@SimonCocking a version of this appeared at.

We’re delighted to have interviewed Charlie Cheever,  @ccheever early Facebook hire, cofounder of Quora , serial investor, and, for a while, serious Ultimate Frisbee player. (First meeting Mark Zuckerberg briefly on the Ultimate pitch, when Mark tried out for the Harvard Ultimate team Charlie was playing for.)

You invested in a range of companies, what are you most involved in these days? Are you more interested in being involved at a investor / big picture level now? Or do you miss being at the micro level?

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I’ve been lucky to be involved with a number of great companies. Zenefits is a rocket ship; Cover was acquired by Twitter; ZenPayroll is doing really well. It’s always fun to be a part of something successful, especially if you can help.

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But I think I still have a few more years in me where I can do something directly.

What are you excited about now?

In the short term and medium term, mobile devices. So many people are going to have them, more than have ever had computers. I think this is the story of the next 10 years, not just the last 5, and that’s more important than bitcoin and virtual reality and drones (though those things are also cool).

In the longer term, I think having a direct connection between brains and computers will change a lot of things in very big ways, but I don’t know how long it will take to get there or what it will be like.


You don’t tweet much, do you have a social media of choice? Or a time sink to carefully manage ?

I’m never sure what my followers want to hear about. JavaScript? Startup advice? I don’t want to make a tweet and get no faves. I do a lot more @-replying.

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The Irish tech scene is booming, what do you know of it? 

I’ve heard a lot about the Silicon Bog and I know a lot of companies that are expanding internationally are opening offices in Ireland. My friend Patrick Collison is from Limerick and started Stripe which is doing great.

You were here at the Web Summit in 2011, will we see you over here again at it sometime?

I actually haven’t been to Ireland yet unfortunately. I would like to go because I’m 1/2 Irish by heritage and have some family there.

Do you have an interest in having more activity in Europe, or does the US side of your interests take up all your time? Philanthropy, is an active interest for many tech investors, what’s your philosophy on it ? How much should you leave for the kids?

The way I look at it, you just want to make the world into the place you want it to be. Sometimes putting time and money into private companies that are trying to be profitable and self sustaining is the best way to do that, but for other things, non-profit enterprises are the best avenues for that. For example, my mom’s job is running a non-profit that takes care of the parks in Pittsburgh where I’m from; the city wouldn’t be nearly as nice without their work, and I don’t think a private enterprise or the city government could do as good of a job on their own.

Sport, we’re having an ongoing debate about Ultimate Frisbee & tech innovators and investors, you played didn’t you? 

I played on the college team at Harvard and then played on a club team in Seattle somewhat seriously for a few years after I graduated. I was pretty good but not great. I’m playing in the SF winter league right now, but I’m old and slow these days.

There does seem to be something about the sport that appeals to tech people. A few of the people I’ve worked with, I met through playing ultimate. I’m not sure why this is, but there does seem to be something to it.

For more see his comments in this Quora question

I was a few years ahead of Mark at Harvard and was a Teaching Fellow for CS51 (the second course in computer science there,) and so they had heard of me, and I had met Mark briefly when he tried out for ultimate frisbee team.

Do you play any other sport, any relevance to your entrepreneurial activities? 

I play in a flag (American) football rec league, and I ran a few marathons last year, and I like to ski. In general, I love sports both as a fan and playing them. I think doing something aerobic helps my brain focus, and I always feel better about everything when I’m in good shape.

What’s you definition of success for the projects you are now involved in?

For me, I think the best feeling is when you notice someone in the seat next to you on a train using something you worked on, or overhear a story about how great something you were a part of is.

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Harvard is a beautiful campus (even in winter with snow in the courtyards, such an old campus), did it help in terms of meeting like minds, and inspiring each other to go on and do great things?

Funny question. I’ve never really thought about it before. I think the #1 thing about Harvard is you just meet ambitious people there. But there is something about the history — names of Presidents and captains of industry on buildings and plaques, etc. — that constantly surrounds you that makes you feel like you have a responsibility to at least try to do something important or meaningful once you leave. A lot of people have that drive within themselves anyway though.


from MIT, but such a great image!


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