Ask HN: How to deal with a dysfunctional relationship with a 50/50 co-founder?

101 points by throwaway9934 ↗ HN
We’re four years into a bootstrapped B2B startup that set out to solve two ambitious technical problems for our industry. Last year we turned over more than 1m USD. Each of was responsible for one side of the business.

However there were still a lot of technical issues to be solved when we launched. Over the last year I’ve been able to clear all the problems on my side, but he has pretty much done almost no technical work since launch two years ago. Instead he sees his role as the figurehead of the company who basically just does sales and ideas and treats everyone at the company including myself as incompetent PA’s.

This worked for a while because we had a lot of hype around us in our industry and the money was rolling in. However the next round of potential buyers are wisely waiting to see how things turn out with our first round of customers.

My co-founder responds to complaints by telling them that their problems aren’t really problems in a very professional and well written manner, but that’s not working anymore. I now find myself having to mend bridges with customers which causes a lot of conflict because I am “overstepping my bounds.” Additionally I have to “overstep my bounds” to engage with his talented direct reports who now openly despise him, in order to convince them to not leave the company.

Now the money has nearly run out and we need what seems like a miracle.

I feel like I’ve tried everything I could think of to try and turn this relationship around but I don’t I just don’t see how anymore. We struggle to have any meaningful conversations about anything related to the business even when I manage to maintain my composure in response to nearly constant put downs.

107 comments

[ 2.8 ms ] story [ 202 ms ] thread
Tell him to stop being such a child and join the real world. Or become a venture capitalist.
Honestly, it sounds like the ship have done gone sailed. If it's as dire as you indicate (which I have no reason to not believe), sounds like you need a lawyer.

It's also my belief that 50-50 partnerships turn out like this more than they don't. I've made a point to never get into a partnership. Sure, I'll work for someone else, or I'll have someone work for me. But 50-50 means there's no good resolution on opposing business decisions.

But my critique doesn't really help you after it's done. Check the contract. See if there's a buy-out option, or offer to sell your interest. Regardless, you're bringing in a big gun.

Lawyers are generally the last step, not much happens that is good once they are involved. I'd recommend couples counseling of some kind prior to that, and sitting down and laying things out and giving him/her time to think on it at the very least.
As dysfunctional as it is, I don't think either one of us would get lawyers involved. I think maybe I've managed to take the first step towards some kind of reconciliation between us. I think that perhaps the desperation of the situation may have created an environment where we are forced to work together for a common goal (saving what's been built so far).
You make good points but as you say that ship is sailed. I instigated a good long talk today based on the advice here and it was remarkably positive. We decided to focus only on finding a way to make the company survive, and if we manage that to revisit everything in a few weeks or months.
Have you candidly told him any of this?

In your position, it sounds like you two need to have a serious talk about what both of you consider your role to be and about where the company is going. Find a free block of time and figure out where you two go from here, you’re both adults and can and should be discussing these feelings and issues.

Agreed, except: he likely can't because the other guy is a jerk. There's some people who just missed the REASONABLE DNA strand.
I have tried numerous times in the past. However because things were "going well" he had no reason to listen and we kept marching towards disaster.

Oddly enough, based on a rare positive conversation we managed today, it seem likes maybe this crisis might put us back on the same page. Will have to see how this plays out in the coming days and weeks.

If the relationship is beyond repair: Make it clear that either one of you leaves an active role with the company or the entire company dies. Your cofounder may not be aware of the severity of the situation.
It's strange, yesterday I would have said it is beyond repair.

Today, after taking some advice here I see a sliver of hope that it might be salvageable.

I've managed to make myself replaceable at least in tangible ways so I hope to find myself a good way out where everyone wins.

Sounds like your company is in a tough spot. Almost out of money? Regardless of the other issues you probably need to cockroach-up and get profitable right away.

Assuming you are a C-Corp, the rest is going to depend on your equity structure, board structure, etc. I hope you have dotted i's and crossed t's, legally speaking, to cover situations like this. Not enough info here...

Have you had a serious sit down conversation with your board? This is exactly why you have a board of directors.

If you don't have an external board, start making the rounds to see if you can raise a series and buy him out. (if you see the company going anywhere)

I don't think "buy into our startup so I can get rid of my cofounder" is a great pitch
"We're failing and I hate my cofounder. Now's the perfect time to jump on board!"
In a dark moment in the past it had occurred to me to try and sell my shares to a company in our industry that would like to see us gone. I don't think I could do that though.
We don't have a board. We raised money by taking deposits over a year before delivery. It's just between us to figure it out. I've followed a lot of the advice I've received here and so far it seems to have worked. First positive conversation in a long time today. The first step is to try and survive what's left of this month now.
There are people who specialize in therapy to get founders to talk to each other. Have you tried such a session?
This. Both of you should see a professional counselor/therapist together. Google for ‘business partner therapy’ or ‘therapy cofounder’ for details and practitioners.
Without any accusations, tell him the path where you‘re heading in written form. You can add potential remedies and the end, but in essence, describe what will or might happen. A good phrase in these kind of messages is

“Unfortunately you didn’t have time to look into XYZ. I’m truly sorry that we now face ABC. But if we do EFG we might still have a chance in fixing this”

In general: use written form, avoid any phrases that put the blame on him, describe accurately what happened and the consequences and end on a hopeful note or idea.

To me, that reads as passive aggressive. "It's unfortunate you didn't do your job..."

I think it's a better approach to say "The problems are X. We know this because of Y. My proposed solutions are Z. If you agree, let's get together and figure out how to do Z. If you don't agree, let's get together and figure out where our analyses diverge and how we can come together."

It is a fine line, yes, but if you abstain from any accusations in the rest of the text, then my formulation is generally received as empathy. This is supported by the fact, that there are no lies there. OP _is_ sorry that things went as they went. And it also is objectively “unfortunate” in the sense that with a little luck there might have been a different situation.

The general point is that OPs partner is in a corner. Empathy is needed to allow him to be cooperative and understanding of his own mistakes.

I realize now that at some point in the last few years I totally lost any sense of empathy for my co-founder. As I write this I realized that today was the first time I've shown him any real sense of empathy in a really long time. Coincidentally I think we may have actually made some progress in turning things around today as well.

Thanks for taking the time to respond.

I'm really happy to hear that. All the best.
You are right, it's really hard to get to a consensus if one person feels attacked.

It's really hard to describe some of the major problems without coming across as blaming though since we've more or less followed a path that I attempted to explain monthly for at least 6 months (sometimes nicely and sometimes badly to be honest).

I've taken the most blameless approach I can and I think it might actually be working now though! We may have come to a common realization today that if we don't come together as a team right now it's all over.

Yea, don't do business with non-programmers. Programming is thinking. If you can't program, you don't know how to think in 2018.

Tech people have traditionally kissed up to business entrepreneurs in the past (for their money, network and supposed "experience"). It's a price so many of us have had the negative experience of having paid. The space is so competitive now (all niches), that you BOTH must be an expert in a niche AND know how to program.

Your partner likely doesn't know how to think, and compensates for it through playing politics and overbearing manipulation like most "business men" (aka "scare tactics"). It's a short-lived strategy that ALWAYS falls apart in the long run. There's no short-cuts around having hard technical skills and respect from people that know you get it when it comes to the all-important details that they will be tasked to focusing on day in and day out.

My advice is to get out as soon as possible.

The only solution is open, factual, non emotional discussion about the situation, backed up with both attending a marriage counsellor. I'm not kidding.

Discuss issues with the behaviors, not of the person.

And I presume of course that your shareholders contract defines how this situation will be handled in nthe event that the conflict cannot be resolved?

> backed up with both attending a marriage counsellor

Is that even doable for a non marital relationship?

Yes. A counselor is a great idea.

I wish I done that with my ex-partners. Sometimes an objective and impartial third party is exactly what you need. People can get dug into their points of view and be quite honestly unable to see it any other way - until a third party points out the elephant in the room.

I've not thought of that, but it's something I'd be willing to try.

Our contract does not define how things will be resolved in a conflict. Basically we end up deadlocked and nothing happens until one capitulates. This has resulted in absurd scenarios that I would be too embarrassed to admit.

If we manage to survive this crisis I there is a lot of work to do in order to fix things. There is a lot of built up damage.

Step 1: Lay down the cold, hard facts (not your interpretation) in a tactful manner meant to assist in helping him vs. attacking him. Do not issue threats or ultimatums ("I will go to the board", "I'll quit if...", etc.), that will often make things much worse--hurtful to your employees/executive team. Give your co-founder some time to determine whether those facts are true or if it's just you (~2 weeks).

Step 2: If that doesn't breakthrough, then your next step is escalating with the board and letting them do a real investigation to the merit of your claims. Ultimately, they'll likely speak to someone on his team.

Step 3: If you can't do that, consider stepping down since the opportunity cost could be very high. It's much worse for the two co-founders to be at odds and potentially blow up the company at this stage. The company is learning to scale around 4 years in (usually) and if he's a first time CEO, he's probably going to be struggling.

* Try your best to remove the emotion. Consider therapy during this time as it's going to be a bumpy road especially if you've built up resentment over the last four years with each other and care a lot about your company that you started.

Email me (click on my profile) and I am happy to help you through this while keeping it confidential.

Thanks for taking the time to respond first of all. The post hadn't picked up yet by the time I shut down for the night so I didn't see these responses until this morning.

I think writing my original post and reading the responses here released some pent up frustration on my part.

1: I've managed to take step 1 today. The response I received was surprisingly positive. By that I mean a sort of grudging acceptance. I'm not sure if that's because of the desperation of the situation we are in; or if it was a change of manner on my part. Probably a bit of both. This was probably the first work related conversation we've had in over 24 months that was free from negative emotion on both sides.

2: We don't have board; we retained 100% of shares for ourselves. We raised our seed capital by taking deposits based on the proof of concept we had when we started. Really lucky I know.

It sounds like you've let anxiety and panic take control.

Remember that your co-founder cares about the business, and is probably doing what he thinks is best with his time.

I'd writing a letter to him (and not sending it), taking a full day off, and then read your letter imagining you're him.

It's important to communicate how you're feeling, but don't make your co-founder responsible for that--his work/role in the company is his responsibility, and the way you're feeling is your own. Communicating both (what you think needs to change, and also how you feel about it) but keeping the two distinct will help.

No. The co-founder doesn't care about the business. He thinks he cares. He may even want to care. But he doesn't. He cares about himself.
That's an amazing leap to make considering everything we know about the situation is coming from OP and thus is, by definition, one-sided and surely biased to some degree.

I don't know who the OP is nor is it my intention to cast doubt on his or her view of the situation, but I find it incredible that anyone's immediate reaction upon reading this is so absolutely sure that the co-founder doesn't care about his own business.

It's not a leap at all. If what the OP is saying about the co-founder is true, then that's my take. People who act like the OP described are not acting in the best interest of the business. If what the OP said cannot be believed, even for the sake of argument, then there's no discussion to be had at all.
> If what the OP said cannot be believed, even for the sake of argument, then there's no discussion to be had at all.

Disagree.

1) One can read a text with an eye toward the ways in which the narrator might be misinterpreting the situation and can hold in ones' head the possibility of that misinterpretation...while also making suggestions for how to grapple with the problem that the writer presents.

2) Taking as given the way OP presents their problem, you are correct that the co-founder is not acting in the best interests of the business. However, it is an unjustified leap to say that the co-founder does not care. There are a multitude of reasons why the co-founder could simultaneously care very deeply and be acting this way:

- The co-founder is mistaken on matters of fact about the problems.

- The co-founder is making a judgement call about maintaining product focus vs responding to customer requests...and making a mis-judgement

- The co-founder lacks skill at listening to and interpreting feedback[1].

- The co-founder is overcorrecting from making an opposite error previously in life/career.

- The co-founder is missing some other very important leadership skill.

Point is, it is possible for people to fail very badly and obnoxiously at something that they care a great deal about.

----

On second read, I think you might be using the phrase "does not care" in a way that isn't making sense to mean. Could you expand on what it means for someone to think they care about something but to not actually care about it?

[1] This is a skill. https://www.amazon.co.uk/Thanks-Feedback-Science-Receiving-W... is a good book on it.

To your question about my use of "does not care":

Consider a personal relationship. You can say you love someone. You can want to love them. You can even convince yourself that you do. But you may not, in fact, love that person, and your actions will bear the betrayal.

What I'm talking about when I say "care" is caring about the business in and of itself. That's a very different thing than caring about what you get from the business. My interpretation of the OP is that the co-founder's behavior indicates that they care about what they get from the business but not the business itself. Someone who truly cares about the business itself doesn't act in ways that harm it unless they absolutely have to.

Businesses are full of people at every level who profess to "care very deeply" but don't, or who genuinely care about things that are immaterial or even detrimental to the business's success. So when I say that people like that "don't care," I am not saying that they don't care about anything or that they have no feelings of caring.

I am talking about the CEO who "cares deeply" but refuses to fire poisonous employees or make other difficult but necessary decisions, the dev who "cares" about his work but not enough to overcome procrastination, the HR people who "care deeply" about employees but actually fear them, the managers who "care" about their direct reports but treat them like shit, and so on.

Ah okay. It seems we fundamentally disagree about my point #2 because of a meaningful difference in semantics. You use "I care about X" as a statement about the externally-visible operations of the speaker. A nurse cares for patients even if she is tired, achey, and annoyed. If you will, "caring" is a property of a one-person system's public API.

I use "I care about X" to be a statement about the internal state. "I care" is a description of emotions and motivations. So which meaning is correct?

Well... its semantics, so no "correct" in the same way that there is a correct measurement of the gravitational constant of earth at sea level above average-density crust. I like to say "All models are wrong; some models are useful", and the purpose of words is to communicate. So which definition is more useful? I assert that it depends on your time horizon and your ability to convey relevant insights.

In a short time horizon where OP doesn't know what this guy's problem is, your definition is more useful for deciding how OP should act. OP has little way to open a heart-to-heart conversation where the cofounder can open up with his worries or commit to starting on a path to change his habits. OP probably doesn't have time to wait for the cofounder to change his habits unless they sit down and rigorously design those habits and the communication protocols to reinforce them -- something I've only seen from my wife and I. In a short time horizon, OP has to deal with his or her cofounder as-is.

So why am I still blathering on?

Because reading "he doesn't care" struck a nerve. I've been "the dev (or student) who 'cares' about his work but not enough to overcome procrastination" for multiple chunks of time from 2004 into early 2017. What changed wasn't my level of concern for productivity but instead several types of growth:

- Getting access to tools that allowed me to block distractions.

- Developing good habits of diet, exercise, and especially sleep (and escaping from a uni culture which said "sleep is for the weak")

- Learning skills of breaking down projects, insisting on understanding the 'why' of projects, asking well-structured questions, and planning out steps to execute.

- And 14 months ago, learning what discipline even actually was and how to build that muscle.

This growth all happened over the course of a decade of trying to debug myself which included 4 PIPs and 3 firings, so quite a long time horizon and empirically a longer time horizon than anyone but my wife could reasonably have had the patience for. If you had told me during this time that I did not care about my work, I would have been internally seething with anger, but not even known how to counterargue. So just so you know, concluding that about someone can be rather inflammatory to them.

-----

By the way, thank you for answering me. Writing that all out was really useful for me. If you'll humour me again, I'm curious: What are some ways to tell that you don't love another person? What is love? When I've asked about this sort of thing before, I've just gotten the response " Baby don't hurt me; Don't hurt me--no more ", which is unhelpful.

Probably the single most important characteristic of love is an empathy-driven willingness to make sacrifices (existential or material) in the name of helping another person or preserving your relationship with them. Pretty much all betrayals of love ultimately stem from an unwillingness or inability to do so. That's at least true of all the reasonably clear examples of "not loving" that I can think of. Loving someone doesn't necessarily require that you make sacrifices but it does require that you would. That may be one reason it often takes a while for people to realize that they don't love or that they aren't loved. You never really know until it's put to the test. Maybe it's a single thing that's so significant, a loving person would obviously do or not do it. But it's probably more often a series of smaller things over time that individually seem ambiguous or minor but amount to a pattern.
If I had to make a guess he cares about what the business can do for his own status; in terms of recognition and validation more than money.

Sometimes that's aligned with the interests of the business and sometimes not.

You are absolutely right about the anxiety and panic taking control. Writing my original post yesterday seems to have fulfilled the function of writing the unsent letter. Seeing all of these responses today has totally changed my outlook. I guess it's clarified my perspective a bit. We had a positive work related conversation for the first time in in a really long time today.
You need to bring in a third party that has no stake in the game and that both of you trust (your board won't work if they are also shareholders).

Only then will you be able to move forward without risking either your business or your co-founder relationship.

Read "Traction" by Gino Wickman.

You're an integrator. Your co-founder is either a visionary, or he's lazy, or maybe both. I don't have enough info to know for sure.

At any rate, each of you handling separate sides of what is basically two different businesses is a mistake. Sure it does a nice job in giving each of you autonomy, but it's terrible for maximizing each of your unique skill sets.

Thanks for the response and for the book tip. I will read it.

You are right that it was a big mistake to not get involved in what the other was doing. In retrospect I think our egos prevented us from allowing "interference" in what the other was doing so it naturally developed like that.

It sounds like the core problem is that you're unhappy about how the division of roles was made. Is it that your co-founder isn't contributing as much as you to the company or that he doesn't respect your and others contributions? or both?

You say each of you was responsible for one side of the business, did you agree on this split together or did it just happen? when was it apparent that you weren't happy with how the roles were split?

If you could go back in time, would you rather both of you contributed on technical work? Do you feel it's unnecessary to have your co-founder dedicated to sales? Are the main problems the company is facing technical, sales or something else?

I assume that if there was a partnership agreement in place you'd have mentioned it, which means you are in a general partnership. I've been in this position – twice! I'm sorry to tell you: if you don't have a signed agreement that specifies each of your obligations to the business, then you have very little recourse except to offer to buy him out, at whatever terms he'll accept. You can't fire him, you can't dilute his equity, you can't take the team and start over without him. You can't even really quit; you'll still be liable for half the partnership's debts. The only threat you can make is to dissolve the partnership, discontinuing the business and splitting its assets and liabilities. Which, given that you're almost out of cash, may be your best next step anyway.
This is why there is a clear chain of command, there can only be one CEO who is it?
Neither one of us would have started or continued if it meant ceding control to the other. It is literally 50/50. I don't think I'll ever be doing that again.
A neutral third party to the dispute? Serving as a mediator?

If you can't argue with him, maybe suggesting that someone, other them you guys, should hear your and his complaints and problems. Like a marriage counseling, i guess.

I think you may have just grown differently, he might very well think you're not focusing on the right things either at this point. Assuming you're both reasonable people and you want to fix things with him. You could try this;

Get away from the office and have an uninterpreted "strategy session". Sometimes leaving town and relaxing a bit helps. Do something fun, not business related for a night then the next day have a conversation. Start with facts he can't dispute that are not personal. Something you can both agree on. Like, can we both agree that the business is sinking and only has X months left? If you can agree on that, the next question is what do we need to change to fix it? You can bring up some of the issues without personally attacking his style. A la "I think we need to listen closer to customer feedback and focus on revenue generating opportunities within their feedback"

I've worked with a lot of personalities that sound familiar to your co-founder, the trick is planting the seeds so they think it was their idea/or they were at least apart of the ideation process - when really it's exactly what you wanted them to do and your purpose for engaging in the conversation. Not everyone can just be directly reasoned with or is receptive to direct feedback.

Thanks for responding and please accept my apologies in the delay in my response.

I had a long overdue positive interaction today. I think we've both realized that if we don't work together on this we're finished. So that's a good start.

I'm going to take your advice about doing something that's not work and then try to have a conversation later. I have noticed that in the past he can totally reject an idea but then accept it a few days later.

I have also had more success previously with presenting a course of action as me attempting to support him or his goals. My ego gets in the way of doing that too often though. It's been tough.

I think I may also have some internal insecurity in regards to him trying to hog the limelight whenever possible. I like to think that I'm above feeling that but I do often have to check myself to make sure I'm doing things for the right reason and not as some kind of passive aggressive retaliation.

Sounds like an issue for the board of directors. Do you have a board of directors? If so, I suggest reaching out directly to board members one-on-one to raise these issues with them.
We don't have one. I need to either find a way to fix it or quit. I've taken a lot of the advice on here and I'm actually feeling hopeful for the first time in a long while.
Based on the direct reports despising him and wanting to leave, wouldn't you say it's time for him to go? If he's been like this for two years a weekend retreat won't fix things.

Explain to the board your position and go fix your company. He'll thank you for it later when his shares are worth something.

I’ll echo this from the position of having been one of the direct reports under a person like this. He was eventually fired and replaced by the board, but not before costing us months pursuing what everyone knew was the wrong strategy, and costing us three excellent people who had enough and quit.

It’ll likely be painful and messy, but the best thing you can do is force him out in some way.

Neither one of us can be fired unfortunately. I would have done that already had it been an option.
So I'll speak a bit from my own experience in a similar startup situation. Similar in that I had a co-founder problem but we were pre revenue and only a little over a year in. Ultimately having money coming in changes the equation.

So any decision that's made is a big cost/benefit analysis. My life was made miserable and sleep were suffering. I simply couldn't continue and felt my time could be better spent on higher productivity projects.

So I left... Now with a few months of hindsight since the departure, my quality of life is better. I've moved on to projects that are more fun. I miss the old startup and what we built, but it wasn't worth continuing in that situation.

If I were to reflect quickly on how that situation arose: slow loss of mutual respect and breakdown of communication. So always keep communication open and always keep it civil.

Outcomes and measures. These quantify your success.

Sounds like these outcomes are failing:

* Technical Issues Cleared * Deliver on requirements of existing customers * Understand complaints of existing customers * Strengthen relationship with existing customers * Retain talented staff * Strong leadership from leadership team (co-founders)

But these outcomes are succeeding:

* Successful brand awareness in market * Gain initial revenue from customers

So based on this, what outcomes are important? How do you measure their importance? And then what is their role in this? Obviously they're not happy with you either - the put downs, the lack of respect in conversations means there's some unresolved resentment from their end as well.

Personally, I'd recommend both parties write down their concerns, outcomes, and measures, and then with a mediator work through what's important. Contact me if you need a hand.

It's a bit like a marriage - it can be saved, but you both have to acknowledge your 50% in contributing to this situation.

If what the OP wrote is true, then the "marriage" should not be saved. Anyone who acts the way the co-founder allegedly acts should be fired.
This is really clear advice and thinking; thank you.

We had a positive interaction today, first in a long time. I took a lot of the advice on this board and the result was good. Hopefully we can make it continue at least in the short term.