Ask HN:paying customers but annoying co-founder: should I stay or go

You'll want to read business books and consult a lawyer. Figure out what your options are. Dissolve the company, buy him out, get bought out, etc. A lawyer can best advise you on these matters, also did you assign your IP to the company? If not as others have suggested, just change the name on the door as the code is yours (or, your employers if you didn't get that sorted out). Also, consult a lawyer as there may be implicit agreements present, or legal obligations you are unaware of.

Don't cut and run just because you are the tech guy and he is the biz guy. Figure out the business side of things and get the guy out of YOUR company. It's not going to be the first time you'll have to get someone out of your company who has equity. This is a valuable opportunity to learn how to do this.

If your site sucks, change it. I assume as tech guy you've got control of the DNS records?

Stop asking for permission, and start taking control of your life and your business.

This might have been assumed, but it's worth reiterating that this could get really stressful and distracting for your business. To avoid that, you should do everything in your power to leave on good terms with him. First, talk to him in a non-confrontational way: ask him if there's anything that's getting in the way of his giving the project more attention. Politely let him know that you expect more of him, as a business partner, and see if he steps up. Set a concrete but reasonable goal date (I'd do about a month from now), and on that day, decide if you want to keep working with him for the next year or not. If you leave, suggest getting back together after he has a chance be more focused/organized/whatever.

I wouldn't bring lawyers into something like this until the very end, as they can put a very grim aura on the conversation. Have a heart-to-heart, figure out what you want, what he wants, and how both of you can be satisfied. Once you're sure of that, see a lawyer about making a legally binding agreement.

It's OK to be confrontational to a certain degree. He doesn't sound like the indispensable kind of co founder and would be in rough shape without OP, who is therefore in a position of power.

Power best unused, for the good of the customers, if no one else. One sincere but difficult conversation can substitute for months of fighting, stress, and legal threats. The ideal break-up, if one can't be avoided, would be to part ways amicably and get back to work.

yes certainly nothing to the degree of fighting/stress/legal threats but op should be assertive in the initial conversation imho

You're jumping the gun here. Two prerequisites must be met before you consult a lawyer:

1. You've exhausted all other options; and

2. You decided that what you're fighting for has enough monetary value to justify the time and money you'll spend exploring and pursuing legal remedy.

Of course it's worth knowing your position. If you have no contract it's a mess. If you don't have founder vesting it's a mess. He can walk away with half but then again so can you.

You can take the lack of such formalities as pretext: say to your cofounder you meed some structure. Say you need founder vesting and clear division of responsibilities. Make yourself CEO and then you can decide who designs the website. If necessary you can fire him then (without cause he'll still end up with a piece but that can be better than half).

Or simply talk to him about your grievances and concerns.

If those conversations fail just wAlk away.

1. You've exhausted all other options; and

Many times it's worth consulting a lawyer earlier rather than later, as such a consultation can do all sorts of things for you - eliminate options you might have otherwise wasted time pursuing, illuminate options you weren't aware of, and also keep you from making any mistakes that could come back to hurt you later.

That last point is most important and most overlooked by non-lawyers, I think. I've learned from friends who have learned the hard way that in disputes like this involving money or business, it's crucial you know the applicable law from the outset and adhere to it, even if you only intend a legal solution as the absolute last resort.

If it does come to that, your case is strongly bolstered in court if you can show that you were aware of the applicable law and diligently followed it from the outset. For example, if your adversary in court broke the law, and then you broke it too to counteract him, the court will look unfavorably on both. Two wrongs do not make a right, especially in the eyes of courts. So it's worth positioning yourself from the beginning of any such dispute as completely in compliance with legal requirements.

If you don't know what those requirements are, an early consultation with a lawyer could be valuable.

PS - it's also less stressful to simply rely on the law to guide your decisions in this uncharted territory, rather than trying to make it up as you go. Don't reinvent the wheel here, instead leverage the hundreds/thousands of years of codified dispute resolution and legal theory.

I guess my point is that you want to avoid a situation where your cofounder is an "adversary".

Yes absolutely. Solve the problem by anticipating it and completely avoiding it > all. Unfortunately the OP appears past that point.

Not necessarily. His cofounder may simply be oblivious to his level of concern. Until he's sat down and said "I'm not happy with A, B and C and if I can't get satisfactory resolution I'm going to have to stop doing this" (perhaps leave out the ultimatum part at first) then it's premature to either fight or run.

> I has happened that I asked him 3 times in the same email conversation 'did you read X', without him saying 'yes I did' or give any other indication that he read what I said or asked. Or that I tell him 'please make sure you do X or it won't work' and then he emails me back "it doesn't work", where after a couple of mails back/forth it turns out he just didn't do X.

That is normal. Basically 90% of non-nerds, and 50% of nerds, do that a lot. Get used to it. Get over it. You aren't going to be able to only do business with people who think in the same detail-oriented way that you (and I) do.

As annoying as it is, you should not make your decision based on that. What you need to consider is: what does he bring to the table? Can he effectively do something that brings substantial value to the company? If he can pull his weight for making a profit, then it doesn't matter if he's not as smart as you.

Astonished that this was voted down:

> what does he bring to the table?

is a very good question I didn't notice anyone else asking.

You talk about the negatives, and seem to imply there aren't many positives, but are there any?

Another thing I didn't notice anyone else saying, is maybe you could take a cooling out period. Back away for a little bit (tell him you're doing this of course) and see what happens and how you feel if you get a little "space" for a week or two. I bet you'll get some clarity about what you want to do, one way or the other.

E-mail is not a conversation. If you are not communicating, pick up the phone or meet face to face. Pick one or two things that are really bothering you and tell him. Ask him what you are doing that bothers him. At this point it's just poor communication. Other folks have pointed out it's a question of his complementary skills, which I agree with. The real question is one you two are communicating more effectively is he able to do things that add significant value to your startup.

Run.

Been there, done that. (I didn't run soon enough)

The heart-to-heart stuff is nice and warm for about a week. If you have been having problems for a long while, trust your senses and leave before you are more heavily invested.

Remember all those books/articles/posts about how having a great co-founder is important. (Anyone got good quotes for this ?)

I've heard so many breakup stories recently that I'm starting to believe in many cases it's less risky to not have a co-founder and just get to the point where you can hire people.

I concur - it's worse than being married.

I'll be the contrarian...

As a techie you have to take a step back and ask yourself: are my expectations like a programmer or like a person? People aren't machines and partnerships are usually far from perfect at first.

Being inexperienced, your partner is not going to grasp (and hold on to) X-tech concept as quickly as a veteran like yourself. It also sounds like he is wearing a lot of hats (on top of family and day job) so his attention could be very divided.

It may not be time to pay yourselves, but it may be time to consider outsourcing stuff that neither of you can manage - such as the website redesign.

Throwaway account, since I don't want to link this to my real name. But: Leave. Your feelings will only get stronger, and it will be harder to leave if things seem to go better business wise. But you can't ignore your feelings, and will only get unhappier with the situation.. I did, and am happy I left, only should have done it earlier.

It sounds like a lot of passive aggression on both sides.

Here's your problem - he thinks he's the boss, and you think you are the boss.

He asks you to implement a feature. You don't think it's a good idea. You both give each other a bunch of reasons why. He ends the conversation with "OK, it's sounds like it's a bad idea then". He retreats for a while, then decides to go another three rounds.

My S.O. and I have similar conversations, though it's usually about tech vs. clothing purchases. Who wants to spend 1000 on a sweater? A DSLR lens is a much better purchase. Anyway ...

The point is, you have unaligned goals or unaligned strategies for reaching those goals. As you've said, you aren't on the same wavelength. That's not really unhealthy - sometimes other people are right when they disagree with you. Sometimes not.

You have two options (IMO):

* You both have to agree that you trust each-other, but you are aware that you disagree at times (due to your separate skill sets, expectations, etc). You both have to work to minimize the impact of the quibbling, and you need mechanisms to help you here - most companies have minute books to record decisions for this very reason.

* Split.

You're still very early in the project. You have paying customers, but it sounds like that's more-or-less just covering hosting costs, etc. You have a long way to go if you're going to turn this into a real business that makes you rich. A long way to go where you'll be working with this guy and splitting your profits with this guy.

Talk to him about your concerns and see if you can work something out. But if you have any doubt that he's the right cofounder for you (which it sounds like you still will after talking to him), get out now. The longer you wait, the more it'll feel like you should just stick it out because of how much work you've already done and how well it's going.

But though it may feel like things are going great right now, you really haven't invested that much time in this, and you don't want to spend 5 years with a cofounder that you don't feel is pulling his weight. If you don't think you can spend 5 years working with this guy, get out now.

Pure business cofounders always seems to me as a wrong choice. MBA guys generally don’t understand what goes into coding; they see tech guys as replaceable robots. I tried so far to work on friends projects or have friends working on my project with no success when the guy is pure MBA; most of the time project won’t event take off.

I will say you are deep in it, you should fight and try to acquire more control and swing things your way.

You really should be talking face-to-face as much as possible and I do not understand why you are sending e-mails in the first place. It sounds like you two live and work far away from each other and in that case I believe you are doomed anyhow.

But yea just leave, a conflict like this just gets worse and worse. Specially when one of the parties in the conflict doesn't realize there is one. If you really believe in this business you could always take in outside help but I believe that is your only chance to fix the actual issue.

If you aren't prepared to do that, run.

IMO, In this particular case, face-to-face discussions will make the matter worse.

The co-founder doesn't READ his emails/IMs let alone remembering what has been discussed.

Newsflash. Nobody reads (I mean really reads) e-mails. Get used to it.

Are you saying that I was doing it the wrong way the whole time? :D

I mean, you really can't make that a rule. I read (and re-read) important mails, I guess I'm not the only one, am I ?

Of course you're not the only one who reads his emails. JabavuAdams is FOS as far as I'm concerned. I've been a developer for almost two decades and I always read my emails -- CAREFULLY.

In fact I have every client agree with me from the beginning that our emails serve as the written terms our agreements when we both agree in writing. And I ask them to always save every email they send me and every email they receive from me, so that we will both have a written trail of correspondence to refer to when (not if) there are any misunderstandings.

This system has served me well for many many years, so for someone to make an all-encompassing claim that no one reads emails is just plain ridiculous.

Come on, do you seriously believe that I'm arguing that 0 people read e-mails?

What I was trying to convey is that you'll constantly be surprised at the number of intelligent, educated, detail-oriented people who did not in fact read what you wrote.

If you optimize your communications to assume this, you will become a better communicator.

EDIT> There's another important subtext here. I've often seen the following pattern: developer is confronted with user behaviour, but continues to talk about "I do this, I do that", rather than internalizing that others do not do as he does.

> You really should be talking face-to-face as much as possible and I do not understand why you are sending e-mails in the first place. It sounds like you two live and work far away from each other and in that case I believe you are doomed anyhow.

This is the biggest red flag I saw. You guys should be talking voice or meeting face-to-face more often. You will not solve personality issues via email that neither of you have a lot of time to spare for.

If the OP doesn't make at least a serious attempt to re-connect with his founder then he's at least half of the problem here.

Make time to work with your cofounder vocally, in-person if possible. It's too easy to dismiss concerns via email.

He's counting on you and you both have to put up with a lot. If you can make it through this by stepping back and realizing that it takes two to communicate, then the business has a chance. You might have to try harder to communicate with him but can you honestly say you've tried your absolute best to make it work? Are you going to let communication breakdown without trying as hard as you can to fix it?

Things will get harder as you go on-- this kind of a problem isn't a great sign either way, but if you don't try your hardest the bad sign may very well be about you. Be absolutely convinced you did everything in your power to compensate for his weaknesses (and yours).

If your heart isn't in it enough to try your damnedest, then perhaps that's the problem and not the communication issue. I'd still try to address that because it doesn't sound like it can get much worse if you're considering leaving.

Have you directly brought these issues to his attention? If you haven't...

I'd list the items that are bothering you most and how'd you like to have them resolved. Maybe run it by a trusted friend - someone who will be directly honest with you. Then, break the list into two categories - can live with it and can't live with it. For the former, make like a duck - let them roll off your back. Just shrug your shoulders, roll your eyes, and say 'Oh that <cofounder name> is silly'. For the later, I'd look to directly address your partner in a manner that is meaningful to him. If you come to some consensus, set ways to monitor it to see if things are improving.

After this, you will have accomplished 2 things. One, you took ownership of the situation in a mature and constructive manner. This helps, especially if things don't work out, since you know you gave it your best (read: less regrets). Two, you'll have a better idea of how likely things are to improve.

If you have done this and things are not working, then look at the options. Is it worth sticking it out? If not, list your options. Often times, the black and white options (quit cold turkey and stick it out) are not the best. Consider options like decreasing your role, decreasing his, bringing in a third party (e.g. a design guy), having distinct boundaries of responsibilities, or you taking over the design element.

If it is time to part ways, I'm sure you'll do it in a professional manner that doesn't burn bridges.

Best wishes.

It doesn't sound like this is the right co-founder and if you have any inclination that this is the case at this early stage of the company then do something about it NOW.

Aside from the personality issues it doesn't sound like he's bringing enough to the table to help your company elevate to where it needs to be - that's business and in addressing this you might get better mileage using this as the grounds for action because they are explicit and practical.

"You can't keep the site looking the way users want it" and "You don't have the product development skills needed as you are raising feature ideas that are not being asked" are all explicit issues you can use. "I don't like the way you communicate" is not, even if that is really the issue.

I would be VERY careful about dissolving the company and then taking IP with you to a new company, as others have suggested. He would be in his right to lay claim to his share of the IP.

There are ways around that however. Getting the company to grant each of you a non-exclusive perpetual right to the technology, then dissolving the business, then you going off and setting a new business with it is one way (that also lets him do the same, with a new co-founder perhaps, so be confident he won't be successful).

But you MUST see a lawyer (retained personally, not on the business of course)

Sounds like you do a lot of emailing. Email is a tough way to communicate. Have you considered trying another medium? (chat, texting, phone calls....etc.)

From the sounds of it, do you even need him? Seems like something you can get an employee to do, and for cheaper.

Judge if your other co-founder brings value in terms of the business network with potential markets, partners or investors. If you feel that he is needed for the business to function then you should probably be looking to outsource the website. Since you have paying customers for your project, you can do a simple A/B test by announcing that you are going to release the feature in question and provide a sign up/ i am interested form. You can tell be the number of customers who would be interested in the feature versus your existing customer base.

If you genuinely feel that the non-tech co-founder is not bringing enough value to the table, you must probably be looking at buying out part or whole of the stake. However, I suggest that you get knowledge of the other aspects of the business such as accounting, tax filing norms and such. Most of the other stuff, you can find others to handle for you without parting with your equity.

You already have the technical aspect down. So disband the project, find a better co-founder and simply restart the same thing anew. You can be up and running in a fraction of the time.

Basically, do what Arrington did with Calacanis (with regards to running the TechCrunch conference).

"What would you do?"

First I would get on his case, tell him the website needs to be updated because the service will not grow into a real business in its current 1990s design. Show him websites that I feel are a good standard and what I expect our site to be like. If he can't do that then it is the wrong partnership for me.

I would stop working on the project(in relation to his ideas/feedback/requests), tell him I need the website updated a few decades or I'm on my way.

and then plan do the whole thing on my own while keeping an eye out for another co-founder with some technical ability aswell as business interests.

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You should take the positives out of this project in its current state. You have the technical side down and you know you can get customers to pay for the service.

Have you sat down and had a heart-to-heart with him? Cover all these points. I think his response will be a better indicator of whether you should stay or leave.

Talk with a few advisors and lawyers individually, and then if you still don't have a clear idea, maybe meet with some advisors/lawyers with both of you in the room.

If all else fails, I'd re-write the business plan in terms of who does what. What are you good at? What aren't you good at? If he has a bad sense of design, maybe he shouldn't be handling that aspect, etcetera.

With that said, I hope that all goes well and that this startup succeeds!

I think this is a typical 'go with your heart' situation. If your gut feeling tells you you're not enjoying it for such and such annoying reasons it is a clear sign that its not the best thing for you. In these situations ending is better than mending. That is because mending will take up your time only to have you end up in a marginally better condition. If you feel this is the case start from scratch.

I was in a similar situation but with a much more competent partner. But for different reasons we just weren't headed in the same direction.

I said hey, here is a deal I am happy with. I am happy to be on either side of this deal, because it is fair.

Not sure how much I can talk about it, but it had to do with one partner getting the company and the other getting an X percent royalty for Y years.

Thanks for all the advice and different point of views. I though I'd be lucky to get 1 or 2 responses. I hadn't expected more than 40. It sure offers some food for thought.

Some people said: live with it, people don't read their email. Well, I send at least 20 mails a day at the daytime job, and I know quite well how much the average person reads from your mail and that when you ask a direct question, it usually gets answered. I've also seen the same email issues with customers.

What does he bring to the table? Well, basically he handles all things I prefer not to. Does he bring something unique that can't be replaced? No. It's pretty hard to find someone who wants to be an entrepreneur though and who wants to put in hard work that might make a profit later. For me it seems to be an almost impossible task to find someone who wants to be an entrepreneur, that is a complement to my skills, who I get along with and is fairly local to me.

I know lots of competent people, but none of them are interested in becoming an entrepreneur unfortunately.

I know from experience though that when working solo, once the fun technical part is over, it's too easy to find another interesting technology or idea and start hacking at that. I've got several of such unfinished projects. That's a big motivator for me to get a co-founder.

Concerning that it seems that we both like to be boss: well, we both have a management function (during the daytime job) where we need to coordinate/steer people. We both are used to being right.

I don't want to bring any lawyers to the table though and I don't want to just run with the project and leave him in the cold (although I could). I wouldn't want him to do that to me, so I won't do that to him. I also know that this would make me feel too guilty, which isn't worth it.

I thought having a working product and paying customers is pretty much, but the comments on here have made me realize that this is just the beginning. Which is it, we'd have to grow the number of paying customer at least 10-fold to be able to replace our current income from the daytime job.

Basically I've decided to give it 1 month and then re-evaluate. I'm planning on putting all issues in a notebook or file somewhere together with the date, because I tend to concentrate fully on work and family and forget about what happened when. Sort of a diary, to get a better view on things.

Thanks for all the advice and insight!

Listen, if he's your partner and he's doing the stuff you don't want to do and you have paying customers, it seems to me it's worth trying to salvage over the next month. If your partner is doing more harm than good in certain aspects, why not agree that you need to formalise those aspects to accelerate growth, and then do it in a way that actually helps him not screw up?

For example: you say your website is a mess. If he can make it ugly, then he has too much control. Move to a CMS with a tight templating system and eliminate this pain point. If he's making repeat (and poor) feature requests, move to a formal feature request system with upvoting and make it public. Then you can point out that a particular feature has no user support. If you're answering the same questions over and over, institute an internal helpdesk system and just refer him to the answered, closed tickets and the search when he re-asks.

Basically, look at it as a management issue. The human factor is always going to be an issue no matter what startup you pursue; if you lack the soft skills to deal with it well, a systems approach might take you 80% of where you need to go until you've expanded enough to bring in another person who's designated job it is to take responsibility for these decisions.

If you are looking for boolean answer: GO

What's the point in staying in a company where you are not happy (in this case because of cofounder). You can either resolve the issue or separate and start something of your own.

Talking to your co-founder will not help, from what you have written seems like he has a personality issue and this will take a long time to correct......you first have to get him to accept the issue is with him. My advice would be to be smart, put personal feelings and emotions aside and try to engineer a way to get him out of the company or you and the company away from him. Time is so precious, you can't waste it on someone not ready/mature enough for the start up world yet, especially when you have a family.

Be careful-- We all know from experience that there's two sides to every story. The other guy's perspective could just as easily make it appear as if the OP has the personality issue.

The truth is that every founder is different and every one of them has issues. The successful team is going to be able to compensate for each other's weaknesses.

The key here is to really step up the communication-- if you do that and still nothing works out, I'd say only then start the plan to leave.

The day you believe in your heart of hearts that you did your best, but it wasn't enough to compensate, then you've fulfilled your obligation to the partner. I don't sense the OP has yet tried his true best-- or else he'd know there isn't more he could do to make it work.

Would you want him to bail/cut-out on you because he felt like you two couldn't communicate? At least without coming to you first to figure out a way to improve the communication issues?

"The day you believe in your heart of hearts that you did your best"

Sometimes when u wait that long, the opportunity has been taken by someone else, you running out of money or your customer's are just too frustrated with your business. I believe that you are correct that stepping up communication is important but we also have to keep in mind that time is money. My advice would be to put a time frame on it and if the issue is not solved start executing your plan. Also always remember that the health of the business comes first.

Tell him you're leaving, and offer him (as an alternative) to buy him out for a low price.

Could you potentially buy him out? Just replace him.

If you decide to go solo or drop the project (so as to not have to worry about buying out your partner, or maybe because you're over this one and want to move on), have you considered selling the company?

I'm interested in hearing more about the company and would consider buying it. You can contact me via email on about.me/sir

(ps. I'd probably want to hire you back ;))