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Ask HN: Horror co-founder stories.
66 points by kimcheeme on May 24, 2014 | hide | past | web | favorite | 35 comments
Anyone have stories on nasty co-founding team relationships and/or recommendations on what to look for in a co-founder?

I had a friend who would "test" girlfriends by taking them camping for a few days.

Camping or other intense travel that raises the level of discomfort (no running water/flush toilets/electricity/internet/air conditioning etc.) reveals someone's true nature very quickly. You'll see whether they get cranky or stay optimistic, whether they're disorganized or not, whether they carry more or less of their fair share of the load, whether they get on your nerves, etc.

[Replying to my own post, since I can no longer edit for clarification.]

A lot of commenters have let their imaginations run wild and turned "travel/camping trip" into some kind of "survival of the fittest/Navy SEALs/I WILL BREAK YOU" type endurance test. This was not the case at all.

An example of what I'm talking about... The next time you're traveling, watch how the other travelers react if things don't go exactly according to plan, like an unexpected delay. You'll see all kinds of reactions, from calm and taking it in stride to completely loosing it. It's incredible how some people will let even the tiniest inconvenience throw them off of their game completely. That type of person is not someone who will be an ideal cofounder, because nothing about a startup is going to go exactly as planned.

Also watch what happens when things get boring. Once the initial excitement of starting a company has passed, there will be many, many days that just aren't that exciting. Disney World is exciting, but driving from LA to Orlando in the shortest time possible can either be a blast or drudgery depending on who you're with.

Some commenters are also reacting negatively to the idea of "testing" someone. Let's be clear here: Every question you ask your potential cofounder is a "test" of some sort, since too many wrong answers will result in their rejection.

Loosing a cofounder is so traumatic to a startup that you really should put good effort into learning whether your potential cofounder is just "talking the talk" and will jump ship at the first sign of trouble, or if they can actually "walk the walk", and stay committed to the venture for the long haul.

If this happens organically, then that's one thing (e.g. going on a hitchhiking/whatever journey for two weeks or more, etc. - it does kind of work (get to know person as side effect, and so on)); but institutionalizing it (so to say) just sounds shitty.

Maybe because the person doing the 'test' would always (at the back of their mind, etc.) know that it was being done deliberately. And this kind of informational asymmetry is, simply put (imho), not ethical. (Nor does it sound sexy or spontaneous or groovy or really interesting.)

I think the difference between male and female "testing" is often just in the rationalizing process e.g. if you were approached by girls since the age of 12 you would have established by now unconsciously some "filters".

Sure, but i think there's a nontrivial difference between these kinds of (usually) spontaneous and (often/usually) unconscious filters, vs. a whole streamlined process (which takes a longer time; though it does yield more information, as a rule (imo.))

Then again, maybe this is just, uh, institutional ludditism ;) (i.e., everyone has their own process, some have simply industrialized it a bit (e.g. for want of a more spontaneous set of filters, as you said.) But this metaphor probably doesn't work that well.)

I agree that it's a nontrivial difference, but I don't know if one approach is better than the other. It's something that has been on my mind a lot.

I studied marketing (among other things), and it's essentially the study of manipulating people to achieve a desired effect. And while I noticed that knowledge about manipulation doesn't automatically translate to a practice of manipulation/persuasion (in the same way that knowing a lot about addiction might not shield you from being an addict), having this knowledge, at least for me, feels like an uncomfortable responsibility.

Take approaching a potential romantic interest. There are some very effective techniques to increase your chances of 'success' (however you would define it). We generally frown upon doing this (too) explicitly; it very quickly seems sleazy. And yet 'womanizers' (or the opposite equivalent) apply these techniques without really thinking about it and we don't judge these people as strongly.

Is this unfair? If someone who is naturally less skilled at flirting uses 'techniques' to do better, is that worse than someone who does this naturally, assuming that in both individuals have the same 'pure' (or 'impure') goals? Or is it perhaps better because the individual in question is at least conscious of his persuasion or manipulation, and can question his motives?

I think about that a lot, and I haven't found an answer yet.

For me personally, I'm lucky, in a way, that I feel guilty very quickly. I simply cannot lie very well, for example, not because I cannot lie, but because I have trouble facing myself when I do so. So I try not be too conscious about manipulation and persuasion. And yet I know that applying well-tested techniques is very effective.

If anyone here can point me to literature on this subject (I suppose it's a matter of ethics), I'd greatly enjoy exploring that.

Yes, I see your point. Or at least, this made me re-think things that I've also been considering, namely: this kind of 'shunning'/etc. of explicit techniques is a biased selector of certain kinds of people (natural womanizers, whoever.) Hence the resulting ethical framework is not as egalitarian as it may appear to be on first glance.

> Or is it perhaps better because the individual in question is at least conscious of his persuasion or manipulation, and can question his motives?

That's also a fair point, it makes a certain amount of sense.

Again and again I wonder how much of our ethics is derived from 'folk psychology' which is itself biased towards 'intuitive' behaviours (whatever they may be; but in this case it would e.g. include unconscious/natural flirting, whatnot), and is biased against 'uncanny valley' reflexive mindstates (e.g. "i am aware `(that she is aware that i am aware)^n` that i am currently deliberately employing subtext in the current dialogue", etc.)

..and this could simply be a kind of aesthetic bias (that might make sense for us, humans), but whether it says anything about ethics is a wholly different question, say.

..this might have been a bit of a ramble. Interested in pointers towards literature, too.

> ..and this could simply be a kind of aesthetic bias (that might make sense for us, humans)

I think that sounds very plausible. We generally don't seem to like it when someone 'pulls aside the curtain' when it comes to things that feel hard to control or define.

For example, the best way to escalate a fight is to say something like "are you on your period?" or "did you not get enoug sleep last night?" They are perfectly valid questions in themselves, but asking them (assuming you mean well, of course) is not a good idea.

It makes sense that our minds don't like being treated like the often irrational, physical organs that they really are.

For example, while I feel perfectly comfortable treating a 'physical' headache with pills, I feel much less comfortable taking medication that alters my mood (although doing so for fun, and being 'in control' makes it significantly more acceptable).

Yes indeed, and now I recall my curiosity about the fact that kissing with our eyes open doesn't really work (in most cases / as a rule, etc.) You can't really explain it away by saying that 'one needs to divert (cognitive, whatever) resources from the eyes / visual stimuli': there's a specific kind of eeriness that is sometimes present, etc. Very interesting.

Is his name Dwight Schrute?

This is really good idea :)

I concur, I feel like this or any other situation to bring out true emotion is what is needed.

Such as dumping you as soon as they find out you'd rather challenge them with physical tests than communicate?

Also a good way to find out if the don't like camping or if it's their first time. Interesting but I don't like the idea of 'testing' people.

Those hardly matter; in fact, if the person was an avid camper the test would be useless, because it's designed to put them under stress in ways considered socially acceptable, and see how gracefully they degrade.

I have a story in the making that I hope will have a happy ending.

I started a company with two of my good friends whom I also happen to be living with at the moment. We're profitable and growing, but that doesn't mean we don't have problems. I am the technical co-founder while the other two handle operations and the business development side. However, they seem to be just going with the flow while I on the other hand am pouring my blood, sweat, and tears into this company. And I feel my work isn't being respected because they have unrealistic demands and sometimes complain about things not working or things not being done while they on the other hand aren't making any effort to see how they can help. It's easy for them to just delegate their tasks to our assistants but for my work, it isn't so easy. They should be hustling and trying to grow the company with their free time, but they aren't. My resentment has been growing against them and lately it's been putting a strain on our relationship. I think us starting out as friends has made us avoid talking about the deep issues that underly this predicament. In the end, I can't do this without them and they can't do it without me. How can I approach this situation? The obvious answer is to sit down, talk, and make my issues be known but before I do that, I need some good advice.

I also want to mention our equity is split three ways evenly with no vesting.

Please please please communicate with your co-founders! Communication is absolutely necessary for your continued survival and success. Do not avoid talking about the issue because it's uncomfortable. Rather, you need to face it head on.

My co-founders and I are constantly discussing uncomfortable but important company issues. We've built up enough trust such that we understand everyone has the company's best interests in mind. Sometime we get upset while having these conversations, but the long term result is always better.

We also have regular 1-on-1s with all of our employees, and one uncomfortable question we always ask them is: "what is the worst part about working here?" Then, we fix it. Our rational is that if we can always fix everyone's worst problem, then everyone will be very happy in the long term.

On a semi-related note, I'm sorry to hear that your co-founders aren't working as hard as you. That's unfortunately a terribly common issue, and it's exacerbated by the fact that they don't appreciate the technical work that you do. I wish there was some easy way to fix that, but I fear that that along with the lack of communication among you will spell doom for your company.

I also want to mention our equity is split three ways evenly with no vesting.

Woah. Never ever do that again. You've given away the one tool that is used to deal with the issues you list.

Not to mention no VC will touch you until you include vesting. But may be you've no plans to raise funding.

Now on to your question, I would begin by making sure that they are assigned goals that are as challenging as yours. If you feel they can help with growth, make that an official part of their day to day job. They will either succeed or fa at it. They will either work hard to achieve it or not make an attempt. Either case, when you make it "official", its good for everyone and gives everyone clarity.

Run don't walk from a cofounder who refuses vesting. Vesting is non-negotiable. This is the easiest and most painful formation mistake you can make with a new venture.

I don't have any specific advice, but I would encourage you to read the book Non-violent communication (it's short). There are some "cheesy" aspects to the book (mainly the poetry that introduces some chapters), but a lot of really good / specific tactics for communicating without putting others or yourself on the defensive, which I think it one of the most important aspects of having a conversation like the one you will need to have.

This is a classic "entrepeneur death trap". http://webcache.googleusercontent.com/search?q=cache:tdyrtET...

That's from 1996. This is what people in start-ups would mail around to each other before we had svbtle links to email each other.

A few thoughts, which could be helpful:

* Founder vesting schedules can be implemented at anytime, including backdating the start date. For example, the standard 4 year vesting with one year cliff could be be set to start 9 months in the past so that in three months from implementation, all of you would have hit your cliff. This could be used as a negotiating tactic if they are averse to the idea of vesting in general.

* What's best for everyone is what's best for the company. The company is at risk without better founder communication, so to help the company, communication should be improved. Remembers, this isn't about being combative or competitive. When they win, you don't lose. When any of you wins, everybody wins.

* Everyone is biased to appreciate their own work. This goes for you as well as your cofounders. Do they think they're working hard? If this is just about hours worked, them working a fairly normal schedule and you working double-time is only unhealthy for you. Maybe there is a happy solution in some expectation setting.

I've had these issues as well and am happy to talk anytime. Contact info is in my profile.

I hope with you but that looks like something that needs attention, don't wait too long with addressing all this, once tempers get frayed it is a lot harder to re-establish a dialogue.

For the most part it seems that you have legitimate issues that, as others have said, you should probably talk to them about. It's quite possible that they don't realize how much work you're putting into this.

But one practical thing you could consider is to not live with your co-founders. Living with people in itself can put a huge strain on things, and can sometimes be enough to break up friendships! I've seen it happen.

In my experience the important things are:

1. Do they proactively do the tedious stuff when things aren't exciting? Passion waxes and wanes and good co-founders dig deep and push through the bottoms of the motivation cycle.

2. Would you feel comfortable with the, representing YOU if you were not around?

3. How quickly can you find a comfortable and systematic way to constructively criticize one another?

There are more specific details, but these are the non-negotiables

I did a course in founder dilemmas this semester at MIT taught by Professor Matt Marx. The recurring theme from the course was that poorly considered early decisions could have lasting consequences. One of the main issues was how homophilous relationships (classmates, family) between co-founders had significantly lower success rates than non-homophilous. From this, the one lesson I've definitely learnt is to look for someone drastically different to myself when trying to find a co-founder. A suggested read is 'The Founder's Dilemmas' by Noam Wasserman, full of a lot of lessons that can often be avoided.

Key takeaway: Ensure your cofounders are competent through third-party verification if you can't do it yourself.

I know of company cofounded by a skilled business guy and a technical guy. That's a fairly typical split, except the technical guy is absolutely useless. He hasn't learned anything new since his internship days, and insisted his code was perfect despite obvious security flaws.

The business guy just took the technical guy at his word without checking to see if his skills really were at that level. What followed was a tremendous waste of investor money as the technical guy insisted on doing everything his way and creating massive loads of technical debt.

Had the business guy had an independent party verify the technical guy's skills, he'd have saved himself $X00,000 in opportunity costs and years of his life.

i'd do a small throw-away project with the person before you attempt anything. if you can complete the project, then tackle something bigger. it's like training camp before full-season play.

Not always practical. I've almost completed a 7-year project and now find myself in the unusual position of being a technical founder in search of a non-technical co-founder. I could go out alone for sure and yet know that I'm just not good at carving out a market for my product, no matter how good I know it to be.

My challenge isn't knowing what to look for (if I have a skill it's reading people) - it's finding someone suitable.

That doesn't mean you couldn't take a break for a hackathon, Startup Weekend, etc. to meet and try out other people.

Paying attention to how the person treats the wait staff at dinner can also give you a quick insight into their character (this works for both business and personal relationships). Treating the waiter like scum is a gigantic red flag, at least for me.

Here's an example of non-alignment of founders, and ownership that did not have vesting periods...with a consequence that departing partner-founders had to deal with a major fraction of the entity owned by non-participants.


The ability to think independently is the key. A cofounder who is constantly looking to you for the next step will bring you down. Look for people who have proven track record of motivating themselves and executing their own ideas. This does not necessarily need to be in the form of a startup.

Of course there are other things like chemistry and skill, but independent thinking is absolutely critical.

What do they say? What do they do? What do other people say about them?

That will usually weed out most of the procrastinators, wannabes, "difficult" people etc...

A bit of interpersonal chemistry going, some complimentary skills (you're looking for compatibility, after all), and some level of emotional investment on the problem being solved, wouldn't hurt either.

Make sure you do background checks (references + backchannel).

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