At Velocity/OSCON 2015 in Amsterdam a couple of weeks ago, the conference committee approached me to ask if I’d be up for doing an Ignite talk. It was rather last-minute and I had only hours to prepare. I said yes and then tried to think of a topic. I turned to Twitter and asked, if you could have me talk for 5 minutes on any topic, what would it be? A couple of people responded that they wanted to know what founding a company was like, so I sat down in the speaker lounge at the RAI and started trying to figure out what it’s like to be a founder/CEO.

You’d think I’d know after three years, but truthfully, it’s still hard to really know what I feel.

Anyway, I did it. I sent O’Reilly twenty slides of uncaptioned images that moved through an arc, and tried to write a story I could tell on stage. If you’re not familiar with Ignite, it’s a format in which exactly twenty slides advance automatically after fifteen seconds each, for a total of five minutes.

I had to wing it to some extent, and while speaking I thought one of the slides might even have gotten lost in the void of the internet and I had to skip some stuff I’d planned (it was really confusing to see what slide was on screen), but I got through it. Below I’m sharing my notes—which I did not exactly follow, because I changed things until the moment I spoke—and at the end is a video of the talk.

If you’re a founder/CEO or similar, and you’d like to talk about your struggles, I’d encourage you to reach out to me or to peers. (I can’t be available for everyone, but if you’re desperate you need to talk to someone.)

The working title of the talk was either “What it’s like” or “Why I do this” or something similar.

OK, enough preamble, let’s do this.

Why I Choose Technology


Years ago my friend Eliane asked why I love databases, and it took me years to answer. I always loved knowing how things work. I used to disassemble clocks and put them back together. Eventually I realized that technology is how I express my creativity.

Creative Expression


Creativity is a vital part of being human. All forms of expression are equally valid: dance, music, art, writing, athletics, coding. Whatever you love, whatever brings you alive, is valid. That includes being a nerd.

The Importance of Creativity


Creativity is self actualization. It’s how we express agency in the world. It’s how we say “I am alive and I choose to live, not just exist.” I want this for you, and for me, all of us.

So I Founded A Company


Three years ago I founded company to amplify my personal mission, to give to others what I wanted for myself: a life of purpose and validation that being a nerd is just as honorable as being a sculptor. I speak today because I want to share this experience with others.

What’s It Like Being A Founder?


In a word, stressful. Words to describe it don’t really exist. It’s a roller coaster from fear to joy and back, sometimes every 20 minutes. I can describe specific dimensions of the experience, but it’s like becoming a parent. You have to live it to know it.

Demands From Everywhere


Everyone wants something from me. Customers, employees, investors, community, family, vendors, governments. The amount of time and energy left over for myself is very small. Personal and company demands are often in conflict.

No Comfort Zone


My comfort zone is mostly off-limits now. I am a reserved person, but I must be outgoing. I prefer to support people, now I must sometimes challenge them. I’m a single-tasking focuser, now I have to multitask. I deny myself the pleasure of a job well done.

Compounding Effects


It’s hard to find time or motivation for exercise. I constantly forget things and people. This becomes a self-reinforcing negative spiral quickly.

Sleep Is Elusive


Sometimes I wake and cannot deal with intrusive thoughts and a racing pulse. At 2 in the morning, jacked on adrenaline and fear, I’m not solving anything. When I do sleep I have repetitive dreams of being late and unprepared.

“I sleep like a baby: I wake up every three hours crying.” - Ben Horowitz

The Struggle


Ben Horowitz’s book The Hard Thing About Hard Things is the best description of the experience I’ve read yet. to get a taste, read The Struggle.



Being a founder and CEO forces me to constantly destroy the old person I used to be. He is no longer what I need. He got me to this point, but now the task is to systematically amputate the parts I do not want and grow new ones.

I have bitten off the pieces that I did not want
I have bitten off the pieces that I did not want
- Jann Arden, Saved



This is way beyond “productivity tips” and “life hacking.” It’s self transformation. This is what it means to be committed. The only way through it is through it. It’s often a brutal process.

So Much To Lose


It’s hard to ask for help because there’s so much to lose. Everyone is looking for the slightest sign of weakness or fault. Honestly admitting a shortcoming could mean not winning a customer or investor, losing an employee.



I’m not alone in the struggle, but I’m lonely. Most founders suffer in silence and isolation. Depression, sickness, addiction, breakdowns and even suicide are the result. It’s rare for founders to break the silence. I’m doing it today because we deserve it.

Not Impostor Syndrome


It’s popular right now to talk about impostor syndrome, but this isn’t impostor syndrome. This is real and honest. This is a valid experience. I take comfort knowing that my discomfort with this unnatural experience is an appropriate response to the position I’m in. If you are feeling the same thing, know that you’re not damaged goods.

Daily Rededication


To cope and adapt, I have to make an effort to help myself and ask others to help me. I begin each day by dedicating myself to the service of something greater than myself. I resolve to be fully alive, present in the moment, and to suppress my self-will. I read sacred literature. I journal. Then I go do my best. I end the day by forgiving myself.



Meditation is a huge part of what keeps me sane. Meditation does not still my mind or stop the intrusive thoughts. It helps me notice and accept what is happening to me, within me, and around me. I worked with an architect, an old man with a lifelong transcendental meditation practice, for years. But I lost it. I had to find a system that actually worked for me. The Headspace book and app helps.

Asking For Help


I also ask for help. I’ve reached out to a lot of other founders and talked. They may not know it but they’ve made a huge difference for me. I hope you reach out to me if you need help, too.

Working as a Team


I’ve also had to learn to stop trying to do everything myself. I have a team of people who are better at their jobs than I am. I don’t ask them to be my confidantes, but they support me whether they know it or not. And I have advisors, mentors, and a professional coach who make it easier day by day.

Alternate Conclusion 1: You Make A Difference


It sounds hard. Why do I do it? I do it because of you. You are here for a purpose. You have impact. The world needs you and cannot replace you. You make a difference. But really, I do it for you because doing it for you is doing it for myself. I must be to the world what I want the world to be for me. I get back more than I give. My lows are lower, but my highs are higher too. Thank you. [I wanted to end with a note of inspiration and encouragement, gesturing towards each person’s irreplaceable role in life, but I changed this ending at the last moment.]

Alternate Conclusion 2: Why Do I Do It?


I believe that the product, company, and the team serve a greater good. It’s true that it’s hard, but I believe I must be what I want to see in the world. My low times are worse, but my highs are higher. [I chose this ending because I thought the note of encouragement, although important and true, was not consistent with the rest of the talk. The sentiment of the first alternative ending still holds, though.]

Video Of The Talk

Done! Now Read These:

On Focus

Your free will lies in the directing of your attention. Whatever you concentrate on will become central to your life.

The Goal

Teams are systems, too.

Personality Assessments

What kinds of personality assessments exist, and when are they useful?