Toast (TOST) RSU sell-vs-hold
Calculator · free · no signup · TOSTSell at vest or hold? Compare after-tax payout from selling Toast 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 TOST today.
Most diversification frameworks would advise against a purchase that size in a single name; the right answer depends on your conviction in TOST. 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 Toast
Toast (TOST) is a public Vertical SaaS company, headquartered in Boston, MA. IPO'd Sep 21, 2021.
Last close: $25.07 per share (as of 2026-06-16).
Equity grants at Toast typically include incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs).
Toast, Inc. is an American cloud-based restaurant management software company based in Boston, Massachusetts. The company provides an all-in-one point of sale (POS) system built on the Android operating system.
Source: Wikipedia (CC BY-SA 4.0)
Steve Fredette, Aman Narang, and Jonathan Grimm founded Toast in Boston in December 2011 to replace the legacy, Windows-based point-of-sale systems used by restaurants with a cloud-native Android platform built around the restaurant workflow. Toast handles tableside ordering, kitchen display, online ordering, payroll, and scheduling through a single subscriber platform, charging processing fees on card payments. The company serves over 112,000 restaurant locations in North America and processed more than $140 billion in gross payment volume in 2024. Toast IPO'd on NYSE as TOST in September 2021.
Sources: en.wikipedia.org · alphaspread.com
Equity comp at Toast
- 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 Toast.
Toast (TOST) 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 Toast (TOST) RSUs vesting at $25.07 per share is $12,535 of ordinary income on vest day. After roughly 32% combined federal + state + FICA (~$4,011), the post-tax share value is ~$8,524. 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 Toast tools → · Use the generic RSU Sell-vs-Hold Calculator for any company.
Toast equity questions
- Should I sell or hold my Toast RSUs at vest?
- Toast 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 Toast grant ISOs, NSOs, or RSUs?
- Equity compensation at Toast typically takes the form of incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs). Incentive stock options can trigger the alternative minimum tax (AMT) when you exercise. Restricted stock units are taxed as ordinary income when they vest.
- Do Toast RSUs use double-trigger vesting?
- No. Toast 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.
One piece of the puzzle.
OptionsAhoy plans your Toast equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.