Your Equity Compensation Is Not a Windfall. It's a Planning Problem.

RSUs and ESPPs generate real wealth. They also generate real tax bills, concentration risk, and decisions most people aren’t prepared for. The difference between having a plan and not having one compounds over time.

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What Happens When Nobody Is Managing This

For most tech executives and senior professionals, equity compensation is a significant part of total income. It’s also the part that gets the least strategic attention.

RSUs vest on a schedule. Most people look at the deposit, note the automatic withholding, and move on. ESPPs get purchased at a discount, maybe sold immediately, maybe held, without much analysis of the tax consequences or how it fits into the broader portfolio. Year after year, decisions get made by default: hold everything, sell everything, or whatever the HR financial wellness presentation suggested.

The result is a growing concentration in a single stock, a tax situation that’s more complicated than it looks, and a collection of shares that haven’t been connected to any broader wealth strategy.

The Specific Problems We Solve

Vesting events that land in the wrong year

Every RSU vest is taxable as ordinary income in the year it vests, at the value on the vesting date, regardless of whether you sell. If that vest lands in an already-high-income year with no offset strategy in place, the tax cost is whatever the bracket says. If someone is looking at the vesting schedule in advance, identifying whether there are deductions, losses, or other strategies available in that same year, the outcome can be meaningfully different. The window to act is before the vest, not after.

Concentration that builds without a plan

The second you receive RSUs or ESPP shares, a portion of your net worth is tied to a single employer. Most people know this is a risk in the abstract. Few have a formal plan for how much concentration is acceptable, at what threshold they'll diversify, and how they'll manage the tax cost of doing so. Without a plan, the default is inaction, and the concentration grows.

ESPP decisions made without the full picture

ESPPs offer a discount on company stock, which creates an immediate return on paper. But the tax treatment of ESPP shares is specific and often misunderstood: qualifying versus disqualifying dispositions, holding period requirements, and the interaction with ordinary income versus capital gains all determine what you actually keep. Most people know they got a discount. Few know what they're actually keeping after taxes or how the shares fit into their overall portfolio.

How We Approach Equity Compensation Planning

We look at your full equity picture, vesting schedule, unvested grants, ESPP participation, current holdings, alongside your tax situation, investment portfolio, and liquidity needs.

From there, we build a strategy: when to hold, when to sell, how much concentration is appropriate at your net worth level, and how to manage the tax cost of diversification over time. That strategy gets revisited at every major vesting event, not just once and forgotten.

For clients with significant unvested grants or meaningful company stock concentration, this coordination with your broader investment and tax strategy — and the full picture of your financial life — is one of the highest-leverage things we do.

Turn Equity Compensation Into a Long-Term Strategy

If you have RSUs vesting, an ESPP you’re participating in, or a growing concentration in company stock with no formal plan for managing it, the right time to build that plan is before the next vest, not after.

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Investing involves risk including possible loss of principal. No strategy assures success or guarantees against loss. Results vary based on individual circumstances and are not indicative of future results.