PayPal (PYPL) RSU sell-vs-hold
Calculator · free · no signup · PYPLSell at vest or hold? Compare after-tax payout from selling PayPal RSUs at vest vs. holding through the LTCG cliff at 12 months.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your vest
Tax inputs
Hold strategy
Best after-tax payout — at year 1 yr
$47,709
Sell + invest wins by $4,981 over Hold 1 yr.
Estimates only. Not financial advice.
Heads-up: under-withholding. Your employer withholds federal tax at the IRS supplemental rate (22.0% on this vest, ≈ $17,600). Your marginal federal rate on this vest is 32.7%, owing $26,171. Expect to settle the $8,571 gap at tax time.
The hidden purchase
Tax was paid at vest either way. Holding is mathematically equivalent to taking $44,509 in after-tax cash and buying $44,509 of PYPL today.
Most diversification frameworks would advise against a purchase that size in a single name; the right answer depends on your conviction in PYPL. Holding past one year converts the gain to LTCG.
Sell + invest
Best payout| Vest value (shares × price) | $80,000 |
| Federal | |
| State | |
| Medicare | −$1,160 |
| Additional Medicare | −$720 |
| Market gain over 1 yr at 10.0% | $4,451 |
| Cap-gain tax on diversified gain — LTCG (federal + state + NIIT) | −$1,251 |
| Net at year 1 yr | $47,709 |
Sell every share at vest; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.
Hold 1 yr
| Vest value (shares × price) | $80,000 |
| Vest tax (federal + state + FICA) | |
| Net at year 1 yr | $42,728 |
Sold 444 shares to cover vest tax (net-settled); kept 556 shares 1 yr to qualify for long-term capital gains.
Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're still employed at vest.
Both columns are stated in year-1 yr dollars. The sell side compounds at the market return; the hold side compounds at your single-stock expected return after a 20% volatility drag.
Estimates only. Assumes net-settled (sell-to-cover) vesting; double-trigger and pre-IPO RSUs are out of scope. Excludes multi-state moves, AMT interactions on other equity, and 83(b) elections. Not financial advice.
You evaluated one RSU vest. The beta plans every vest of every grant across years, with concentration and AMT in the loop.
Request beta access →About PayPal
PayPal (PYPL) is a public Fintech company, headquartered in San Jose, CA. IPO'd Jul 20, 2015.
Last close: $43.65 per share (as of 2026-06-16).
Equity grants at PayPal typically include restricted stock units (RSUs).
PayPal Holdings, Inc. is an American multinational financial technology company operating an online payments system in the majority of countries that support online money transfers; it serves as an electronic alternative to traditional paper methods such as checks and money orders. The company operates as a payment processor for online vendors, auction sites and many other commercial and company users.
Source: Wikipedia (CC BY-SA 4.0)
Founded in 1998 as Confinity by Max Levchin and Peter Thiel, the company merged with Elon Musk's X.com in 2000 to form PayPal. eBay acquired the firm in 2002, then spun it off in July 2015, when shares began trading on NASDAQ under PYPL. Headquartered in San Jose, California, PayPal operates the namesake consumer wallet alongside Braintree, Venmo, Honey, buy-now-pay-later products, and the PYUSD stablecoin. Alex Chriss took the CEO role in 2023. Fiscal 2024 revenue reached roughly $31 billion.
Sources: en.wikipedia.org · investor.pypl.com
Equity comp at PayPal
- RSUs use single-trigger vesting: shares become yours as each portion vests on schedule, and the value is taxed as ordinary income at that point. No IPO or acquisition is required.
Researched 2026-05-07.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by PayPal.
PayPal (PYPL) RSUs vest as ordinary income at the price on vest day. The decision is whether to sell at vest and reinvest, or hold the shares through the 12-month LTCG cliff. This calculator runs both paths through the same after-tax math so you can compare like-for-like.
Example: 500 PayPal (PYPL) RSUs vesting at $43.65 per share is $21,825 of ordinary income on vest day. After roughly 32% combined federal + state + FICA (~$6,984), the post-tax share value is ~$14,841. Holding 12 months for long-term capital-gains treatment then only matters for the price change between vest and sale; the ordinary income at vest is already locked in. The calculator runs both paths through the same after-tax math.
All PayPal tools → · Use the generic RSU Sell-vs-Hold Calculator for any company.
PayPal equity questions
- Should I sell or hold my PayPal RSUs at vest?
- PayPal restricted stock units (RSUs) are taxed as ordinary income on their value at vest whether or not you sell. The only open decision is what to do with the shares afterward: sell at vest and reinvest, or hold past twelve months for long-term capital-gains treatment on any further gain. The calculator above runs both paths through the same after-tax math so you can compare them directly.
- Does PayPal grant ISOs, NSOs, or RSUs?
- Equity compensation at PayPal typically takes the form of restricted stock units (RSUs). Restricted stock units are taxed as ordinary income when they vest.
- Do PayPal RSUs use double-trigger vesting?
- No. PayPal restricted stock units (RSUs) use single-trigger vesting: each tranche becomes yours as it vests on schedule, taxed as ordinary income at that point, with no liquidity event required.
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