While equity compensation can be a powerful wealth-building tool, it also introduces a unique set of financial planning challenges, especially as your position becomes more concentrated.
Having built my practice in the Bay Area, a large portion of the families I’ve helped have worked in the tech space in one form or another. If you work in tech, there’s a good chance a meaningful portion of your net worth is tied up in company stock—often through RSUs, ISOs, or non-qualified stock options. While equity compensation can be a powerful wealth-building tool, it also introduces a unique set of financial planning challenges, especially as your position becomes more concentrated.
Over the past decade, I’ve worked with engineers, product managers, and executives at fast-growing companies that have built a great life by keeping their eggs in the company basket. While it worked out for them on the ride up, they end up grappling with the same question:
How do I reduce risk and minimize taxes without losing out on the future upside?
To help clients navigate this, I use a four-part framework called M.I.L.O, designed specifically for professionals facing the complexity of concentrated stock positions. Here’s how it works.
You don’t have to sell all your shares to protect yourself. Using options strategies—like protective puts, covered calls, collars, or exchange fund replication—can reduce downside exposure, generate an additional source of income, or diversify your exposure to traditional indexes like the S&P.
By using complex options strategies, we can protect the wealth you’ve accumulated and take some of the risk off the table. This gives us breathing room to be more tax-efficient while we divest over time.
When you’re in your peak earning years, the basic tax levers matter. We focus on the no-brainer strategies—things like:
These aren’t flashy moves, but they’re foundational. They create long-term tax savings and open up room in your income plan to realize gains from your concentrated position more strategically. In other words, we’re building a clean, tax-smart base to work from.
When markets fluctuate—or when you’re diversifying—tax loss harvesting becomes a key lever. This means intentionally realizing investment losses to offset gains elsewhere in your portfolio.
For many of my clients, we use direct indexing to automate this process, aggressively capturing losses without disrupting overall market exposure. This allows you to keep a diversified portfolio and use the losses that arise throughout the year to offset the gains from your concentrated position and sell more tax efficiently.
Selling shares isn’t just about the price—it’s about the tax context. We build a forward-looking strategy that allows you to exit in phases, with minimal tax drag.
A big part of this is setting a “capital gains budget”—a target amount of gains we can realize in a given year without pushing you into a higher bracket, triggering the Net Investment Income Tax (NIIT), Alternative Minumum Tax (AMT), or affecting Medicare premiums. We coordinate this budget with your salary, bonuses, deductions, and other planning goals.
This structured approach takes the guesswork out of “when to sell” and helps you stay in control of your tax exposure over time.
While the MILO method serves as a strong foundation for addressing concentrated stock positions, there are additional strategies we often incorporate that can be just as impactful.
If you have charitable intent, we can use that to your advantage. By grouping charitable contributions into years when you’re realizing significant gains, you can reduce your tax bill while supporting causes you care about. Tools like Donor Advised Funds (DAFs) allow you to donate highly appreciated assets directly—avoiding capital gains tax and still receiving a full deduction for the fair market value. It’s an efficient way to give and a smart way to chip away at a concentrated position.
Another strategy that often comes up is the Exchange Fund. When implemented correctly, it allows you to contribute your concentrated stock into a pooled fund and receive a diversified portfolio in return—without triggering capital gains at the time of the exchange.
It’s a compelling concept, but it comes with trade-offs. Most exchange funds require multi-year lock-up periods, complex tax reporting, and higher fees. And while gains are deferred, they’re not eliminated. On top of that, access is limited—these funds are typically only available to accredited investors, and allocations can be hard to secure.
In many cases, we use options strategies to replicate the diversification benefits of exchange funds while retaining more flexibility and control. It’s not about ruling out the tool—it’s about understanding where it fits and going in with eyes wide open.
Equity compensation is complex—but with the right plan, it doesn’t have to be stressful. The MILO method gives us a structured, proactive way to reduce risk, lower taxes, and preserve the wealth you’ve worked so hard to build.
We call this framework the MILO method—a structured, tax-aware approach to managing concentrated stock positions. It also happens to be the name of my cat, who (like many tech clients) is independent, strategic, and occasionally way too concentrated on one thing.
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