I’m a founder. And I’m not depressed

Update: I received a number of appreciative, heartfelt emails from entrepreneurs thanking me for sharing my experiences. And a few friends also sent me messages like, “Hey Kevin, I know you mean well but …”

In retrospect, I should have exercised better judgement in how I wrote about depression because this is a complex issue. Sorry. People who understand the disease have advised me that depression isn’t the opposite of happiness. I believe them – giving people simple tips I’ve used to make myself happier won’t help people who are clinically depressed. I should have written a post called How to be a Happier Founder since that’s all I’m qualified to talk about.

I thought about re-writing this post from that perspective but decided to let my mistake stand as it is. Hopefully others will learn from it.


A real disease with horrible consequences

Brad Feld just wrote a great post about startup founders, depression and its horrible consequences. I’m not refuting his points – we need to do more to understand depression and prevent these tragic suicides. I know of startup founders who have suffered from depression.

(Feeling depressed? STOP reading and get some help.)

Can entrepreneurship cause depression?

I don’t know. Actually I don’t know … well … anything about depression. I don’t know if being a founder can cause it or if the pressures of entrepreneurship exacerbate the disease. I only know that being a startup founder hasn’t made me depressed. On balance, I love being an entrepreneur and can’t imagine doing anything else.

But it can be brutal at times, so over the last 20 years I’ve learned a few tricks for being a happier founder – I hope they help you.

I am grateful for this opportunity

I’m so thankful to be alive in this amazing time. I’m 5’7”, weigh 145 pounds and can’t run or jump. For most of the world’s history I would have been lion meat or the village’s poorest farmer.

But I was born into an era of computers, the Internet, and capital markets, so I can make a living sitting on my rear and “working” in air conditioning. I can choose what to do with my life.

You know what I really enjoy doing?

  • Making software.
  • Writing.
  • Trying to improve the world.
  • Working with creative people.

There’s a career where I can do these fun things every single day – entrepreneurship. How did I get so lucky?

And yet I have the same problems that you do

I’m glad entrepreneurship is challenging but sometimes I wish it wasn’t THIS hard. My currently startup, SoHelpful, is about 18 months old and still an experiment. I often think about the opportunity costs of not having a more traditional career – I’d be wealthier and better at golf.

Everything seems to take 10x longer than I expect. I make rookie mistakes. I second-guess most of my decisions and have days when everything goes against me. My family is amazingly supportive, but I can’t often share what I’m going through because they won’t understand. It can get awfully lonely.

So, yeah, I understand how hard it is being a founder.

A few choices I’ve made that made me happier

But there are a few things I can control that have made entrepreneurship more rewarding.

I started by picking my market

I’ve tried starting companies based on making money, doing what investors wanted me to do, or working on some tech I found interesting. None of this worked … at all. So this time I decided to pick my market first – other entrepreneurs like you – and then look for solutions to serve them.

I now find myself working for people I really like. I don’t mind cranky support emails, I like learning more about my customers, and coming up with creative ways to help them succeed. Work is much more rewarding when you really like your boss.

I planned for 20 years

My worst entrepreneurial experiences have resulted from my own impatience. I didn’t just want to be successful … I wanted fame and riches TODAY. I tried to speed everything up by raising more money, hiring faster, and rushing products. It didn’t work and only resulted in frustration.

I still try to go as fast as I can, but I have no expectations of overnight success. I pick projects I would be happy doing for 20 years. Now I can judge 1 year of hard work in the context of a long-term goal – not based on some imaginary expectation of overnight success.

I don’t read TechCrunch

I don’t read popular startup entertainment sites like TechCrunch. These “news” sites are fiction and bear almost no resemblance to what I’ve experienced as a founder and investor.

Whenever I do read them I feel worse about myself – it seems like everyone else is succeeding but me. So I don’t read them.

I work very hard

Since I like what I do … I do more of it. I don’t count the hours and the line between social and work activities doesn’t exist (another benefit of picking your market first). I don’t sacrifice my health, I get enough sleep, and put my relationships ahead of work.

But I work hard. It gives me a sense of satisfaction and makes every small victory so much sweeter.

I hire happy people

The best part of entrepreneurship is the people. At SoHelpful we have periodic “staff meetings” over Skype where Joey, Chiara and I give updates. We spend half of our time laughing, all of us happy to connect after so many hours of toiling alone.

We’ve all got the same frustrations as every other team that struggles to build products and sell them – but we do our best to enjoy it. Whenever I visit Manila we have a ritual of buying (incredibly unhealthy) ColdStone ice cream. That’s us in the picture!


I help a lot of people

I spend most of my time helping people – my customers, my team, other founders. I always feel better about myself for doing so. It isn’t a distraction from my work – it IS my work.

I met Joey and Chiara as a result of helping people. We got all of SoHelpful’s first 100 customers by being helpful. Being helpful is a great way to start a company.

You have choices

Trust me – I know all about the ugly side of entrepreneurship. Sometimes things are out of your control. But you have choices and can take control of your crazy life.

You can pick your market, be patient, hire happy people, stop reading TechCrunch and work hard just like I do.

You can go get a job and come back to entrepreneurship when you’re 30, 40, 50, or 70. I’ve done it and have no regrets.

You can “fail” … again and again. No one is keeping score. You’ll just get more fun stories we can share over beers together.

You can travel to developing countries and see happy people living in abject poverty – it will give you a whole new perspective.

And you can be helpful

And you can spend less time … on you. Work less on your product, your blog, your landing page.

Instead, try spending more time helping your customers. You’ll feel better about yourself – and your business will be more successful.

Photo credit: ૐ Didi ૐ


  1. Someone you know October 5, 2014 at 5:14 pm #

    Hey Kevin. Felt compelled to write back after reading this article.

    I think I’d like to make a point about depression. It’s not the opposite of being happy. Being depressed is not the same as being sad (it’s one part of it but theres also the hopelessness on days and lack of motivation amongst other things) . Unfortunately, no one chooses to be depressed.

    Just like you can’t tell a person who has cancer or a fever to snap out of it, telling someone who is depressed to be happy is perhaps symptomatic of how little people know about mental illness.

    • Eike Post October 5, 2014 at 5:48 pm #

      “Someone you know” you are very right that there are physical causes in the brain that can cause depression, and that it can be impossible to just turn the switch to happiness. Nonetheless, what Kevin and also I have found, is that it is possible to for us to do certain things that keep us positive.
      From my own experience I see that a certain life style makes it more likely that I feel bad and am negative, and that I can do certain things to become more positive. Over the last 10 years I have observed these negative factors and positive factors and now I am able to stay positive even in face of adversity.
      These factors for me are:
      1. General Life Conditions
      1. eat healthy
      2. interact with friends
      3. go to warm and sunny country
      4. go out in nature

      2. Activities
      1. do sport
      2. work less
      3. restrict news uptake and computer games

      3. Positive thoughts
      1. make plans for future and have goal for future
      2. stop thinking about the past, no regret
      3. think about the people that are worse of than you not those that are better of

    • kevindewalt October 5, 2014 at 6:13 pm #

      Great points. Hopefully I didn’t give anyone the impression they can “snap out of it” with the simple suggestions I offer. Like I said, I don’t know anything about the disease and hope anyone who suffers from it gets help.

      But there have been lots of articles linking the pressures of entrepreneurship to stress, depression and ultimately suicide. So to the degree that our profession causes it, I hope people can make some simple choices like I’ve chosen to do to make the experience more enriching.

      We have more choices than we realize.

  2. Ruslan Dorfman October 5, 2014 at 5:43 pm #

    I’m telling my co-founders that after founding the company made me a “bipolar”. When I was salaried employee I was adhering to my routine I was “emotionells” and content (most of the time). But being a self-funded Entrepreneur is an emotional roller coster – one day you are happy when (customers come and you are achieving next milestone), but the other day I’m hitting rock bottom after having a look into the (almost empty) bank account and wondering whether how cover next payroll and pay the invoices.

    • kevindewalt October 5, 2014 at 6:20 pm #

      Hey Ruslan,

      Man, I hear you. We’ve all been there. The pressures can be brutal.

      I can only offer that it gets easier with age. At 44 I don’t let the highs get to high and I realize that the lows aren’t as bad as they seem.

      The worst that can happen is that I fail, lose everyone’s money and have to fire everyone. That’s happened to me before, life went on, and everyone I worked with still talks about how great the experience was.

      The best that can happen is that I make lots of people rich, become famous, and can do whatever I want. I have friends in this position. They’re still the same people, facing the same demons, and no happier or sadder as a result of the experience.

      The worst isn’t all that bad, and the best won’t change who I am. The years teach us things the days never knew.

  3. Anup Ghosh October 5, 2014 at 7:51 pm #

    Good advice Kevin– I like it!

  4. Ankit Jain October 5, 2014 at 10:38 pm #

    Thanks Kevin. Feeling lonely is one of the things that’s occurs often while doing a startup and that makes us feel negative. But when there are people like you who are trying to help entrepreneurs like us, who can stop our great team!!

    I am really grateful to you and all those who hav commented on this post to make us feel that we are not alone. This helps us keep motivated and inspired. We all together will achieve great heights some day. Pretty sure of that I am. 🙂

    Cheers everyone! 🙂

  5. Rico October 6, 2014 at 2:14 am #

    Hey Kevin,

    I’ve appreciated your honesty and the will to show the behind the scenes your journeny as an entrepreneur 🙂

    Great post.

  6. Richard Garside October 7, 2014 at 8:53 am #

    I found the ideas in this video very helpful when I felt like nothing was going my way and everything was just too difficult. The video starts off a bit slow (and I thought it was a bit cheesy at first), but it really flipped how I was looking at things:


    The gist is that you learn the most from the things that are most difficult and learning is good and not something to be afraid of. She puts it better than that though. It’s well worth a watch and her book is good too.

  7. blog admin October 7, 2014 at 11:57 pm #

    It’s hard to be honest about the roller coaster ride we call entrepreneurism and you’ve done that well. I was especially inspired by your statement that you pick work/startups that you’d be happy doing for 20 years. For me, that’s the gist of this. We are all caught up in the day to day, and when you do that, things never (or rarely) go fast enough, there are never (or rarely) enough customers soon enough and bank account figures don’t up quickly enough either. Until they do. Everything changes. It’s hard to depend on anything else but yourself. But depending on the inner self, if you can, is the way you ‘win.’ Every day. It’s a skill that doesn’t grow out of loneliness but instead out of self-sufficiency.

  8. Wojtek October 9, 2014 at 11:45 am #

    Thank you Kevin for sharing this!

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