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How I feel quitting my own startup

aquiles.me

91–99 of 99 posts

Re: How I feel quitting my own startup

#91

Earlier quoted context omitted.

okay, so your position is that he should leave because everyone is too mean. that's valid.

Don't put words in my mouth. OP mentioned significant equity and the possibility to be acquired, without any details. This could both provide them with something to show after enduring all the suck, as well as with a real chance of changing management. If the question was to join the company, or no equity was at play (including if there's either no realistic chance of that equity being worth something, or if the equi…

> because it sounds like a business bordering on dysfunction

yeah, that's what a startup is.

Re: How I feel quitting my own startup

#92
post #62

Earlier quoted context omitted.

How can that happen and how do you avoid that happen without ones' own knowledge?

It happened because it all seemed legit -- we were both going all-in, we had the exact share split in writing, did reverse vesting, received founders stock, etc. I even noticed that the shares seemed to exceed the total, and my business partner sent minor corrections, explicitly affirming I had the most shares of anyone. You have to trust your business partner at some point. Legally speaking, my business partner secr…

> I now know that startups often first allocate 10M shares, apparently for psychological reasons.

Heh. My company has exactly one (1) share, probably also for psychological reasons.

Re: How I feel quitting my own startup

#93

I've made > 100 pre-seed investments and the #1 cause failure in the first 3 years is founders quitting because of unresolved cofounder conflict. The first time I saw an obviously valuable, fast-growing company blown up because the founders couldn't agree on a $5000 travel expense I was astounded. Now it's something I've grown to expect - just one more risk to be managed. To try and mitigate this my #1 question each…

>> I've made > 100 pre-seed investments and the #1 cause failure in the first 3 years is founders quitting because of unresolved cofounder conflict. Can you comment on the most common cause of conflict? You mention something trivial to make the point that they can be over trivial things, but what is the most common cause of conflict?

There’s no one specific cause that stands out as common. All happy families are alike; each unhappy family is unhappy in its own way.

What IS common amongst terminal cofounder conflict is a series of ruptures in the relationship without any corresponding moments of repair. Over time the ruptures build up into complete relationship breakdown over an issue that seems trivial. People gradually work themselves apart and can’t come back. Some of my biggest failures as an investor have come from not understanding this dynamic.

What I’ve observed is that great cofounder relationships display a pattern where conflict is followed by a moment of restoration so that a strong positive relationship builds over time. The biological analogy of this is muscle hypertrophy. You repeatedly lift something heavy and your bicep muscle fibers are damaged. Under the right conditions of rest your body repairs the damaged fibers by fusing them, which increases muscle mass and so you get stronger over time. Or you don’t have a repair cycle and instead keep lifting heavy things without rest until you eventually get a traumatic failure and can’t lift anything for a long time (if ever).

In the stress of a startup conflict is inevitable, and to a certain extent at times it’s also required for progress. So the insight here is not “great cofounders have zero conflict”, but rather “great cofounders follow conflict with moments of repair”. If you consider each conflict a small tear in the relationship with your cofounder then for every tear their needs to also be a compensating motion of repair.

What I’ve learned to do now as the investor in the loop is to help cofounders notice early when ruptures are occurring without repair. Most of the time merely drawing attention to this dynamic is enough for them to course correct.

Re: How I feel quitting my own startup

#94
post #87

I think this is mainly an issue of a lack of formal structure. A bad way to start a company with your cofounder is to expect to reach a consensus on decisions and only that moves forward. It’s hard for 2 people to consistently reach consensus, it’s impossible for more than 2. There needs to be a clear formal hierarchy, people lower in the hierarchy can always disagree voice out the thought but they must commit once t…

There is never a real lack of hierarchies tho. It is just that everybody has their own (which turns out to have a similar effect). If you are lucky all of the hierarchies people have in their heads align with each other. But it helps to have this formalized. As someone who worked on quite some film sets: Contrary to the assumption many people have, clear roles and responsibilities are good for creativity. In the end…

That’s a great point, never thought of it that way. Hierarchies always exist, if everyone’s aligned you need not formalize it (very rare), else formalizing it helps.

Re: How I feel quitting my own startup

#95
post #11

Although it wasn’t as a founder, but I can relate, in one of a small startup I got hired as the first engineer, rest were a founder and sales guy and a part time HR girl, so as expected, I solely built the architecture, few fully fledged platforms, dozens of PoC, successfully delivered projects, then after 1.5y the second engineer got hired, now I’m guilty as probably you mentioned being emotionally attached to my wo…

As long as you have significant stock it probably doesn't matter much. Like for that engineer with 10% of Yahoo, or chief cook at Google. If you are ambitious, then you need an assistant to do what you are doing now. Better a small team under your leadership ;) The difficult part is to make them believe it.

I wouldn't want to hold stock in such a situation. His ability to influence the business positively and therefore increase the return on his stock is limited.

Re: How I feel quitting my own startup

#96
post #88

Earlier quoted context omitted.

So, since the a hole engaged in fraud the veil was broken, no? That makes them personally liable iiuc...

Perhaps I was too nice. Most VCs recommended dropping/settling the case, since (1) it was only a year and many startups go bust anyway; (2) the best people spend their energy on the future, not the past; and (3) regardless of the facts, many people are wary of working with someone who sued his business partner personally. (As Trump shows, portraying yourself as the victim of a baseless lawsuit often elicits sympathy,…

I'd say you were too nice.

Even if it didn't help you personally, having pursued it more vigorously would have been a public good as it would ensure a documented record of the misdeed which future prospects could use to avoid the bad actor, as well as discouraging new bad actors from developing as they would see the loss rate as exceeding the win rate etc.

As long as everyone keeps letting shit go, letting bad actors off without penalty just because it would take more effort than it was personally worth, then we will continue to see these behaviors manifested and likely at an increasing rate as it proves it's effectiveness.

Re: How I feel quitting my own startup

#97

Earlier quoted context omitted.

>> I've made > 100 pre-seed investments and the #1 cause failure in the first 3 years is founders quitting because of unresolved cofounder conflict. Can you comment on the most common cause of conflict? You mention something trivial to make the point that they can be over trivial things, but what is the most common cause of conflict?

There’s no one specific cause that stands out as common. All happy families are alike; each unhappy family is unhappy in its own way. What IS common amongst terminal cofounder conflict is a series of ruptures in the relationship without any corresponding moments of repair. Over time the ruptures build up into complete relationship breakdown over an issue that seems trivial. People gradually work themselves apart and…

This is a great insight, explained well. Thank you for it.

Re: How I feel quitting my own startup

#98
post #89

Earlier quoted context omitted.

This reads like reasonably normal high growth growing pains. Miserable but common as everything is constantly breaking (not just the product but organizational systems and processes) as the company piles on new hires and new customer demands. Communication breaks down completely as you leave the “everybody knows what everybody else is doing” stage and need to figure out coordination across siloed teams and work strea…

> This reads like reasonably normal high growth growing pains. Not the parent, but I don't see how this is normal. Your sales team giving customers high expectations is a recipe for customer disatisfaction. Releasing broken things binds resources on unnecessary things that would have otherwise been used to stabilize foundations or add new features. So you essentially have a sales teams sabotaging the plans of the eng…

Completely agree with the ideal situation you present. The problem is that this doesn't hold up under the pressures of small teams chasing high growth.

Nobody is intentionally sabotaging anyone else (usually) but everyone stretches a little bit in the name of growth and things break down at the edges. Revenue growth can be life or death for small companies so, even though it sucks, promises are made and things are rushed. A perfect foundation and completely bug-free features don't matter if the business is dead.

There's a lot of sub-optimal juggling going on around this growth phase where you sometimes need to just focus on keeping the ship afloat until you hit the next set of milestones -> prove your worth -> raise -> grow the team to help shore up the foundation. Even if you aren't raising VC it can still be a similar grind where you need more cash flow to hire more to meet the exploding customer demands.

I will note that this only applies to high growth companies. If you have a pile of cash, strong product conviction (and skill), and the willpower to keep your feature set limited while turning away potential customers, you might be able to build the solid foundation -> sell the rock solid product. That isn't how most startups operate though and once you take VC the clock is ticking.

Re: How I feel quitting my own startup

#99
post #48

Earlier quoted context omitted.

Cofounder conflict is one of the biggest untold stories of the startup world. Happens all the time, but no one wants to admit the scale of the problem or get into their own specifics.

I'm grateful that I experienced "cofounder mismatch" at a young age (23) and when the stakes were small. Basically, building an app with two friends when one wasn't committed at all, and the other was about half as committed as I was. Ended exactly how you'd expect (though thankfully, we're all still friends). This is the chief reason why I'm the sole founder of my current venture. I'm not militant about avoiding cof…

I too am glad my first cofounder flaked on me when I was just getting started. Learned a bitter lesson that I will never forget.

This is also why I went the solo route for #2 (ignoring the investor/"expert" insistence on multiple founders). 10+ years later my bootstrapped (non-tech) company is profitable, has a strong dedicated base of customers, and allows me a degree of flexibility in my company direction and life that I would not have otherwise.

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