to all discussions about company stock. Any reason to vary from that approach is gonna have to be Pretty Damn Persuasive.

What is an Exchange Fund?

Let’s just consult Investopedia for its definition:

An exchange fund, also known as a swap fund, is an arrangement between concentrated shareholders of different companies that pools shares and allows an investor to exchange their large holding of a single stock for units in the entire pool’s portfolio. Exchange funds provide investors with an easy way to diversify their holdings while deferring taxes from capital gains.

After you keep your money in the exchange fund for at least seven years, you can “redeem” your shares in the fund (this has no tax impact). Now you own a collection of shares of the individual companies that were represented in the exchange fund. You can choose to sell those shares (or not). At the moment of sale, you will pay long-term capital gains taxes on the gains, i.e., the value of the shares over your original cost basis. That’s what the above definition means by “deferring taxes.”

An example:

  1. Your investment portfolio is $3M. $2M (67%) of that is Airbnb stock. You acquired this stock by exercising ISOs way long ago, and so your cost basis in that stock is only $20k.
  2. You are invited to participate in an exchange fund and to reduce your concentration in Airbnb, you accept.
  3. You move all $2M (for simplicity’s sake) into the fund. This happens with no tax consequences. Now, instead of owning $2M of Airbnb, you have $2M of a mix of Airbnb, Meta, Datadog, Fastly, Amazon, Microsoft, Tesla, Nvidia, etc. (all the other stocks that were invited to join the fund). You have moved from ownership of a single stock to (indirect) ownership of many stocks, without incurring any tax bill.
  4. In seven years, you redeem your shares in the exchange fund and now own stock in all those companies (Airbnb, Meta, etc.). All that stock is worth $3M.
  5. You choose to sell all that stock and now you owe taxes: The taxable gain is $3M- $20k = $2.98M. You pay long-term capital gains tax on that $2.98M.
[Added 10/4/2024 for clarity’s sake:] Please note that you don’t have to sell the company stock after seven years. That’s just the earliest that you can.

Why Would You Consider Using an Exchange Fund?

Because taxes suck.

I mean, I’m not one of those types who think taxation is theft. I very much like my paved roads and national parks and national defense and public schools and feeding the hungry. But I know as well as anyone that paying taxes is painful.

Having a lot of your money in a single stock creates a concentration risk. The opposite of concentration is diversification: having a little bit of your money in a lot of stocks (or, more broadly, in a lot of investments, including bonds and, for some people, real estate and commodities and precious metals, to name a few). You get easy diversification when you invest in something like a Total US Stock Market fund or a target-date fund.

If you sell your company stock in order to reduce your concentration and invest the proceeds in a diversified portfolio, you’re gonna have to pay taxes on the gains in the stock you sell. (Notice I said gains; you don’t have to pay taxes on the total value of the stock, only on the growth it has experienced since you acquired it.)

Exchange funds promise that diversification without the tax hit.

Ooooh, that sounds niiiice.

What’s the catch?

Cons of Exchange Funds

Oh, my friend, the catch is big. And multi-faceted. Let us count the ways this can bite you in the butt.

Your money is locked up for seven years.

I’ve already mentioned the seven-year holding requirement in order to get these tax benefits. You might be able to get your money out earlier (check the terms of the exchange fund), but if you do, you won’t get the tax-deferral benefits. The seven year holding period is actually a legal requirement.

Why is this lockup a potential problem?

Well, there’s the obvious “But what if I need the money?” problem. For my client who inspired this blog post, this wasn’t a problem: she has plenty of money outside this company stock and shouldn’t need the company stock money for many years.

Then there’s the not-so-obvious “If the performance of the fund starts to tank, I can’t do anything about it” problem. You gotta leave your money in, watching helplessly as your investment falls in value. And considering that exchange funds are often created after a huge run up in a particular industry’s stocks, it can easily happen that you put the stock into the fund at or near the top…and then watch the stock prices run down. 

[Added 10/4/2024 for clarity’s sake:] Even if you were invested in typical stock funds, it’s not as if I’d recommend selling out of them as soon as the market starts to go down. There’s a reason why the saying is “Buy Low, Sell High” and not vice-versa. If you’re invested in the stock market, you have to be okay with the “down” part.

If your stock is Qualified Small Business Stock (QSBS), you already have the best tax benefit!

[Added 11/13/2024] If you acquired your company stock while the company was still small/early stage, it’s quite possible that your stock is considered Qualified Small Business Stock (QSBS). Why do you care? Because if it is QSBS, you can sell it, at a gain, and not owe any federal capital gains taxes on some to all of those gains. (It’s possible you can avoid state taxes, too, but that is, naturally, state-specific.)

If you can sell stock at a gain without paying taxes (or by paying far less in taxes), your tax need for an exchange fund might be eliminated. So, if you want to participate in an exchange fund, please first make sure that the shares you’ve contributing to the fund aren’t QSBS.

Some of your money is probably invested in crappy real estate.

Twenty percent of an exchange fund must be invested in “illiquid” investments. Usually, this means real estate. So when you participate in an exchange fund, yes, you own a portion of Airbnb, Meta, Datadog, Fastly, Amazon, Microsoft, Tesla, Nvidia, etc. You also own a portion of a real estate investment that the managers of the exchange fund pick.

Here to comment on said real estate investment, Mr. Kochis:

Excellent real estate opportunities can be packaged and sold on their own merits. Real estate used to meet a tax requirement for the packaging of some other main event is not likely to be the kind of with the very best investment characteristics.

In other words, you’re likely not getting the crème de la crème real estate in the fund. Probably not even the plain old crème. And yet 20% of your investment in the fund now depends on that real estate investment’s performance. Not ideal. [Added 10/4/2024 for clarity:] But, you know, check out what this 20% actually is in the exchange fund you’re looking at. I’m not opining on any specific fund.

They’re expensive.

Historically it has been white-shoe firms like Goldman Sachs and Eaton Vance who have offered exchange funds. The fees have been hefty. It’s not surprising to find an annual cost of 2% of your share of the fund. Have $1M in the fund? You’re paying $20,000 each year.

That said, Cache, a much newer company, charges a much-lower fee: 0.50% – 0.95%.

Not-so-diversified diversification

Exchange fund managers try to get stock into the fund (by invitation) in order to recreate/track a diversified market index. That’s the whole point after all: Diversification! (without a tax bill)

Alas, this promise of diversification often doesn’t turn into actual, meaningful diversification.

Again, Kochis writes:

The opportunistic timing of the creation of exchange funds can diminish true diversification even more. These funds are especially likely to be brought to potential investors when a particular market sector has recently enjoyed exceptional growth. [Sound like the tech industry, anyone?] Such growth often leads to many newly wealthy investors looking for ways to manage their new problems—far too much of a single holding in proportion to the rest of their portfolio. They are often found in the same industry or market sector at the same time making for a rather dubious attempt to minimize the downside risks of market exposure for a closely correlated position. This is especially problematic since investors in exchange funds are precluded for 7 years from taking any other action on the stock they contribute.

Traditionally exchange funds have usually tried to track the S&P 500 (which as of earlier this year, was 40% in the tech industry). Cache tries to create a fund that tracks the Nasdaq 100 (when I looked, it was 62% in the tech industry).

So, yes, you diversify away from the risk of your one company. That is valuable! But you’re still wildly exposed to the vagaries of one industry: tech. You own little of US companies in other industries, and probably very little to no international stock, bonds, smaller companies, etc.

Some offerings are very new.

Call me a luddite (I prefer “realistic based on experience”), but at this point I instinctively distrust fintech offerings that haven’t been around for probably at least a decade. I have been burned by a sexy new fintech startup—and have seen many people be burned by others—as the companies “pivot” to find a business model that is actually sustainable. That pivot often completely undermines the value to the early adopters. I daren’t name names for fear of crossing some unknown-to-me legal line, but if you harken back over the last five years, I’m sure you can think of a fintech tool that ended up really damaging some people’s finances and lives.

As much as I instinctively turn up my nose at Goldman Sachs, at least they’ve been offering exchange funds for years and years. I don’t have personal (direct or indirect through my clients) experience working with Cache, but it was founded in early 2022, and frankly that alone is enough for me to be wary of them.

Exchange funds are hugely complicated tools and tech has a history of flouting either the letter of the law or the spirit of best practices (tidily summarized in the euphemistic phrase “disrupting the industry”). Occasionally, yes, the tech folk get punished for it. Much more often, however, the end consumer is the one who suffers.

Your taxes aren’t eliminated, just delayed.

This isn’t a con per se, but it can still hurt you if you think (incorrectly) that exchange funds allow you to avoid taxes. And I fear many people do.

Even if you use an exchange fund and get some level of diversification, when you sell (after at least seven years), you still owe taxes on the gains in the fund. There is value to tax-deferral, for sure! That’s why so many of you likely contribute to your 401(k) pre-tax. But the tax bill is still gonna be there, and, if the exchange fund hasn’t lost a lot of money, the bill is still gonna be big.

When Are Exchange Funds Most Likely to Be Useful for You?

After reading this far, you might wonder, as did my client, “Who, then, would actually benefit from using an exchange fund?”

As best I can tell, you’re most likely to benefit if you’re in the following situation:

  • You’re currently in a high-tax situation (because of your income and/or state), and it’s possible you’ll be in a much-lower tax situation in seven years (because it’s at that point that the taxes will be calculated).
  • Your stock has very low cost basis. That means your gain is large, and the tax bill upon sale will be large. By contrast, if your company stock is all from vested RSUs, it’s probable that your cost basis is actually pretty high (because you paid taxes on the RSU shares when they vested, setting the cost basis equal to the value of the stock on the day of vest), meaning the gain is small. In that case, just selling the stock would actually not create that big a tax bill.
  • You have lots of broadly diversified investments outside the concentrated stock so that the inability to access the money for seven years isn’t a big deal, and the continued lack of broad diversification in the fund isn’t that big a risk to your total portfolio. This is more “you can afford for the exchange fund to go poorly” and less “the exchange fund will actually help you.”

the snark

As I’ve already mentioned, you have to be invited to join an exchange fund. That makes sense, because the managers are trying to construct a fund that tracks a certain market index (ex., the S&P 500). They can’t just take all comers.

You also need to be an Accredited Investor or maybe even a Qualified Purchaser in order to participate. That means that you have to have a certain (high) minimum household income or household net worth.

As you might imagine, this creates a sense of exclusivity, of elitism that can be very tempting.

Kochis writes:

On rare occasions you may have a client who prefers the exclusivity of an exchange fund, despite all its limitations, or one who finds the seven-year lock-up helpful for reasons unrelated to investment optimization [ex., they want an excuse to not give money to family].

Heh. Well, the world takes all kinds. And there probably are some cases where these considerations are important enough. Though, if they are, I’d suggest you might benefit more from some personal or family therapy.

One of the basic rules of investing is: Don’t invest in anything you don’t understand.

As you now perhaps understand, exchange funds can be wildly difficult to understand (well). So, either avoid exchange funds, acquire the knowledge yourself to analyze the opportunity (but lord, why would you spend your one wild and precious life doing that??), or work with a financial professional who already has the knowledge (not only of exchange funds, but also the knowledge of you and your goals).

If you want help thinking through all the complicated “but maybe they’re good?” financial opportunities in your life, from someone who knows you and cares about you, reach out and schedule a free consultation or send us an email.

Sign up for Flow’s twice-monthly blog email to stay on top of our blog posts and videos.

Disclaimer: This article is provided for educational, general information, and illustration purposes only. Nothing contained in the material constitutes tax advice, a recommendation for purchase or sale of any security, or investment advisory services. We encourage you to consult a financial planner, accountant, and/or legal counsel for advice specific to your situation. Reproduction of this material is prohibited without written permission from Flow Financial Planning, LLC, and all rights are reserved. Read the full Disclaimer.

Focus on these Few, Important Parts of Your Auto Insurance

Block Woman stands in focus in the background with two blurry red cars in the foreground that have crashed into each other.

My husband pointed me to this recent, kinda insane Twitter thread about auto insurance: 

It tells story after story of people doing or saying “dumb” things about auto insurance.

You get enough such stories strung together and you start to realize, “This isn’t the consumer’s fault. It might be their problem, but it’s (often) not their fault. They’re not doing these ‘dumb’ things because they’re dumb or subject to magical thinking. The system is simply too complicated to understand (alongside the umpteen other systems they need to understand…oh yeah and don’t forget their job and family obligations).”

That plus the fact that some clients have been goggle-eyed at the increase in their auto insurance premiums and, lo’, this blog post was born.

We are not insurance agents or brokers (originally typed as “borkers,” and let me tell you, that almost stayed) here at Flow. Such people have already written lots of articles across the internet that explain every aspect of auto insurance. I’m not interested in recreating that. (You should absolutely work with an auto insurance agent or broker in order to fully understand your coverage.)

I’m coming from a perspective of knowing enough about auto insurance and having worked with many a client to figure out the most appropriate coverage for their total financial picture. I have learned what to focus on…and what to safely ignore.

Auto insurance policies can provide a lot of different kinds of coverage. I don’t care about most of them. They’re nice-to-haves.

I want to discuss the short list of items in an auto insurance policy that we review on our clients’ policies—and that you therefore might focus your energies on. We believe they are the most likely to protect you against catastrophic (or even just really painful) financial damage, while keeping premiums as low as possible.

Liability Coverage

When I look at my auto insurance policy, this is formally called “Bodily injury and property damage Liability.” It covers your legal liability when your accident injures another person or damages someone’s property, i.e., when you’re sued by the person you hit.

Now, if you get an Umbrella Liability coverage—which we generally recommend to our clients—you’ll likely need to max out this coverage anyways. But even in the absence of that requirement, this is probably The Most Important Part of your auto insurance.

Why? Because it protects against the most catastrophic financial costs: being sued. While the cost of repairing or replacing your car is bounded (by the value of the car or a replacement car, more or less), people can sue you for any amount they want.

We generally recommend our clients max out their liability coverage.

Deductibles

Setting deductibles too low is probably the most common mistake we find amongst our clients. They’ve set their deductibles to, say, $250 when they could be much higher (usually $1000 is the highest available).

Why do I recommend they raise their deductibles? Because it will lower their premium.

What makes that an acceptable trade-off? The fact that they have plenty of cash to pay that extra $750 if they submit a claim. If you don’t have much cash lying around to pay the possible bill yourself, then yes, you should probably keep your deductible low. In my opinion, deductibles should be set in coordination with your cash emergency fund: the bigger your cash cushion, the higher you can afford to set your deductible.

This logic applies to both Comprehensive (covers the cost of repairing damage to your car by an event other than a car collision, such as theft or vandalism) and Collision (covers the cost of repairing damage if your car overturns or if it hits another car or object) deductibles.

Underinsured/Uninsured Motorist Coverage

That Twitter thread mentioned at the start features a “Plaintiff’s personal injury litigator” who says he recommends to all his friends and family that they get lots of underinsured/uninsured motorist coverage.

Anywhere from 5% to 25% of drivers are uninsured, depending on the state.

Which really really sucks when they hit you. Their lack of insurance, it turns out, ain’t payin’ any of your bills.

There are two parts of this coverage:

  • Underinsured Motorist Bodily Injury: This covers costs for damages you (and a few other related people…see your insurance policy for details) incur, including medical expenses and lost wages.
  • Underinsured Motorist Property Damage: This covers the cost of repairing your car. If your car is a beater ?, then it’s not very worthwhile.

We generally recommend our clients pay for underinsured motorist coverage and tailor the “property” damage coverage to the value of their car.

So, take a look-see at your auto insurance and make sure that you at least have these three categories of your policy set appropriately for your situation, okay? 

And yes, your premiums have probably gone up and they’re probably high…and there’s probably nothing for it but to pay the bill.

That or trade in your vehicle for a 20-year old Toyota Sienna that’s worth about $13 and move out of California. See? Easy!

If you want to work with a financial planner who will take a look at all parts of your financial situation, reach out and schedule a free consultation or send us an email.

Sign up for Flow’s twice-monthly blog email to stay on top of our blog posts and videos.

Disclaimer: This article is provided for educational, general information, and illustration purposes only. Nothing contained in the material constitutes tax advice, a recommendation for purchase or sale of any security, or investment advisory services. We encourage you to consult a financial planner, accountant, and/or legal counsel for advice specific to your situation. Reproduction of this material is prohibited without written permission from Flow Financial Planning, LLC, and all rights are reserved. Read the full Disclaimer.

How Much Can You Safely Spend from Your Investments?…for the Young and Financially Independent

Block Woman stands at the start of a blurry game board of Life.

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How I Created My Own Charitable Giving Plan: The Final Installation (Probably)

Block Woman reviews a hand-written list of potential charitable donations. There is a pile of cash underneath the list.

Two major iterations (and several years) later, my charitable plan is finally where I want it to be. That said, even my original plan was good enough as it was! After all, the charities were still getting our money, and that’s the whole point. So, please, if there’s one lesson you take away from my “journey,” let it be: Just Start Somewhere.

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What Are Estimated Taxes? How Do They Work? What Should You Do About Them?

A few weeks ago, I was talking with a client about his 2023 taxes. About the fact that he hadn’t paid estimated taxes in 2023. And that a probably big, but who-really-knew-how-big tax bill was looming before April 15. And that his CPA would give him some recommendations for paying estimated taxes in 2024. And that he should pay those estimated taxes so we’re not in this position again next year.

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