Founders Guide: So You’re Leaving Your Company
Talking through the hardest decision a founder has to make
Founding a company can feel a bit like being a parent. Founders pour their hearts and souls into their companies. They dedicate years of their lives to growing these fledgling organizations. Their identity becomes wrapped up in their companies, which in turn come to reflect their founders. And if they stop giving love and attention and care, especially in the early days, the company dies.
The ironic thing about the founder journey is that after all is said and done, most founders will eventually leave the companies they create. Sometimes this is because you had a great exit. You get out of the souped-up car that you’ve worked on, polished, slaved over, and hand the keys to an exec at a mega corp. Sometimes it’s because the company is dead in the water. You turn off the life support and return any cash you have left and lament what could’ve been. And sometimes, most painfully, it’s because you can’t stand your company and your cofounders any longer, and you need to get out (or risk jail time for assault).1
In the span of a month, two close friends left their companies. One had a buyout that couldn’t meet the company pref-stack. The other was pulling his hair out due to co-founder conflict and needed to quit. They’re both still going through it. It’s hard.
When I left my first company, I left on pretty good terms, and I still had a pretty rough time of it. With a year+ of hindsight and a lot of writing in between, I think there are a few things that make leaving a company really really hard for founders.
Most founders that I have met are ambitious, hyper energetic people. We can’t sit still. I suspect half of us are borderline manic most of the time. That energy is what sustains a founder. But it also makes leaving hard, because leaving means a vacuum. What do you do with the time? How many times can you do the routes at your local climbing gym, how many runs of Ascension 20 Slay the Spire before all of that sitting around starts to get a bit boring? Related: many founders are not exactly in tune with their emotions. Huge competitive edge when slugging through hour 33 of writing code, less good when left alone with your thoughts.
Leaving a company is like leaving a family. Founders have close personal relationships to the people they hire; the best founders love and live for their teams. Leaving a company feels like a betrayal. “I joined this company because I wanted to work with you, and I put my faith in you, and now you’re leaving?” “How could you not see how hard this has gotten, why did you not do more to help?” Some founders lose their entire social network when they leave their companies, especially in the Bay where social life and work are so closely tied together. If you have a big co-founder fight, are you supposed to just meet up at the next ML Paper Reading Group & Cuddle Pile and chat-slash-cuddle like nothing happened? Founder breakups are more toxic than most actual breakups.
Founders can’t actually talk about their departure, at least not publicly. Certainly not to the people they are leaving behind. Founders often have non-disparagement clauses tied to their equity. So you can’t share why and how you left with anyone in the industry, unless you do so with a smile on your face. Which, again, is many of your closest friends! Also, many founders are pathological rule breakers and misfits who see their work as part of their identity and self expression (myself included). Restrictions on speech hit especially hard.
Founders wrap so much of their personal identity and self-worth into the success of their company. If the company failed, it’s because I failed. I am a failure. I didn’t work hard enough, or smart enough. That same mentality keeps founders in terrible working conditions.
All of this lends itself to a really common failure mode. Founders instinctively try to control the ambiguity — the moment they leave, they are setting up their next thing. This time I’ll make it. Some founders go further and try to recreate their first company. I’ll do it better this time, I won’t make any of the same mistakes.
Don’t do this.
If you spend months-to-years working on whatevercorp.ai, your entire way of thinking is clouded. You will see everything through the prism of being the founder of whatevercorp.ai, and as a result you will make bad and probably incoherent decisions.
Instead, you have to do something that is basically impossible for a lot of founders: slow down, sit back, and reconnect with yourself.
To the extent that I have advice, here are some notes:
You need to clear your thinking, let the oil and water separate. The best way to do that is to dramatically reduce the timeframe of your thinking. You’re used to thinking weeks or months or years ahead. Stop that. Bring your timeframe down to one month. Then one week. Then one day. Then five minutes. What do you want to do five minutes from right now? Answer that question honestly, and then go do that thing. For the first month after I left my first company, I had huge plans about starting all sorts of projects. But what I really wanted to do was eat Costco taquitos and play Pikmin. I am so grateful I did the latter, because that eventually led me to what I was naturally curious about (coding agents!).
Related: avoid the impulse to answer questions about what’s next too early. It’s fine to not have an answer when someone thinks they are being helpful and “a good friend” when they inadvertently ask ‘what are you planning to do next?’ It’s fine to say ‘I don’t know’ and mean it. There are no hard and fast rules, but I think if you have an answer within a month you didn’t spend enough time thinking. You should seriously consider whether you even want to do the startup thing. It’s fine if you don’t!
Write. Write a lot. Write your founder journey. Don’t use AI. All this serves two purposes: first, writing is thinking, and you need to make time and space to think and process; and second, future you will want that memoir as something to look back on. Writing has this beautiful way of cutting through emotion, because you can look back at what you wrote after a night’s sleep and see in your writing a different version of yourself, and recognize that that version isn’t you now.
Don’t travel. Stay in your hometown and let yourself be bored. The brain is remarkably efficient. It builds routines — including emotional states — around physical memory. You spent months working on your company. Your apartment / home and your city and of course your office will trigger certain emotions, and you need to rewire. Travelling is great, and can be relaxing, but travel is about creating new routines in new places. You need to give yourself some amount of time going about your usual day so your brain will understand the new normal (alt: just move. This is obviously less immediately attainable for most people, but would have a similar effect!)
Get advice from other founders who have previously left their companies. This is not always easy to do, because you may not know other founders who have left their companies, or you may not feel like you can approach them. One of the things I don’t like about Bay Area founder culture is that everyone is constantly showing off to everyone else, which means there is little space for vulnerability. Even when people are really going through it, they will grit their teeth and smile and give the pitch for the ten millionth time. So, yea, not easy to find folks who are good to talk about these things with. But if you do have someone in your wheelhouse who has gone through it before and who you can talk to, call them. They will have a lot of detailed things to say, and will likely appreciate the call.
These are the things that were most useful for me. There are also the usual canned-but-useful bits of advice — spend time with friends, pick up new hobbies, get fit, sleep, read, etc. etc. Those are all helpful, but I think far less so than the five things mentioned above.
The last thing I’ll add here is that if you are reading this because you just left your company and it resonates:
first, I’m sorry that you had to leave under less than ideal conditions;
second, congratulations, this is basically always the right decision, and I hope you feel a lot of relief;
third, it gets better, and you will eventually become your previous company’s biggest ally (because, you know, you are likely heavily financially incentivized to do so);
And finally, if you need it, feel free to reach out, happy to chat.
Mostly this piece is for folks going through the last one in this list. Founder breakups and disillusionment are far and away the most common reason founders leave their companies, and also the most difficult to work through. If you had a great exit, some of this advice may still apply, but a lot of it won’t because you will likely be embedded in a larger company and most of the battle is watching your company change from underneath you.