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

77 points stuck12345 | 2 comments | 11 Apr 25 16:16 UTC | HN request time: 0.671s | source

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?

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fzwang ◴[11 Apr 25 17:31 UTC] No.43656317[source]▶
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.

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fzwang ◴[11 Apr 25 23:26 UTC] No.43659805[source]▶
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.

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1. stuck12345 ◴[14 Apr 25 15:00 UTC] No.43682059[source]▶
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?

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2. fzwang ◴[23 Apr 25 00:44 UTC] No.43767636[source]▶
After seeing a ton of teams and failed companies, I think people fall into two categories. The first group don't care much about what they work on, as long as it grows quickly. The second group is emotionally invested in an idea/space. This is obviously a gross generalization, but you get the idea. There are good and bad manifestations for each group. The anything-that-pops group can over-pivot and never stick it out, but obviously rolls the dice more which improves chances of a good outcome. The my-life-calling group can get too ideological and be stuck on something that's just not working/isn't the right time, but the endurance is necessary for building great companies. There is no right way. I think the most important thing is for you and your co-founders to understand each other's stances and the types of sacrifices you're willing to make. Your stance could also change with experience, so you should check in regularly. Nobody's born with a "calling" and it's developed over time. But should your stances diverge in a significant way, a lot of conflict can result.

For a good breakup, I usually think about 3 perspectives:

1) Relationship with your co-founder(s) - Unless there's some major violation of my values, I'd like to be on good terms even if the team fell apart. That means you might still grab dinner/beer with them and even help them out in their next venture. You all may end up co-founders in the future when you're all wiser and the opportunity presents itself.

2) Reputation with your investors - The VC space is smaller than you think, and you need to maintain goodwill. These investors did make a bet on you, and I think you'd want to demonstrate you tried your best. You might even return some of the money left (it's mostly symbolic, but w/e counts). Most VCs understand failures are inevitable, but you don't want to leave the impression that you were the problem.

3) Self-image/self-esteem - I think many founders underestimate the benefits of a good closure emotionally. A good breakup means you sleep well at night and are content with how you handled things. You don't want bad vibes to fester and ruin your motivation and focus for whatever you do next. Building a company is already hard enough, you don't need the debuff. Doing rash things you'd end up regretting will likely cost you more time and opportunities later.