Video Of The Week: The Jack Dorsey Interview

A bit over a week ago, I was asked to interview Jack Dorsey at the NYU Entrepreneur Festival. I posted that news to AVC and all of you helped me compose the set of questions I used for the interview.

The livestream and archive was/is hosted on an NYU student built service, which is great. That said, the stream has a few hiccups and starts a few minutes in. It's about 50mins long.

#Web/Tech

Comments (Archived):

  1. James Fuller

    Who is Jack talking about at the beginning of the video? The beginning of the story is cut off.

    1. fredwilson

      himself. he is talking about how he got into programming

      1. James Fuller

        I mean the person who was offering the $1000 bounty for bugs in his code, and wrote his one C functions because he didn’t trust the C standard library. The way he’s talking, it doesn’t seem to be in reference to himself.

        1. fredwilson

          you are right. it was the creator of a mail program. i forget who.

      2. supine

        But the mention of code “like literature” and the $1000 bug bounty are references to djb, or? http://cr.yp.to/qmail/guara

  2. Dale Allyn

    Weird. No embedded video visible for me. I’m presently in Thailand, so maybe it was eaten by sharks while attempting to cross the Pacific.Is there a direct link?

    1. Luis Correa d'Almeida

      Can’t see the video from London either.

      1. Dale Allyn

        Perhaps an issue with the NYU servers regarding IP addresses outside the U.S. I suppose we’ll learn as other A VC ‘ers chime in.

        1. Tom Labus

          sharks very hungry in NJ

          1. Dale Allyn

            I’ve heard that about NJ sharks.

    2. Dale Allyn

      Digging a bit deeper into the embeded source, it looks like the stream.circles.io server is down/overwhelmed. I attempted to visit the src url and timed-out. Same for visiting the root domain. Looks like AVC might be bringing a bit more traffic than provisioned for.

      1. Antonio Pelle Pellegrino

        i was quickly updating the proxy didn’t realize that this was being posted today .. im participating in a hackathon and had to make a quick change sorry.

        1. Dale Allyn

          No worries. It worked out. Thanks for letting us know.

    3. fredwilson

      yeshttp://stream.circles.io/em…

      1. Dale Allyn

        Thanks, Fred. That’s the path I tried (dredging it from your source code), but alas, it couldn’t deliver. I’ll keep trying. I suspect it’s just a load issue.

        1. Cam MacRae

          Still down as far as I can tell. Oh well, at least I’ll get some extra work done.

          1. Dale Allyn

            Sorry to hear that, Cam. The direct link finally worked for me, and now the embedded iframe is showing up for me as well.

  3. Geoff Judge

    I’m in NY and can’t see a link to the video on the iPad! So not an international issue. Will look on a pc later

    1. fredwilson

      here is the linkhttp://stream.circles.io/em…

  4. Geoff Judge

    Link is there now thanks for fixing

  5. William Mougayar

    It was a great interview and the twitter stream was going nuts during.

  6. John Revay

    I enjoyed fred’s candor about passing Square…USV (Fred Wilson) passing on square. Reminds me of the Bessemer link on their portfolio page. http://www.bvp.com/portfoli

  7. Dale Allyn

    Great interview. Previously I didn’t have the impression that Jack possessed the humility he exhibited here. Based on this example I was quite wrong. (Hint: a trait I value and respect above most others.)I loved the exchange near the end where Jack explains that his “proudest moment” was not represented by a photo with a politician, but one in which his company’s service is being used in a way that fulfills his dream and vision for his entrepreneurial efforts.

    1. fredwilson

      that’s Jack in a nutshell

      1. Dale Allyn

        I’m happy to hear this, Fred.

    2. John Revay

      Hey Dale,I enjoyed watching the video…..Jack seemed like a very interesting guy, very intelligent as well.I was taken back when he said use to have a nose ring and dreadlocks – I have always pictured him – fairly straight laced.

      1. LE

        “when he said use to have a nose ring and dreadlocks”I think it may come as a surprise to some of the younger entrepreneurs out there how unusual (and somewhat distonic) the behavior and mannerisms of the current crop of entrepreneurs are to the older generation. I’m not making a judgement as much as simply stating facts based on my view and observation of business people since I was very young. To be taken seriously you dressed and acted a certain way. You didn’t put a cat on your head and you didn’t post around pictures doing yoga in your underwear. You would never show up in a hoodie when courting investors. That doesn’t mean you have to wear a 3 piece suit and pocket square either btw but there are limits to what type of dress is expected in old school business depending on who the customer or the situation. (That said I landed my first big deal dressed casually in dungarees against guys in suits.)Forgetting even how they dressed, business people (I’m not talking people in the entertainment business, people in creative businesses or even academics obviously) were almost always serious and generally strait laced. You wouldn’t act goofy any more then you would expect to see goofy immature behavior from your Physician, the guy who is piloting the plane you are flying, a policeman with a weapon in his hand, or the attorney defending you in court.Things have changed and it is different now no doubt about that.

      2. Dale Allyn

        I wasn’t absolutely sure if that was a joke or serious remark, John. I’d not seen him pictured that way – only pretty clean-cut. Interesting history.

        1. fredwilson

          That’s how he was when i first met Jack

          1. Dale Allyn

            It’s can be fun to look back through the stages of metamorphosis of each other… and ourselves.

  8. Renu

    I also can’t see any video or link here. Really want to watch this interview. I am from India.

    1. Donna Brewington White

      Fred shared the link in another comment below. Seems like the server is overloaded at the moment.

  9. Renu

    Also given link in the previous comments is also not opening.

  10. Marius

    New York aggression. I love it. Great interview Mr Fred. Thank you for sharing.

  11. Antonio Pelle Pellegrino

    If anyone has a problem with the video you can message or email me at [email protected]s.io ill be more then happy to help and make sure it is as smooth as possible.

    1. ShanaC

      thank you

  12. takingpitches

    New York aggressiveness (in contrast to SV passive aggressiveness). No better endorsement of Fred or NYC tech!And go Charlie Chaplin!

    1. osbournreinap4ef

      New York aggressiveness (in contrast to SV passive aggressiveness). No better endorsement of Fred or NYC tech!

  13. Aaron Klein

    I almost never have time to watch videos like this, but I had to watch this one. One of my favorite entrepreneurs and one of my favorite investors.The commitment you both have to connecting the world – through information, through commerce, through networks of all kinds – is inspiring.

    1. LE

      Your opinion and the others quoting “New York aggressiveness” have peaked my interest now.

    2. awaldstein

      You and I both.I interested in people who talk from the learnings of success that impact the broader world I live in.There are thinkers and pundits. There are lots of people who work hard and smart and just don’t succeed.Then there’s a few who bend luck and gut instinct to just do it and can talk about it. They get my time all the time.You can learn by not succeeding. Everyone though is interested in emulating success.

      1. Aaron Klein

        And Jack isn’t even quite there yet, though you can argue that even a failure at this point would be a relative success. 🙂

        1. awaldstein

          You touch on something important here.With secondary markets for private stock and huge valuations, companies like Twitter and others, are perceived aspirationally like we look at the stock market.Who really knows if they are real or long lasting businesses or not.Engagement is just so really hard to build (Charlie Crystal reminded me of this recently), so hard that it creates its own value scale.

          1. Aaron Klein

            Indeed. I guess I judge the milestone of “success” as a profitable exit for all the early investors who helped you build the company.I’d argue Evernote has already reached that milestone, for example. They’ve used a secondary offering to take out all of the early investors and let founders sell the stock they want to sell.An IPO at this point is just changing one set of investors out for another.

  14. awaldstein

    I’m a big fan of Square. Just like tech that changes life at a street level.Are there any figures public that provide a sense of how wide spread they are used and the health of the company?Company’s feel successful cause they are part of your thinking and your want for a future. Hard to know though when they are private.

  15. dsjoerg

    Anyone have a transcript?

  16. Patrick Mulder

    very inspiring dialogue.I like the discussions about creating deeper meaning and jack’s passion for mobile applications.

  17. mstearne

    One of the things pointed out in this interview and many other tech interviews is the fact that Jack Dorsey is a college dropout along his co-founders at twitter, the founders of tumblr, facebook, Microsoft, Apple and famously many more.When I talk to younger people that don’t want to go to college or are dropping out of college they always will bring up people like Bill Gates and maybe one day Jack Dorsey.The question I would like to see asked to these business owners is how many college dropouts or high school drop outs do they hire within and to run their their businesses. Do they make an effort to recruit college dropouts like themselves or those who’ve followed the advice of Peter Thiel?

    1. Joel Valdez

      Or even worse… Someone who can report on the number of dropouts that don’t make it like they did. I don’t think dropping out is mandatory to get their success. In fact, I think that college education is important. Actually, Bill has said it multiple times, and he even went back and finished his degree.

  18. Michael Molino

    I like Jack’s view on entrepreneurship – that it’s more of an attitude and that you don’t need to start a company to embody the entrepreneur spirit. I work at a pretty big company and the people that I see rise the fastest and become successful are those that have an entrepreneurial mindset inside the organization. More companies should train employees to think like a founder.

  19. Antonio Pelle Pellegrino

    also if your interested any other talks or background info on the NYU entrepreneurs festival go to http://stream.circles.io/ once again sorry if anyone had video issues that should all be resolved…awesome job fred your had a great conversation with jack even better with the Bieber and Obama photos on the projector

  20. Kirsten Lambertsen

    That was hugely interesting. These interviews often are better when it’s two friends talking. The interviewee is so much more at ease.I had no idea he used to have a nose ring and dreadlocks (blue ones)! He just went up a few notches in my book 😉 Seems like a really soulful person.

  21. Antonio Pelle Pellegrino

    I was able to get on my server more of the beginning of the conversation http://stream.circles.io/#e…great insite on coding education from both fred and jackill look to update the video for you with both in one

  22. Margaret E. Federico

    Peyton. I see what you mean… Joanne`s st0ry is nice, Ijust bought a top of the range audi after having made $4616 this past 4 weeksand-also, $10k last-month. it’s realy my favourite-job I’ve ever done. Istarted this 3 months ago and practically straight away started to earn minimum$84, per/hr. I work through this website,, jump15.comCHECK IT OUT