Today marks the one year anniversary of my running of the Seattle Marathon, a 26.2 Mile race through and around my home town.  The marathon was months of training, slowly building up endurance by running a little further each week, until a final 20 mile session two weeks before the actual race, and then a steady set of maintenance runs until the actual event. It was the first and last marathon I have ever, and will ever run. Towards the end, I was holding back tears of pain, and even after crossing the finish line, I had to consciously fight to not collapse to my knees and burst out crying. I lost four lbs. just from that one day of running.

News programs the days before the Marathon talked about the race, and the history of racing, and many of them ended in a similar fashion; some anchor would look sternly into the camera and state “Do not just decide to hop into this marathon and run it! Marathons require serious training! You cannot just do this on a whim!” Why anyone would decide to do a Marathon with zero training, is beyond me. While I was running 5k regularly at least once a week for most of the prior year, I started seriously training in August, and even then, with multiple hours of running logged each session, I often wondered what the hell I was doing. When people asked why I ran it, I told the truth: I wanted to run it while I still could. Before turning 40, before exercise would get seriously difficult, before my metabolism and ability to heal started the slow, inevitable decline of middle age, I wanted to run 26.2 miles so that I could say I did, and know what it was like.

In many ways, a startup is a marathon. There are plenty of milestones along the way, it takes a long concerted effort, there are definitely moments when it feels like exhaustion will drive one to tears, and one cannot just jump into it with no training.

But a startup is more difficult than a marathon, in that a marathon has a definite and obvious finish line. In a marathon, runners always know how much farther they have to go, and some simple pace calculations can tell them when they’ll get there. Not so much in a startup. It’s more like a Triathlon, but one where the distances are changed continuously during the race, and while you thought you would hop on a bike next, you actually have to pivot and switch to a unicycle (despite the fact that you don’t know how to ride a unicycle, just hop on, son!). Startups are difficult, they’re long term, and there’s no finish line at the first round of funding, or second or third, or potentially even the first product launch. Even at an IPO or an acquisition, they can still be in “startup phase”, proving their business model to the satisfaction of their shareholders, new owners, or the bottom line.

Jumping into a startup with no training is also highly hazardous. It’s easy to believe that one is doing the right things, just putting one foot in front of the other (how hard can that be?), but even YCombinator founder Paul Graham cautions about founders who are “playing house” and not actually well trained to run a startup. Only after eighteen years of software development and leadership did I feel even slightly qualified to jump into this new venture, and I would be lying if I said I don’t watch the milestones pass by and wonder how much longer I’ll be running.

So why do this? Why dive in to an incredibly challenging adventure that requires immense training, and even if we succeed, will leave us exhausted and potentially on the verge of tears? My great friend and mentor David Sobeski was discussing his search for a new executive role at a challenging company, and knowing that he’s already highly accomplished and well off, I asked him why he was looking for a new challenge. “What do you hope to get out of this that you don’t already have?” I asked. He told me that there’s always a larger goal, a newer and more difficult opportunity, that he’s always looking for what’s next, and even though he’s been part of eight-figure acquisitions, he’s always asking himself what the next thing is. Is it a Billion Dollar company? Is it being the CEO of the undisputed leader in the marketplace?  Is it demonstrating peerless Product Leadership abilities? There’s always something bigger.

I had to nod my head, because while from time to time I certainly feel that I have “enough”, it is always the next great challenge that drives me. I could be content with the current state of gaming and entertainment, but I ask myself, what’s next? How can I lead that? I could have continued to work for my comfortable Amazon compensation, but I knew I would never really know what it was to be a millionaire if I stuck with that path. (Not that money is my primary motivator, but it certainly unlocks opportunities.) At Amazon, I would battle bureaucracy and paperwork and endless politicking just to convince the right set of people to let me do what I already knew was the right thing to do, instead of just going out and making a product that plenty of people have already told me they’re exited about. I could have run an endless series of 5k races that I knew were tiring but possible, but instead I challenged myself for the big race, tears and all, so that I could say that I did it and knew what it was like.

A startup is like a marathon, but it’s far more difficult and far more challenging. I’m running it now, and I’m thankful for the training I’ve had, eighteen years of work experience, 3.5 years of college experience, and a youth spent enjoying and creating entertainment before that. I’m running it because I want to know what it’s like, because I want to say that I did, and because this is a race that I genuinely believe I can win, and when SyncBuildRun wins, all our customers win with us. What else could be a better prize?

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