It's going to be a fun friday because I get to interview Jack Dorsey late this afternoon at the NYU Entrepreneurs Festival. The festival is sold out but the interview will be livestreamed here. We plan to go on at 5:30pm eastern.

I love interviewing entrepreneurs I've had the opportunity to work with. Last year, I interviewed Dennis Crowley at the first NYU Entrepreneurs Festival and I think it was great. I hope to do as well with Jack today.

And you all can help me. Please tweet out the questions you'd like me to ask Jack. Please include two hashtags in your tweet, #askjack and the festival hashtag #nyuef.

Thanks for your help and I hope we see you on the hashtag and on the livestream at 5:30pm eastern today.

#NYC#VC & Technology

Comments (Archived):

  1. William Mougayar

    Question to you: Between Ev, Biz & Jack, how were they different?And did you know back then that they would not be able to continue leading Twitter.

    1. fredwilson

      Ev Jack and Biz are all very similarthey are visionaries, big picture thinkers, and great evangelizersthey are john, paul, and george. all extremely talented and capable of doing great things on their own. and they have done that.thankfully we had Jason Goldman who is the fourth member of the founding teamJason is a “get things done” oriented person and was key in the early days to doing exactly thati did not think much about the leadership of Twitter when we made our investmenti just knew it was going to be something very important and i wanted to get involved

      1. William Mougayar

        Interesting insight.Jason stepped down too in 2010.I meant later on, – when did you start to see signs that the 4 of us would have to let go.

        1. fredwilson

          Its a long and complicated story with no easy answers or insights. The books will be written at some point

          1. William Mougayar

            :)I’ll try to plant an easier question on the hash stream.

      2. John Revay

        You need both visionaries, big picture thinkers, and great evangelizers…and the people who are able to take the vision and translate into a product, service, companyOne probably does not work w/o the otherJOBS/COOK?

        1. Rohan

          Jobs-CookWalt-Roy disneyGates-Allen/BallmerWhy-How

          1. John Revay

            Good list!

          2. Shola Abidoye

            Yeah, I agree – neat list!

          3. Cynthia Schames

            Wow, that’s great.

      3. John Revay

        Re: john, paul, and georgeGreat photo on Andy Swan’s tumblr site – with the caption – as most of them are….”The millions of moments before “the moment” are what make the moment.Think. Plan. Execute. Create”With Andy’s sign-off tag of WINFun Friday to you all!

        1. rmchrQB

          so cool! Must borrow this from you.

      4. takingpitches

        found an LA times interview of Jason Goldman, who I did not know about. Seems like a grounded cat:”In the early days of Twitter, all three of the co-founders never graduated from college. I felt like the token Ivy League student,” Goldman joked. “I obviously wasted my money on higher education.”

      5. takingpitches

        And he makes this observation in 2010. Still a long way to go.Just delivering a raw stream ultimately is not enough,” he said. Twitter has to find a way to make the experience richer for users by surfacing the content most relevant and important to them, he said. “That’s why people keep coming back.”

  2. John Revay

    #HeadLiners – Jack & FredFeatured Keynote SpeakersConfirmed Keynotes By:Jack Dorsey, Co-founder of Twitter and Square, in dialogue with Fred Wilsonof Union Square Ventures

  3. LIAD

    #askJack – ‘what did you think when USV chose not to invest in Square?'(–oh come on. stop tutting! it is meant to be fun friday.)

    1. ShanaC


    2. fredwilson

      That we made a huge mistake!

      1. takingpitches

        maybe, but dwolla seems like a much more disruptive bet

        1. Matt A. Myers

          Both disruptive. Could be 10-20 years before credit card companies lose hold.

      2. Matt A. Myers

        Was USV approached by Jack for Square (no pun intended)?

        1. fredwilson


          1. Matt A. Myers

            Curious if what they presented was different from the direction they ended up taking.. a less clear of a picture to be able to make a decision from?

  4. kirklove

    Alas, another missed Friday Night Pizza Night. ;)Have fun. Last year’s with @dens was great.

  5. JimHirshfield

    “…see you on the hashtag…”So hip. Love it.

  6. Rohan

    Existential question – why do you what you do?Do you see a gap and just want to fix it? Have you always wanted to change the world in someway?

    1. fredwilson

      Pls put it on the hashtag. Good one.

  7. Abdallah Al-Hakim

    #askJack how do you convince investors to put huge amount of money upfront for something that takes years to perhaps become profitable

  8. btrautsc

    I’d really like to hear his thoughts on wearing dual hats @ twitter & square (as well as your’s Fred – from an investor & operator perspective)…Turning brain on in one shop, then decompressing (or switching costs) to turn brain on for different shop and problem set – which as an aside, I believe may be very healthy for creativity.also how did they resolve disagreements early on with their foursome? feats of strength? sporcle contests? circumference of thighs? (just throwing out options we’ve used…)

  9. awaldstein

    #asjack–‘Did they ever imagine a model other than media?’

  10. Tom Labus

    #askjack Did you think the “fail whale” period was good for getting users persistent about getting on?

  11. William Mougayar

    Fitting to use Twitter for asking one its co-founders questions. One of the million things that Twitter is good at.

  12. mikenolan99

    @fredwilson #askjack at #nyuef – Square has transformed mom & pops and farmer’s markets-what’s next to help the micro entrepreneur?

  13. ShanaC

    I wonder what he thinks of the limitations of design

  14. Richard

    I see square as the amazon of brick and mortar retail. What is the road map to make this experience “smarter” for the retailer and consumer?

    1. awaldstein

      Not till it connects to online POS systems.They don’t connect nor interface to any POS systems to my knowledge. POS online and off is the huge hurdle and tough to solve.

      1. LaVonne Reimer

        Strangely, I woke up this morning thinking about Square and wondered if it wouldn’t obviate the need for POS. I think about new models that will revolutionize old enterprise apps. It’s a hobby. But this is a question. Will Square need to interface with POS or just make it unnecessary?

        1. Richard

          My sister has been a sole proprieter in the healthfood space for 10 years. 1000’s of plu’s, POS is surely required.

        2. awaldstein

          Without POS with real goods you don’t have commerce.It’s that simple honestly.

          1. Cynthia Schames

            @awaldstein My husband’s family owns a paint & hardware store on the Lower East Side, and it’s been in business since 1927. They do millions of dollars in business a year (primarily to contractors).Their POS system ran its very first end of month billing cycle on Friday, just about the time Fred was talking to Jack.So, you can have real commerce without a POS. But to paraphrase Chris Rock, you can drive a car with your feet if you want to… but that don’t make it a good f*ckin idea.

          2. awaldstein

            I love this comment….thanks.One point though. Hybrid models, storefronts with online catalogs though can’t ‘really’ do biz w/o one. W/o real time inventory updates disaster looms!

          3. Cynthia Schames

            Oh that’s so true! Thankfully, he isn’t trying to do anything online 😉 My 77 year old father in law couldn’t handle the stress. Ha. He can barely get AOL to forward chain emails as it is.

          4. awaldstein

            With my clients, and I like hybrid models, there are kinda two stages:-online as catalog ordering. Customer simply order what they know they need. Easier.-online that not only is a place to buy but a place to be sold. A customer acquisition tool. Wild west, exciting area.What interests me most though as a combo of all three(sorry for the rant) is for terrestrial businesses using the web on a neighborhood bases to drive local customers to the store.This is the NY issue where tens of thousands of customers in the area never even know you are there.

          5. Richard

            Shopkeep has this

          6. awaldstein

            Weak info on inventory control on site. Glossing over the issues and connecting to other systems.Cool on front end.

      2. Richard

        Shopkeep is doing a pretty good job out of the gate. POS is low hanging fruit for square that they should pick.

        1. awaldstein

          I’m not as positive.At retail in the wine business as one example, maybe 80% of retail in NYC pushing probably around $200+m in revenue is home grown.How is POS the low hanging fruit where it needs to work on and offline together, tied into warehouse and shipping systems and working to tie into now developing systems for distribution?Normalizing POS by replacing all existing with another is insanity or maybe brilliance. It won’t happen simply though.What am I misunderstanding? I so want you to be correct.Technical and human issues aside (wouldn’t that be nice) I have to wonder whether fixing POS is where the money is. Just because it flows through it doesn’t necessarily mean it’s where the money is to be made of course.

          1. Dayna Gant

            Founder of Shopkeep ran high end wine/grocery stores in NYC. Needed a POS system so created Shopkeep. Their website explains quite a lot.

          2. awaldstein

            Thanks…I’ll take a look.Not an expert but deeply familiar with the issues.Built a store on Shopify recently. Even the rigid rules to make ordering ‘universal’ were unbelievably limiting and they have a really good platform.If ShopKeep deals with the transition from legacy, the move from years and thousands of SKUs and scads of data and logic, then they are onto something. If they don’t address legacy then they are only useful for the new and starting fresh companies. A market but restricted.Surfing over there now.

          3. Richard

            The timing couldnt be any better for shopkeep et al., the legacy systems are mostly hosted on the client. Over the next 10 years, with the legacy system being so super expensive, virtually all small retailers will be running the shopkeep cloud based POS type system. Shopkeep obviates the need for back end systems and soon will tie into vendors systems as well.

          4. awaldstein

            Agree on the size of the need and the mess to untangle.Went to their site and feeling dense as it is not inspiring me with clarification.I both get asked this very often and in spec stage for something that will connect to multiple POSs.I’m interested. If there is a contact that wants to spend 30 minutes with me, could be a useful call.Thanks for pushing on this.

          5. Richard

            On a unrealated topic – What are your thoughts on fostering a miniwinery platform?  (similar to the minibrewery market) 

          6. awaldstein

            Depends where you are going with this?We are building in local wineries, spirits makers and possibly the artisanal brewery market on our next rev so starting to touch that [email protected] if you’d like to discuss. Glad to.

  15. Richard

    Fred, it’s not fun, but can you speak to the ousting of a founding CEO?

    1. ShanaC

      sure, why not?

    2. fredwilson

      i wouldn’t bring it up but others might

      1. Richard

        Fixed the typos. Discus and ipad sure seem to struggle interfacing.

  16. Richard

    Is there an opening for Square to be the google of brick and mortar retail search and advertising?

  17. takingpitches

    #askJack – “Lessons for making it through tough times between the founders”

  18. William Mougayar

    Jack said once “The strongest thing you can cultivate as an entrepreneur is to not rely on luck but cultivating an ability to recognize fortunate situations when they are occurring.”How do you cultivate an ability to recognize fortunate situations when they occur? Any signals or is it all gut feel? #askJack #nyuef

    1. TBodily

      ^This^ And assuming he can articulate an answer a book needs to be written as well…I’ve met many people who are very talented at identifying “fortunate situations” but very few who can actually explain how they go about it.

      1. Matt A. Myers

        It’s really just identifying what could have / add benefit to what you’re doing. This just means good at thinking through every possibility, every strategy, every option, etc … and then of course making decisions and aligning resources with priorities – whatever those are decided to be. In part this is relating to serendipity.Today I walked into a cafe where I frequent, and someone I had talked to in the past waved me over. He let me know about an organization who has a large amount of money ($30 million) and that he’s meeting / involved with them. For what the money is available for he thought I could help, that there could potentially be money available to me as part of a partnership.I would say that is a fortunate situation, though there was a fortunate situation prior to that, that happened months before – and that was to talk to this person and spend time going into detail of what I’m doing, and gain his interest by gearing it towards his own interests of what he’s trying to accomplish. I gained his interest and attention, and I’m very thankful for that – and I hope we can help eachother out in the future.

  19. mgwitham

    Can you ask him…Elon Musk is changing humanity. Tesla kinda…definitely with Space X.What does Jack want his legacy to be?Does he have plans to influence his children’s children’s children? (he’s already done that with Twitter, but let’s go for round 2 or 3 or 4 or whatever number he’s on)

  20. takingpitches

    One of my favorite AVC posts ever is Long Roadmaps.I would love to know what Twitter 5.0 and Square 5.0 look like in Jack’s mind.

  21. andyidsinga

    have Herb Kelleher playing in the background – he is awesome.

  22. LE

    I setup http://nyuef.com/ and http://nyuef.org to forward to the festival page.If the festival organizers want those domains please contact me at any time.

    1. fredwilson

      You never cease to amaze me Larry

    2. William Mougayar

      I wonder why they didn’t buy these themselves.

  23. andyidsinga

    I liked Jack Dorsey’s point about “new york agression” vs “silicon valley passive agression”.

  24. Shola Abidoye

    I’m curious how growing up as a kid in the midwest interested in technology affected his outlook. Curiously, I’ve noticed a few interesting tech firms popping out of MO (which is admittedly sometime I know little about!).

  25. William Mougayar

    It was fun watching the live stream, after the #askJack foreplay.I liked hearing that Data was supposed to be bigger than payments to Square.

  26. fredwilson

    It was done by a student run company. The festival is promoting student entrepreneurship. I understand why they went with that although I agree the video is poor

  27. Matt Zagaja

    The source video appears to not be broken, but it was jumping and having trouble in my Google Chrome browser on OS X. I did some googling and found a way around this (a little hack). On a Mac computer you can actually download the file using a script called AdobeHDS.php available on GitHub (https://github.com/K-S-V/Sc…. No need to learn how to use GitHub (although a good skill to have!) but just click the Zip button to download the scripts into a folder.On your Mac open “Terminal” and type “cd /folder/name” where folder/name is the path to the folder with the script you just downloaded.Once inside the folder type “php ./AdobeHDS.php –quality high –delete –manifest http://w.pp3.me/dvr-erevn/j…”It will then do some stuff and download the fragments of the video to the folder the script is in. Navigate to that folder in your finder and you will see an .flv file. You can open and play this with VLC media player: http://www.videolan.org/vlc….Viola video without skipping 🙂

  28. fredwilson

    I may need to do that because I want to embed it on AVC at some point

  29. Drew Meyers

    Is it posted somewhere else online already?Last night I watched it at – http://stream.circles.io/#e…I want to send it to a few people, but the video is no longer on that page.

  30. Drew Meyers

    Awesome – thank you