Something to listen toCompensation
Beyond One Size Fits All for Startup Employee Options
A 33-minute podcast episode where two investors weigh the 90-day option exercise window and its alternatives
Why it’s worth your time
This a16z episode treats the deadline for buying your startup options after you leave as a design choice. Two investors talk through why the standard 90-day window exists, what longer windows fix and what they cost, and why they think no single design suits every company. Horowitz admits that as a young startup employee he didn't understand his own window, which is a fair reason to check yours well before the week you resign.
What happens to your options when you leave
- Listen to the episode.
Sonal Chokshi hosts Horowitz and Kupor. The early part explains where the 90-day window came from and what a 10-year window changes. Later they discuss other designs, such as back-loaded vesting and smaller grants up front with more for strong performers, and toward the end Horowitz describes what he'd do if he were running a company today.
- Find your own exercise window.
In your option agreement or plan documents, or by asking whoever handles equity at your company, find three things: how many of your options have vested, the strike price, and how long you'd have to exercise after leaving. Multiply vested options by the strike price to see roughly what exercising would cost before taxes. If you're weighing an offer, ask the same questions.
Good moments for this: before accepting a startup offerbefore giving notice at a startupwhen your company changes its option plan
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Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
Exercising can create a tax bill even when you can't yet sell the shares, and how much depends on the type of option and your situation. Horowitz and Kupor are talking about how companies design the rules, so it helps to understand the tax side of your own grant before you spend money.
What might make this harder
Before you resign, ask whether the company has ever extended the window and what that would mean for the option's tax treatment, then talk to a tax professional before deciding.
Questions people ask
What is the a16z podcast on startup employee options about?
A 2016 episode of the a16z Podcast (now The a16z Show) in which Ben Horowitz and Scott Kupor of Andreessen Horowitz, with host Sonal Chokshi, discuss the 90-day window startup employees get to buy their options after leaving, the case for and against 10-year windows, and other ways to design option plans.
What is a 90-day exercise window?
The period, commonly 90 days, that a former employee has to buy their vested stock options after leaving. Options not bought by then usually expire. In the episode, Horowitz traces it to accounting rules that once made longer windows costly for companies.
Why don't all startups offer 10-year exercise windows?
In Kupor and Horowitz's account, longer windows make grants more valuable but mean fewer shares return to the pool when people leave, which dilutes those who stay, and they can make leaving right after vesting more attractive.
How do I find out my option exercise window?
Check your stock option agreement or the company's equity plan documents, or ask the person who handles equity. Do it before you resign, since the clock usually starts when you leave.
What it says, and how it holds up
Picture leaving a startup after four years with your options fully vested, and learning you have about three months to pay for them, in cash, for shares you can't yet sell. That was long the norm, and this 2016 a16z episode explains how it came about. The 90-day window was set for a time when companies tended to go public within a few years and longer windows carried accounting costs, and both of those have changed.
Horowitz and Kupor, investors who sit on startup boards, agree the old system is broken; the argument is about what replaces it. Adam D'Angelo's 10-year window at Quora solved the problem for people who couldn't afford to exercise, they say, but it has costs of its own. They walk through alternatives: Snapchat's back-loaded vesting, Tesla's smaller grants up front and more later for strong performers, Andrew Mason's progressive equity, and Horowitz's own idea of bigger grants vesting over a longer stretch. Their refrain is that people follow incentives, so a founder should pick the incentives on purpose.
It's an investors' view from 2016, and they're open about where they stand: Kupor stresses that CEOs, not venture capitalists, drive these decisions, and Horowitz recalls losing options he couldn't afford to exercise when he was a young employee with a family. What counts as typical may well have moved since, so it makes sense to treat their picture of standard terms as dated and check your own documents. The episode describes US startups and US tax rules; option terms and taxes can work differently in other countries.
If your company has already gone public, the squeeze the episode describes tends to ease, since you can usually sell some shares to cover the cost of exercising, and the questions that matter shift to taxes and timing. This explains how things usually work; it isn't financial, tax or legal advice for your situation.
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Picked by Truest and described in our own words. The original belongs to its creator. Last updated October 9, 2026. We sell a career membership; where that’s relevant above, we say so.