Plan for the tender, not the IPO.
Stripe’s tender offers are how your equity becomes money — and each window is a tax decision as much as a selling decision. This guide covers how the Stripe tender offer process works, what your annual grants actually give you, and how to diversify without handing the gains back in taxes.
Stripe has stayed private while becoming one of the most valuable companies in tech.
For employees, liquidity isn’t an event you wait for. It’s a rhythm you plan around.
Suhas Joshi
// ADVISOR, PROSPERO WEALTH · FORMER STRIPE EMPLOYEE
Suhas worked at Stripe and has held Stripe equity himself — he’s been inside the tender windows, weighed the same elections, and made these decisions with his own shares. He has helped Stripe employees navigate everything this guide covers. For him it isn’t theory; it’s felt experience.
// THE LIQUIDITY RHYTHM
Two tender windows a year — and they are not equals
A Stripe tender offer is a company-arranged window in which eligible current and former employees can sell a portion of their vested shares at a set price, typically to outside institutional investors and to Stripe itself. Because Stripe is private, these windows are effectively the only sanctioned way to turn shares into cash — which makes their structure worth understanding in detail.
In recent years the pattern has been consistent: a major tender offer early in the year, and a smaller liquidity window late in the year. The February 2026 tender — with participation from Thrive Capital, Coatue, a16z, and a share repurchase by Stripe itself — valued the company at approximately $159B, up from $91.5B in the February 2025 tender.
Stripe valuation at recent liquidity events
Feb 2025 tender offer
$91.5B
Sept 2025 secondary
$106.7B
Feb 2026 tender offer
$159B
Valuations as publicly reported (CNBC, Crunchbase News, Stripe newsroom). Confirm all terms through Stripe’s official tender documentation.
The two windows, compared
Pricing
Anchored by outside investors negotiating to buy in — real price discovery
Based on the prevailing 409A valuation, with little external pressure on price
Size
The year’s primary liquidity event
Limited — employees report caps in the neighborhood of $50K
Typical timing
Q1
December
Planning role
The decision window that matters most
A modest release valve, not a diversification plan
Based on recent tender cycles as described by current and former employees. Stripe sets timing, eligibility, and terms for each event, and they can change without notice.
Why the price barely moves between tenders
Stripe conducts 409A valuations quarterly, but a 409A is an appraisal, not a market. Because Stripe isn’t raising outside capital, there is usually little forcing the appraised value upward between tender events. The practical effect: the early-year tender, where outside investors actually negotiate a price, is where the real number gets set — and public-market events like major fintech and AI IPOs may influence what those investors are willing to pay.
// YOUR GRANTS
Annual grants, one-year vesting — equity that behaves like a bonus
Stripe grants equity to most employees as annual RSU refreshers that vest over a single year, rather than the four-year initial grants common at other tech companies. The structure changes what your equity actually is: less a lottery ticket on long-term appreciation, more a recurring component of annual compensation.
Each year’s grant is priced at that year’s valuation. If the 409A keeps climbing, the same dollar grant buys fewer shares — you participate in upside one year at a time, not across a four-year window.
Grant size scales with level, and the equity share of total compensation generally grows as you move up.
Vested shares are yours. RSU shares stay with you if you leave Stripe. Some longer-tenured employees also hold legacy stock options — covered in section 04.
Taxes happen at vest. RSU value is ordinary income (plus payroll tax) as it vests, whether or not a tender window is open — one reason concentration builds quietly. See our RSU planning guide for the general mechanics.
The cash-or-equity election
Stripe has reportedly begun offering some employees a choice: take the annual refresher as RSUs, or take it as cash. At vest the two are generally tax-equivalent — both are ordinary income. The real question is what you’re left holding afterward.
One way to think about the election
Little or no existing Stripe stock
Taking equity may be a reasonable way to participate in upside you don’t otherwise have — your exposure starts near zero.
Years of accumulated vested shares
Taking cash may be worth considering — the election is a rare chance to stop adding to a concentrated position without selling anything.
Educational framing only — the right choice depends on your full financial picture, goals, and risk tolerance. This is not individualized advice.
// FROM SOMEONE WHO’S BEEN INSIDE
Your job depends on Stripe. Your bonus depends on Stripe. Your future grants depend on Stripe. The question is how much more of your net worth should.
— SUHAS JOSHI, FORMER STRIPE EMPLOYEE
There’s no scientific threshold for “too concentrated.” Some advisors treat a single position above roughly 20% of net worth as a flag worth examining, but the honest answer is that the right ceiling depends on your goals, your spending needs, and how much of your future earnings already ride on the same company. Our concentrated positions guide covers the framework in depth.
// THE IPO QUESTION
Stripe gets the benefits of being public without going public
As of mid-2026, Stripe remains private and has announced no plans for an IPO. In January 2026, co-founder John Collison told Bloomberg the company is “still not in any rush” to go public — consistent with years of similar statements.
The traditional IPO pressures are largely absent. Employees get liquidity through tenders. Early investors get liquidity through the same events. The company is profitable and isn’t raising capital. The constituencies that usually push a company public have already been accommodated.
Nobody can predict an IPO — including Stripe employees, and including us. Stripe could announce one next quarter, or stay private for another decade.
The planning answer doesn’t require a prediction. Treat tender offers as your liquidity path. If an IPO comes, it’s upside to a plan that already works — not the event your finances were waiting on.
An IPO is a possibility. The tender calendar is a plan.
// THE LEGACY ISO CLOCK
If you still hold old ISOs, the calendar is not your friend
Some longer-tenured Stripe employees still hold incentive stock options (ISOs) granted before Stripe shifted to RSUs — employees report grants as late as 2017–2018, typically carrying 7-to-10-year expiration terms. Unlike RSUs, options expire — and at a private company, the squeeze between taxes, liquidity, and the expiration date can get genuinely tight.
// THE CASH PROBLEM
Exercising costs money today
Strike prices on old grants may be low, but the check is real — and it buys shares you can’t sell yet.
// THE AMT PROBLEM
Exercise-and-hold can trigger AMT
The spread between strike and the current 409A may be taxable under the alternative minimum tax — a bill on paper gains.
// THE LIQUIDITY PROBLEM
No sale until a tender window
Exercised shares can generally only be sold in a company-arranged event. The December window’s limits rarely help much.
// THE DEADLINE
Expiration doesn’t wait
What if there’s no meaningful tender the year your options expire? That’s the scenario to plan against.
The broad choices are well defined, and each carries trade-offs worth modeling carefully: exercising early and holding may start the clock toward long-term capital gains treatment at a future liquidity event, but creates AMT exposure and ties up cash in illiquid shares. Exercising and selling within the same tender is generally a disqualifying disposition — the spread is taxed as ordinary income. Letting options expire forfeits them entirely. Borrowing against private shares to fund an exercise is technically possible through specialty lenders, but terms are often punishing, and employees who took such loans in past downturns sometimes lost most of their equity value.
None of these is universally right. The point is that ISO holders have a decision with a deadline — and the worst outcome is usually the one that happens by default.
// THE TAX REALITY
Selling in the tender: what you’ll actually owe
For most Stripe employees, shares sold in a tender offer are taxed as capital gains on the appreciation since vest — because RSU value was already taxed as ordinary income when it vested. That makes lot selection, holding periods, and full-year tax projection the three levers that matter in a tender year.
Which lots you sell matters. Shares from older vests may carry more gain but qualify for long-term rates; recent vests may have little gain at all. Selling your highest-basis lots first may reduce the tax cost of the same dollar of liquidity — in some cases substantially.
Holding period sets the rate. Shares held more than a year from vest are generally taxed at long-term capital gains rates; shares held less, at ordinary rates. The difference can run into double-digit percentage points depending on your bracket and state.
Withholding on a tender is not your tax bill. A large gain can push you into estimated-tax territory — confirming safe-harbor payments with your tax preparer before year-end may help you avoid underpayment penalties.
ISO sales play by different rules. Same-window exercise-and-sell is generally a disqualifying disposition taxed as ordinary income; previously exercised shares that meet both holding periods may qualify for long-term treatment (see section 04).
Illustrative — why lot selection changes the bill
Vested 3 years ago
Long-term capital gains
Vested 14 months ago
Long-term capital gains
Vested 5 months ago
Short-term capital gains
Hypothetical figures for illustration only — not Stripe’s actual share prices or any client’s holdings. Your basis, holding periods, and rates will differ. Consult a qualified tax professional before making lot selections.
// AFTER THE TENDER
The short menu: what private stock allows, and what to do with it
Private company shares can’t be hedged, exchanged, or borrowed against the way public stock can — most of the standard concentrated-position toolkit simply doesn’t apply to Stripe equity. That narrows the menu to a few levers — which makes using them well matter more.
// OFF THE TABLE WHILE PRIVATE
Options collars and protective puts — no listed options on private shares
Exchange funds — generally limited to publicly traded stock
Variable prepaid forwards — same constraint
Margin loans at standard terms — specialty private-stock lending exists, but terms are often severe
// THE LEVERS THAT EXIST
Sell in tender windows — deliberately, with lot selection and a tax projection
Elect cash refreshers to stop adding exposure
Donate shares to a donor-advised fund — in some cases, with Stripe’s approval
Transfer to a spouse or trust for estate planning — in some cases; specialized advice required
Reinvest tender proceeds in a tax-aware diversification strategy
Turning tender proceeds into a diversification engine
Selling concentrated stock creates gains; the question is whether anything offsets them. This is where a tax-aware long/short portfolio may earn its keep: funded with tender proceeds, it can harvest losses that offset the gains from this year’s sale — potentially positioning you to sell more in the next tender on better tax terms. Sell, offset, repeat: across several tender cycles, some employees may be able to unwind a concentrated position while deferring much of the tax bill. Direct indexing offers a simpler, long-only version of the same idea.
What this looks like across three tender cycles
We’ve written a hypothetical case study following a Stripe employee with a concentrated position through a multi-year sell-down — tender sales, a long/short portfolio generating offsetting losses, and the trade-offs at each step. It’s representative of client scenarios we see, not an actual client account.
Read the case study →
// COMMON QUESTIONS
Stripe equity, asked directly
How often does Stripe do tender offers?
In recent years Stripe has typically arranged a major tender offer early in the year — February 2025 at a $91.5 billion valuation and February 2026 at approximately $159 billion — with a smaller year-end liquidity window also reported by employees. Timing, eligibility, and terms are set by Stripe and can change.
Will Stripe IPO?
Stripe has announced no IPO plans, and co-founder John Collison said in January 2026 that the company is in no rush to go public. Because tender offers already provide liquidity to employees and early investors, many of the usual pressures to IPO are absent — which is why many employees plan around tenders rather than waiting for a public listing.
What is Stripe stock worth?
Stripe shares have no public market price. Value is set by quarterly 409A appraisals and, more meaningfully, by the price outside investors pay in tender offers — the February 2026 tender valued Stripe at approximately $159 billion. Between tenders, the appraised value typically moves little because Stripe isn’t raising external capital.
Can I sell my Stripe shares outside a tender offer?
Generally no. Stripe shares carry transfer restrictions, and sales typically happen only through company-arranged tender offers. Loans against private shares exist through specialty lenders but often carry unfavorable terms, and hedging tools like options or prepaid forwards aren’t available for private stock.
Should I take my Stripe refresher as cash or RSUs?
The two are generally tax-equivalent at vest — both are ordinary income. The more important question is concentration: employees with little existing Stripe exposure may value the equity upside, while those already holding significant vested shares may prefer cash to stop adding to the position. The right answer depends on your full financial picture.
DISCLOSURES
This guide is for educational purposes and does not constitute personalized investment, tax, or legal advice. The information provided is based on publicly available reporting and general tax principles as of the date of publication, supplemented by the recollections of current and former Stripe employees. Stripe equity program details — including tender offer timing, eligibility, refresher grant structure, and any cash election — are set by Stripe, may change without notice, and should be confirmed through official Stripe documentation. Prospero Wealth is not affiliated with, endorsed by, or compensated by Stripe, Inc.
Tax-loss harvesting, direct indexing, and long/short strategies involve risks, including market risk, short-selling risk, leverage risk, and active management risk. Losses harvested may defer but do not eliminate tax liability; the wash sale rule and other limitations apply. Hypothetical examples are illustrative only and do not represent actual client outcomes. No guarantees are made regarding tax outcomes or investment returns. Consult a qualified tax professional, attorney, and financial advisor before making decisions.
Prospero Wealth is a registered investment adviser. Registration with the Securities and Exchange Commission does not imply a certain level of skill or training.
