Archive for December, 2013

The Money Ain’t a Thing

Posted on December 13, 2013. Filed under: Uncategorized |

I’ve been thinking a lot about career decision making lately…we have been assembling a small army at Wildcard over the past few months and that means talking to a lot of people and listening to how they are thinking about their next moves…it is deeply fascinating to me how different the frameworks can be from one person to the next. For me, career decisions have always been easy. I have taken a very long term view that money is just money…it’s important as a reflection of how much my employer or investor or whoever values my effort and contribution…but I have always optimized for people and opportunity first, and put faith in the idea that with these two dimensions way out in front…some time or another…money would follow. Chris Dixon was an investor in my very first startup and I remember him talking about differences between east and west coast engineers in terms of west coast being more “equity minded” and that it was a weakness in the startup ecosystem that New Yorkers didn’t think like this (not having grown up around models of people who made it big through options that hit when companies went public, etc…). I think that there is an argument to being equity minded about a company you believe in, and forgoing cash for the upside of what you help to create…but I think even this calculation is not how to make a career decision…I posit that thinking even longer term is the true optimization of wealth. Yes, the half a point you might get in an incredible startup could, in fact, be worth tens of millions of dollars…but I find it much more likely that the experience you get and the people you learn from if you pick the right startup, is what earns you the knowledge to own 50 points in the thing you create after that startup…and it’s in those points, combined with the deep investment you made in your own knowledge and relationships, that positions you to truly make bananas money…But even this is not the calculation that I find interesting…because a goal of making bananas money is so fucking empty…bananas money is not a goal, it is a side effect of some truly great and ideally positively impactful accomplishment. It is the side effect of great work…work that fills your heart and makes you smile when you look back at it. Work that you are proud of…that exemplifies the mastery of a craft, or the relentlessness of your drive, or the expansiveness of your creativity…it is the work itself…and the joy that comes from doing it, not in isolation, but rather in concert with others who share your pride and some dimension of excellence themselves, that feeds you…I know it is nice to buy a house, and I know it is nice to go on vacation, and I know it is nice to buy nice clothes, and I know it is nice to make a salary you can tell your parents about that makes them proud, but these things are not how you make career decisions…career decisions are about finding the place you can be the deepest expression of your excellence, and finding the people and the work that can help you realize that…and it is in that deepest expression where you actually find the optimization of wealth as well. I watch young, deeply talented people walk through my door, feel the potential of Wildcard and the people in this room as that context where they will reach their deepest expression, and then walk out the door to work at a large company that pays them an extra $50,000 a year…and I wish I had a way to tell them, from a non-biased perspective, that they are doing it wrong…but the nature of our relationship impedes my credibility in sharing this thought…so I write, so you can read it, and apply it not Wildcard, but to wherever fills your heart…take that your gut…fuck the dollars and cents…make sure you can live and make sure you can pay the bills…but life is too fucking short to live bird in the hand when the bush is where you were born to live…

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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:

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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