Tripadvisor (TRIP) RSU sell-vs-hold
Calculator · free · no signup · TRIPSell at vest or hold? Compare after-tax payout from selling Tripadvisor 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 TRIP today.
Most diversification frameworks would advise against a purchase that size in a single name; the right answer depends on your conviction in TRIP. 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 →Related calculators: RSU Lot Order Calculator · Stock Concentration Calculator
About Tripadvisor
Tripadvisor (TRIP) is a public Consumer Internet company, incorporated in Delaware and headquartered in Needham, MA.
Equity grants at Tripadvisor typically include restricted stock units (RSUs).
Tripadvisor is an American company that operates online travel agencies, comparison shopping websites, and mobile apps with user-generated content.
Source: Wikipedia (CC BY-SA 4.0)
Stephen Kaufer founded the company in 2000 in Needham, Massachusetts, originally intending to aggregate professional travel reviews before user submissions took over. The review corpus became the asset, and the business monetizes through hotel meta-search auctions, plus Viator for tours and TheFork for European restaurant bookings. Traffic depends heavily on search engine placement, which makes Google's own travel products a structural competitive concern. The company separated from Expedia in 2011.
Sources: tripadvisor.com · en.wikipedia.org
Equity comp at Tripadvisor
- 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 2026-08-17.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Tripadvisor.
Tripadvisor (TRIP) 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.
All Tripadvisor tools → · Use the generic RSU Sell-vs-Hold Calculator for any company. Diversifying multiple RSU lots? See the lot-by-lot sell order →
Tripadvisor equity questions
- Should I sell or hold my Tripadvisor RSUs at vest?
- Tripadvisor 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 Tripadvisor grant ISOs, NSOs, or RSUs?
- Equity compensation at Tripadvisor typically takes the form of restricted stock units (RSUs). Restricted stock units are taxed as ordinary income when they vest.
- Do Tripadvisor RSUs use double-trigger vesting?
- No. Tripadvisor 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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