Making Ambition Useful

This notion of a billion dollar company is steeped in silicon valley lore. It’s a maxim, a battle cry and a wish rolled into one and tucked under the pillow of every founder each night in hopes the startup fairy will deliver the goods. Yet, there’s a funny thing about this number. Quite often, the companies that state it as an early goal fail while those that end up being the wildest of successes, start out with a very different objective. What's in a Number?

So, Bryce posted this thing this week about entrepreneurs wanting to build billion dollar companies, and for a variety of reasons, it got me thinking. Ambition is a funny thing in our culture. We fetishize it and fall in love with the stories of young entrepreneurs taking on the world and building huge companies. But I've always found ambition as a kind of deadening emotion.

I think ambition feeds into the image of an entrepreneur as this inhuman entity, mechanistic and determined and unfeeling. I think this is why we all pass along the story of Jack Dorsey's two full-time jobs - it came up the other day and Jack was described as, "excessively productive." 

But from Monday to Friday, he clocks in eight hours at Twitter and then walks two blocks over to put in another eight hours at Square.  cnn

This sounds to me, however, as a kind of horrible way to live. I have nothing against productivity and hard work, or ambition as part of a healthy diet of emotions, but all alone, this portrait just feels cold and unfulfilling. I do believe that many successful entrepreneurs work hard and put so much of themselves into their companies, but for many of them, it's not solely driven by ambition or ego.

It reminded me of a particular email that I can probably safely say has been the most important email in my life - I received it when I was a freshman in high school and ski racing. I'll share some parts, change names, and go from there.

What I mean is what I have said before, enjoy skiing for what it is, not what you want it to be... he eats, sleeps and breaths racing, not skiing. [redacted] on the other hand eats, sleeps, and breaths skiing, that is why he loves racing. It is just another part of the rush he gets being on skis. ... Enjoy the ups and downs, and grow with the sport, do not fight it.

It was an important email because it was the first time I realized I could take the huge amounts of energy and excitement that I had and direct it in a way that was productive and useful. I think that's not something we emphasize or distinguish much as a culture - the difference between passion and ambition. Being passionate about your own success is just not a thing. Actually, it may be self-centeredness, but whatever. In the case of startups, the thing I think is pretty consistent with some of the more successful entrepreneurs is passion for a specific thing - not generally a product, but a kind of sensation. For Dennis Crowley it had to do with location, for Mark Zuckerberg it was connecting people, for Larry and Sergey it was organizing the world's information. Starting a company is just a vehicle for that passion. 

I think a lot of this has to do with forming and building a connection. There isn't really a way to learn about your own success, or build a connection to your own success - that's just gibberish. So, if that's your motivator, and that's what you really spend your time thinking about, it's hard to really benefit from that obsession, mentally or emotionally. But when you're passionate about something external, it means you can experience that thing and learn more every day. Even when, by all external measures, you may be failing, you can still be learning and growing. 

I love the profile of Jack Dorsey that Vanity Fair did for this reason, because I think it really brings this idea to life. Jack may be ambitious, but he is also guided by and obsessed with a very specific set of phenomena and sensation, and he chases that relentlessly whatever he does. 

Little Jack Dorsey was obsessed with maps of cities. He papered his walls with maps from magazines, transit maps, maps from gas stations. His parents had resisted joining the emigration to the suburbs, and their shy, skinny son supported them by becoming a passionate proponent of city life. He was mesmerized by locomotives, police cars, and taxis. He would drag his younger brother Danny to nearby rail yards, where they waited just to videotape a passing train. Vanity Fair

The funny thing is, while the blind pursuit of ego can be dehumanizing, the pursuit of something else can make someone feel incredibly human and alive. These are the kinds of people who are incredibly inspiring, whose love for what they do is so palpable that when you talk to them about it, that passion drips off every word they speak like an ice cream cone that just cannot be consumed fast enough in the heat.