A Different Kind of Paycheck

For most executives, the real risk isn't the market, it's concentration. Between vesting RSUs, ISOs, and an employer stock purchase plan, a meaningful share of net worth often ends up tied to the same company that pays the salary. It's easy to let that happen: loyalty, inertia, insider trading windows, and the tax cost of selling all conspire to keep a position exactly where it is. But when a career and a portfolio are riding on the same company, a downturn doesn't just affect one part of the picture. It affects all of it, at the same time.

Equity compensation isn't something to manage in isolation. A 10b5-1 trading plan, the timing of a deferred comp distribution election, the difference between how ISOs and NSOs are taxed, and a broader retirement income plan all need to be built around each other, not treated as separate problems solved separately. Deferred comp in particular carries a risk many executives underestimate: unlike a 401(k), it's typically an unsecured promise from the company, not a protected asset, which changes how much of a retirement plan it's wise to build around it.

Fairfield County is home to a dense concentration of corporate headquarters and senior leaders commuting to or from New York: which means multi-state tax exposure, blackout periods and insider trading rules that constrain when stock can actually be sold, and a cost of living that makes even a strong equity package feel less secure than the number on paper suggests. A generic approach to equity comp doesn't account for any of that. One built specifically around how executive compensation actually works here does.

We help executives turn a compensation package built by someone else's HR and legal teams into a retirement income plan that's actually theirs: one that manages concentration risk deliberately, times equity and deferred comp decisions around taxes rather than around the calendar, and doesn't leave a career's worth of hard-earned equity exposed to a single company's fortunes.