How to Avoid the Founder Depression Spiral

Oct 2015

(Based on an Office Hours)


“He awoke each morning with the desire to do right, to be a good and meaningful person, to be, as simple as it sounded and as impossible as it actually was, happy. And during the course of each day his heart would descend from his chest into his stomach. By early afternoon he was overcome by the feeling that nothing was right, or nothing was right for him, and by the desire to be alone. By evening he was fulfilled: alone in the magnitude of his grief, alone in his aimless guilt, alone even in his loneliness. I am not sad, he would repeat to himself over and over, I am not sad. As if he might one day convince himself. Or fool himself.

Or convince others–the only thing worse than being sad is for others to know that you are sad. I am not sad. I am not sad. Because his life had unlimited potential for happiness, insofar as it was an empty white room. He would fall asleep with his heart at the foot of his bed, like some domesticated animal that was no part of him at all. And each morning he would wake with it again in the cupboard of his rib cage, having become a little heavier, a little weaker, but still pumping. And by the midafternoon he was again overcome with the desire to be somewhere else, someone else, someone else somewhere else. I am not sad.”

― Jonathan Safran Foer, Everything Is Illuminated


Failing fucking sucks. It’s absolutely the worst emotional feeling there is except maybe heartbreak. But when you try to measure why it hurts to much, an interesting conclusion emerges. It isn’t the failing itself that intrinsically sucks. It’s the social proof that adds the sting.

People failing in a bubble by themselves, without anyone finding out about it is just called trial and error. What adds the layer of depression and sadness to failure only comes from lots of other people knowing about it. Particularly when they expected you to succeed but the result was failure.

The differential between other peoples expectations and the outcome of their company is the match that starts the spiral into depression. And when 90% of new companies fail in the first 3 years, it means this spiral is is very very common. The sad part is how easily avoidable it is with just a few small social tweaks.

One kind of startup depression worth mentioning comes from stress and burnout. Thankfully this is easy to fix. Lots of sleep, plenty of exercise, taking breaks, reading a good book, a great holidays, a loving family, a healthy diet, good work life balance and generally happiness are the keys to fixing this type of sadness.

Burnout is surprisingly easy to avoid but most people glorify those who sacrifice themselves to achieve great things. They then try to emulate that same quality, thinking it will give them similar results and so knowingly throw themselves under the bus.

The optimal way to combat burnout is actually by removing yourself from the equation entirely. The best cure is happiness. Walk away. Do something else. Come back when you’re ready and take lots of breaks and delegate. This type of startup depression caused by burning out is a real problem but is not what this essay is covering. We’re covering the other kind.


Managing Expectations


The first half of the equation is managing expectations.



One of the best pieces of advice I was ever given is very frankly, don’t tell anyone. Whether you succeed or fail. Don’t tell anyone. Only tell the people who can very directly help you. They’re the signal. Everyone else is just noise. It is better to succeed or fail in secret. I never appreciated the wisdom in this. But it’s true and is the remedy for large parts of startup depression. Managing expectations. The easiest way to do that is for there not to be any.

There is an uncanny habit with startup founders to tell every person they know about their new company before their own users and the people who’d want to use it. What this accidentally does is two things. It starts the benign positive feedback loop. And it accidentally starts a timebomb in peoples minds that is the expectation of you becoming rich and successful.

Your friends and family think you’re smart. And when you announce that you’re trying to build a company, most people assume you’ll be successful at it, when the statistics say quite the opposite. What then happens is a drawn out death by a thousand knives. Every time you see them again, the small talk will be around your company.

They’ll ask how it is, how it’s going, whether you’re succeeding, how long it will take etc at every opportunity. It’s all intended benignly. But most startups aren’t doing well. Most die. And when they win it takes a long time and lots of hardship. The cycle forces a founder to put on a brave face and pretend like things are great when 90% of the time they are not.

This creates cognitive dissonance, amplifies imposter syndrome and makes founders feel like they’re shams. If you’ve ever been sad, there is often nothing that makes you more miserable like trying to instead pretend you’re happy. Their own company becomes a shackle of the expectations of other people. They can’t discharge it without looking like a failure in the eyes of all their peers.

The hack is to only start talking about a company after it’s already started succeeding. By then you’ve already won in the eyes of everyone around you and have nothing to prove. There aren’t any expectations to meet because you’ve already met them. This model is actually from the art world.

A young singer or standup comic is usually made to hone their craft in smaller venues over years by more experienced agents. This lets them fail in private and try new things in inconsequential environments without the eyes of the public. Only when they’re really good are they unveiled to the public.

The reason for this is agencies don’t want to present unfinished products. They only want to present a singer or comic once they’re sure they’ll become a star. Otherwise the weight of the publics expectations will crush the spirit of the young artist if they ever start to struggle. And even if they start to succeed in small ways, the expectations of bigger success from other people often stops it in its track.

This same thing happens to founders, except they are usually the arbiter of their own misery. Most people who start a new company work outwards from their inner circle to strangers who are their users. They tell all their acquaintances, friends and family about their new company while users find out about their company after all the people closest to them. This is the perfect recipe for startup depression. Everyone starts waiting for you to succeed but you have no users.

The optimal way to avoid depression is actually the opposite. You want your inner circle of acquaintances, friends and family to hear about your company last, ideally from other people you don’t even know, before knowing that you are involved in it. You want to start talking to your users first and to have so many users that eventually your inner circle can’t help but hear about you. When a person has heard of a company then finds out someone they knew is part of it. They are almost always very impressed.

Even if you start succeeding. Most people don’t understand the world of startups. For example, if you manage to raise money at a good valuation. Most people will think the valuation is actually how much money you have and that you’ve already won. Most people not in the startup world think if you raise money at a 5 million valuation, it means that you actually have 5 million dollars sitting in a bank. This is totally wrong. It’s a common misconception by people who don’t know any better. They are often the same people who conflate raising money with being successful. Raising money is not a guarantee of success. But to most people, they see it that way.

It’s why so many people congratulate a young startup for raising capital, as if they won the lottery, rather than just topping up a fuel tank, which is what a capital raising really is. A similar phenomena happens in the arts. When you start to hear a young singer on the radio or a young comic does their first few tv gigs or a stadium. Most people immediately assume they’re already very successful and are earning huge amounts of money, when this is frequently the furthest thing from the truth.

Back when I was an artist, my first ever TV gig was aired to nearly 3 million people. Everybody I knew came and started congratulating me on what a “huge success” I’d become and telling me how “eagerly” they were anticipating my shows. How much did I make for that gig? $3,000. That’s about how much I made from every TV gig I did my first year. Most people didn’t understand the art world and so to them, me being on TV meant I must’ve been making a ton of money. They expected me to be more successful than I was. I saw that pattern play out in the lives of tons of artists and it caused an immense amount of angst. You see the same thing play out with founders of young companies.


Feedback Loop


The other half of this equation is the feedback loop.

When a founder hears a bunch of useless but constant praise and it goes to their head. When a 5 year old child creates an artwork. Nobody will tell them how terrible it is and that it sucks. In fact, most people will do the opposite. They’ll praise it and give it lots of compliments. Why? It’s to protect the child’s feelings and not make the child lose confidence in their own abilities. And children receiving lots of praise for their art will start to feel like they are good artists. But the market for art will almost definitely value their work at zero.

Much of startup feedback is like that. If you show your friends your new company, almost universally they will tell you how much they like it. It’s usually not because they actually do like it, but it’s because they like you and want you to succeed. It’s their equivalent of trying not to tell you your artwork sucks.

So founders start to judge their products based on the opinions of their friends and not their actual customers. And so many a founder who’s friends love their work find themselves in a situation where the market doesn’t. Nobody wants to buy it. It’s not useful. But they’re told constantly how great it is by all the people they know. They have a completely different image of what their company looks like than from how their customers see it.

Listening to innocuous advice from friends, acquaintances and family, ruins good products. The only opinion you should really care about and listen to is that of your users. And finding genuinely blunt and helpful users is quite rare.

That cognitive dissonance based on their experiences showing it to their friends, and the experience of users actually using it creates a depression when things aren’t working and they don’t understand why. Because they built all their assumptions based on people who just want to be nice to you which sends them into a spiral of despair and failure. Much the same way a real art auction might crush the artistic aspirations of a 5 year old. Markets are much less forgiving or accepting.