Ask HN: Co-founder wants me to leave but won't entertain a buy out offer

399 points by fortydegrees ↗ HN
I'm the technical co-founder of a pre-revenue startup. We were 51/49% to them and took a small round of pre-seed funding (~$100k) so our cap table is approx 40% for me and co-founder, 10% option pool and 10% investor. We have very standard shareholder agreements for 4yr reverse vesting with 1yr cliff.

My (non-technical) co-founder spent $10k to create the initial website over a year ago with the idea. I joined about 11 months ago and since then the idea has changed a bit, we've built loads of products, grown from 2k users to 60k users and continuing to grow due to dominating SEO for our niche.

Recently my co-founder said they wanted to work on it themselves. I said I didn't want to leave. They suggested I go down to 3% equity and they continue. I said they would need to buy out my equity at a fair price.

My co-founder doesn't have the money, and the business only has around $40k cash in the bank right now. My co-founder also won't entertain the idea of raising external money to buy me out, or monetizing the site right now.

To me this seems ridiculous as I'm literally just giving away my equity after spending 11 months building the tech and growing the business. Right now if we stuck adsense on the site, we'd generate $5k/mo, and we have inbound sales leads looking to spend upwards of $40k with us. Basically, the business is primed to make money.

They will not entertain the idea of me buying them out for cash.

What are my options here? It's basically being presented to me as "Take the 3% otherwise you'll own 40% of nothing". I don't really want any equity in the company at this point if I'm not involved.

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Did they really pose it to you that way of take the 3% or they'll torch the company? Was it just a bluff because they'll own nothing too? I would talk to a lawyer and possibly the seed investor, but the lawyer first.
The seed investor is remaining neutral.

It's not so much that they'll torch the company. They're just saying they don't have the cash so need to reduce my stake. They will budge on the 3% I'm sure, but I don't value the equity much if I'm not involved.

I'm not too sure what a lawyer would recommend at this point? I also can't really afford one personally - especially as I may be out of work soon haha..

I don’t understand how “the need for cash” and “reducing your stake” are connected. If they need cash, they can raise another round and everyone gets diluted like normal.

If you don’t value the equity, offer to sell it to the seed investor at a discount.

You need a lawyer, not internet advice.
If you're not valuing the equity if you're not involved, then honestly you need to look at this from an opportunity cost perspective.

The trust is fundamentally broken, so it's not really worthwhile to pursue this as collaborators. Unless you're keen to run the business yourself, there isn't much point in fighting this beyond getting your 1st year vesting.

It's honestly not worth your time and energy fighting for something you're not keen to do. And it's definitely cheaper for them to give you 7% more than the 3% offered, and avoid all this hassle and potential legal expense.

If you do want to persist, then you need the investor on your side, as otherwise you can't force the other person out (they'd still keep their 10% but that's the price you pay for that move).

I have to say I find it really odd that someone who's invested $100k is being silent on this, or isn't worried about this situation, especially if the future of the business is now more of a lifestyle business. I fail to see how they'd get a return they'd expect. I'd assume they're actually on the other side, but want to appear neutral.

FWIW if you end up leaving, I'd advise not agreeing to a non-compete or a non-disclosure. It's not about you starting a competitor, but more about them not being able to restrict your future options as they're forcing you out, and they will have to potentially consider the threat of you competing with them at any point in the future.

It's a credit to your efforts that you've built the tech of business that's gotten such good traction and numbers, so you've got learnings and experience that will serve you in good stead in the future.

It's just unfortunate that you ended up with such shitty partners.

Good luck, and I assume quite a few of us will be hoping you bounce back from this, and rooting for you.

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keep 40% of nothing. do not capitulate. you have the upper hand here, and an honorable position.

3% of nothing is nothing also. i’d go with 40%.

it’s absolutely ridiculous because the other founder isn’t prevented from working alone because you hold 40%. the 2 things aren’t connected. so just agree to sell all your shares in the next raise. then it’s his choice: take on debt now to buy you out (cheap) or pay later (expensive). the latter is likely far, far too expensive so more likely you can only sell half your stake in the next round.

EDIT: it has occured to me that you are only 11 months vested. this is a bait and switch. make their lives hell, even after and if you get to keep 10%. he probably can't fire you so you'll just keep vesting. make it very clear you will make it impossible to fundraise unless he buys you out.

The problem with your ask is that early stage capital is for growing the business, not liquidating founders, and investors are not interested in giving anyone cash to liquidate a founder. Additionally, your valuation is currently underwater and even that is assuming a functional founding team.
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It's not OP's ask!

Please explain more what you mean about the valuation being underwater. I don't understand how that is, nor how that is even possible.

The investment was at a $1 million valuation and the company currently has 40k cash + allegedly, the possibility of 60k/year from ads. Unless there is significant growth potential, the net present value of the company is much less than $1 million.
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ah thanks. yes, all startups operate "underwater" then. that is the operating model.

as to the use of venture capital, indeed, no investor will ever allow this -- if they have a say. seed stage funding is most often convertible debt, and the investor does not have a say (legally; but you damn well better do what they say anyway). i'm actually quite surprised that a seed investor would be noncommittal on it. however,

1/ that's the other cofounder's problem, not OPs. the way you phrase it is as if the OP is putting the other cofounder out on a limb with an unreasonable request; that is not the situation here.

2/ the other cofounder doesn't have to use capital, they can take on debt (convertible or straight debt).

It's an absolutely wonderful tradeoff if the business will be run better and more efficiently with just the one cofounder. A no-brainer really. Not doing it indicates a scam. In both cases, OP should insist on a buyout. So there's really no difficult decision here -- on OP's part anyway.

Of course with the business being "underwater" we are talking about a personal guarantee on straight debt. So again, how much does the other cofounder believe in the business and that his motives are pure?

The other cofounder can sidestep this whole thing with various shenanigans, however that doesn't mean OP should just submit. A year of OPs life is worth it to stick to his guns, even if the outcome is inevitable. It's not as if OP has to invest any effort to see through his position.

Sorry to hear you're going through this. I went through something similar and it wasn't fun.

As much as you have shareholder agreements etc. none of that matters too much if the business fails and so it's basically about what the two of you can negotiate.

In my case, I've paid off a former business partner much like a loan. You can negotiate all sorts of parameters on this: monthly payments, grace period, cash triggers, funding triggers etc.

Basically you set a valuation for the business (at least as set by the price of the round of the last investor, if not more because of growth) and then he buys your ownership.

Idk what "reverse" vesting is, but if you had normal vesting it sounds like your 49%, after the 1 year cliff, would be worth e.g. 12%. So you can either keep that 12% or if he wants to buy you out he could pay you your 12% vested * last valuation * growth factor.

It sounds like it's not going to work for the two of you to work together, so now it's just about negotiating the details before the conflict kills the company

This seems like the most realistic and likely answer. My co-founder hasn't really been budging so far and I feel like they don't fully understand the situation. They think that because it was their idea that they are entitled to a lot more than me.

One issue for me is that I don't have that much faith in them being able to execute on the company vision by themself, e.g. they don't want to monetize right now or do a revenue split for reasons I'm unclear about, which makes the practicality of monthly payments tricky.

Have them pay you with a loan and then start a competitor.
Take it from me, a negotiated buy-out is the way to go. I had to buy out a former partner and negotiated a payment over 12 months. It worked out for everyone.

Current valuation should be valuation at the time of the investment multiplied by a small growth factor (1.5x perhaps).

Your stake is the amount you would have owned as of the first cliff (and not any sooner), which is 10% after the investment round.

if the company was valued at $1M at investment, then it would be worth maybe $1.5M at time of the 1yr cliff given the growth factor.

Your 10% of that is $150,000. The company should pay you $12,500 per month for 12 months to fully buy you out. And the company should time the payments to reduction in your equity. If they speed up payments, it speeds up the buy out. If they slow it down, it slows down the buy out.

You should also renegotiate any non-compete.

Seriously? If you are asking these questions, your understanding of the binding contracts belies the casual verbiage in your post. So which one is it?
Is it possible to play the long game? I.e., before your partner tanks the business, lay the groundwork for you alone to rebuild it from the ashes.

E.g., make sure you have copies of all the source code, and any other intangible assets. After the business tanks and he too is short on cash, buy out all claims he has on those assets, and restart the business?

Also consider including your investor in the planning. He/she might be more willing to help you save the business at your partner's expense, if the alternative is losing their entire investment.

If you're willing to buy out his share, I would approach the investor, explain the current dead lock, and get his support to force your partner to do a BMBY (Buy Me Buy You), where you offer him a price per his shares, which he either accepts or have to pay the same sum to you and buy your part.
Agreed with this. Retain your own counsel and do this.
I think this works if fourtydegrees has some bucks in the bank.

Reading between the lines, I suspect fourtydegrees is young and doesn't have the kind of money to do this.

(I also suspect that lawyers may be out of fourtydegrees' budget.)

Suppose I did have some bucks in the bank and did get a lawyer - how would they help? So far my co-founder has been pretty unreasonable with regards to compromising and/or negotiaton.

The investor so far has also been very neutral and I think will remain so.

Basically: Were you negligent?

Assuming you weren't, it's very strange to force someone out right before their equity vests.

Basically, your lawyer can understand the situation better than an internet message board can. Then, a phone call from your lawyer to your co-founder could help make your co-founder become a lot more reasonable.

> it's very strange to force someone out right before their equity vests

If the business-minded folk don't fully value the tech solution I can easily see this happening. This "devil's advocate" hypothetical is not an unheard of occurrence.

That was my thought. This is exactly what you would do if you thought you needed a little tech work up front but that it wasn't actually all that important to the future of the thing.
Which is where the lawyer can help.

If this is the case, (and we don't know the details,) it means that the other founder was acting in bad faith. Hopefully the threat of a lawsuit is enough to solve the situation.

I have worked with lawyers. Once litigation is threatened, everyone suddenly loses all the neutral stuff and becomes reasonable.

If you can afford it, find a good lawyer.

100% true. The non-technical cofounder is doing this because he thinks he can get away with it easily. The investor will go along because he's in it for the money. Involving a good lawyer makes it clear that you won't go down without a fight. A fight that could destroy the business. It's amazing how reasonable people can be when they realize that it's in their best interest to be reasonable.
Whilst the investor might consider that taking sides in personal aspects of the dispute looks unprofessional and might not see your compensation as a priority, surely the only way they could actually be truly 'neutral' on the future of the business is if they've already written the investment off as a bad one. (Which in itself would be useful to know)

Otherwise I would expect them to be (i) interested in ensuring the underlying tech was maintainable in future, which if nothing else might result in more reasonable earnout possibilities for you and (ii) concerned that one of the founders apparently wishes to cut others out of the business to turn it into his personal cash cow, particularly if the other founder is the one with monetisation ideas.

It's not guaranteed that the investor is your friend (another possibility is that replacing you and taking the business in a different direction is something they quietly encouraged) but I wouldn't expect them to be 'neutral' on whether the business has a chance of generating them a return or not.

Exactly what you should do depends on a lot of details about exactly what your business setup looks like, what your personal situation is, and what the other parties to the situation think. Way more detail is needed than you'd provide to any of us internet randoms. A good lawyer who understands these kinds of contracts is somebody you can actually give all of the important details to and who can give you accurate advice for your situation. This is not a good time for some weird quirk of your contract or any related laws to surprise you. If your co-founder is being unreasonable, you need to know what your escalation options are, and you may need to communicate that you are prepared to execute on them promptly if they don't give you what you feel is a reasonable deal.
The typical tech lawyer has seen this exact scenario ~20 times. You probably have some leverage, and spending $1-2k to figure out how much and how best to apply it, given the lawyer's experience, makes tons of sense.
Yeah, spend the money and a good lawyer. The 1000bucks I spend on a lawyer to send a you suing the wrong person letter to a company that’s now worth over trillion was the best money spend.
You don’t hire a developer just because they can say some jargon. They need to show proof of skill, either through code of theirs you can see, the interview process, whatever.

Similarly, business people don’t take shit like this seriously until lawyers are involved. They see no evidence of your ability to actually hold them to account and so believe they can just push you around.

Hiring a professional who knows how to actually hold the other side legally accountable, or make them hurt (tens of thousands of bucks in lawyer fees and months down the drain if the case goes to court) shows you mean business.

Otherwise it’s just talk.

A lawyer is also an expert and can give expert advice, both strategic (what should we do?) and tactical (how do we do it?) based on knowledge and experience. Exactly the same way you do in your technical domain. Would you want advice from a non-engineer on how to architect or build something? What database to use? No.

Like developers, lawyers cost money for a reason, and it’s because of the value they can bring.

I can't imagine my co-founder accepting this as they don't have the cash to buy my shares, so they would be forced to sell?
Well that's the situation the co-founder is creating by making these unreasonable demands...
This is commonly referred to as a shotgun clause.
Do NOT sell. keep 40% of nothing, matter of pride first and for all. Secondly, they are more than likely bluffing. They don't want to put advertising that would generate 5k/mo means they are trying to make things look artificially worse so you leave and keep the rest for themselves.

Don't fall for the 40% of nothing once you are close of making money. They just don't want to share the pie.

I’ll just add: write down everything. Guy is trying to run a bait and switch on you and there’s a very good chance this ends up in court. Be ready.
OP make sure you do this, it is incredibly important. I was in a similar situation with a real dick of a co-founder who constantly pulled these bait and switch tactics. I would even go so far as to write down behaviors they exhibit and times where they tried to strong arm you in the past. Keep logs of everything, insist on communicating through means by which you can record the conversation. Writing things down may not stop their behavior, but it will seriously help your case should this turn into a legal fight.
If it really were 40 percent of nothing, the other party wouldn't want it so bad ;-)
This. 100% this. No sell, no deal, that’s not in the contract...
Try turning the tables and offering them a buyout.
OP said "They will not entertain the idea of me buying them out for cash."
Unfortunately it doesn't sound like an option:

> They will not entertain the idea of me buying them out for cash.

That's a negotiating position.
Then they have established a lower bound on the value of their shares.
Bingo! Now you know it’s BS. This really sucks. It’s not a good place to be. The fact that they won’t take a buyout from you means they are pulling a fast one and someone probably said “You know, it would look better if it was just you” somewhere down the road.

Don’t sell, don’t give, don’t walk away. Stand firm. This was a binding agreement they can’t get out of. You have all the power here. You know you have something. They have established a lower bounds on its value. It’s way more than 40% of 400k.

Best of all. Don’t let your customers know it’s founders are going through this. It’s obvious, but make sure you keep your cool and composure. It will pay off in the long run.

>> It will pay off in the long run.

For both of them if partner can separate head and ass.

Could one really re-establish trust at this point? How would you know things may not head south at any future point with a big outcome at stake?
How do you figure NTF can't get out of it? Couldn't they fire TCF with the investor's cooperation?
I was assuming there was some sort of binding articles of incorporation that guarantees the TCF rights in this case.
Then they are in lots of trouble, assuming the OP has a rock solid legal agreement...
>the other party wouldn't want it so bad ;-)

Value to a founder does not imply value to the market.

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Hmm... a few objective points here:

- If OP keeps 40% and doesn't do work for the company, the company is highly unlikely to succeed. The company needs to be able to dish out equity to future employees and likely investors to succeed, and having 40% locked up in an entity that doesn't do anything for the company is not going to be attractive to those future participants.

- If OP keeps any equity, they should be doing it with the hope that the company succeeds, so that the equity will be worth something. Don't keep equity to spite your co-founder. It's not going to benefit you in any way if that causes the company to fail and your equity ends up being worth $0.

- If OP wants a fully cash deal, it's not realistic if the other co-founder doesn't have a ton of personal cash (most don't). Raising a round to buy out a co-founder at 40% of valuation isn't something ANY investor is going to want to do. That's almost half of an investment thrown in the trash, from their perspective, and they'd probably rather invest in a less complicated competitor.

- It sounds like the human relationship between OP and co-founder is broken and it is not worth pursuing working together, as that alone would likely lead to the failure of the company even if everything else works out.

That said, my thoughts would be:

(a) Stall for a month to get to the cliff so you have slightly more leverage.

(b) Work out a deal where you're not keeping that much equity, but you're keeping an amount such that the company is still bound for success, and that your smaller amount will actually be worth something. Owning 40% of $0 is still $0. Owning maybe 5% of $1 billion is something.

Good analysis. It sounds in principle that for OP there isn't really much options to win big, sometimes that happens in startup land - mentally it is good idea to admit that this project wasn't personally very successful and start thinking about next moves.

Most important here, I think, is to act in polite and professional manner. It is not uncommon in these situations for everyone to lose because things get personal. Just try to find some kind of deal where you are likely to get some value.

Vesting schedule means he has 0% right now, 10% in a month, and then 1/48th of 40% every month thereafter.
The OP said it was a 4yr reverse vesting schedule and that they currently owned 40%.
With a 1 year cliff, I’m pretty sure he effectively owns 0 right now.
With a reverse vest, you own the shares immediately, and the vesting schedule defines how much of the shares you retain if you leave (i.e. if he quits now, 100% will be clawed back).
Yep, which means he effectively doesn’t own them right now, in any meaningful financial sense. For the purposes of control, sure.

The parent comment of this thread was talking about keeping 40% of nothing.

There's a decent chance that the other founder is in the same position, in which case the investor is the only one with a real stake in things
Agreed. And also: if you give up that 40% then for sure there will be a play to give up the rest.
What if the other party switches activity over a new company in the meantime?
The founder and investor can fire him and easily dilute him down to 3% without violating any agreement. He’s got zero leverage here unless his agreement had anti dilution protections.
I am not a lawyer, but...

Dilution of the sort you seem to be describing would expose the founder and investor to a minority oppression lawsuit from OP which could result in monetary damages, and/or the forced sale of all or part of the company at a price determined by the court.

You can't just dilute people without there being any consequences, unless the new shares are being sold at a justifiable price and at an arm's length. The attempts made so far by the founder to push out the OP would color any future dilution, making it harder to justify that dilution in court, even if on the surface it appears legitimate.

If the shares are not sold to a third-party arms-length investor, OP would have to be given the opportunity to participate in the share issuance on a proportional basis. If the founder and investor conspire to issue shares to themselves with the sole purpose of diluting OP, not only would that dilution possibly be reversed in court, but further sanctions could be imposed on the founder and investor as well.

I’m not a lawyer either, but these risks are easy to skirt.

First they have time to just fire him, and without contractual protections she/he’s out before vesting a single share. Most US states are At Will employment, meaning they don’t need a reason. If the CTO wants to contest the firing, where will they get $30K+ to pay a lawyer sue over a nearly worthless business?

If he/she is able to vest their first year before getting fired, but they then dilute the CTO further, where is the CTO going to get $30K+ to pay their lawyer sue over 10% of a nearly worthless business?

Can you expand on why they want you out and what happens if you stay?
We've spoken a fair bit and they don't have anything specific to say. It's mainly that they don't like or want the stress of working on a startup, and want to run it more as a lifestyle business.
That's tough. I think they will need to realise that the commitment to having seed funding and a co-founder are not the same as a lifestyle business - especially when they do not have funds of their own to fall back on and revenue is not presently hitting the numbers that would be needed.

Even a lifestyle business requires more than just 'coding'. That person at least is likely to have an unpleasant awakening. I just hope it doesn't hurt either of you too much

If they want to run it as a lifestyle business, that might be some leverage with your investor. Lifestyle businesses are great, but they do not return the same as high-growth venture businesses.
lol! too late for that! he took seed money.
They are trying to kick you out a month before you vest! These guys are not acting in good faith. Do not trust them. Wait a month and vest. Then quit.

You were the technical lead. More than anyone, you built it. Don't let these suits steal it from you or bluff you. So often business types take advantage of financially unsophisticated technical people.

It's important to see if you are before or after the cliff.

If before then depending on your employment agreement and other docs there could be a scenario where you are fired/let go and get 0% shares.

Your last round valuation was $1,000,000 post so that price would be $141,000 or so for your 14% stake, can include some triggers on when that occurs that doesn't impede the business (ie $xm raised, $y profits).

If not then your ownership of the company is basically 10% on good leaver terms and that is the floor you should accept.

To illustrate assuming 100 total shares

Now: 40.8: him 39.2: you 10: option 10: seed investor

Goes to new cap table of: 40.8 him (57.6% ownership) 10 you (14% ownership) 10 option (14%) 10 seed investor (14%)

You're not going to get bought out now although you could say that your stake is purchaseable in the future at the last round valuation, which is very reasonable and keeps the cap table clear, probably $140,000 per the above with some sort of trigger for that (eg $xm raised, $y profits)

he is a cofounder not an employee
That may not matter here, depending on how the company is structured. If his partner has the right to sever him from the company, for ex. by dint of his share advantage, and he hasn't cliffed, he'll get 0.
Just because your co-founder just now feels like "working on it alone" doesn't give him/her the right to force you out, specially if he or she doesn't have any leverage (as you say, the investor is remaining neutral). So what is preventing you from just saying "no, thanks, I'll keep my 40% and keep working on this". What would he/she do, then?
What keeps the OP from saying they'd rather work alone on it and the other cofounder leave instead, then see what the co-founder want to leave. If they come with some amazing demands, the same demands can be used by the OP to leave.
Why does your co-founder want you to leave?
They're not enjoying working on the company together. It's mainly that they don't like or want the stress of working on a startup, and want to run it more as a lifestyle business.
That is so bizarre and seems unbelievable. Feels like there is another reason they arent telling you. If you didnt want the stress, why boot the cofounder? If I didnt want the stress I'd try to maintain some ownership and have you step up more.
Something smells fishy, if they don't want the stress why would they want to do all the work alone? And there would still be investors bringing some pressure. They also didn't ask you if you agreed to run the business like a "lifestyle business", they directly ask you to leave. That sounds like a made up excuse.

You probably can't work together anymore now, but you both seem to think the business can be profitable, so if you decide to leave you should be compensated for what you built.

Don't rush the decision. You've worked for 11 months, you can take 2 weeks to talk about it and think things over.

I worked with someone for about a year without making any money. We had to part ways without anything to show for it. I can empathize.

You didn't say why your co-founder wants to fire you. I suggest digging deeper into those reasons before you haggle on your exit terms.

Assuming you weren't negligent: I would try to point out that pushing you out one month before your equity vests is bad faith on your co-founder's side. Offer to leave voluntarily after your one-year cliff. Otherwise, if your co-founder just wants you gone now, request that you keep your 1-year equity and some severance.

Furthermore: Sometimes it's cheaper to just close the company and use the "lessons learned" to restart a very similar company... And that very similar company won't owe you anything.

[Edit: Deleted some text that, after reading the discussion, isn't relevant.]

Sell nothing. Do you want to leave? It doesn’t seem like you want to leave.
Stories like this make me wonder if there's a form of pre-business counseling much like premarital counseling where you discuss with your cofounder expectations going into the business and talk about worst-case scenarios like this and how each party would handle it at the time of the counseling (considering people change over time).
I thought that's what involving a lawyer in these kinds of negotiations is supposed to do?

That requires having the bucks in the bank to pay for a lawyer. If fourtydegrees is young with a thin wallet, I don't think lawyers were involved.

Not all lawyers will cost 100k. You can get a good lawyer for 2-3K for basic consultation and if you don't even that type of cash, then it is tough for sure.
> You can get a good lawyer for 2-3K for basic consultation

Maybe it's just my style, but that's a lot for me to shell out on "day one" of working with someone. I prefer to trust the people I work with.

But, in a situation like this I'd happily spend that kind of money to get something straightened out.

Not experienced in this by any means at all, but I still am interested in what are the legal, social, and professional responsibilities here.

Legally, you are entitled even though the market is no longer the same as which you were brought to help in. Professionally you have put in lots of un-tallied TLC. Socially, there seems to be no effort for an amicable resolution.

On the business side it doesn’t make much sense for you to continue with the company if this is not your area of expertise. So you should taper off the position of founder and become a silent investor. Do not budge on percentage. It is your right.

If the other person does not accept this, then the option is to dissolve the company. Keep all assets as is. And license to new entity for royalty or one time debt.

If you want to continue with the company, negotiate a position that is optimized for what you can do. And remain shareholder. And board member.

Either way, assess the true value of the company in terms of current potential revenue, future growth, and future risks. Use that as as premise for negotiation. And set aside a BATNA. A best alternative to negotiated agreement.

Don’t focus on the torch and burn scenario even if the other person insists is a possible outcome.

(All this comes from someone who doesn’t know a single thing about this other than how businesses merge, split, and dissolve.)

> Legally, you are entitled

He's not. He's 11 months into a 12 month cliff.

First of all, in a case like there where you have founders at odds so early on, your company is basically on life support and probably dead already.

You have very little to lose by digging in and waiting for your co-founder to fold. If your co-founder has done this at this point of the business where the stakes are so low, they will absolutely try to screw you out of the 3% through other nefarious means.

It sucks that a single founder can tank a promising startup, but that's how it goes (unless you've already got a shotgun clause or equivalent in your shareholder agreements).

I would propose structuring the buyout in the form of convertible debt instead of a cash buyout. You give up your equity today, but the LLC gives your a convertible note to cover your valuation conditional on some future funding event.

Set a specific valuation target, at which point the note will pay in cash equivalent to a certain percent of the company's equity. That defers the issue of liquidity until if/when the company gets sufficient funding. But it gets you out of the equity today, particularly with regards to voting shares. Which is probably what your co-founder cares about the most.

This makes a lot of sense. An issue I have with this is that one reason my co-founder wants to split is that they don't really want the pressure of running a startup, and so are unlikely to go on to raise additional money.

Could a situation where I get a cash payout, say $20k from the company to sell a certain %, and then the convertible debt to sell more in the future work?

If the co-founder doesn't think there will be a need for any new funding, then that would imply that he expects the company to be cash-flow positive in the near-term.

I'd sit down and work out what are the cash flow forecasts and milestones. Contextualize what's a reasonable rate of return for implicitly funding the company by foregoing an immediate cash buyout. If/when the company achieves certain profitability milestones, then the note will pay back in installments.

Each successful milestone draws down the principal, each missed milestone increases the principal. If profitability isn't sustainably achieved, the note converts back into common equity. If/when there's a major funding event, the note converts to common equity or cash equivalent of the common equity valuation.

Essentially you're planning for three scenarios. 1) The business becomes profitable without further funding. You're paid off over time from the profits. 2) The business goes the fundraising route. You're paid off at the liquidity event. 3) The business succeeds at neither route. Your share of the equity reverts back to you, so you receive your fair share of the scraps.

"An issue I have with this is that one reason my co-founder wants to split is that they don't really want the pressure of running a startup"

Whereas it sounds like you have a solid plan to grow the business and generate revenue. As @jedberg says, this makes your interests aligned with the (neutral) investor, and the other founder at odds with the investor.

a) You and your cofounder can't work together

b) One must leave

The investor and one founder can push out the other founder. Who do you think the investor thinks should leave if you reread your quote above?

> An issue I have with this is that one reason my co-founder wants to split is that they don't really want the pressure of running a startup.

I’m confused. If they don’t want the pressure of running a startup, why isn’t the co-founder leaving, instead of trying to force you out and remain in charge?

Could you privately find a potential buyer for your 40%? Then tease that info and magically they may prefer to buy you out and suddenly find a way to do so...
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Your co-founder likely has no ability to just kick you out. What do the documents you signed say? Is there an operating agreement?

Who brought in the investor? Who has that relationship? If you're friendly with them, you could ask for advice or feedback. Do you have business mentors near you who can help you navigate this?

Why does your partner not want to continue working with you? Are your views on how to continue opposite? I understand how you see this as unfair but it also doesn’t make sense if he/she builds the product alone and owe you 40% for 12 months of work
Since you have a 1-year cliff and have only been there 11 months, sounds like as of today you have 0% equity. So the immediate question may be whether your co-founder can fire you.

In 1 month, you've vested 25% of your grant, or 10% of the company. So I would try to get to that mark to strengthen your negotiating position. Any references to 40% are red herrings at this point.

Unless there's a specific buyback clause in your stakeholder agreement, they're under no obligation to buy you out at any time. (They may have the right to do so. That's not uncommon.)

Of course, you're under no obligation to resign, either. So this is a negotiation.

So the way I see it, you have a few options:

1. You take your 10% and leave. You "don't want any equity", but better something you don't want than nothing.

2. You agree to a buyback, potentially at a discount to FMV. If you don't know what FMV is, it's hard to negotiate one way or another. It's v. likely not $1M. Sounds like this is a no-go.

2B. You agree to a non-cash buyback, e.g., in IP. You spent 11 months building the tech: what if you took that with you?

3. You flip the script and buy your co-founder out.

In any case, your relationship is over. You might walk away with nothing.

10% might be a good target from another perspective -- the investor put in 100k to get to 10% -- is that about how much "sweat-equity" that the OP has put in? Alternatively, just pretend the vesting was happening monthly.. how much is that 9.16%? The surviving founder does need enough incentive to continue. The OP should make sure it is hard equity of the same class as the investor's shares, where there are tax liability distributions and other preferences. If the OP is before the vesting cliff and your co-founder is fixated 4%, then perhaps think about the balance as unpaid sweat equity, disbursed as deferred compensation at a reasonable interest rate, as a percentage of revenue, to be paid off before co-founder raises their owner draw? Critically, the OP should assume best intents and look for win-win situations. Finally, seek competent legal advice!
I think people should be careful with the "seek legal advice" thing. Obviously, you need to talk to a lawyer. But:

(a) You need a lawyer who deals with this kind of stuff regularly and has a realistic and well-informed view of what the outcomes are going to be. Most lawyers aren't like this.

(b) Legal gets expensive very fast, especially as it transitions from advice to negotiation and document review. At this scale of opportunity (the way the company is described), I'd stick to get getting advice!

(c) Past the "can I be fired" question, which I agree is urgent (and probably predictable), a lot of the negotiation here isn't going to be about the law so much as it's going to be about what both sides are willing to accept. If you have friends who have been in founder disputes like this, their input is going to be just as valuable as the lawyer's.

Agree completely that poster would want the right kind of lawyer – someone who specializes in this kind/scale of business, and that reaching out to acquaintances/etc who've been in relevant situations may be as valuable or more than legal advice.

Agree also that lawyer-billing-on-the-clock gets expensive fast. But unless poster already has a go-to trusted counsel – which seems not to be the case – the mere act of "shopping around" can get 15m-1h of unbilled pre-engagement discussion from a bunch of lawyers. Essentially, poster could type up a 1-2 page brief, in more confidential detail than the post here, and have dozens of short conversations with lawyers (some of which would read the brief 1st) about key issues, tactics, & potential outcomes. The contrasts between what lawyers say, & what they ask about, will be as informative as any one conversation.

> the investor put in 100k to get to 10% -- is that about how much "sweat-equity" that the OP has put in

Another way to look at it: their sweat equity is more like $1 million e.g. $100k “time” invested with a risk of success of 1 in 10 means you need to get $1 million out to be “even” (ignoring Kelly Criterion).

Obviously there is some Bayesian that goes on now that there is more information, but it seems like it has a better chance of success than when it started, which makes numbers more difficult to calculate than complete failure ($0).

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Hold out. Keep working and keep proof you are working and do what is required to keep your stake. Don't give them anything that could be used to justify firing you or the upper hand in any legal battle. Keep any evidence of them violating the contract. Try to get the upper hand in any negotiations. You'll get a better deal at the very least
Sorry you had this happen to you. I had something similar just when the startup looked like it was going to take off the other co-founders tried to shake me down for my shares, threaded me with complete theft of my shares if I didn't accept some insulting, contract breaking amount. The company went on to do unsuccessful ICO scam and things worked out well for me getting out