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How I feel quitting my own startup

aquiles.me

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Re: How I feel quitting my own startup

#51

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…

> Is it practically possible to shift the culture?

Yes. But it requires saying no to lots of things you used to say yes to (and vice versa), which can be extraordinarily difficult

It may not feel like it, but if you have been around since day 2 you’ll be respected enough to try anything you like, as long as you actually do it and don’t complain (not saying you’re a whiner but some people are). You basically have tenure.

Re: How I feel quitting my own startup

#52
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…

Sorry to hear that. How did you end up in a situation where you're the only founder working full-time but the other founders have more equity and control over the business?

Re: How I feel quitting my own startup

#53
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…

It sounds to me like the two perceptions of your previous startup are pretty well aligned. You felt your partner was coasting so you checked out. They felt that you checked out. Maybe they were doing more than you realised, or maybe they were just freeloading.

Re: How I feel quitting my own startup

#54
> Going away at this moment sounds like an irrational choice, but I was one I had to take, I had to place myself and my peace of mind ahead of anything else.

I can relate to this. No, I didn't leave my startup. I've worked with three startups altogether, including one of my own, which started off with a co-founder back in 2012. In the not-my-own ones, I was once the founding engineer, and once the fourth engineering hire.

Why didn't I leave my own bootstrapped startup despite the amount of pressure, chaos, uncertainty, and pain, all of which were setting in at the same time? Not to mention immense difficulties in dealing with co-founders and all the social pressures (home life, relationships, real day job at a fortune 500) and burning hard-earned cash to keep the thing running in the face of uncertainty and the very real likeliness of failure.

Why I nearly did walk out:

- Extremely unpleasant co-founder. Unsociable, condescending, biased - for instance I'm quite sure he perceived me as being worth less than himself because I had no wife and kids situation going on. Treating me as employee despite having equal shares in the company. - No VC capital or outside funding. The expectation of having close to 0 in the bank account once the pay-day happens from the "real" job (and rent+bills have already been covered) sucked really, really much.

A few things spring to mind as to why I did not walk out:

- Luck. We seemed to have the right timing. There were almost no products on the market which attempted to solve the problem the way we did. There was a tremendous interest in our product, but we just couldn't get any significant number of people to convert, despite seemingly offering the right product.

- Having listened to feedback and tweaking the product (most notably the pricing/business model), we managed to achieve decent market capture (it took almost 3 years from) and that came mostly as a result of persisting through the cash-burn, listening to and evaluating all customer feedback, and iterating on many aspects of the product dozens of time. Fixing broken things and solving weird edge-cases which weren't weird in retrospect pointed to the fact that we were simply inexperienced. We still pressed on and sought to break through this barrier of having no freaking clue about this emerging market.

- The real break was the actual realisation of the for-reals breakeven. It changed the game - the point at which no money needed to leave our personal bank accounts to pay for cloud services, domains, tax accountants, templates, logos, you name it, was one of the greatest feelings ever. At point-breakeven the whole thing went from a "somewhat successful side-project which has been draining our personal bank accounts" to a project which could potentially provide enduring sustenance, and we might be able to take it further. At that point it became all the more compelling to press on.

Re: How I feel quitting my own startup

#55

Earlier quoted context omitted.

Great way to ruin a great friendship.

I don't necessarily agree with this statement - if I know my best friend inside out we will have a super large room for flexibility, and that often prevents conflicts.

My practical experience is that there is no way of separating the two things, friendship and co-worker. And I believe there is more to lose than to gain in this arrangement. When a problem comes up I rather not argue with my friend (sorry, co-worker) about how my position is right and his is wrong.

Re: How I feel quitting my own startup

#56
post #52
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…

Sorry to hear that. How did you end up in a situation where you're the only founder working full-time but the other founders have more equity and control over the business?

Maybe they funded it?

Re: How I feel quitting my own startup

#57
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 people be so sketchy and still sleep at night is out of my mind

They use their stolen money to buy very nice mattresses.

Re: How I feel quitting my own startup

#58

Earlier quoted context omitted.

I don't necessarily agree with this statement - if I know my best friend inside out we will have a super large room for flexibility, and that often prevents conflicts.

My practical experience is that there is no way of separating the two things, friendship and co-worker. And I believe there is more to lose than to gain in this arrangement. When a problem comes up I rather not argue with my friend (sorry, co-worker) about how my position is right and his is wrong.

Thanks for the insight. In that case, I'm wondering what would your preferred network be, if you're looking for a cofounder?

Re: How I feel quitting my own startup

#59

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…

Wtf… 100 people and you’re still doing 18 hour days? Y’all are past the point of needing the switch to sustainability.

Re: How I feel quitting my own startup

#60
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…

It is probably no consolation for you, but now your former co founders have "their" own company that's four years old, still has no customers or an MVP, and apparently no one really working full time on the company... Seems like they get what they deserve...

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