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Ask HN: How to deal with a dysfunctional relationship with a 50/50 co-founder?
101 points by throwaway9934 on May 7, 2018 | hide | past | favorite | 103 comments
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.

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.

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.


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.


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.

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.

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.

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.

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.

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.

Well, this may be contrary to the flow here, but I think the problem may be you.

Please, allow me to explain: you asked a question portraying yourself as the victim in the relationship. Then bunch of people are trying to help you out, but you didn't respond to any of their questions.

For anything to succeed, you will need synergy and thus, communication.

I respectfully advise you to engage here with the 35 people that are trying to help you out.

Right. I think a better question is how do you deal with a co-founder who posts something like this on HN, where they know you and other people you know will see it, as if the story doesn’t contain obviously identifiable info? Someone who attacks by attempting to frame public opinion? (not speaking as that person, just an observation)

I chose my words carefully to make sure this remains totally anonymous. I was not trying to frame public opinion, just genuinely feeling low and desperate.

It was 3 hours since the OP when you posted. I'd give him more time; being a founder he may have just had time to post this and intends to follow up later.

Thanks for your response. An hour after posting my post was at 1pt and no responses and I thought it died in new. I've only just seen these messages now but I'm at work.

I'm actually overwhelmed that so many people would answer. I will engage with everyone as soon as I get back from the office.

What do you say to the idea that your posting is underhanded and passive aggressive? People involved will recognize your business based on the description you give. Everyone else will take your side of the story for granted and crucify the picture you paint of your co-founder.

There are plenty of avenues you could take to seek the advice of other entrepreneurs for this without doing it on a public forum. It seems you’re looking to create an effect upon certain people in your situation who you expect to read HN.

You don’t come off well in this, IMHO.

I do concede there is a passive aggressive element to my post, caused by a lot of internal resentment and frustration.

But no one will recognize our business or who we are. But I can't really go into detail on that topic without actually risking revealing something.

I genuinely reached for advice in a desperate moment.

I'm sure I'm part of the problem. I can't say that I've been some kind of angel. I have reacted quite badly and at times immaturely. I did not however intend to portray myself as a victim. It's a situation of my own making. I did choose him as a co-founder after all.

It has been a very difficult few years though. I've taken a lot on board from what I've read today and I think it's made a positive difference. We finished the day feeling like we were on the same team for the first time in a long while.

This sort of relativist approach only makes sense if you assume both people are right, wrong, or lying. If one of them sees things how they are and the other does not, then "synergy" isn't going to get anyone anywhere.

Also, you should be "respectful" by entertaining the possibility that what OP is saying is true.


There is a lot of very good advice already given here. Granted, some of it might not be applicable, but some feedback would allow these HN contributors refine their suggestions.

There is indeed a lot of good advice here and I'm touched that people have gone out of their way to give it. I couldn't respond right away since the post didn't get any responses for the first hour and I had already turned in for the night. I didn't see the responses until today.

Dude it's only been 2 hours since he posted.

Are you sticking up for yourself by pretending to be a different poster?

*Edit: reworded this

100% that wasn't me. I'm at the office now and will engage with everyone as soon as I get back.

The usernames seem stupidly similar, this is becoming an interesting roller coaster of a story!

Weird that the username is green even though it doesn't exactly match OP's.

green just mean newly created account

I also find that colorscheme plainly confusing, maybe a tooltip or something to explain the color will help?

Oh thanks for the correction. I thought green meant OP

I considered that before I replied, but then it has to be contrasted with the fact that the guy claims to be suffering for a year.

Since people end relationships in much less time if things aren't going well, I was instinctively expecting the op to care more.

Whether or not people end relationships "in much less time if things aren't going well" is an empirical question and I don't think it's necessarily true. Anecdotally, lots of people seem to "stick it out" in various kinds of personal and business relationships for much longer than a year even when things are terrible.

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.

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.

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.

This isn't a situation I have experience with so I can't offer qualified advice. It sounds really difficult and frustrating. My general advice is when you find yourself at odds with someone, remember that the two people who most need compassion in that moment are you and the other person. That just means recognize the suffering you are both going through. Also, recognize the suffering that the other people at the company will go through if things continue along the current path. That's not meant to engender dread or anxiety. It's just a way of cultivating awareness and compassion.

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?

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.

> 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.

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.

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.

Agreed, except: he likely can't because the other guy is a jerk. There's some people who just missed the REASONABLE DNA strand.

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.

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.

Does "bootstrapped" mean self-funded or that you have only taken seed money? I think you need to call on a higher power but if you don't have a board you can call on you might have to make sure you are leaving (when the time comes) on the best possible terms.

throw him under the bus. do not pull any punches or try to cover his mistakes. i'm not saying to air your dirty laundry to customers and others, but don't treat him favorably in any convos you have ... if he derails a customer relationship, so be it.

if it's really as bad as you say, that you need a miracle, you're done. make sure that you leave with some dignity. don't tolerate insults. you can be calm if you keep in mind that it says more about him than it does about you. "that's unacceptable, do you want to restate that?" and then if there's no correction, "this isn't productive" and leave the room.

We're self-funded so there is no higher power to call upon.

It's a cooperate or die situation, and yes we need a miracle.

I've taken advice today based on what I've read here and I somehow managed to speak frankly but with empathy. For the first time in I can't remember how long we managed to get along and talk about the problems. It felt like a good change. I don't know how much of it was me, him, or the situation.

I don't expect that to last indefinitely but if we can survive this I think I can create a win-win situation and find myself a way out.

If self-funded then the question needs to be asked as to who provided the funds -- was it 50:50 or sweat equity (technical partner) and money (sales and marketing partner).

In my experience the person proving money + sales experience tends to grossly under-value the technical contribution, even if they come from a technical sales background.

We're both technical and we've both made similar financial contributions and sacrifices. One thing that has become painfully clear for both of us is that we need professional sales and marketing help from someone who knows our domain inside and out.

The problem is that we can no longer afford to bring such a person into the company until we dig ourselves out of this hole.

I had similar situation. I just decided to leave. Transferred my shares to the other party and resigned. That was a such relief. That business never gone any further and I saved myself from all the wasted time and frustration.

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.

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...

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.

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.

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.

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.

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?

One option is seeing is discussing a buy out. If the company is under-funded and on life support, seeing what one can get out of it is might be the best business decision you can make.


- write up list of potentially irreconcilable differences that drive you bonkers, keeping list as short as possible

- present list to co-founder, and offer to discuss resolving the list items or one of you buying out the other

- if you can't work something out, be prepared to walk with your equity & cross your fingers for a future payday

P.S. when breaking up, the one with the deeper pockets probably has more leverage.

P.P.S. sorry you are in a tough spot, and I hope you figure something out!

Problem is recapitalization might mean never getting that payday, even if the company does well.

Personally I think such things should be illegal but that’s how it goes...

From your description you seem to be dealing with a narcissist. They are often great sales people, but when hubris takes hold, they turn into insufferable managers / leaders. Perhaps you should research the many web sites that provide techniques in dealing with them or even engage some appropriate therapy -- yes! for yourself. There are ways to preserve your sanity in the face of their attacks. In many cases the sanest approach is to dis-engage. In your case you most likely need legal advice on how to do that without creating even more problems for yourself.

Thanks that hadn't occurred to me. I've found myself bewildered by some of his statements and actions, maybe that will help me understand whats going on inside a bit better.

This sounds =EXACTLY= like a company I was doing some product consulting with recently.

Sounds like a fairly dismal working relationship. Since you're technical, I suspect you wouldn't have too much difficulty finding other work.

My experience reminded me that entrepreneurs get to work on literally whatever they want so it makes little sense to work on something that is obviously not working.

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.

Radical candor.

This is very familiar and I've been dealing with it for a lot longer.

Unfortunately my conclusion has been that I cannot grow my company any further with my co-founder, and I instigated a search for a buyer a few months back.

I'm not sure how much of my advice is going to be useful if your money has nearly run out, but I can share what I went through to try to resolve the situation, and how it came to this.

Can you agree on what the company is trying to do? Can you write it down? This is so important and took me & my co-founder years! Pick a performance metric for the company, share it with everyone and hold yourselves accountable. (we didn't do this for >10 years, until the growth had slowed - we had to backtrack through our random walk to find a model of why we'd grown, and therefore how we might grow more deliberately in future!)

If you can do that, great! Now can you agree on what your individual roles are in achieving those goals? Can you give them titles? You say you've turned over $1m but I assume you have funding as well - what to do next really depends on how many staff you have, and whether you need them all to achieve your goals.

If you have <10 or so, the "overstepping your bounds" dynamic sounds like a big worry - that might be your co-founder trying to build a comfortable wall where there probably shouldn't be one. At that size it's more important that you can trust each other to step in where necessary. If you have e.g. >20 staff, it's more important you cultivate autonomy among your two management chains, and try to hold each other accountable to higher level goals, accepting a bit of inefficiency in the process.

I'd not write off someone who wants to take on sales & figurehead (CEO) stuff. Business need contributions that are not just "technical work", and you might be guilty of undervaluing what your partner does. The company dies without sales, and a figurehead needs to take primary reponsibility for the company's mission and keeping it accountable for that. They should also be the first person to spot customer problems, and want to air them out. At your size there should be a really tight loop between "sales person" and "product problems person", and the CEO needs to be in charge of that.

So don't be tempted to talk down your partner's role as you've done here. Talk it up, then hold them to it. Ask why your CEO-in-waiting is letting customer problems are going unaddressed, and why he's not taking charge of sales while you solve real operational issues. Give him the shape of the business as you see it - that you're going to lose buyers because it's clear that the company is not solving current customers' problems well enough. Ask what his plan is to resolve that, and ask that he take charge of that plan- he's the figurehead, the salesperson-in-chief.

(from what you're saying, it sounds like your CEO might need to get down with the product like he did at the start, and make a plan to step back up when more sales effort is required - is that about right? This kind of temporary change of role falls out of the targets you agree.)

Management failings are really really hard to address. Unfortunately telling your partner that they are a bad manager, despite all the evidence you can muster, will not work. If you're expected to fill in for their managing - bring that to their attention. Tell them what conversations you've had with "his" staff, why that's a problem, and what you'd like him to do to resolve them.

(This was probably the biggest red flag in my business - an elaborate shadow management structure to prop up a bad manager is torture for everyone. If your co-founder is motivated by fealty, flattery etc. rather than having his staff achieve cool things - that is such a hard attitude to shift, and especially to recognise in yourself. Being as absolutelly charitable as possible - what do you think they are motivated by? Has that changed since day 1? Can you work with that motivation?)

So ... I'm not sure if you've had a direct conversation, or what personal stock you might have in being blunt to the point of risking your relationship. But the financial situation sounds like you may not have a choice (is this subscription revenue or a predictable set of one offs? I'm guessing subscription and investment has taken your burn rate too high?).

Lay it on the line to your partner, with the greatest respect to his past achievments. You had nothing, you now have a company & professional respect. Leave bitterness and ego at the door. Put the crucial problems of the business on the table, and see if you can build fresh confidence between you to resolve it.

If you can't do that in one or two meetings, where the stakes are very clear to your partner, make your own plan to leave because at that point it won't be mutual. Don't give yourself the pain of trying to agree a mutual exit plan - decide what's right for you, and execute on that.

The line about "struggling to have meaningful conversations" is exactly where I was years ago - and still am in some ways. It took me a while to get from that point to actually pushing to leave, but I've had to do that on his schedule. I'll miss the wonderful team we've built, but I know that I'm wasting theirs and my time by staying. I wasted real value in my company by hoping my partner would change for much too long.

Take my advice, lay it on the line for them as a matter of priority, and if you don't get real commitment, get your head in your next opportunity ASAP. The team, the customers and everything you've built can't come to anything if you've correctly identified such a big structural failing in your company. Act on it! And good luck.

Hey thanks for responding. I'm sorry to hear you are in a similar situation.

Okay so yes we can agree on what we're trying to as a company and we can write it down. We even have a performance metric. So that's a good start but you'll see things start to break down for us soon.

There is no accountability, and we absolutely cannot agree on individual roles let alone come up with titles.

Turnover was > $1m, we have no funding, and < 10 staff. Both of us have a technical background. Our model is basically one large up front set up fee and then an ongoing subscription.

Your comments about the CEO type role are interesting and really accurate. Right now I'd guess that I'm 80/20 tech/sales and he is 20/80. So he is the initial primary contact for most of the sales although over time I seem to become the primary contact. I think this is because I am more willing to recognize and admit the problem exists.

Some of the technical problems are only currently solvable by one of us because of specific domain knowledge. Otherwise I would have taken responsibility for everything technical.

We cannot agree that the company is not solving current customers problems well enough. I hear a lot about managing expectations and T's & C's.

I feel like I often have to step in and fix relationships with customers because of this. Then I end up making a plan, taking charge of the plan, and making myself accountable to the customer for executing that plan. I seriously piss him off when I do this, especially if it is one of "his" accounts.

I've taken on board a lot of the advice I've read here today, and I just maybe think that I may have been able to finally get the idea through to him that happy customers will make his sales job a lot easier. I've also (I think) managed to make him see that it would only take us a maximum of one month to solve all the remaining problems that I (and most of the customer base) classify as major.

I'm going to do everything I can to make sure the company will survive the next couple of months (that means sales) and then I'll need to revisit the idea of what's next.

Feel free to hit me up if you want to talk, my email is in my profile and happy to jump on voice. I am happy to go into more detail on what I tried with my co-founder what worked. Over the last couple of years, I've talked to a lot of founders so I've got a good collection of what others tried too (slowly writing content for https://healthybusinesspartnerships.com/).

I went through something similar with my 50/50 business partner in 2014. Not quite the same, but close. My co-founder had a bit more of a mid-life crisis that he took out on me, although with your partner it might be similar under the surface. I tried meditation with someone who helps on this store of thing, time, some alternative work arrangement proposals, a coach to work with him, and so on. I was prepared to talk to our only investor and fire him at the time, but it would have created a lot of problems due to our structure. So I tried to buy him out... but in the end that didn't work out and I decided the best course of action for my stress was to sell. It sucked but happy to be out of it.

What would I recommend? *With the caveat, I don't know more of the details.

1. You guys have hit a million run rate, that is impressive and a huge point to reach. Don't throw away the company so quick until you figure out if you can salvage this, or if you want to salvage this. I would stress that not many companies get to $1 million. I don't know how that first batch of customers is doing, or if you can be profitable without an investment round so there are two big questions I would ask myself.

2. Do you still like this business? Do you want to keep doing it even if you only own 50%?

If you want to continue on this project...

3. I'd recommend going to couples counseling. I kid you not. Tell him that you want to go to a weekly couples counselor and find someone who focuses on business partnerships, this could be a mentor, this could be a therapist. Find someone and have a place you guys can start talking to see if this is going to move forward. If you can't talk this isn't going anywhere.

If after that you still can't talk... - Can you work with the investors and fire him from day to day and take over? I wasn't sure if there were any investors... - Can you find an investor who will buy out a portion of his ownership or all of it?

PS. I'd love to hear more on the business and possibly buying him out as well. Always interested in that.

Read “The Anatomy of Peace” and “Crucial Conversations” they might help you out of your problems.

thank you

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.

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.

Thank you everyone for taking the time to read and respond. I'm honestly touched. I thought my post died in new.

I am at the office now so cannot engage with all of the responses for a few more hours.

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.


Not Michael :)

50/50 ?

Should be like 10/10/90 .. 50/50 only makes sense if you are making enough to bootstrap.

We got the first sale before we incorporated. 50/50 happened because neither would accept less than 50.

I would declare the startup failed. You have two company-ending problems, one of which is unprofitability and a lack of investment funding, and one of which is the fact that it sounds like you work with a total douche. Odds seem slim that you will solve both at once. Even if you get an infusion of funding, you still have Mr. Douche to deal with (and of course he'll take the credit for getting the funding too), and life's too short for that kind of stress. However, on the other hand, if you did get more funding, it might suddenly become worth it to try to work out the problems with him. Which might include some that you're contributing to, and therefore have control over. But unless funding arrives, I would advise you to take the lessons from this business experience (including, don't go into business with this person or anyone like him), cut your losses, move on as quickly and cleanly as possible (pay off anyone you can who needs paying[1]) and go find something more exciting & fun to do!

Another potential lesson: Michael Gerber in "The E-Myth Revisited" recommends parsing out all the different roles in the company: CEO, CTO, Director of Sales and so forth... all the roles you imagine being there after it "scales up." Because guess what, they are there before you scale up too, each one just doesn't take up 40 hrs a week yet. So if you're a sole proprietor, you end up handling like 10 jobs or something. (Gerber says literally draw an org chart, and then write your own name everywhere.) It seems like playtime/fantasy but it's to remind you you have all these different jobs to do, so don't drop any of the balls. And as you grow and hire people you offload/delegate specific duties to them.

Anyway if your company is made up of more than one person, you can probably see by now that defining roles and responsibilities is even more important. Sounds as though there has been a poor definition of the roles, and/or a violation of the expected roles. For example your partner seems to have declared himself CEO (except his own fantasy version of one, rather than a grown-up value-adding one who fulfills his promises) and made you, I guess, the CTO? The ideal time for assertively correcting this was before it happened (see above), or failing that, as soon as it started happening, or failing that, as early in time as possible. It will never again be as early as it is right now, so now's the time.

Is there a possibility of getting the many people who hate him to vote in a meaningful and legally-binding way to oust his ass? That would be cool. Or we're talking a focused group intervention along the lines of the ones they do for drug addicts. The guy sounds (from your admittedly one-sided view) like a narcissist and/or con-artist though, so he may actually have no interest whatsoever in working on or saving any "relationship."

[1]https://en.wikipedia.org/wiki/Fugazi#Business_practices - "Occasionally, Fugazi would have an unrepentant slam-dancer escorted from the concert, and give them an envelope containing a $5 refund (the group kept a stock of such envelopes in their tour van for these occasions)." (The point being, use money, if necessary, to pay for a clean break that is fair and non-complainable by the "breakee.")

Tell him to stop being such a child and join the real world. Or become a venture capitalist.

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