Your Four-Year Vesting Schedule Is Broken. Here's How to Fix It.

Last year, I spoke to a partner at a tier-one San Francisco VC. He asked what I thought about founder vesting. I told him: the standard schedule is too short, and founders should revest at every meaningful funding milestone.

He asked me to write about it. His reasoning: only VCs ever bring this up, which makes them look like the bad guys protecting their own interests. He wanted a founder to make the case — because revesting isn't there to protect VCs. It's there to protect the founders who stay, and the company they're building.

So here it is.

The math doesn't work for a ten-year journey

Across three companies, I've parted ways with two co-founders and got stuck with one who owned all his shares and barely showed up to work. Those experiences made me understand, viscerally, why the standard vesting structure fails everyone involved.

The problem is the assumption baked into four-year vesting: that the company's journey — from zero to exit — takes about four years. It doesn't. Most meaningful company-building work begins after the Series A. Getting from zero to $3M ARR might take four years. Getting from $3M to $100M ARR takes another eight.

When your vesting schedule ends at year four, you've created a cliff. And the scenarios on the other side of that cliff are ugly.

Here's one: you incorporate, split equity with your co-founders, do the standard four-year vest. It takes two years to raise your A round. Your co-founder leaves right after the raise — or better yet, stays one more year, vests 75% of their shares, and then leaves. They walk away with the majority of their equity while you and the remaining team do the actual scaling work. That's more dilution for everyone, less equity for future hires, and a co-founder who has every incentive to leave and no incentive to stay.

Here's a worse one: you hit your B round four years in. You're at $3–5M ARR. Your co-founder is now fully vested. They get an offer for double their salary somewhere else. Why would they stay? They can leave with 100% of their ownership, make more money, work less, and wait for the exit that you and your remaining team will grind to deliver. Same upside, half the work.

That's not a hypothetical. I've seen it happen.

What I actually recommend

Starting a company is a ten-year commitment. Most of the company-building — the scaling, the real hard work — happens after the A round. If you're at seed stage and feeling proud of what you've built, that's appropriate. You're also maybe three percent of the way there.

The vesting structure should reflect that reality. Here's what I advocate for companies with more than one co-founder:

Six to eight year vesting periods instead of four. The journey is longer. The incentives should match it.

Full revesting after the seed round. Everyone resets to day one. The company you're building now is not the company you incorporated — the real journey starts here.

Revesting of unvested options at the A and B rounds. If at the B round you have 50% of your options still unvested, those remaining shares vest over the next six years instead of two. The runway extends with the company's ambition.

Granting additional options over time. As the journey lengthens, give co-founders more equity — so the decision to leave becomes genuinely costly, and the decision to stay is genuinely rewarding.

I know the instinctive reaction: "I earned those shares. Why should I give them back?"

Here's my answer: if you're planning to be there for ten years, you lose nothing. Revesting is costless to the people who stay. It only matters if you leave — and if you're going to leave, your equity shouldn't be a reason to stay for one extra year and then bail.

Revesting protects the founders who are in it for the long run. It protects the company from incentive structures that reward leaving at exactly the wrong moment. And it protects future team members who deserve equity that reflects the work still ahead.

The people who should fear revesting are the ones who were never planning to be there for the full journey. If that's not you, sign the paper.