Visualizing the seat you want

Posted on August 11, 2013. Filed under: startups, venture capital, wildcard |

Friday night I had dinner with close friends who were in town after a few months on the road. While we were waiting for dinner to be served, the subject of Wildcard came up. After explaining what we are working on (which is always fun and interesting, especially to a non-tech crowd), my friend Jess asked me what my goal for the company was. She said “Are you gonna try to sell it to Google or someone like you did last time?” She saw how cool that experience was for us…I guess it’s sort of natural to assume that we would want to do that again…

Instead, I explained that my goal was to become a Google, or Amazon, or something of that magnitude.  Like all good friends would, she accepted that goal as possible, without doubt or hesitation (thanks Jess). As we talked through what that might look like, I admitted that I was having a hard time visualizing a future where Wildcard was, in fact, a company with tens of thousands of employees and global impact/reach. I explained that it wasn’t hard for me to visualize our product on that scale of influence/import, but rather it was hard to visualize myself running a company like that.

For my entire career, I have always paid very close attention to the traits and characteristics of people in positions that I aspired to have. At General Catalyst Partners, I had 4 or 5 models of what General Partners at a top tier VC “looked like.” If I wanted to become one, I had some kind of picture in my head of what that was, and therefore I could see my path to attaining it, and also what I looked like in the seat. Sure enough, I became a General Partner at Lerer Ventures, and I think I behave sort of as I pictured I would even back then. When I was preparing to become an entrepreneur, I talked to thousands of early stage founders…again, built the model in my head of “what that looked like,” and then it became easier to see myself in the seat. Once you can see a picture of yourself in the seat…it’s not so hard to execute toward that reality. As Hyperpublic grew, I had models of my peers as well as CEO’s who were two, three, four years ahead of me…I saw our path to twenty people, and probably even 40 or 50, and I could visualize myself  in that reality.

With a goal like becoming the next Google or Amazon, I must admit I don’t have very many first hand accounts to look at…it’s hard to build the model of what “that seat” looks like. I spent a few months at GRPN post acquisition, and caught a couple glimpses of Andrew Mason in action…so I guess that’s a little input, but I’ve never really worked at a giant company, and have had very little interaction with those who run them. An email here and there, or time spent with former captains of these types of companies, for sure…but no real, first hand, “this is what the person looks like who started and is running this mega-company.” It’s a bit of a blind spot for me that I’m going to have to work on, as someone who gets places much faster when I can visualize them and then make them real.

I suppose there is something to growing into that seat organically…and I think all those who are in it, must have done so their own way…but organic matter grows faster when atop a scaffolding that provides structure. I’m not quite sure how I’m going to attain this scaffolding (good thing, we’ve got quite some time before it becomes necessary), but this is a bit of a strange feeling not having a visualization to run at of the seat I want. Maybe the first time in my life where I can’t clearly see exactly what I want to become. I guess that’s a sign that we’re shooting appropriately high.

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2 Responses to “Visualizing the seat you want”

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conversely, do you think an entrepreneur should be able to visualize folding a business before taking the risk to do something disruptive? (if that makes sense)

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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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