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Ask HN: Has anyone quit their startup (VC-backed) over cofounder disagreements?

Ask HN: Has anyone quit their startup (VC-backed) over cofounder disagreements?

83 comments

·April 11, 2025

hey fam, i'm at a crossroads where i'm considering quitting my startup and taking a job or alternate paths and wanted y'alls opinion.

i've been working on a startup for the past 24 months with my cofounder - i'm technical and she's mostly focused on business side (with basic frontend skills). we got funded roughly 18 months ago for an idea i came up with, was excited about, and found some traction.

since then we pivoted away from it. we've roughly pivoted almost every month to something new. there is no longer any vision or clear problem we're trying to solve. each month is our team simply fishing for ideas in different industries and domains hoping to strike gold.

my cofounder and i don't see eye to eye on most things anymore and the relationship has also deteriorated significantly. my cofounder and i disagree upon what problems to focus on. for her, ideas only resonate if there are competitors who've raised $X million or hit certain revenue targets with no regard for interest or insights for a problem/industry. i'd much rather work on problems where i have some inherent interest and/or urge to solve the problem but it's hard to drive a shared vision between us both. this is a constant point of friction.

after 24 months of working together, i'm now considering quitting my own startup to either go do another one or take a job where i can find problems and a future cofounder. has anyone been through anything similar in the past? how did you navigate this?

fzwang

I used to work in VC and have seen a few examples of this. Every case is a little different, but from what you've described I'd focus on salvaging the co-founder relationship. Conflict like this is totally normal. IMO, a pivot is when you change directions based on new information. It sounds like you're not pivoting, but lost. If you haven't already, addressing this head-on and having a candid conversation about being lost would be beneficial. Think of it as an exercise to possibly strengthen your relationship via conflict. Few other thoughts:

1. At this early stage of the business, the core asset is really the co-founding team and their relationship. Conflict is very much normal, but how you resolve it is important. You should be able to articulate your co-founder's concerns. For ex. she might feel the pressure to show "progress" to your investors.

2. It takes a lot of time and energy to build a good working relationship. Moving onto something else might seem like a good idea at the moment, but you could be right back with the same issue with another co-founder.

3. If you do decide to move on, end the relationship as amicably as you can. Note that this is not necessarily the "quickest" route, but it'll help keep your reputation intact.

Edit: spelling.

willseth

100%. This is an opportunity to lead, not walk away. Maybe he still fails, but it's a valuable learning experience either way and a much better story to tell assuming he wants to found another company. Conversely, walking away in frustration will be a red flag for many investors.

tptacek

Counterpoint: unless there's an opportunity for the company to be a success --- which, 18 months into its seed investment, it does not appear to be --- nobody is going to care whether this person stayed on to the bitter end.

JamesBarney

The ROI of investing another year or two of frustration and failure so a handful of investors might have a marginally better opinion of you is poor to say the least.

willseth

VCs don’t care as much about failure as you might think. They make investments expecting 90% failure and understand that timing and luck are big factors in success, so they are simply looking for people who they believe can lead through rocky stages and navigate difficulty. Assuming you want to continue to be a founder, bailing on the company you founded, even in the face of very frustrating conflict, reflects poorly.

ra0x3

OP seems trapped between a rock and a hard place. Doesn't seem bought in, not having a good co-founder relationship (a recipe for failure). But walking away would be a HUGE red flag for his future. I don't envy OP's position.

necubi

It's really not a huge red flag. Co-founder breakups are incredibly common. In this case the company is also flailing and has been likely written off by their investors, so they're not going to care.

Something I've learned doing a startup and talking to a lot of other startup founders is that one of the biggest risks is sticking around for too long just because there's still money in the bank. Your most precious resource is time, and if it's pivot-hell for 18 months you're well into sunk-cost land.

fzwang

Working through a really difficult situation like this could actually make their working relationship much stronger. To your point, even if they fail they'll learn from the experience, which will be useful for their next venture (either together or going separate ways).

fzwang

Some additional personal observations that OP might find useful:

- Building a company is really emotional, as you already know. Most founders are under-skilled when they start, and are forced to learn quickly. As a result, you get a lot of scars along the way and the experience will test all of your insecurities. Learning how to resolve existential crises again and again is part of the package. And it gets worse. Wait until you have whole teams of smart opinionated people that you have to lead.

- It'll be good to revisit why you and your co-founder decided to start a company. You've both spent 2 years of your lives living in the trenches, so to speak. Someone decided you two were worth the risk. Why didn't your co-founder quit after the first idea failed? Why does she keep trying? I obviously don't have enough info to make any judgement calls, but I've seen situations where people make the wrong call because they've failed to truly appreciate the emotional baggage. For example, sometimes the first failure hits really hard and triggers all sorts of insecurities in a co-founder about not being good enough. And if their team starts questioning their judgement over and over without diffusing the insecurities, it just makes things worse.

- There are good and bad breakups. Good breakups are worth it for the emotional closure and the reputational upside. Bad breakups can create all sorts of fallout that will affect you in unexpected way (sometimes without you even knowing, ex. if the drama resurfaces during due-diligence). All the legal mechanics are also much smoother and drama-free when the breakup is on good terms.

- I am probably biased because these types of co-founder blowups are what keep investors up at night. Losing a technical co-founder is not only emotionally draining, but usually lethal for the investment. People problems are gnarly and take a lot of skill and precision to diffuse. If anything, use the crisis as a personal challenge to figure out how to resolve it on good terms.

stuck12345

my cofounder has been pivoting across different ideas for the past 4 years now after their last company failed. while admirable, the inability to stick to idea/industry/persona, to me, seems like a massive red flag. we started the company for the sake of starting a company, ngl.

what does a good cofounder breakup look like?

stuck12345

thanks for the advice here, fzwang. when these relationships end, what have you usually seen? have there been scenarios where the company/remaining funding is split between the founders? or is one usually bought out?

bruce511

At the risk of an unpopular view, and the inevitable downvotes, I think it's worth stating the following;

If your business model is raising money from VCs then doing things VCs want is important to getting paid.

All businesses tailor their output to suit their customer. Your customer is VCs. So you need to tailor your output accordingly.

In this sense your business partner is not wrong. There's no point on working on things that excite you, if it doesn't excite them. That's a hobby.

Sure, pivoting too often is also wrong. So you should try to improve that.

At this point it's probably worth sitting down with your partner with the fundamental understanding she is right; You need to find something to attract the next investor. However you need to stick with it, success or fail. You've thrown a lot against the wall, now it's time to choose.

Of course you'll likely fail. Most businesses do. VC based businesses at an even higher rate because your customer base is so small. But even failure is OK because VCs are looking for founders, not successes.

Make no mistake; founding a startup is hard work. Not fun stuff. Not interesting stuff. Mostly it's just work.

Being a founder isn't about coding. It's about business. You need to bring more to the table than just coding. Just like your co-founder takes an interest in the technical side, so you need to take more than a passing interest in the business side.

In any business, sales is the most important thing. Without them you will fail. Tech supports sales, not the other way around.

I'm sorry that this sounds harsh. I don't mean it that way. I wish you success. That success starts with you realizing the truth at the heart of your partners position. Start there. Fix your relationship.

Good luck!

ezekg

The one I was a part of wasn't VC-backed, but yes, I've quit due to bad cofounder fit. No equity, no payout, just straight up left for my own sanity. It was my idea, too, and I was the only technical cofounder. It's a nightmare to be stuck in that situation, and it's not worth it imo. I've known other founders who have done the same, including founders of VC-backed companies.

tptacek

How you navigate this is you quit. You don't have a startup; you have an unstable pair of cofounders flailing to pick a startup to build. Every dollar you draw from your initial investment before securing product/market fit devalues your work. You and your partner have lost respect for each other and will likely sabotage any success you do find.

It's not clear to me what you're preserving by staying.

JamesBarney

100% this. If you guys had significant traction with your startup then it might be worth it to work really hard to try to salvage the relationship.

But right now you're just wasting your life. The most valuable resource you burn through at a startup is your life. Startups are stressful, they wear you down, they're not great for your finances, and many of those are doubly so if you don't get along with your cofounder.

Just quit, you don't owe anyone your life. You are less likely to find traction with two cofounders with a bad working relationship, and if you do find traction you are less likely to be able capitalize on it.

tptacek

I won't shut up about this, because I don't think most people can understand viscerally how much more valuable their time is than almost any other consideration until they've spent a lot of it already. People here obsess about equity stakes, but almost never about opportunity cost, which is what's really killing most of them.

Also? Working your ass off to save a shitty business relationship has a psychic cost. You do not have an unlimited reservoir of relationship energy to spend. If you want to keep doing startups, you need to guard your morale reserves. Wringing yourself out here won't just mess up your current startup (which seems fucked enough already); it can mess up your next one too.

its_down_again

First off, that sounds incredibly frustrating. I’ve seen this archetype before—a business person with just enough technical knowledge to chime in on complex product decisions, but without the patience or interest to develop any real depth. Instead of building real understanding, they rely on mimicking what looks successful. Always chasing whatever has funding or buzz.

That kind of thinking lacks vision and makes it really hard to build anything meaningful. Over time, it wears you down. Even if the product “works,” it doesn’t feel good because you know you're forcing it. These folks tend to say things like “this should be easy,” then only show up to question why something isn’t done. They manufacture urgency instead of clarity, and when things inevitably fall short, the blame falls on the technical team.

Second, you’re not a first-time founder anymore. Life’s short. For me at least, you’ve earned the right to walk away and build something you actually care about again.

nsypteras

Cofounder splits are extremely common. Cofounder "couples" counselors are a thing you could look into to help resolve your differences. Your VC might have recommendations for one. If you ultimately decide to split, I'd recommend at least one of you (or "the company"?) getting a lawyer to draw up a formal separation agreement you both sign in order to split in the cleanest possible way.

tptacek

Do you really need a lawyer here? Presumably the mechanics are pretty simple: you're vested halfway to your share (in what is probably going to be worthless equity), which is what you walk away with.

I ask this because I have on several occasions lawyered up (sometimes adversarially, sometimes just to keep my own ducks in a row) during separations and (if you're working with someone serious who is qualified to manage a founder separation) it's always expensive, but not always valuable.

I also ask this because this is the Nth "I'm splitting up from my startup" I've participated in, and I've noticed that for better or worse, this community has a bias towards dramatically satisfying resolutions, like ensuring for instance that each founder in a doomed startup receives precisely the allocation of company assets that they're entitled to. In the real world, the smart play is often just to walk away.

mizzao

Agree that these are extremely common but you don't hear about them when you're constantly reading TechCrunch.

I've seen almost 10 breakups from startup friends in the last year and have been through one myself. It's like dating — very few end up in marriage and most marriages end up in divorce. Except maybe worse, because people get married after knowing each other for just a few days, in order to apply to YC.

taw1285

This is very interesting to me. From this thread: https://news.ycombinator.com/item?id=43472971, I am wondering if there are anecdotal stories of how equity is being handled after a split.

On one hand, if the leaving co-founder retains all equity, it creates a sandbagging situation on a cap table that's no longer useful to the business. On the other hand, it feels right for the leaving co-founder to enjoy some upside for the years they put in.

tptacek

This problem is what vesting is for.

necubi

Standard 4-year vesting doesn't work well for this situation. A founder leaving a worthless startup with 20% of the equity is a huge problem. The remaining founder will need that equity to offer outsize offers to senior (and eventually C-level) folks to replace them. And it's demoralizing for the remaining founder and team to be working extremely hard to make the company successful, while the departed founder reaps the rewards with no effort.

Opinions will differ here, but I think if you're leaving a pre-PMF startup you've created essentially no durable value, and should return nearly all of your equity.

I've heard of startups doing 10 year vesting for founders (with double trigger) to align this better.

BhavdeepSethi

I thought this was satire before I looked it up. I mean, it makes sense but it's still so hard to believe.

serjester

Pivoting every few months? 0 cofounder alignment?

Decisions like these are tough to make in the moment, but looking back you almost never regret it. Trust your gut.

tylerneylon

I have been a similar situation before. Yes, walk away — and learn what you can.

There's one easy part of your situation, which is that your immediate next step is clear. I think it's clear because it sounds like the two of you have a fundamental disagreement about how to choose a direction. There's also a power imbalance if you've consistently been going along with pivots that you don't want to execute on. If you think you can resolve things, then maybe I'm wrong. I'm basing my advice on the fact that this is 24 months in — enough time for you to know how easy it'd be to get back to "we like working together and are on a path to success."

Now for the hard parts: * You want to act as professionally as possible in walking away. Communicate clearly, being fair to both yourself and the other people involved. I think it's easy to err to far on either side (either too defensive/passive "nice to yourself" or too deferential "nice to others"). * It can be tempting to think of this is as your cofounder's fault, but that's not constructive, and it's better to learn toward your future actions. For example, how could you have seen this problem earlier? My guess is that you were never "cofounder compatible," and this is a chance to get better at identifying that compatibility with others (useful for both startups and other jobs).

It's not a fun situation, and I hope things go well for you.

stuck12345

agreed - in hindsight, cofounder compatibility was low. i met them at a networking event and then started tinkering on ideas.

indymike

> since then we pivoted away from it. we've roughly pivoted almost every month to something new. there is no longer any vision or clear problem we're trying to solve. each month is our team simply fishing for ideas in different industries and domains hoping to strike gold.

I've parted ways with cofounders in two of my five startups (they left, not me... I could afford a zero paycheck for a little while, they couldn't). In both cases we did better after the split. In both cases our original business idea didn't work out, and we were trying to stay alive. It felt like pivoting from idea to idea. Reality was it was just trying to sell and collect enough to make payroll in six weeks. So we went from whatever we were doing to custom dev shop... Survival mode sucks.

When got down to a single founder, it wasn't that one person was right or wrong about what the business could do. It was that the business could execute well enough (without cofounders fighting and second guessing) so it could survive, and eventually find something to productize.

jononor

Pivoting every month! After 24 month and after raising VC money. That does not sound good. There are very few things that can be uncovered/learned in one month that would justify pivoting away from it, even in B2C. Even while throwing things at the wall and seeing what sticks, one needs to actually wait for the thing to actually hit the wall, at the very least...

rozap

Pivoting every month fishing for ideas in different industries? What in tarnation? Yea dude get outta there.

ra0x3

As fzwang mentions, your co-founder relationship IS the business at this point. I'd talk to your co-founder 1:1 and really have some uncomfortable conversations. If you both feel like the relationship is not salvageable, amicably walk away without burning the professional bridge (someone might ask her how you are to work with). If your heart is not 100% in it (for whatever reason) I'd suggest walking away. The opportunity cost of dragging the dead weight of a business that you're not bought into (and that you aren't seeing success with) is simply too high - and can have real life consequences (finances, stresses, etc). There's nothing wrong with walking away - there's a reason the overwhelming majority of startups fail. And most tiny startups fail due to co-founder relationships - doesn't have anything to do with PMF or anything. Think about it over a weekend - have the tough conversation(s) - don't burn the bridge. Live to fight another day. The sun is still shining outside and the NBA is still rigged to always make sure the Lakers are relevant ;)

uptownfunk

Move on, you’re not married. If You can’t align on how to vet the problem then you can’t align on the dozen other things you need alignment on. Cut your losses and move. It’s not failure it’s pivoting. Take the learning and move on, and make sure you vet your next cofounder throughly along what you learned from this experience. I will say, she wants to work on something that she has data she can sell. Selling, users, and traction will make the fundraise much easier. So try and see where she is coming from. But it sounds like at this point better to go your own way.