Co-founder exiting after pivot – what's a fair exit package? | Hacker News Reader

Co-founder exiting after pivot – what's a fair exit package?

44 pointsthrowaway-xx79 comments

Throwaway for obvious reasons. I’m a co-founder of a venture-backed startup currently valued at ~$20M. We raised a strong pre-seed, built a team, shipped v1, generated revenue, and recently pivoted into a related idea that I think could work—but I’m no longer the right person to lead it. My co-founder is passionate about the new direction and wants to take it forward. I want to step away cleanly and with integrity.

I have ~10% vested. I led our early fundraise, worked unpaid for months, and contributed personal capital. I’m not trying to maximize my return—but I also don’t want to walk away empty-handed after 1.5 years of building.

My question: 1. What’s a fair exit package in this situation? A formula/rule I can use?

2. Should I just keep the vested equity? Future investors may see this as dead equity.

3. Is a cash buyout common or appropriate?

How would you approach this with the board/co-founder in a way that’s constructive and protects long-term relationships?

Would love to hear from anyone who's seen this play out—on the founder, investor, or legal side.

View on HN

Equity: Walking away, your stake should be whatever you've veseted -- this is why you have vesting. If you purchased your shares (I hope!), then there's nothing more to do. If they were options, ask for conversion from ISO to NQO (IRS-mandated) and an extension (10yr) on the exercise period. If the post-pivot company wants, they can keep you on as an advisor for a period at some reduced equity vest (e.g. 1/20th your founder vest). This is a nice way to transition and can be worthwhile in some scenarios.

Cash: You should expect none. If you all documented the unpaid work in the form of contractual deferred compensation (unlikely), then you can insist this be paid out as a requirement of labor laws. If it wasn't documented, then it's a sunk cost. Cash is the company's life blood, so they cannot waste it on employees that are departing or terminated. You shouldn't expect an exit package.

Realistically... If you own 10% in a "new" company (post-pivot), this is a great position for you. Their alternatives are (1) to nuke the cap table in a reset and pivot without you; it's not really worthwhile for anyone to duke it out this way; (2) if they're itching to buy you out (unlikely), you can consider whatever offer they put forward but you have no legal obligation to accept; or (3) everyone just accepts the current state of affairs as sunk costs and parts amicably. (3) is best for everyone involved -- it's mutually non-ideal.

I used to work in VC. Although I've never deal with this situation myself, I've talked to other founders who've had similar experiences.

The general thinking is that the new team is essentially a new business. This new business needs cash, and taking that away is more or less a non-starter at this point. Fundamentally, founders are compensated for seeing things through, not for partial work. It's a really hard sell to either ask a cash-poor company for cash for non-productive purposes or to ask new investors to put up cash that's going towards an exit-package (ie. someone who's not going to be contributing). The only leverage you may have is how much pain you can cause by not being bought out, which puts you in an adversarial relationship with everyone else. I don't think that's good for you.

So I'd recommend you'd just hold on to your vested shares to build good will. Indicate your intent to exit, but you like the new idea and wouldn't put additional pressure on the business at this stage. If the business is successful in the future, you may get bought out by later stage investors to simplify the cap table and reduce governance complexity. But for that outcome, you'd need to be on good terms with current investors and the new team.

I've commonly seen grants like this diluted to almost zero. I would think carefully and strategically about how you can get some sort of value for the equity you vested. Its probably harder than you think to get decent liquidity on it.

Is it legal to dilute this to zero? Can't you sue post-exit (e.g. Saverin and Facebook)?

At a normally-papered startup? Yes. No.

The juice has to be worth the squeeze. No sense in fighting against fiduciary duty, minority shareholder oppression, etc., etc. unless there is some sort of value there. This usually means a successful exit before taking action.

I think we're saying the same thing --- that none of this matters, just walk away with the vested shares and be a friend to the company. Diluting his founder shares in subsequent rounds is going to be a nonevent, and diluting him to zero in an acquisition --- unless it's a seller's market or a bidding war --- may be as well. It's just not worth worrying about; I think the only real question here might be "do I take a buyout if offered", and this person is nowhere near that yet.

Ahhh yes same thing

It happens all the time, I have seen it in NYC. Usually its an early stage thing, cofounder leaves after 1 year etc. Much harder to do with a complicated cap table. Investors I could name even suggest it

Suing would only make sense if the dollar value is very high.

Some good advice here; couple qs: did you get shares for your personal capital contribution?

Simplest thing to do if you think it will work and don't need money is just sit on your vested shares, perhaps ask for a little more as an exit package, be supportive, offer to join the board as an advisor, and move on.

If you'd like a clean break and some cash, you could call your last round investors and offer them a discount to the last price for your vested shares. Depending on the state of the company and what's next, they may be interested -- there's an implication in these conversations that you'll find SOMEONE to buy eventually, which they may or may not like. I'd guess unless things are gangbusters, you might look at 30-50% discount from the last valuation, knowing nothing about the common, the company or the pref stack.

Another possibility - you could offer to sell your shares at a discount to your cofounder, leaving him in a good spot - he could ask around for a loan / investment (in which case the company would be the buyer, and he'd benefit pro-rata).

Personal advice - keep some, sell some, stay available to help.

I agree with Joel Spolsky that nobody should get shares for personal capital contributions (at least, not unless they're investing in a round). If you want to be fastidious, set up IOUs.

I'm 100% the opposite. It's wrong for one group to expect preferred stock for their capital contributions, while they ask the usually less experienced CEO to make a tacit capital contribution (lower than market salary) and then on top to ask them to put cash in that won't be given the same terms -- nah.

Now, if the founder capital went in pre-round, and a round was raised, I'm with you -- that's fine - and between the founders at that point; they got paid in equity valuation. But otherwise; nope.

We're talking about arrangements between founders, not arrangements between operators and investors. Investors don't ask you to put up cash; that is literally the opposite of what they do.

Actually they do it all the time - asking to ‘top up’ employee stock option pools before a round is closed, keeping exec salaries low, or cutting them when the company is running low on money - these are all forms of founder capital contribution that are not compensated. I’m not saying they’re not market, or even that they’re a bad idea. But, consider an exec who could make $300k base plus ISOs at a public company going from $170k to $100k for lean times — what would raising that 70k cost the company in stock? A fully level capital stock playing field would see the 70k investment from the founder independently priced in a fair round and deliver preferred stock. I’m unaware of this ever happening in my last 25 years of startup and venture experience.

As someone who had a co-founder exit 3 years into our 8-year journey, here's my take: keeping your full 10% might actually hurt everyone involved, including you.

Think about it from the new investors' perspective. They see a former founder holding 10% who left because they didn't believe in the new direction. That's a red flag. They'll either demand you reduce it significantly or they might just pass on the deal entirely. I've seen this kill funding rounds.

More importantly, it can destroy motivation for the team staying behind. They're busting their ass on the pivot while someone who checked out still owns 10%? That breeds resentment fast.

My suggestion: voluntarily reduce your equity to something like 2-3%. Shows good faith, removes the investor concern, and keeps the team motivated. In exchange, ask for a reasonable cash package - especially if you've been working unpaid or below market for months. That's just settling up what's owed, not "taking money from the company."

When my co-founder left, he went from 26% to 3%. Seemed harsh at the time, but it let us move forward clean. We raised our next round 3 months later partly because investors saw we handled the transition professionally.

The cash part really depends on your financial sacrifice. If you've been unpaid for 6 months while getting the company to this point, then yeah, getting compensated for that makes sense. It's not about "exit package" - it's about getting paid for work already done.

Just keep the vested equity. That's why there's vesting.

10% is a large drag on the cap table.

If that actually becomes material, they'll offer to buy shares in the next round. That's the point at which this whole conversation becomes interesting; right now, it's complexity for its own sake.

I know the feeling! I left a company some years back in a complicated way, and my instinct was to drill in as well. It seems like a big deal! It really isn't, though.

Or they'll find a way to dilute the co-founder's shares so they don't have to buy them out.

If that's going to happen, it's going to happen. I've heard as many stories of it happening as I've heard stories of people unhappy with the amount of liquidity they were able to achieve early in the life of a company that later became successful.

What does that mean?

That theoretically future investors will be reluctant to invest because the founder 10% is crowding out equity that could otherwise be used to attract key performers down the line.

Nah, they can just issue more. He's already giving up 40% -- plenty of head room.

I'm not saying I agree with the concern, I'm just articulating what it is. I think the answer here is super simple: walk away with the 10% vested. (Also: stop thinking in terms of %).

The exact details are unclear from the original post, but he definitely isn't giving up 40%. If they've only raised the pre-seed (a reasonable inference given the low valuation), then 10% ownership after 18 months points to two co-founders and a combined investor and option pool dilution of 20%. Anything is possible, of course, but unless the deal terms were very non-standard, this scenario makes the most sense.

You're right that 10% isn't necessarily a huge deal for investors, though. Early-round investor models target a specific ownership stake, and the company has to issue the same number of shares for that no matter what the composition of existing shareholders is.

The challenge with founders leaving is more psychological, like an early engineer who's vested a quarter of their 1% grant realizing that they still have to work hard for three years just to get a tenth of what the guy leaving already has. That's an easy way to suffocate the remaining team's motivation. Potential investors will (and should) look into it, but most of the time it's fine.

This is a joke right? Seed investors will get 10-30% of a company for under a million dollars which will be blown through in less than a year. That’s means they’re a drag on the cap table right?

Important Questions:

1. How much did your involvement lead to the fundraising success?

2. How much did your involvement lead to the products' early success?

3. Does it make sense to take the IP early idea that you were passionate about as part of your exit package?

==========

Expectations:

* you should expect no cash. taking cash will lead to a lower chance of a return on your equity. if you desperately need cash, you should get a small package based on your salary.

* you have no way to protect against being diluted. you have no idea how much work it will take to make this project successful. making it successful will require dilution. at best you could negotiate never being diluted under a certain amount, and making that based on successive valuations. if you leave at pre-seed, and it becomes a unicorn, you likely don't deserve 10%. what do you think you realistically deserve if this is a massive runaway success AFTER you leave.

* one way to think about this, is what would your time have been worth at a company with a higher TC. if you would have been paid $500k including equity somewhere else, maybe you should get the same amount of equity as someone investing 500k in cash, and get the exact same dilution as they would.

* you will not find a standard answer anywhere. you need to find the best solution between:

  1. your ego
  
  2. your cofounders ego

  3. giving this startup the best chance of success so that all of this time will be worth something for everyone. even if thats less than you want it to be, its better than $0. because all of the hard work lies ahead.

Small nit - protection against dilution - that may not be true; there are laws in the west coast about minority investor treatment. Your overall point -- do what you can to stay a little long and make sure the company is worth something -- is absolutely the right way to think about it.

I’ve been through this type of thing a few times and there aren’t many good solutions. The new business needs cash so taking some is a tough pitch to the new team’s executives. New investors are rarely keen to see funds going to an exit fund. You can make threats and indicate you won’t go quietly into the good night, but that makes things adversarial. At some point in the future, your equity could become a problem that will be worth taking care of. At this point, your best path to dollars is to become the problem, but if you do that, it’s a lot more difficult to see one of those future exits shape up.

Curious, what was doing your friend, who is ready to take over and lead? Why not switch sides, take over his functions, and offer your stake for sale during the next raise at that valuation?

Why not offer your stake to the company’s investors at the previous valuation?

A pivot, by definition, means turning away from the original course of the business.

If you were really motivated by the previous goal, and you're disinterested in the new goal, why stick around?

I've seen companies pivot from "we are going to solve plastic trash recycling using automation" to "we are a trading platform for bales of plastic trash" - much more achievable, but much less interesting.

If you have PMF, everyone staying behind is taking full market salaries and your valuation is based on a priced round then you should likely keep all your vested equity undiluted.

However, I assume that, as a pivot implies, you are pre-product market fit. In which case here are some questions to consider.

What is the value of the company after the pivot? How much of what was done pre-pivot has any relevance to the post-pivot company?

Is the startup valued at $20m or do you have SAFEs with a $20m cap? If the company is _worth_ $20m that means you've probably had a priced round and someone would likely pay $2m for your vested equity. Is that correct? Sell to them with a substantial, say ~50%, liquidity preference that goes to the Company (likely the Board's approval is required for a share transfer).

In large part the purpose of the SAFE is to avoid valuing the company. What valuation did you put on your 409A? Are you equating your "given a win-state valuation" (the cap) with your actual valuation (409A).

There is a Michael Seibel video where he talks about founder equity. In it he suggests that you should give back a lot of equity if pre product market fit as this will actually maximize your total return.

Remember if you raised $2m at $20m cap but have spent $1m your remaining co-founder is essentially taking $1m at $5m cap if compared to starting again (since they still have to hand over 10% to the investors and now they have to hand over 10% to you too but you spent $1m so they are giving up 20% for $1m).

Would it be more sensible for your co-founders to start a new company and offer the investors a substantial chunk or all of their remaining money back or to come with? Did they invest in them, you or both of you? In a liquidation how much would you get?

I would suggest that you should look to offer at least 90% of your vested equity to not have the remaining equity diluted. A good rule of thumb here would be what could you sell the company for today with no one staying (more than the a few months for minimal hand over) and divide the amount you raised by this number and this is the dilution you should be looking for.

You don't mention how much cash the company raised, or how much cash is left. These are key questions if you want to know how much of a buyout is appropriate.

If there's not a ton of cash, they are going to be very hesitant to give much of it to a departing founder.

At the same time, you should be hesitant to just hang onto your equity on the promise that it will be bought out later. If the company isn't successful, you'll get nothing. And if the company is successful, future investors will convince your founder that you don't deserve anything and that they should do shady stuff that will dilute your shares to nothing.

Keep the vested equity and move on. Anything else is asking too much.

My two cents…

1) They buyout the shares. If they don’t want to do that then…

2) Sell the company.

If either of these can’t happen the company is dead and everyone parts ways. It’s as simple as that. No free rides here.

What? No. A departing founder doesn't necessitate either a buyout or an immediate sale. This happens all the time.

Sorry, you’re right. There should be a third option

3) You keep the shares and hope for the best outcome. (If they don’t want you to then go back to 1 or 2)z

No, you don't.

You don’t keep the shares?

You don't have recourse to force a sale, buyout, or wind-down of the company.

Have been in that situation. If you leave, you're done. It's up to the other co-founders if they want to throw you a bone to keep a relationship in place. The leaver is dead to the board and the investors. It's your business now, move on.

is it tho? like i agree if i just took the equity. but if i own a ton of equity and the board wants to clean up the cap table, don't they still need to deal with me by offering me a fair number instead of "just moving own"?

Not sure they need to do anything. Maybe in the interest of smooth sailing, and closing things off, then the board might be motivated to reach a mutually acceptable conclusion. Whether this be a little buyout, an advisor tie-in, etc, completely depends. Situations like this is why founders create equity agreements.

Went through a similar scenario a few years ago, similar valuation range and stage. The person was nice, so we amicably decided to settle at around 3% sweat equity.

interesting, i might end up doing something similar. if you don't mind me asking, how much did you sell the remainder of your shares for? was it close to your FMV? i feel like i'm already being negotiated hard by being forced to sell my equity to minimize dead equity and then instead of selling at the 409A valuation, being sold at the FMV seems like i'm losing another battle. thoughts?

They're forcing you to sell?

Buy sell agreements are common.

seems like i'm losing another battle

If you frame it as a battle, you are already losing.

Because it is a battle where you are outgunned and out organized.

And in a battle you go from being a former employee/founder to an existential threat while burning your relationships.

If you need your initial investment back you could also take a note payable.

Oh, also: if you feel like you're being forced to do anything, or negotiated hard against at all, or losing battles, just lawyer up. Depending on your jurisdiction you could start saying things like, "I dunno, sounds like oppression -- let's just do what's best for the company here".

Yes, so i had another cofounder join in, with the previous cofounder exit, so first we sold the shares to the new cofounder at FMV and the company returned the sweat equity to him at FMV. Honestly, the best thing is to get a lawyer who has done these transactions before and once you have amicably communicated let the lawyer take this up, it will drain your energy otherwise.

Isn’t the 409a valuation FMV? I thought that the whole point of the 409a valuation was to find FMV? Do you mean par value?

If the company is pivoting, 0% beyond asking them to buy out your vested shares unless you want to keep them.

As someone who has never been in this situation, some of the replies in this thread are very disappointing. They basically seem to amount to, "eh, go pound sand, quitter."

You've put in a ton of work during the hardest period for a startup. That's not worth nothing.

In opposition to these other people, I'd say maybe a frank but congenial discussion with your co-founder is in order. Something along the lines of being burnt out or not agreeing with the current direction of the company, those details don't matter so much. If think you'd want to ultimately fall on you wanting to "pass quietly into the night."

Sometimes people come up with solutions on their own that would surprise you. You just gotta not pigeon hole them into a particular type of response from the start.

The issue has nothing to do with whether he worked hard, it has to do with the fact that the work the company did ended up being not very valuable, so much so that the company is doing something completely different.

Ultimately he created very little value and therefore is entitled to very little value. The company can just go out of business and start fresh!

Raising money is not value.

2-5% could be appropriate. 10% is completely insane.

Bullshit. He helped build a company that could even continue past a year. That's better than literally 80% of the startup market. Look up BLS statistics. Not only that, he helped build a company that could even bother to attract the attention of investors. Prima facia, someone thinks there's value there.

The world is full of jokers talking about starting a business and jokers who have "started" a business but are faking-it-to-make-it off of credit cards. You can't do that for a 18 months. OP has built something. It may not be the software he started out to make, but it's certainly a business that some investor thinks has a chance of being a going concern.

The investors invested on a previous idea.

The fact that the other founders are deciding to pivot is just a luxury of the fact that the company has inertia, not value, which is why they are switching ideas.

Our OP doesn’t want to work on the new idea, the one that might have value, therefore he is entitled to very, very little.

You do not understand the economics of VC backed startups.

Attracting investors is hard, but it's still the easiest part of building a company. If the company pivots, then it's pretty likely that the vast majority of the previous work no longer has any (monetary) value.

None of this has anything to do with anything. In the immortal words of William Munny, "deserve's got nothing to do with it". Any properly papered company has a legal structure based on 20+ years of SFBA lawyers predicting that founders are going to leave their companies, which will need to remain going concerns for any startup ever to be investable.

If you're an exiting founder in an LLC without an operating agreement, you can kill the company. Otherwise: you leave with whatever you vested. That's really all there is to the discussion, for now!

Very similar situation.

You can think of your equity in terms of buckets: you get some for having the courage to start, some for the grind, and some for future returns. You're giving back the future returns bucket, not the other two. The vesting mechanism imperfectly maps to this.

Keep the equity. It's not "dead" in any real sense (though people will describe it that way to talk the value down). Dilution will hit it anyway. Again: you are already relinquishing the future value when you stop vesting.

If you have a board seat, consider staying in that capacity. Then at the next round perhaps sell the seat and equity to an incoming investor. Early on, board seats are more valuable than stock and selling that package, perhaps at a discount to the incoming valuation, is fairly compelling. Your exit then fits the playbook for exiting early angels -- it's not weird.

Taking cash is a bad signal in a couple of ways: it signals that you don't believe in the new direction and it signals the remaining founder is making poor financial decisions. Unless the framing is that you took a low buyout to walk, which isn't a great look for anyone.

Message it as what's best for the business, and be firm when they ask you to relinquish the equity. You said it very well in your post: "this is a great idea, but I'm not the right fit. I'll stay on in an advisory and governance capacity, but my last day as an officer and employee will be end of next month." Give the company lots of time and help to move on.

Help the company by setting it up to be so valuable that an incoming investor will want to remediate the situation by sweeping you off the cap table (again, like an early angel).

Depending on your counterparties it might not be possible to preserve relationships. Make sure you can afford litigation. Depending on your financial position this means get a new job or start a new business. When someone says, "relinquish or I'll sue" then you generally want to answer "my counsel will accept service at this address: xyz".

You're not going to sell a board seat. Not how it works. You probably can't even sell the shares!

Depends on why you have the board seat.

No it doesn't. It's very difficult to imagine a plausible circumstance where you have a company that took significant investment where you could hold a board seat that the board could not eject you from after you left the company. You can't sell a board seat.

"Yes, I'll put another hundred grand into the company, but I want a pref issue with an attached board seat."

This person isn't an investor, but even an investor can't sell their board seat. This is getting silly. "Hold on to your founder board seat and sell it later" is not real advice.

Depends on why you have the board seat.

As a hypothetical, kind of? But not really. The board is written into the company's bylaws, as a rule, and requires a board vote to change. 'Selling your board seat' really means engineering a complex deal that requires a bunch of other people to sign off.

The same is true of selling your equity, by the way. As a founder you have common shares, but early-stage investors want preferred shares with QSBS treatment. Even if you're allowed to sell your shares, which most startups don't let you do, it's not in your power to convert them to preferred or give the buyer QSBS treatment.

The problem we have in all these threads is that sometimes people just say stuff, because it sounds interesting or it's fun to fantasize about, and it's hard to tell that stuff apart from actual advice.

This person probably doesn't even have a board seat, but either way: you're not selling a board seat.

> 'Selling your board seat' really means engineering a complex deal that requires a bunch of other people to sign off.

The company is at (pre-)seed, so the next round is this exactly: they're probably rewriting the shareholder agreement, for example.

I wouldn't call it more "complex" any other round.

A startup that has a board is a company you can't sell a board seat at. This is past silly. Despite what you wrote earlier, "holding on to and selling" board seats is not a thing.

You're simply wrong, I have done deals like this. You are clearly quite upset about something, and are not providing a clear argument -- relying instead on personal attacks and "no true Scotsman" goal post shifting.

Good luck to you, all the best!

I have no idea who you are and there's nothing personal about any of this, but I am concerned that people are going to read this and come away with the idea that departing founders with board seats generally sell them, and when they try that, everybody is going to look at them like they're both naive and irrational --- exactly what the original poster said they were trying to avoid.

What’s a fair exit package in this situation?

What is fair is to be open with your cofounder and investors.

Should I just keep the vested equity?

Should the other stockholders just dilute your holdings?

Is a cash buyout common or appropriate?

Probably less common that telling you to pound sand. Cash is the life blood of a company and giving you cash is very damaging to the startup.

To put it another way, you need to negotiate. To negotiate you need to care about the interests of the other people and in the case of a startup recognize that the vast majority of the work is in the future. And that there is no value in sunk costs. Good luck.

1. Don't ask for cash or an exit package imo. This isn't a mature, profitable company. It's a startup. You took a shot, you missed, and you're quitting. I think it's fair for there to just be a clean break there. Either that, or stick with the company and see it through.

2. Keeping the vested equity seems fair to me. The entire point of that vested equity is to represent the sweat you put into the business.

Agree, but asking for his personal investment contribution back is totally fair. Also, make sure you understand how future investment will affect your 10%. Don't want to be left in a Eduardo Saverin (Zuck) situation.

talk to your lawyer, imo.

By all means pay $1300 to hear "walk away with your vested shares".

Might not be the answer you want but ask for a vacation. A long month away might be enough to clear everything up. Doing startups is tiresome.

Reply on news.ycombinator.com