My journey out of the startup world

After more than a decade working with tech companies, I no longer believe in the startup dream. 21 Oct 2018


For those in the tech world, there’s a constant stream of reinforcement about which values you should embrace if you want to build a successful company. People hang on the tweets of VCs and the blog posts of entrepreneurs, looking for the secrets to success. For a long time winning at this game was the most important thing in my life. I moved from the US to Sweden to further my career without giving much thought to the huge challenges it would introduce to my life.

As my career progressed and I took more senior roles, I came to realize that my values were actually quite different from those of the people I was encountering at work, especially within the financial sector. I saw that I often felt the need to adapt my personality to fit the environment I was in.

Then, three years ago, I experienced a serious health scare that hit me in the midst of a major crisis at my then job. I was told by doctors that my illness was almost certainly caused by the extreme stress I was under. I believe people can learn to adapt themselves to many situations that aren’t a natural fit for their personality. But staying in a situation like that for too long eventually forces you to pay a price. I paid the price when I arrived in the emergency room that day three years ago.


In private conversations with friends and colleagues I occasionally hear stories of disillusionment with the startup scene similar to my own. At this point, it’s nearly impossible for me to take seriously the culture and beliefs that dominate this scene. From the fundraising process (bullshitters bullshitting each other) to the absurdities of the hiring process (don’t get me started on ‘cultural fit’) the whole thing is ripe for mockery.

It’s useful to remember that every employment arrangement is built on a foundation of coercion. That may strike some as needlessly conspiratorial or downright Marxist, but flexible hours, unlimited vacation time, beers in the fridge, and company retreats do not erase the truth of it. Coercion has become subtle (‘We want you to want to do a good job.’) rather than overt (‘Back to work!’).

I don’t think most people want to hear these things. It feels cruel to discuss the inspiration modern management takes from slave practices with people who need a job to pay the rent and buy food. As a friend once said, ‘An ethically uncompromising job is a privilege, not a virtue.’ But I refuse to believe that the current situation is the best we can hope for.


This spring I was granted Swedish citizenship and no longer have to worry about the intricate employment rules that apply to work permit holders. I’m now focused 100% on my own projects.

Working by yourself on a laptop at a coffee shop isn’t the right choice for everyone. I suspect that where you fall on the ‘freedom vs security’ spectrum will determine your happiness with this path. But it’s a natural fit for me. When I’m working on an idea I’m excited about, there’s nothing better than moving between writing code, designing interfaces, sharpening marketing messages and talking to users.

‘Lifestyle Business’ has become a term of derision among a certain segment of people who believe the ‘go big or go home’ model of Silicon Valley is the only real way to build a business. The funny thing is that I’ve been intimately acquainted with a few stagnant startups that could have been excellent lifestyle businesses if they hadn’t already raised money from VCs. Once you take someone else’s money you can’t think about keeping it simple and doing it for the pleasure of building something. It turns into a game of juicing the numbers to justify further investment to eventually secure the big payday. It’s not a game I’m interested in playing anymore.

See my collection of resources about meaningful work.