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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

#61

Post by ab-dm »

aqui_c wrote: 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…

I had to check I hadn't written this in my sleep overnight. You're describing a very similar experience to mine, and I'm honestly shocked at how common this experience seems to be.

2 weeks ago I signed the contract to "sell" my shares for my startup of ~7 years. I'm just now starting to realize how utterly miserable I had been for a long, long time.

It's a very difficult decision, but it gets easier every day (on average, some days can still be tough).

It's only going to get better.

Re: How I feel quitting my own startup

#62

Post by psyklic »

DelightOne wrote: post #45
psyklic wrote: 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?

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 secretly created a small equity pool for all co-founders excluding himself. There was no reason to believe we were in a pool, since co-founders split the entire pot.

This caused the percentages to seem about as expected. To the best of my knowledge, there were only two tells in the written contract:

1. The total shares were listed as ~1M, which at the time sounded perfectly logical. Unbeknownst to me, this was only the shares in the pool. I now know that startups often first allocate 10M shares, apparently for psychological reasons.

2. The vesting documents were titled an "equity incentive plan". At the time, this made perfect sense to me; the entire reason for us all reverse vesting is to provide incentive to stay. However, I now know this specific phrase often indicates an equity pool.

I recommend all founders speak with the lawyers jointly, instead of delegating it to the CEO. Ideally, also pass the contract by a startup-savvy lawyer. (In our case, one of our co-founders showed a CPA who said everything looked normal.) I recommend not signing until the exact cap table with zero errors is jointly signed. (As I mentioned above, I pointed out a mistake to my business partner then signed after he replied I had the most equity.) I also recommend contacting your business partner's references if you haven't worked together, especially since they will be providing those to VCs later.

Re: How I feel quitting my own startup

#63

Post by [deleted] »

benjimouse wrote: post #20

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…

[deleted]

Re: How I feel quitting my own startup

#64

Post by AnonymousBison »

benjimouse wrote: post #20

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 quitting would kill any confidence remaining in the company and trigger an exodus.

Re: How I feel quitting my own startup

#65

Post by z3t4 »

throwaway778 wrote: post #14

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…

Tell the owners that the train might derail and that you wont be on it when it does, so they either have to slow down or risk crashing.

Re: How I feel quitting my own startup

#66

Post by pbj1968 »

Well, frankly, it’s a real shame he’s hanging up on this one. There’s much to be done with light sheet. I only exist at the fringes as a bystander but have seen some incredible imagery come out of it. Compared to all the “disrupt the phone sanitizing market!” cruft I’m used to reading about, this one actually seemed worthwhile.

Re: How I feel quitting my own startup

#67

Post by opmelogy »

taneq wrote: post #53
opmelogy wrote: post #32

Earlier quoted context omitted.

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.

> You felt your partner was coasting so you checked out. They felt that you checked out.

Yes that's basically what happened. I get that this is their perception, but find it funny how much self-awareness is lacking as to what they contributed. I'm still friends with them and still like them, but they are firmly in the camp of "nope" moving forward.

> Maybe they were doing more than you realised, or maybe they were just freeloading.

I'd love for it to be the case where they were doing more than I realized, but considering we're all engineers and I'm the only one working on designs and implementing code...and driving all the discussions...you get the idea.

Re: How I feel quitting my own startup

#68

Post by hinkley »

aqui_c wrote: 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…

Why is it always that the most practiced storyteller on a project seems to tell themselves the story that their contributions matter head and shoulder over those of everyone else combined? "We wouldn't be here if I hadn't pushed thus and such."

At some point they forget that the value others brought to the table was a big part of what made them participate in the first place. Now they devalue all of those other players.

Re: How I feel quitting my own startup

#70

Post by hinkley »

quickthrower2 wrote: post #38
JonChesterfield wrote: post #13

Earlier quoted context omitted.

If the full time people don't identify a founder leaving as an existential threat and look for their way out that's on them.

Also it is a job. People can get fired (impacted I mean) at any company. They weight it all up like any other job. Company is family never really existed.

You can keep people off balance enough that they don't have time to think about finding another job. That's what a 60+ hour work week is for, after all.

You work and sleep.

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