How I feel quitting my own startup

I left the startup I co-founded 4+ years ago. The entire process was an emotional roller-coaster.<p>My co-founders (and business partners), who are the majority shareholder, made it abundantly clear that the company was &#x27;theirs&#x27;. 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.<p>At some point, when this behavioral pattern started affecting other team members and I realized I had nothing left to do, it was time for me to move on.<p>I tried to write down how I felt, keeping it politically correct.

I&#x27;ve made &gt; 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&#x27;t agree on a $5000 travel expense I was astounded. Now it&#x27;s something I&#x27;ve grown to expect - just one more risk to be managed.<p>To try and mitigate this my #1 question each time I meet with the founders I invest in is &quot;how&#x27;s your relationship with your cofounder(s) going?&quot;. If the answer to this question is anything less &quot;fantastic!&quot; we have a long conversation about why, before we talk about anything else.<p>A low cadence of communication between founders is also correlated with higher failure rates, so another fun question is &quot;when was the last time you spoke with your cofounder?&quot;. Again I&#x27;ve stopped being surprised by the amount of founders that answer with &quot;last week&#x2F;month&quot;, which again needs to spark a conversation about why.

I went thru this seven years ago, leaving my startup which I&#x27;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.<p>For me it was as close as I could imagine giving up a child would be like, but in hindsight it was the best choice and I grew hugely as a result.

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 work, after all, I really was invested in it, I even designed the icons for these platforms and the proper catchy names in addition to the software&#x2F;hardware engineering design, to writing the docs and even pitching the work for technical clients since sales guy had no idea what the work was beyond the concept.<p>After a while, same thing started to happen, promises were made these platforms can deliver even though technically is impossible (so you can guess later when the client know these promises were BS), not getting invited to critical meetings, sales team (grew later than one guy) is gatekeeping the communication and only dripping to engineers the client requirements after they add their own unrealistic expectations, started to exclude me for training clients on how to use these platforms as only sales team are doing those (funny as most of the time, the first question they get asked and they are stuck, and ended up they calling me during the session remotely), and after long discussions that it isn’t possible to be carried by sales and need a technical team, they quickly hired a co-op to act as one during these sessions… among other issues, I call these situations are simply sabotaging the company&#x2F;startup based primarily on greed, in this case it was by the sales and CEO followed later.<p>Now I had my lessons learned in that experience, but I’m sure your situation is worse being the founder, but I felt a good peace of mind after leaving them so hopefully you did the good thing.

I’m struggling with making this decision at the moment and it was interesting to read this.<p>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. Enough equity that if we were acquired now I’d be set for life.<p>But I just don’t know if I can hack it anymore. The commercial and product teams are pushing wildly unrealistic timelines for new features, which then the technical teams end up the bad guys for not being able to deliver on. Internal communication is all over the place, with nobody seemingly aware of deadlines and deliverables. The CEO is pretty visibly complaining about some teams not working hard enough, because he doesn’t see them in the office or working evenings and weekends. Meanwhile I’m on 18 hour days, under pressure to squeeze performance out of a team that I already think is delivering good quality at a pretty rapid pace, and being badgered constantly to provide KPIs and metrics for them so that the C-suite can deicide if they’re pulling their weight.<p>It’s almost exactly the opposite of the culture I’d want to create in an engineering team. Instead of teamwork and transparency aimed at producing a cohesive vision, everyone’s pulling in a different direction. Everyone is overworked and making mistakes, and instead of trying to build systems and processes to avoid these issues, it’s become a blame game. The answer to any problem always seems to be “work harder”, rather than providing the resources and support that teams require. Features are being rolled out to customers against engineering advice before they’re finished, meaning a massive drag factor as we scramble to patch them – and engineering leadership desperately trying to protect the rest of the team from having to pay for these decisions. And there’s this message being communicated from the top that suggests technical teams aren’t working hard enough that just feels utterly toxic. I’m probably making it sound worse than it is, but for certain the last six months have stopped being “I’m excited about working on this”.<p>How do you make the decision that it’s time to call it a day? Is it practically possible to shift the culture? Or is it feasible to detach yourself a little bit from it – concentrate on the areas you can change, and stop caring about those you can’t? I’m a well-paid engineer in an interesting field, and I’m invested financially and emotionally. It’s hard to be objective about whether it&#x27;s time to quit.<p>Basically I can sympathise with the emotions you’re going though and thanks for writing about it. Hang in there!

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 the decision has been made (Disagree but commit). If as the leader you see employees doing things behind your back, first you fire them especially if it is duplicitous. Then you have a long reflection on why your decisions were bad enough that employees felt the need to do this. It may be time to hire a new CEO if you think you cannot hold employee respect and trust. There is a sort of prevalent myth in Silicon Valley, that friends start startups and the company structure is flat in its initial days. There are far too many examples disproving this (Amazon, Facebook, PayPal etc) and even in the case where you have friendly cofounders, you still find an implicit hierarchy built on respect and trust which is probably the ideal form of hierarchy. However lack of hierarchy is a recipe for a mess of a company, formalizing hierarchy kills a lot of politics.

Hi OP, it&#x27;s a truly sad event when people conspire against you. Have you received legal advice? Even though you are not working for the company anymore, you still have rights as a shareholder. A lawyer can help articulate and fight for those rights.

I&#x27;ve been the founder who has been fired by his cofounder, and I&#x27;ve been the founder who has had to fire a cofounder. It was really terrible from both ways. Hope things get better for you!

Side note, but the small font size + light grey text on the white background made it a bit of an eye strain for me to read your story, would definitely benefit a bit from some more contrast.

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.

This echos some of my feelings planning to move on after 14 years at the same(non-startup) place. Thank you for writing it.

even thoug i dont know u. for me i relate in this way. i love to start things, motivate others, and dream big. however, at some point though it makes me sad, i feel like the idea is better off in other peoples hands. i struggle to focus and .... just want to start new things and motivate new ppl. i dont do startups for this reason but actually you writing this blogpost makes me feel maybe there is a place for me. to get the ball rolling and then leave it to people who are good at being consistent and seeing things through, but maybe less at starting and gathering motivation in the early stages. everyone has their own strengths and pitfalls. each end is a new beginning and i am sure after this tough breakup u will have learned a lot and find a new wonderful thing in ur life! =) all the best!

&gt; 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.<p>I can relate to this. No, I didn&#x27;t leave my startup. I&#x27;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.<p>Why didn&#x27;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 <i>day</i> 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.<p>Why I nearly did walk out:<p>- Extremely unpleasant co-founder. Unsociable, condescending, biased - for instance I&#x27;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 &quot;real&quot; job (and rent+bills have already been covered) sucked really, really much.<p>A few things spring to mind as to why I did not walk out:<p>- Luck. We seemed to have the right <i>timing</i>. 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&#x27;t get any significant number of people to convert, despite seemingly offering the right product.<p>- Having listened to feedback and tweaking the product (most notably the pricing&#x2F;business model), we managed to achieve decent <i>market capture</i> (it took almost 3 years from) and that came mostly as a result of persisting through the cash-burn, listening to and evaluating <i>all</i> customer feedback, and iterating on many aspects of the product dozens of time. Fixing broken things and solving weird edge-cases which weren&#x27;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.<p>- The real break was the actual realisation of the <i>for-reals</i> 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 &quot;somewhat successful side-project which has been draining our personal bank accounts&quot; 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.

This saddened me. Best of luck, truly.

A finishdown, if you will.