Entrepreneur, Innovation, Interview, Technology, Ultimate & Innovation, Ultimate Frisbee

Charlie Cheever, cofounder of Quora, serial investor, entrepreneur & ultimate player


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 ? 

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!


Entrepreneur, Innovation, Interview, Ultimate & Innovation, Web Summit 2014

451 Degrees, a Californian take on Dublin Web Summit, (and zebra donkeys)




Had great fun meeting and subsequently interviewing Patrick Giblin and Jake Jacoby from 451 degrees for this article, oh and their CTO is a keen Ultimate player too, just saying…


How did the Summit go for you?

The Summit was a great experience.  It was difficult for us to measure expectations going in because it was such a young event but the growth that it has shown and the few people I knew that had gone were what tipped us to go.  Its reputation precedes it.  The quality of former attendees is very strong making it an easier leap.  We had the chance to establish a global footprint with those that attended as well as find some interesting strategic partners from San Francisco.  We learned a lot as well

Did it match your expectations?

It exceeded expectations.  The event has really unique and good nuances.  It is unlike any conference I have attended and haven’t we all attended too many of these things…it does a great job with keeping it fresh and giving the companies a fair and equal playing field.  It allows companies that are chosen an opportunity to experience the conference from the other side of the floor.  That is brilliant!  We spent days walking around seeing and meeting other companies of interest and could do so because our booth presence was just one day.  The presentation of every company in the simple form and the stand given is great.  A quick look of the overview of what they do and we knew, “Move along” or “Hmm, let’s chat a bit”.

Not much room for wasted conversations and being a company trying to generate interest with flair.  It just worked perfectly.  Then you add in the Night Summit events and the value got even stronger. Creating locations for people to meet without the pretentious “invites” to THE only cool party is great.  There were things for everyone to do.  A chance to meet many different people.

It seemed as if every door was open when it should be and for it should be.  I am sure we were not invited to some rooms that we would have wanted to be in but we were so busy and gaining relationships that it did not matter.

If you were to do it differently what would you have done?

If I was to do something differently I would create better communication with the companies coming in and while at the event.  A knowledgeable point person at each hotel would be useful. Much of this was a mystery to us and we did not know what to expect.  I heard this from many of my fellow START companies as well as Alpha and Beta companies too.  We all felt unprepared with expectations.  Perhaps that is with intent but it was a bit disheveling.  I also think that the understanding of what dinners we were to go to could have been better scripted.  We never were really sure on how to RSVP to “invited” events as a START company?

There was not a point person for Q&A on these things for the companies there.  Lots of the volunteers were just unaware and said “I was just hired yesterday, I really don’t know?   I think in today’s day and age having a brief video tutorial of “What to Expect?” and “This is a Day…” would be REALLY useful to the companies coming 1st time and most are coming for the 1st time.  I also think more Q&A speakers and having some of the Alpha, Beta and Start companies take the stage would have been great.  We need to see and hear from each other more than we need to hear another speech from an established ‘Giant’ trying to promote their product offering today?


What did people think of your product?

The reception to our product seemed very strong and there has already been follow up to confirm this.  Our SaaS technology is the next generation of Big Data and Ad Technology.  Two subjects that are very hot right now.  We had a lot of visitors and interested parties that we approached.  The tide is rising towards our product. So excitement was there.

People were able to quickly grab the value our product creates.  As Comments become more relevant and definitive to Content everywhere we show more value to the owners of Content. Because our SaaS interprets all Comments using Artificial Intelligence and Machined Learning to create relevant SEO and Ad Delivery it is a natural fit for people.  It was easy for us to tell people that we listen to and make sense of all that “noise” around your content and then make you money from it…people like that message and we have proof that it works so they follow up.

Did you get any useful feedback from people here?

We did.  It is always important to listen closely to the objections and the doubts around your value.  We were quickly reminded that we have a gap in the adoption by the leading Ad Delivery Networks.  At this time, they are not all interested in working with us in a ‘dynamic’ environment.  That can create some friction within our adoption.

We have to find ways through those objections and ways to entice these Ad Delivery Networks to see the gains we can reach for them. So when there was feedback that we cannot be of full use because we do not work yet with their ADN we see a need to cure the problem.

Will you be changing or pivoting your project based on what happened at the summit?

We will not be pivoting or changing the product just building on it and focusing on expanding the API’s that will allow it to create good use cases for all parties.

How did you find Dublin?

Dublin was GREAT!  The people are fine people, kind and welcoming.  Helpful as well.  The city is SO supportive of all of these technology companies and the desire to solve our issues.   Questions about “Why do business in Dublin?” were handled effectively and efficiently.

This is not just about tax breaks and the “Double Irish” it is about support and COMMUNITY.  This city is committed to doing the right things to get things moving forward.  They work together.  City Officials, Banks, Building Owners and People.  They all are giving the same message.  In short, “Come here and stay a while, if not forever, because we like you and want you…we are here to help”  and they all did.  The Summit also gives you a chance to see some of the social side of Dublin.  That was great too.  Nice to see some of the food and spirits that Dublin is known for.  Seeing the history of Trinity College was fantastic!  Guinness Brewery and its meaning and history was great as well.  Just a wonderful city opening themselves up for the good of all of us.

Which had more use for you the day summit or the night one? Why?

Day Summit.  Just easier to get to conversations quickly.  Easy to identify the synergy with whom you were approaching.  Get to the business and move along.  The Night Summit is a great addition and gives social a chance to build relationship that can lead to business for sure.  The let down was in the hype around the Venture Capitalists, Investors and Market leaders being a part of the Night Summit but in reality they were hard to find if there at all.  Most of the Night Summit was meeting of other companies.  It was useful but less precise.  They both are great ideas and Night Summit is a very cool part of what makes this conference unique. But there are no Donkeys painted like Zebras?  Only in TJ… (Tijuana).


Over here we only have zebra mussels, donkeys, or zebras, no donkey zebra fusion yet!