Tax planning and advisory services for stock-compensated professionals at public and private companies, before the vest, not after.
Here's how a typical equity-comp year unfolds when no one's planning ahead.
Without a mid-year projection, there's no way to know what the vest will cost you in taxes, or how to prepare for it. The clock is already running.
Most companies withhold at a flat 22% supplemental rate. If you're in a higher bracket, that gap is quietly accumulating. Nobody told you to adjust your W-4 or set cash aside.
Short-term vs. long-term capital gains is a meaningful difference. Without guidance on timing your sales, you may be paying ordinary income rates on gains that could have qualified for preferential treatment.
This is the moment most stock-compensated professionals call a CPA for the first time. Unfortunately, at this point the planning window has closed.
The good news: every one of those moments is preventable with the right plan in place before January.
Equity comp returns aren't difficult because the math is complicated. They're difficult because the planning happens outside of tax season, and most CPAs only show up in March. By then, the decisions that matter most have already been made.
We work with stock-compensated professionals year-round. That means when your next vest is approaching, when your company announces a tender offer, or when you're thinking about exercising options, you have someone to call who already knows your situation — not someone you're briefing from scratch.
Your equity situation is personal and often tied to confidential company information. You shouldn't have to re-explain your vesting schedule every time you have a question. Your CPA knows your file.
We serve clients in both English and Spanish. For stock-compensated professionals in bilingual households, or those who simply prefer to have complex financial conversations in Spanish, we work fluently in both. Nothing gets lost in translation.
A free 30-minute call to understand your equity comp structure, your current filing situation, and what's at stake in the next 12 months. No obligation, just clarity.
Based on your equity type, vest schedule, and complexity, we'll outline exactly what's included, what it costs, and when we'll be in touch throughout the year. Flat-fee, no surprises.
Quarterly touchpoints tied to your vest schedule, proactive outreach before key events, and direct access to your CPA when decisions need to be made quickly.
Both, at two separate moments. RSUs are taxed as ordinary income at vesting, based on the share value that day, and your employer typically withholds shares to cover it. Then when you sell, any gain or loss measured from the vesting-date value is taxed again as a capital gain or loss.
The trap I see most: employers withhold at the standard 22% supplemental rate, which under-withholds for high earners and leaves a balance due at filing. That's why I plan around the vesting schedule ahead of time, projecting the expected liability and addressing any shortfall before April, so there are no surprises.
Whether to hold or sell after vesting comes down to your situation. Short-term and long-term capital gains each carry trade-offs, and the holding period runs from the vest date. I lay out both sides so you understand the full picture before deciding.
Exercising an ISO and holding the shares past year-end triggers AMT on the "bargain element," the spread between your strike price and the stock's fair market value at exercise. That spread isn't taxed for regular income tax at exercise, but it is an adjustment for AMT, which catches many people off guard.
ISOs carry holding requirements that determine how they're ultimately taxed, which is why planning the exercise matters. A common strategy is to exercise up to your AMT crossover point, the level where AMT would start to apply, and, in years you do pay AMT, to track and use the AMT credit in future years.
Not all stocks carry the same risk. Exercising and holding a volatile position can leave you owing AMT on a paper gain that later evaporates. That's why I weigh the pros and cons of a specific position before you exercise.
Because brokers are only required to report your discounted purchase price as the cost basis, not the amount already taxed as ordinary income on your W-2. Left uncorrected, this makes you pay tax twice on the same discount: once as wages, and again as an inflated capital gain.
This is an error that less experienced preparers miss, because it requires knowing to pull the broker's supplemental statement and adjust the basis on Form 8949. The correct basis is your purchase price plus the portion already taxed as ordinary income, and using it usually produces a lower, accurate gain.
Timing matters too. Qualifying dispositions (which meet the ESPP holding rules) and disqualifying dispositions are taxed differently, and each changes how much of your proceeds are ordinary income. There are cases where a disqualifying disposition is strategically the better move, which is why planning ahead lets you evaluate all your options rather than react at filing.
An 83(b) election lets you choose to be taxed on restricted equity at grant, when it's worth little, instead of at vesting, when it may be worth far more. For founders and early employees whose stock is subject to vesting, it can convert a large future ordinary-income hit into long-term capital gains.
The deadline is strict and unforgiving: 30 days from the grant date, with no extensions and no relief for missing it.
It isn't right for everyone. The best candidates are early-stage founders and employees whose shares are still worth very little, so the tax paid upfront is minimal. The risk is real, though. You pay tax now, and if the stock loses value or you leave before the shares vest, you don't get it back. The election also offers little benefit when the stock is already worth a lot at grant. And it doesn't apply to RSUs at all: because RSUs are only a promise of future shares, you don't own anything on the grant date, so the IRS doesn't permit an 83(b) election for them.