Video Of The Week: Jack Dorsey At The 99% Conference

Back in 2010, Scott Belsky asked me to give a talk at The 99% Conference. That’s when and where I delivered the 10 Ways To Be Your Own Boss talk.

Jack Dorsey followed me on stage and delivered this 15 minute talk. I sat in the audience for Jack’s talk and loved it. So I thought I’d feature it here this week. It’s four year old but as relevant today as ever.


Comments (Archived):

  1. Nikhil Nirmel

    Good talk. I have two follow-up questions.- Are we as entrepreneurs uncovering business opportunities that fundamentally exist, or are we uncovering what we have the personality to create?- How to prioritize an unexpected user behavior or opportune external event over our original vision of what the company should be. I believe Jack refers that process of prioritizing “editing,” but I’m curious what that process actually is for him and others.

    1. Matt A. Myers

      Just my quick thoughts in response to those..- All answers it exists, it’s a matter of finding the right question. Your ability to generate questions, which comes through the experimentation process of the brain, will determine what your mind sees and resonates with. Tie that with personal experience as feed for what your brain tries to solve, and then yes – you’ll uncover what you have the ability to create. This is why you should fully dive into the arena of whatever you are solving the problem for.- The first leading metric for every company should being self-sustainable which means generating enough revenue to pay all bills. For me if a new opportunity or insight will lead to reaching sustainability faster or increase any of the factors of success over what you’re currently prioritizing then IMHO you should shift things or at least plan to do so as quickly as possible. It’s harder when you’re a big company with lots of processes and people because people in fixed environments and systems take time to adjust, if they are even comfortable or able or wanting to fluidly adjust. This is why small companies or startups can seemingly make sometimes fairly large pivots in their focus very quickly.

      1. Jim Peterson

        Great points. As to one’s ability to generate questions: agree with you, and also sometimes out of domain experience contributes since you look at the issue differently than those in the domain.

    2. William Mougayar

      Re: #1. Great question. My answer is that the 2 must collide. Passion about them + their viability.

      1. Matt A. Myers

        Passion evolves or develops through attention or exposure to the area. There of course has to be the seed that results into the direction of that passion existing though.

  2. Matt A. Myers

    It sounds like Jack Dorsey was fairly close to programming a first version prototype of Foursquare!

    1. William Mougayar

      He has hinted at extending Square in that direction. Maybe he will buy them 🙂

      1. Matt A. Myers

        For the right price I imagine it makes good sense.

  3. Brandon Burns

    This reminds me of Brad Feld’s post about how we rewrite our own stories.

    1. Matt A. Myers

      Do you have a link for the lazy?

        1. Matt A. Myers

          Thanks Brandon 🙂

    2. Vineeth Kariappa


  4. Matt A. Myers

    Re: “That is one of the most important things to start doing, is to start drawing your idea, to start getting it out of your head and seeing it from a completely different perspective.”This is why I was naturally drawn towards design (pun intended). I had to get my ideas out, down on paper, and simply writing it out in text form doesn’t translate well back into the meaning of what I see and how I’d see it functioning and existing.This is a very important process and really fits within agile development or design. For myself as ideas come to me I must get them out or they simply sit with me until I process them. Initially, years ago, I wasn’t good at this process. There was a lot of friction and it was slow. Over the years though I became more fluid at it, better at organizing and learning how I needed to output it so I’d be able to understand it. As Jack said this allows viewing from a different perspective. And having a visual representation of it allows a natural evolution and continue to then apply other ideas to what your latest visual representation is.Anyway, I can’t count the number of mockups I made for different projects I have been playing with over the years. I used to think and still do at times get frustrated by how many energy I put into certain things, how many different variations I created, though in hindsight I realize that it’s allowed me to learn and to discover more finely what I like and hoping I have a good sense and good taste – that what will most likely work. Of course there is the iterating for how the crowd will morph what you’re doing – like for Twitter the word Tweet, Re-Tweets, Hashtag usage, etc. came into existence – those all really being part of the MVP (Minimum Viable Personality) that Twitter was lacking as a very basic tool which I am sure allowed a very strong brand to be built up encompassing all of that messaging.I would highly recommend everyone take an interest in scribbling designs out. As you’ll notice none of the first-version scribbles that founders of these highly successful companies create actually look all that great, but they get enough of the idea across. It also allows you to then see what the important parts are visually, so then that can help you focus your messaging or pitch – to perhaps help illuminate where its real value comes from.

    1. Elia Freedman

      Great comment. I keep a pad of paper near by just for this purpose. I do wish I could do this stuff on my iPad but it seems that the process gets in the way too much.

      1. Matt A. Myers

        I do mockups in different ways using different mediums depending on what kind of thoughts or ideas they are or how evolved they are, etc.. I design as a form of procrastination as well, so that’s in part why I feel I’ve gotten fairly good at UX.. 😛

  5. William Mougayar

    3 big take-aways for me:1) I like this part where he describes Luck as being able to recognize a lucky situation:”Being able to recognize when a situation is happening around you; that encourages build-out & execution of an idea.”These are tipping point moments that you sometimes recognize, and sometimes you only see in the rear view mirror.2) “Everything you see at Twitter today was invented by users (despite their initial resistance to them), e.g. RT, @, #, “tweet”.” The power of user iterations (which we call now customer development).3) Knowing when to stop. Knowing when to put something away, and when to be passionate about something.

    1. pointsnfigures

      love that description of luck. it’s accurate and I will reuse it. It really frosts me when people point at wealthy people and say they were just lucky.twitter was great at using jujitsu coming from customers to make their product great

      1. Donna Brewington White

        I think about the Daft Punk song — sort of my theme song … I feel like I’m up all night to get lucky, but not in the way they mean.

        1. pointsnfigures

          for what they mean you don’t need luck ; )

          1. Donna Brewington White


    2. Elia Freedman

      Learning when to listen to my customers was one of the big things I’ve learned in my life so far.

      1. Aaron Klein

        It’s an art form.If I did everything my customers asked for, my product would be unusable. If I hadn’t have listened to them, my company would be bankrupt.

        1. PhilipSugar

          Nailed it.

        2. Elia Freedman


        3. William Mougayar

          Exactly. Knowing what to take, and what to shelve is so critical. Customers can tell you what they want from the product, but they can’t really tell you what’s good for your company.

        4. LE

          Well put. Which really comes down to the same thing over and over again. Making smart decisions given the information at hand.A few days ago my wife (who normally loves my stories) said something which was totally out of character. She said “I think you are thinking to much about this”. To which I said “but that’s what I do I think about things and try to make the right decision (and some more)”. I am not a “throw caution to the wind” type of person (in fact that phrase really annoys me).Yesterday at our date night dinner, I told her about a deal that I just did complete with the play by play which shows it dating back to about 1 year ago. And how it ended up happening in the end. At each point there was strategy and (what others might call) over thinking in order to come to the right conclusion and have the desired outcome. And what I find for me is that this works more than it doesn’t work. It might not work for someone else but it works for me.By the way I hadn’t been to your site in some time. I really like the way you hammer the point in the attached screen shot. I give this the “LE5” award for execution.

          1. Aaron Klein

            Thanks LE! That’s quite the compliment.

          2. Donna Brewington White

            It still amazes me how this has evolved. A much different message than that initial beta. Good for you, paying attention and making the transition. That’s what I call agile.

          3. Aaron Klein

            It’s true. I’m proud of how much has changed and yet our core is very much the same. If we had marble on the side of our building, we could have carved “Aligning the World’s Investments with Investor Risk Tolerance” into it and that still would be true. 🙂

          4. Donna Brewington White

            My bad. Not a much different message, but a differently targeted message. Still solving the same problem.

        5. Donna Brewington White

          That’s powerful.

    3. jason wright

      on 2, i wonder if the lifecycle of resistance to each new iteration shortened as they gained a clearer understanding that the market decides, that the user is the only thing that really counts? it didn’t sound that way, but resistance is futile.

      1. William Mougayar

        What you said sounds right to me.

    4. LE

      With respect to luck of course execution of multiple chosen paths normally can’t happen in parallel.So if you are able to recognize a lucky situation you are also passing on another luckier situation that may happen down the road.And if the path you choose isn’t right (not lucky because let’s face it it’s not really that obvious) you may not have the opportunity to be able to take advantage of the thing “around the corner”. Opportunity cost in other words. People don’t typically factor that into decision making.Let’s take the hypothetical example of a person in the mid 90’s who gets offered a good corporate job, recognizes the potential, and gets hired. Then a few years later the opportunity of the internet comes along and they can’t take advantage of that. So they might still do well but not as well as if they had taken the other path. And in fact most people who did early things in the internet not only recognized the opportunity but were free to do so for various reasons (they weren’t tied up in something else that was “good”). Maybe have been a few of course. Golden handcuffs in other words.Dating is also similar. You get tied up in one relationship which means that you are passing on other relationships “right around the corner” that may be better. Or worse.In anything that is long term there is always the opportunity cost of making a decision which ties you up.

      1. William Mougayar

        Such is life!

    5. sigmaalgebra

      I took “knowing when to stop” as meaningwhen to stop developing the product andmove on to alpha and beta test and offeringthe product to the customers/users. So,first sell them a Model T, and don’t wait until have a BMW 7 series to start selling.Sell them a good French chef’s knife and don’t struggle to make it also a combination fish scaler, bottle opener, can opener, and bone chopper. Get feedback on version1.0 before designing version 2.0.

      1. William Mougayar

        Could that too. Applies to big and smaller ideas.

    6. Donna Brewington White

      Those struck me as well. The 3rd is tough — the “knowing when.” Although I think that it is probably a matter of being honest with yourself and also not being ruled by compulsion. I’m sure there is more to it than that. It is amazing how much timing factors in. It seems that many failed companies are the right idea at the wrong time.

      1. William Mougayar

        True. Maybe timing is half of it, if not more.

  6. pointsnfigures

    Love the comment, “Payments is essentially social”. Bitcoin is essentially social.

    1. Timothy Meade

      Bitcoin is getting shaken out, this is a good thing. The problem with the exchanges is they are acting like Napster (effectively) centralizing the repository of stored value (or the thing of value, such as content), while later protocols either distributed it (Gnutella) or divorced the discovery and delivery (the latter being Bittorrent which is content and location agnostic).Centralized repositories are vulnerable to the exact type of attacks that have occurred, theft by deception (in this case technologically mediated), internal corruption (once possible scenario for Mt. Gox), etc.The difference with Napster is Bitcoin was designed as a distributed protocol, and relies on the power of the network to regulate it, but has been misapplied by people who want to short-circuit it’s path to acceptance, and have thereby soured the public on it.To tie this in with the subject of the article, the Dorsey conception of Twitter was limited in scope, and the full power was only revealed when the network itself created the means (hashtags) and the use case (widely published news and current events). Bitcoin has at its root the potential to be discovered by a network of distributed actors and applied in a way that can’t really be conceived, but it has to break free of the “exchange” (which are acting more like banks storing both Bitccoins and currency for long periods of time) model.

      1. pointsnfigures

        Interesting points. My experience with an exchange is that it’s a lot of things. I don’t see any current exchange operating like a “real” exchange. They are trade matching engines-not exchanges.The most important thing to a market economy is transparent price. Next is the information transmitted by that price-and the information flow that happens between buyers and sellers in determining that price. Then there is the back office which is another core reason exchanges exist.A central limit order book would do a lot for Bitcoin, with a central back office. The centralization will cause all kinds of things to develop around it. There is one Twitter stream, that spawns all kinds of things.The community is afraid of a monopoly. But, the community will also be able to choose not to use that monopoly–so a CLOB exchange will charge low fees.What would you get in return? Transparent efficient markets. Back office support. Security. Information flow.As soon as the Bitcoin community tames the volatility, acceptance will be wider. Wider acceptance spreads the virtues, and allows every thing in the ecosystem to develop.

        1. Timothy Meade

          I think I suggested an amendment to the protocol to track exchanges among cryptocurrencies and other currencies and commodities, allowing an aggregator (like to determine the price across multiple exchanges and relative to many other commodities whose prices are determined by other mechanisms. These messages would be signed by the entity that did the exchange and carried in the notes or as an actual extension to the Bitcoin and other protocols.

          1. Timothy Meade

            Of course, once you have this price information determined in a distributed manner, you could build a centralized exchange (I don’t know the terminology you referenced to use it myself). You would be trusting the network as a whole, not a few exchanges that may choose to manipulate the price. (Similar to the LIBOR conspiracy)If anything we have learned that trusting a single entity like Mt. Gox to be the source of the widely accepted price of a single Bitcoin has contributed to the volatility, though it could be the insular nature of that particular system rather than a symptom of it being a single organization associated in the public’s eye with Bitcoin. (To the extent the public is even aware of it.)It seems the distributed nature of Bitcoin would lend itself to a number of competing exchanges, though that would eventually coalesce by natural market forces.

    2. awaldstein

      I believe that the transactional process should accentuate value…but a social act.I’m missing something.

  7. jason wright

    an entrepreneur needs to think different, but not become too detached from how typically other people see the world and think about it. a padded cell is comfortable, but for all the wrong reasons.

  8. Kirsten Lambertsen

    Sometimes I wish I hadn’t read Bilton’s book. I have a hard time not playing parts of it in my head while Dorsey is speaking. But this is an excellent talk, and he’s very easy to watch and listen to as a speaker. The luck part is extremely interesting.

    1. fredwilson

      when reading Bilton’s book you need to realize that Jack refused to cooperate with him. so he took it out on Jack.

      1. Elia Freedman

        I assume you feel the Jack was pretty unfairly treated in the book?

        1. fredwilson

          yes i do

          1. bsoist

            I am so glad to read your comments on this. I sent you that one email after reading Brad Feld’s post about the book and it was obvious from your reply that 1) I should read the book, and 2) I should probably not talk to you about it again. :)After reading the book, it has been a struggle to resist asking you a few specific questions, but your comments here answered all of them in just a few words.

      2. Kirsten Lambertsen

        Well, now I’m glad I mentioned it. That’s illuminating.

      3. Dave Pinsen

        You’ve said previously though that Bilton’s take was pretty close to the way it happened.

        1. fredwilson

          yeah, but the stuff about Jack was biased

      4. Matt A. Myers

        I haven’t read the book – though was there anything defamatory in it?

      5. LE

        Look people are free to do whatever they want as long as the realize that the chips might not fall where they want. If you are going to not cooperate with someone who has the ability to influence what people think about you, there are going to be consequences [1] to that action.[1] This is closely related to “keep your friends close and your enemies closer”.

    2. Elia Freedman

      I realized I was doing the same thing, or at least the excerpt I read about the creation. But I also reminded myself that the invention of anything doesn’t really come from one source, even if the mythology of it does.

      1. Kirsten Lambertsen

        Ya, the book feels like a Jackie Collins novel. In fact, I’ll go so far as to say it feels amateurish.Bilton isn’t threatening to join the ranks of Halberstam or Kearns Goodwin any time soon 😉

        1. bsoist

          Read very much like it had an agenda to me. I don’t know the players in the story personally, but I started using Twitter in 2006 and I’ve been paying attention to the story since as much as anyone can from the outside. I guess every story needs heroes and villains.

        2. LE

          Do a search for “Kearns Goodwin plagarism”.

          1. Kirsten Lambertsen

            Yes, I suppose that means I shouldn’t have included her. It’s Saturday and I don’t feel like finding a replacement for her 🙂 I take your point.

    3. bsoist

      I feel exactly the same way.

  9. bsoist

    Many people forget to give credit to luck. I finally got to see 20 Feet from Stardom last night. In it, Sting talks just briefly about luck and the role it plays in success.but it’s not blind or random. One should be prepared to take advantage of opportunity. About a year and a half ago I received a surprise in the mail – book called Get Lucky by Thor Muller and Lane Becker. It arrived at my door the day it was available in stores. The authors thought surprising some people with it would be a demo of the concept of serendipity. It worked for me – made me read the book. It was worth reading.

  10. William Berlin

    Thats interesting….It is my understanding that Jack did not invent twitter….my understanding is that one of the devs at odeo with a background in communications theory invented and developed twitter…

  11. rothbriele

    I like this aspect where he explains Fortune as being able to identify a fortunate situation:”Being able to identify when a scenario is occurring around you; that motivates build-out & performance of an concept.”Spybubble Gratis

  12. RowdyFish

    Sorry … I love this blog and Fred’s writing … but this video is complete non-sense. The level of pontification and speaking in circles is astounding. I can barely listen past the pretentious “creation myth” involving “maps at the age of 13”. It is amazing how people in this comment section actually “buy” this stuff. We need to stop blowing smoke up Dorsey’s a%$ and call a spade a spade.He came up with a very cool idea (or arguably his buddies came up with the idea) – and it caught on. Much as Snapchat was a bunch of drunk college bro’s who came up with a really catchy product. This revisionist histroy … and hanging on Dorsey’s every word … has clearly reached a crescendo. If you believe Twitter was inspired by Dorsey’s creation of maps … and he essentially announced Twitter on a playground … you have clearly drunk the coolaid. As far a Fred’s statement that Bilton was biased … Bilton’s reporting has been very widely supported (even by Twitter insiders). Dorsey’s buddies … of which I am guessing Fred is one … are the biased parties.PS – Evan Spiegel gave a similar speech recently talking about how Snapchat developed from his “deep understanding of the tangential nature of human interaction”. Hah!Wake up people!

    1. msuster

      I felt the same way. I had to turn it off.