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Equity Compensation · Silicon Valley

RSU & ESPP —
know what you're
actually keeping.

RSUs and ESPPs look great on paper. After federal tax, California tax, and payroll deductions, the reality is often quite different — and most tech employees don't know their real after-tax number until it's too late to plan around it.

Use the calculators below to see your vesting schedule, net proceeds, concentrated stock exposure, and whether holding your shares makes financial sense given your total portfolio.

Open the Calculator How they work ↓
50%+
Combined CA + federal rate for some
15%
Typical ESPP discount
4 yr
Standard RSU vesting schedule

Equity Compensation Calculators
Total RSU grant size
$
Today's share price
%
Estimated stock price growth per year
How shares vest over time
Used for custom schedule
Your marginal federal rate
%
CA default 9.3% — adjust for your state
%
1.45% standard + 0.9% NIIT for high earners
%
Before this grant vests
Total Grant Value (today)
Total Tax Withheld
Net After-Tax Proceeds
if sold at vesting
Concentration Risk

Vesting value and after-tax proceeds by year

Gross vest value
Net after-tax
Tax withheld
View Full Vesting Schedule
YearShares VestingPrice at Vest Gross ValueTax WithheldNet ProceedsCumulative Net
Concentrated Stock Risk — Company Stock as % of Net Worth

Sell vs. Hold Analysis

The case for selling at vesting

  • You've already paid ordinary income tax on the full value — you're holding with after-tax dollars
  • Holding single-stock carries company-specific risk you're not compensated for with higher expected return
  • You already have significant exposure through your salary, options, and career
  • Proceeds can be diversified into a low-cost, tax-efficient portfolio immediately
  • Future gains from holding would be taxed at preferential long-term capital gains rates — but on a concentrated, volatile position

The case for holding (selectively)

  • If you have strong conviction in the company's growth prospects beyond the market
  • Holding 12+ months converts future gains to long-term capital gains rates
  • If your total company stock exposure is already low and concentration risk is manageable
  • Qualified Opportunity Zone investments can defer capital gains from eventual sale
  • A systematic sell strategy (e.g. sell 50% at vesting, hold 50%) can balance risk and upside
For illustrative purposes only. Tax estimates are approximate and use combined federal, state, and Medicare rates. Does not account for Alternative Minimum Tax (AMT), other income, deductions, or the timing of withholding vs. actual tax liability. Actual results vary. This is not tax or financial advice — consult a qualified advisor before making decisions about your equity compensation.
$
Your annual base salary
%
Most plans cap at 10–15%
Length of the ESPP offering period
$
Price at the start of offering period
$
Price at end of offering period
%
Standard IRS maximum is 15%
%
Most 423 plans include a lookback
Shares Purchased
Immediate Gain at Purchase
discount + price appreciation
Tax on Immediate Sale
disqualifying disposition
Net Profit — Immediate Sale
after tax on discount portion

ESPP value breakdown — contribution vs. gain vs. tax

Contribution
Net gain (after tax)
Tax
Qualifying vs. Disqualifying Disposition

Sell immediately (disqualifying)

  • The discount portion is taxed as ordinary income in the year of sale
  • Any additional gain above the purchase price is a short-term capital gain (ordinary rates)
  • Simplest approach — eliminates single-stock holding risk
  • The immediate after-tax profit is still significant due to the built-in discount

Hold 1+ year (qualifying)

  • Requires holding 2+ years from offering date AND 1+ year from purchase date
  • A portion of the gain is taxed at long-term capital gains rates (0%, 15%, or 20%)
  • Can meaningfully reduce tax on larger ESPP balances over time
  • Introduces single-stock risk — price could fall significantly during holding period
ESPP calculations assume a Section 423 qualified plan with lookback provision. Tax treatment differs for non-qualified plans. Qualifying disposition rules require 2+ years from offering date and 1+ year from purchase date. This is for illustrative purposes only and is not tax advice. Consult a CPA or fiduciary advisor for your specific situation.
How Equity Compensation Works

The basics — and what most employees miss.

RSUs and ESPPs are two of the most valuable benefits tech employers offer — and two of the most misunderstood. The tax treatment alone can make a difference of hundreds of thousands of dollars over a career. Here are the things that matter most.

01

RSUs are taxed as income — not as capital gains

When RSUs vest, the full market value is taxed as ordinary income — at rates as high as 50%+ in California. Many employees are surprised to find that 40–50% of their vested shares are withheld for taxes before they see a dollar.

02

Your cost basis is set at vesting — not at sale

When you eventually sell your RSU shares, your cost basis is the fair market value at vesting — not zero. Only gains above that price are subject to capital gains tax, which can be favorable if you hold 12+ months.

03

Concentration risk is the hidden cost of holding

Every RSU you hold after vesting is a bet on your employer's stock with after-tax dollars. Most financial advisors would never recommend putting 20–40% of a client's net worth in a single stock — but that's exactly what many tech employees do by not selling.

Talk to an Advisor

Equity compensation is complex.
Your strategy shouldn't be.

As a fee-only fiduciary with deep experience in Silicon Valley equity compensation, Hooman Altafi helps tech employees build a plan around RSUs, ESPPs, and concentrated stock — with no commission incentives, just objective advice.

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