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How I feel quitting my own startup

aquiles.me

81–90 of 99 posts

Re: How I feel quitting my own startup

#81

I went thru this seven years ago, leaving my startup which I'd been with for about 15. I still considered it a startup after all that time. The opportunity had long since been missed and all that remained was a long slow grind down to nothing. Which is exactly what has happened as it continued after my departure. For me it was as close as I could imagine giving up a child would be like, but in hindsight it was the be…

I'm in a similar boat currently. I've been in the same startup for almost 6 years now, pretty much since day one of its creation. I've been with the founders through every step of the way and my closest circle of friends is among the employees. But at this point it feels like the product is going nowhere fast. I'm worried about my career (i don't have much else on my CV) but being the very first hire I'm afraid quitt…

If things at your startup have been run equitably, then after 6 years you should have some equity that's all yours.

That makes it fine to quit. You'll stop getting salary, but that equity is your stake in the future as things unfold.

If you don't have any equity after 6 years then it's time to bail anyway.

Re: How I feel quitting my own startup

#83
post #30

Earlier quoted context omitted.

We had well-known lawyers from the beginning who deferred payment until we raised. The problem was that we delegated all legal to my business partner. When we traded the written equity split, he didn't disclose that he held (estimated) >80x more shares than what was listed next to his name.

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

The short answer is always, always have your own lawyer review these things.

The lawyer preparing the corporate documents is the corporation’s lawyer. That person cannot also be your lawyer. Every founder should have their own lawyer review and advise them on the paperwork.

Re: How I feel quitting my own startup

#84
post #79

Earlier quoted context omitted.

The way you explain it makes it sound like explicit fraud which is completely actionable.... Or were all communications referenced verbal rather than written?

Every communication referenced was in writing. The equity was only one of many very unsavory things that happened, and I eventually had to hire a lawyer. He suggested we sue and took the case on contingency, but by that time the company had minimal assets.

So, since the a hole engaged in fraud the veil was broken, no?

That makes them personally liable iiuc...

Re: How I feel quitting my own startup

#86
post #2

I left the startup I co-founded 4+ years ago. The entire process was an emotional roller-coaster. My co-founders (and business partners), who are the majority shareholder, made it abundantly clear that the company was 'theirs'. They made decisions behind my back although I am the only founder working full time on the company. I felt alienated, undervalued, and frankly quite miserable for a while. At some point, when…

That really sucks. I'm sorry to hear it. I tried twice to start software companies with people I knew. Both times the other party didn't invest nearly as much time as I was putting in. And in both cases I figured this out fairly early and started to match their drive and investment into what we were building. As you'd expect, the companies folded within a few months. What's interesting to me is that one of the guys I…

I've found that people live in their own delusions. You have to learn how about how a person perceives the world around them and realise that there is no objective truth but simply what they believe.

Then you can still work with them as long as their incentives are aligned with what you need them to do. That is the intended behaviour fits within their perception.

Re: How I feel quitting my own startup

#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 the director ans the producer will decide on things, but on a good film set the best idea wins and so the director and producer would be idiots not to listen to their team when they have them.

Re: How I feel quitting my own startup

#88
post #79

Earlier quoted context omitted.

Every communication referenced was in writing. The equity was only one of many very unsavory things that happened, and I eventually had to hire a lawyer. He suggested we sue and took the case on contingency, but by that time the company had minimal assets.

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, while justifying bringing a lawsuit often requires a careful factual explanation.)

Re: How I feel quitting my own startup

#89

I’m struggling with making this decision at the moment and it was interesting to read this. I’m not a founder, but I’m the first hire and the first engineer – there since day 2. Six years in, a couple of pivots, and now we have a team of 100 people with a gigantic series A just closed and an excellent PMF. I built most of the product myself – it’s genuinely game-changing and commercial demand is through the roof. Eno…

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 engineering team by extorting them with things they promised to customers.

These are the signs of a dysfunctional and badly managed organization. Your sales guys should have a realistic image of your capabilities and customers should get things when the lead of engineering deems them ready. And if you don't trust their judgement on that, it is either a you-issue or a them-issue.

Re: How I feel quitting my own startup

#90

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?

Given poor communication, trivial things lead to conflict. This is the case in every relationship. The takeaway should be that you need to communicate well, not that you need to pay attention to one specific subject.
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