Going Uncomfortably Fast

Posted on December 5, 2013. Filed under: startups, venture capital, wildcard |

I didn’t learn a lot of things in my time at GRPN…I was only there 4 months after all…but there are a few tidbits that I picked up that have stuck with me as we forge forward at Wildcard. I remember Andrew Mason visiting the Palo Alto office on more than one occasion…he’d come and address the engineering team, talk about what’s going on in the company…and frankly run damage control as the stock continued to get abused in the public markets. He was actually a wonderful orator and his cadence with the team I found inspiring and emotionally intelligent. Now some of his words may have been lip service, and some may have been genuine, but I remember this one phrase which I may slightly butcher…but it will be with me forever. In describing why things were “breaking” at GRPN he would repeat over and over “We intentionally made the decision in the early days of building that we wanted to go uncomfortably fast…that we liked the feeling of the wheels shaking on their axels as we grow…and it is this commitment to going uncomfortably fast that allowed us to defeat an entire market of ‘me toos’ and get to where we are now.” Now his words were through a lens of the costs and required repairs that come with going uncomfortably fast…but the idea that they deliberately sought to exist in this forward moving state of instability I found fascinating…at my first two startups I had always tried to preserve stability…

As I reflect on his words, they echo a hand that Kenny has always put gently and sometimes more forceabley on my back…pushing me forward…faster than my stomach would intuitively dictate…A common phrase that I hear from Kenny when we talk about Wildcard is “You need to go faster…step on it…now.” I think to myself…we are going fast…faster than I have ever gone before…and yet still…it is not fast enough…we need to be going “uncomfortably fast…” I’ve said before that I think the optimal burn for a startup is the amount that causes a CEO to feel slightly uncomfortable with what he or she is spending…and I think this sentiment applies not only to what you spend, but across all operational metrics and decision making…there is a very fine line between irresponsibility and the optimal angle at which you lean forward in your decisions…and I am forcing myself to live on it…every single day…the crazy part is, even though I feel like I am approaching that line…in reality, I am probably still not even close to it…there is something to pointing your skis straight down the mountain that is actually safer and more optimal than sliding down the double black sideways…but it requires this leap and confidence that you can only gain through a combination of experience and gentle pushes from those that have more than you.

I am grateful to Andrew and Kenny and a few other close friends who gently and not so gently continue to nudge our skis into that optimally uncomfortable position…it’s getting us to places that I’ve never been before 🙂

p.s. if you want to come skiing with us…this is where the lift tickets are sold: http://www.trywildcard.com/#jobs

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4 Responses to “Going Uncomfortably Fast”

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Going uncomfortably fast also makes the ride more interesting… I like Mason’s wheels/axles parallel. When we started, our CEO used to always similarly say, “Speed is our only IP.” The sense of urgency and operating uncomfortably fast can produce some amazing output. Sounds like you’re getting ready for Sochi, and it must be a blast.

Great post, I think one of the things you need to go “uncomfortably fast” is exactly what you mentioned, close friends who put their hands on your back and give you the nudge. Hopefully we can give the same nudge forward to our own friends while being pushed by them at the same time.

[…] Uncomfortably Fast (link) – I liked this one because I sometimes think we go uncomfortably fast in our company, but if that […]

[…] Jordan Cooper did a great job capturing the essence of this in his article by the same name. It’s about pushing […]


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    I’m a NYC based investor and entrepreneur. I think there is one metric that can be used to measure the value of a human life and that’s impact. How did you change things? How many people did you touch? How different is the world because you lived in it and how positive was the change that you affected? (p.s. i don’t use spell check…deal with it) You can email me at Jordan.Cooper@gmail.com

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