Stripe told employees on February 24, 2026, that it will run another tender offer valuing the payments company at $159 billion, up from $91.5 billion a year earlier, according to the company's 2025 annual letter. Thrive Capital, Coatue Management and Andreessen Horowitz are funding the purchase alongside Stripe itself, and the offer is open to both current and former employees, giving many equity holders their first chance to sell shares since last year's tender.
What changed
Stripe reported $1.9 trillion in total payment volume for 2025, a 34% increase over 2024, and said its revenue suite of billing and invoicing products is on pace for a $1 billion annual run rate. Co-founder John Collison told CNBC the company remains in no hurry to go public, citing strong organic growth and profitability. The tender offer, rather than a public listing, is Stripe's mechanism for letting employees and early shareholders convert paper wealth into cash while the company stays private.
Who is affected
The tax outcome for a Stripe employee selling into this tender depends heavily on how the shares were granted. Employees holding restricted stock units under a typical private-company double-trigger structure recognize ordinary income under Section 83 only when both vesting conditions are met, generally continued service plus a liquidity event such as this tender. For many employees, participating in the tender itself is the second trigger, meaning the full value of the shares sold is taxed as W-2 ordinary income and subject to withholding in the year of sale. Employees who instead hold shares from an early exercise of stock options, and who filed a Section 83(b) election at grant, may owe only capital gains tax on the appreciation since that earlier vesting date.
The after-tax math
Example: an employee who sells $500,000 of Stripe shares in this tender, where the RSUs vest concurrently with the sale, would generally see that full amount taxed as ordinary income, potentially reaching the top federal rate plus payroll tax withholding, with little room to convert it to the lower 0%, 15% or 20% long-term capital gains rates. By contrast, an early employee who exercised options years ago and held the resulting shares for more than a year before this tender would owe capital gains tax only on the increase in value since exercise, a meaningfully lower rate for the same dollar amount of proceeds. The difference is entirely about grant type and holding period, not the tender offer itself.
| Grant type | Tax at tender sale | Applicable rate |
|---|---|---|
| RSU vesting at the tender (typical case) | Ordinary income on full value | Up to 37% federal, plus payroll tax |
| Exercised options, held over 1 year, no 83(b) issue | Capital gain on appreciation since exercise | 0% / 15% / 20% federal |
| Exercised options, held under 1 year | Short-term capital gain | Ordinary income rates |
Moves to discuss with your advisor
- Whether shares being sold are RSUs taxed as ordinary income at the tender, or option shares eligible for capital gains treatment.
- Whether the concentration of a large share sale in a single tax year pushes other income into a higher bracket or triggers the net investment income tax.
- Whether proceeds should fund quarterly estimated tax payments to avoid an underpayment penalty, since employer withholding on supplemental wages may not cover the full liability.
- Whether diversifying out of a concentrated position, now that a market exists to sell, reduces single-company risk relative to continuing to hold private shares with no public market.
What to watch
Stripe has not disclosed a target IPO date, and Collison's comments suggest the company sees little near-term need to list. For employees, that means periodic tender offers, rather than a public listing with continuous liquidity, remain the primary way to realize value from Stripe equity, and each one carries its own tax timing decisions that are easiest to plan for before shares are actually tendered. Employees at other large private companies running similar liquidity programs face the same set of choices, since the tax treatment turns on grant mechanics that are common across the industry, not on any feature specific to Stripe.
Sources
After TAX is an independent publication. Articles are general information, not tax, legal or investment advice. Consult a licensed professional about your situation.
