Equity compensation
Every type of equity comes with its own decisions.
We evaluate equity in the context of your full financial life, not in isolation. Choose your situation to see the core question, what we model, and the mistakes we help you avoid.
Restricted stock units
Would you buy this stock with cash today? If not, holding vested RSUs is making that same choice.
What we model
- The gap between 22% supplemental withholding and your actual tax rate
- Sell-at-vest versus hold, by tranche
- Company stock as a share of your net worth
- Your vesting calendar against trading windows
- Estimated tax payments to avoid penalties
Mistakes we help you avoid
- Assuming withholding covers the whole bill
- Paying tax twice because cost basis was misreported on your 1099-B
- Letting one company quietly become most of your net worth
Incentive stock options
How many should you exercise, and when, without an alternative minimum tax surprise?
What we model
- Your AMT crossover point each year
- Holding periods for long-term treatment: two years from grant, one from exercise
- Early exercise and 83(b) elections
- The $100,000 annual limit, beyond which options are treated as NSOs
- Post-termination exercise windows if you change jobs
- The optimal time of year to exercise
- Recovering your AMT credit through timed sales
Mistakes we help you avoid
- Exercising without modeling AMT
- Missing a 90-day exercise window after leaving
- Waiting for long-term treatment when the stock risk outweighs the tax savings
Non-qualified stock options
When does the ordinary income at exercise make the most sense for you?
What we model
- Exercise timing across tax years and brackets
- Withholding versus what you'll actually owe
- Exercise-and-hold versus cashless exercise
- State sourcing if you've moved or plan to
- Expiration dates across every grant
Mistakes we help you avoid
- Letting valuable options expire
- Under-withholding and an April surprise
- Exercising and holding without a clear reason
Employee stock purchase plans
Should you participate fully, and when should you sell?
What we model
- The value of the discount and any lookback provision
- Qualifying versus disqualifying dispositions
- The ordinary income piece of each sale
- Cash flow during contribution periods
Mistakes we help you avoid
- Basis reporting errors that inflate your taxes
- Holding for qualifying treatment when the stock risk isn't worth it
- Skipping a plan that's often one of the best deals in your benefits package
Tender offers, IPOs, and acquisitions
How much should you sell when the window opens, and what happens to the cash?
What we model
- Tax character of each lot, including recently exercised ISOs
- QSBS (Section 1202) eligibility
- IPO lockups, trading windows, and 10b5-1 plans
- Deal terms in an acquisition: cash, stock, and escrow
- An investment plan for the proceeds
- Selling strategies that help you recover the AMT credit faster
Mistakes we help you avoid
- Making a large decision under a deadline with no plan
- Forgetting that selling ISO shares early creates ordinary income
- Leaving proceeds in cash with no strategy
- Improper tax reporting
Facing a deadline? Ongoing clients get priority help around tender offers, IPOs, and other liquidity events.
Public or private, the questions change.
At a private company
Your equity may be worth a lot on paper, but you can’t sell it yet.
The big decisions are whether to exercise early, how much cash to put at risk, and how to plan for a liquidity event that may be years away. We look at 83(b) elections, QSBS eligibility, and AMT at today’s 409A value, so you invest in your company’s future on purpose, not by default.
At a public company
Your equity is liquid, so every day you hold it is a choice.
The big decisions are how much to keep, when to sell, and how to diversify without giving up more to taxes than you need to. We build a plan around your vesting schedule and trading windows.
Where equity fits in the bigger plan
Equity can accelerate wealth, or create tax surprises and concentration risk. We coordinate equity decisions with your taxes, cash needs, and long-term goals.
- Evaluate ISO and NSO exercise decisions with a full tax projection
- Decide how much single-company risk you can reasonably carry
- Compare early exercise with waiting for liquidity
- Diversify concentrated positions on a tax-aware schedule
- Turn liquidity into a long-term investment plan
- Create a long-term exercise and sale strategy that fits the rest of your plan
Ready for clarity?
Let's talk about where you are, what's coming up, and how to plan for it. A free 30-minute call, no pressure.