
Ask HN: How to deal with a dysfunctional relationship with a 50/50 co-founder? - throwaway9934
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.<p>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.<p>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.<p>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.<p>Now the money has nearly run out and we need what seems like a miracle.<p>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.
======
suhail
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.

~~~
throwaway9934
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.

------
cowpig
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.

~~~
staticautomatic
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.

~~~
georgemcbay
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.

~~~
staticautomatic
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.

~~~
afarrell
> 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...](https://www.amazon.co.uk/Thanks-Feedback-Science-Receiving-
Well/dp/1611762510) is a good book on it.

~~~
staticautomatic
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.

~~~
afarrell
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.

~~~
staticautomatic
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.

------
cel1ne
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.

~~~
ImSkeptical
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."

~~~
cel1ne
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.

~~~
throwaway9934
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.

~~~
cel1ne
I'm really happy to hear that. All the best.

------
conductr
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.

~~~
throwaway9934
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.

------
dsl
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)

~~~
kingbirdy
I don't think "buy into our startup so I can get rid of my cofounder" is a
great pitch

~~~
mratzloff
"We're failing and I hate my cofounder. Now's the perfect time to jump on
board!"

------
quickben
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.

~~~
throwaway9934_r
Dude it's only been 2 hours since he posted.

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

*Edit: reworded this

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

~~~
staz
green just mean newly created account

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

~~~
rojobuffalo
Oh thanks for the correction. I thought green meant OP

------
nicwolff
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.

------
jordan_litko
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.

~~~
throwaway9934
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.

------
crankylinuxuser
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.

~~~
bwb
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.

~~~
throwaway9934
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).

------
rojobuffalo
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.

------
hoodoof
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?

~~~
77pt77
> backed up with both attending a marriage counsellor

Is that even doable for a non marital relationship?

~~~
gregpilling
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.

------
fardo
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.

~~~
throwaway9934
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.

------
machinecontrol
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.

~~~
throwaway9934
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.

------
matte_black
There are people who specialize in therapy to get founders to talk to each
other. Have you tried such a session?

~~~
troydavis
This. Both of you should see a professional counselor/therapist together.
Google for ‘business partner therapy’ or ‘therapy cofounder’ for details and
practitioners.

------
jiveturkey
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.

~~~
CyberFonic
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.

~~~
throwaway9934
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.

------
merinowool
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.

------
dustingetz
This is why there is a clear chain of command, there can only be one CEO who
is it?

~~~
throwaway9934
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.

------
jconley
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...

------
WaylonKenning
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.

~~~
throwaway9934
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.

------
anonu
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.

------
alexbeloi
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?

------
amorphid
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.

Consider:

\- 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!

~~~
azinman2
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...

------
CyberFonic
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.

~~~
throwaway9934
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.

------
pbreit
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.

------
cncrnd
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.

~~~
jon-wood
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.

------
endlessvoid94
Radical candor.

------
throwaway9934_r
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.

~~~
throwaway9934
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.

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

~~~
throwaway9934
thank you

------
jacquesm
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.

------
rroriz
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.

------
throwaway9934
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.

------
mhale
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.

~~~
throwaway9934
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.

------
justinzollars
Michael?

~~~
throwaway9934
Not Michael :)

------
justonepost
50/50 ?

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

~~~
throwaway9934
We got the first sale before we incorporated. 50/50 happened because neither
would accept less than 50.

------
rdiddly
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](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.")

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

