The Wave not Ridden and Living Fearless

Posted on: August 7, 2013
Posted in Career


You will experience moments of debilitating fear in startups and in life. Fear that hits unexpectedly and with varying intensity. A competitor launches, a deal falls through, or you know what? it’s just been fucking cloudy for the last week, and you don’t feel right. Whatever it is. It will happen.

In tech startups when things feel bad they feel really bad. There’s a manic nature to all of the cycles in tech—no you’re not just “doing okay”, things are either bad or great.  A lot of our own internal extremes are amplified by the way investors and writers help perpetuate stories—information has an unparalleled velocity in the tech world.

This has upsides and downsides.

The upside of technology, which I absolutely crave and love, is that early stage tech, particularly internet-driven,  is a meritocracy. This meritocracy and merit-based achievement rewards outliers whereas conventional industry tends to suppress or ask people to climb a ladder. It rewards people who focus on the average.

But one visible downside of this is that people sometimes measure their current status on what the group thinks right now.

Paul Graham recently wrote a seminal post about how to get startup ideas. One passage resonated with me about how technology ideas develop:

When startups consume incumbents, they usually start by serving some small but important market that the big players ignore. It’s particularly good if there’s an admixture of disdain in the big players’ attitude, because that often misleads them. For example, after Steve Wozniak built the computer that became the Apple I, he felt obliged to give his then-employer Hewlett-Packard the option to produce it. Fortunately for him, they turned it down, and one of the reasons they did was that it used a TV for a monitor, which seemed intolerably déclassé to a high-end hardware company like HP was at the time.

You could be developing the next Apple I that people will brush off—somewhere it is happening, right now. And the funny thing is that, because of the velocity of ideas in tech, it will go from ignored to ridiculed to copied what feels like overnight. Unknown to famous faster than you thought possible.

Don’t be scared of these waves that others are chasing. Because while they are hanging off the crest and tweeting about it, another set will come in from the other direction and wash the temporal legacy of those waves away…

You are best served to ignore the ripples around you and focus on what you are passionate about. Sometimes people will believe in you and say good things, and other times people will look at you as if you can’t see the sky falling. And this changes fast.

I remember this feeling distinctly. When I left business school in 2009 I had such a tarnished view of bigger institutions and the financial crisis that I was sort of numb from a lot of it. So I went off and did interesting things, met people, built stuff, and dreamt about the future. I acted like I had nothing to lose. Because actually, at the time, I didn’t.

I can still vividly recall people looking at me as if I was lost. A year before I had a job offer from Goldman Sachs, and now what was I doing with my life?

Today I  hold on to how innocent it all felt then, of feeling fearless with nothing to lose, digging deep emotionally and trusting my instincts. Of turning down the well-reckoned path for something different, foreign, yet-to-be-validated and scary.

That became a time of unparalleled growth. If I had taken the comfortable or accepted path, I could have been stuck inside the wrong industry looking out. Instead, a year later, I was meeting incredible people, helping companies grow and building things I loved, with the added upside of  TechCrunch, Techstars and Groupme on my paper resume.

This is a fact: If you live fearless and attack life, you can go anywhere. Fear debilitates you from the intrinsic need you must hold on to in startups to take risks. And this carries over to life.  You are powerful beyond measure, and playing small does not serve you or the world.

When friends, industry outsiders, VCs or anyone else look at you differently, or better yet ignore you—whether you are working on new things or have yet to figure it all out—you are probably on to something.  And throughout that process, live fearless. The truth is, they don’t know where the next waves are going to come from, either.

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