How Jack Dorsey BUILT Twitter & Square | The BIGGEST Lessons in Innovation

My goal is to simplify complexity. You have those like shower moments where you're walking at midnight in some town in New York City and you've got these amazing brand ideas and then you start thinking, well, I could really start doing this if only X, and if I had this person, or if this technology existed. I think leaders of companies have to consider themselves editors and you constantly have to edit the team.

He's an American computer programmer and entrepreneur. He's widely known as the co-founder and CEO of Twitter, as well as the founder and CEO of Square. He has an estimated net worth of $1.2 billion. He's Jack Dorsey, and here's my take on his top 10 rules for success. Rule number 1 is my personal favorite, and make sure to stick around all the way to the end for some special bonus clips. And as always, if Jack says something that really resonates with you, make sure to leave it in the comments and put quotes around it so other people can benefit and be inspired. Inspired as well.

Kind of cliché, but just do it. A lot of time is spent thinking about something and talking about it, but when you actually get something down, either on paper or in code or, you know, in front of someone, that's when things start happening. And you're going to make a lot of mistakes.

The important thing is that you make decisions and you keep moving forward.

But you have to get it out there.

You have to start, and you have to be brave enough to take the criticism.

I always go back to the punk movement of the '70s.

People would get out, they'd be on the street, they'd sell their jazz.

Because you were a teenager back then.

Yeah.

Well, and they would be learning in front of people. They get out on the street and it's the first time with a guitar.

Yeah.

And, you know, they're learning how to play and they're getting better and better and better.

Yeah.

And I think it's really important to just get it down.

Do it.

Just do it.

Edit, edit, edit, edit.

My goal is to simplify complexity. I just want to build stuff that really simplifies our base human interaction. Twitter was around communication and visualizing what was happening in the world in real-time Square, was allowing everyone to accept the form of payment that people have in their pocket today, which is a credit card. So we've built the simplest way to accept credit cards, and it's just this little tiny device that we give away for free, and you just download some software from the App Store, and you plug it in to your mobile phone or your iPad, and suddenly you can take credit cards. So if you're a tax accountant, or a lawyer, or a doctor, or you know, even a hairstylist, you can now accept credit cards.

It's really that the users help decide where we go. We are the curators of the technology, and we think we're pretty good at it.

But—

and this leads into my third lesson— is, you know, you need to listen. You need to be still and really listen to what's going on around you and let that inform and let that inspire your next steps.

It seems hard to be still and listen when you've got 300 followers, you're following 300 people.

It's extremely hard.

It's extremely hard. But it's really important that you're able to step back and listen to what's going on and what patterns emerge so that you can really consider those and move them.

I think that's one of the strongest things you can cultivate as an entrepreneur is to not rely on luck, but cultivating an ability to recognize fortunate situations when they're occurring. Odio was a very fortunate situation. Could have taken that idea, not told it to Evan, not told it to Biz, not told it to Noah and all my other coworkers at Odio, and tried to start my own company with that idea. But the fortunate situation was that I was working with some really amazing people.

And we had a great team.

So of course, you know, it makes sense to start there. The fortunate situation for Square was that in 2008, the end of 2008, the entire market was crashing down. Like all of these abstractions we built upon abstraction upon abstraction upon abstraction in the financial world, which no single human understood, were now falling apart. And suddenly we were getting back to basics back to fundamentals. Management teams were being asked to leave, banks were failing, you know, people were clarifying around like, we need to start getting innovative, we need to start treating our customers so poorly, we need to stop encouraging bad behavior to reap fees. Like, we need to really turn this whole thing around. And anytime there's a recession or a depression, that's a great time to innovate, start a company. Start a project, you know, do anything. So, you know, we recognize, we recognize that time. And at the same time, my co-founder Jim, uh, re— you know, recontacted me.

He—

I've known him since I was 15 years old. He was my boss when I was 15 years old. And, uh, he's like, Jack, I want to talk to you. Um, I want to, I want to build an electronic car company. Like, that's interesting. And he was thinking about it because the car industry was failing as well. And he was like, why don't we just give these car companies to well-seasoned entrepreneurs? Like, why don't we give Ford to Steve Jobs? And like, you know—

That would be amazing.

Yeah, it would be amazing. And like, you know, GM to Ellison or like whatnot. And he's like, and also I want to start an electronic car company. I'm like, that's ambitious. But in that moment, we decided not to start an electronic car company, but we wanted to do something together. And we kept having these weekly conversations about what that thing was. And I was researching dealing a lot with finance and healthcare, because I was looking at doing something in those spaces. And Jim called me one day, one of us scheduled meetings, and he said, I just lost a glass sale. He's an artist, he sells glass. And I lost the sale because I couldn't accept a credit card. And here he was talking on his iPhone, his general purpose computer, and I was talking on my iPhone. And we couldn't figure out— A 1 GHz computer sitting in the palm of your hand, but no way to accept credit cards. He couldn't accept $2,000 from someone who wanted to pay him, right? Like, why is that? So we decided that we wanted to answer that question, and we did a bunch of research, and I started writing some server code, and we hired a guy to write some iPhone code, and Jim built some hardware. And in a month, we had a, uh, a little— well, it was actually quite a big device that plugged into the audio jack of your iPhone and could swipe a card, take a payment. It would go through the merchant process and then generate a receipt with a map on it. And I went around, I showed it to a bunch of investors, and they were all amazed that it could even work. So we decided to really focus on it and make it a, make it a company. And it really just comes down to like recognizing that fortunate situation and recognizing the people around you that, that could help and, and just owning it. The biggest thing for me on that, on that path is I need to I need to draw something out and I need to get it out of my head. I found myself very early on thinking about something, like thinking about this early idea for Twitter, and saying to myself, I could build this awesome— you have those shower moments where you're walking at midnight in some town in New York City and you've got these amazing brand ideas. And then you start thinking, well, I could really start doing this if only X, and if I had this person, or if this technology existed, or if this happened or this happened. What I realized I was doing is I constantly making excuses for not working on it. And then the window had passed and then I couldn't do anything. So I think it's really, really important to write it out or to draw it out or to code it. But you need to get it out of your head. And the reason you have to get it out of your head is you need to be able to see it on a surface that is not in your mind. And once you can see it and once you can step back from it, then you can also decide this passes my filter, passes my constraints, so maybe I can show it and share it with some other people. And then they'll be like, you know what, that's the stupidest idea ever, or that's somewhat interesting, but maybe this and this and this. So the sooner you can do that, then you have a lot of momentum around it and you can really decide if you want to commit to it and work on it more, or put it on the shelf for a later date. And the realization that I think everyone needs to have about that latter option, putting it on the shelf, is that you can come back to it, and it'll surface back up in another piece of work or another idea at some point in your life. So having that ability to close off a chapter and move on is really, really important. You can't have all these open threads, and that's what I realized I was doing, and that also encouraged me to really write more and to really think about what is the story? How are people coming to this? And like when I show my friends this, how are they going to react? And I would write it down. I would actually treat it like a play. And when I realized that I was writing plays, I read a lot more plays. For style and for substance and for technique. And I think it's really good. And I think there's another company that I've always looked towards for inspiration, and I know a number of people in this room probably have a similar company in mind, which is Apple. Apple, I think, is run like a theater company. It has a great sense of pacing, has a great sense of story, and has a great sense of execution and it's all about, it's all event-driven, it's all stage-driven. The stage being a billboard or the stage being a keynote or the stage being a product launch. All of it has a very, very cohesive end-to-end story. I mean, you think about what happened when Steve Jobs came back to the company. The first thing he did is he killed every product line the company was working on. And for 2 years they had no product on the market whatsoever. All they had were a bunch of posters all around the world with Steve's heroes. And it said, think different. And it was just focused on bringing up the brand and making people aware of the brand again and how the brand is aligning to this particular feeling and story. And then they came out with the iMac and then built iTunes and then the iPod and they realized that, wait a minute, people are carrying music on their phones now, so we better build a phone, iPhone. And so this unfolding of the plot and the epic story has been very, very interesting to watch, especially if you look back to that time when he came back to the company. So I've learned a lot from that company and other companies who operate in a similar fashion.

Constrain is a big thing for me and this is something that we're constantly learning at Tripur as well. It's important to say no, and it's important to be able to easily say no. And there's many, many things you can do, and especially when you have a successful venture behind you or you're running with it, it's really important to recognize, you know, when, where you need to go, where you'd like to go, and really constrain the process and keep things really simple. In my dispatch days, we, uh, back in 1999, early 2000, um, we built something really cool.

We loved it.

Uh, and then we hired a CEO that didn't really match our personalities and didn't match our vision. Um, and, uh, we grew the company very, very quickly, and that really scattered the focus of the company. So One of the things I've learned with Twitter is that, you know, that singular focus, that do one thing and do very well, that works out.

I think the biggest thing for me, I think for all startups, is that it's really, really easy to consider any hire as like the length of the entire company. I think leaders of companies have to consider themselves editors. And you constantly have to edit the team. You constantly have to make sure that you have the best people in, and if there's any negative attribute within the team, person or element or otherwise, you have to part ways. And deal with it right away. Yeah, right away. I mean, you have to say, like, this is the best thing for the company, and to be fair to both of us, like, it's just not the right time for both of us. Like any other relationship, you need to be able to recognize what's good and what isn't optimal. And take action on it. So that's one thing that, you know, I would— like with Twitter, like we grew very, very slowly and we didn't edit the team in the best way. We didn't get out of the way of ourselves often enough. So that's something I would never do again.

But what I want to talk to you about today is a note which I call daily. So if you create a new note in your Notepad, or something that you check on a daily basis. This is the most important thing. Name it daily and then write the word do colon, and then go down a few lines and write the word don't colon. The one thing I would ask you to do walking out of this is to every single day, just for a week, Wake up to this note, check it throughout the day, and then also before you fall asleep, check to make sure that you did and you didn't do everything. So what you put in each one of these is you have a list of everything that you want to do every single day, and you have a list of things that you don't want to do. And the easiest way to add to the don'ts is to notice something that you never want to do it again— you never want to do again— and you just add that to it. Very, very simple. I'm just going to share some of mine. These might be a little bit personal and embarrassing, but here we are. Number 1 on my do list is to stay present. I think it's so easy to get trapped in the past. It's so easy to think about the future. The most important thing is I stay present, and just reading this brings me back to the present, brings me back to this moment. Number 2 for me is be vulnerable. Show people my mistakes, show people my fears, because they can relate, because they're going through similar things. Number 3: drink only lemon water and red wine.

Great red wine is a great modifier for it.

This goes with one of my don'ts, which is don't drink hard liquor or beer on weekdays. Number 3 is 6 sets of 20 squats and push-ups throughout the day. I just have to do them every day. 6 sets of 30-second planks. Run for 3 miles. Meditate on this list, stand up straight, which whenever I say, I always see posture moving in the audience, say hello to everyone. I just bought a heavy bag, so I'm training with a heavy bag, so I want to spend 10 minutes with a heavy bag every day. I want to do a video journal every single day, and I want to get 7 hours of sleep.

On my don't list, and again, this is one of the hardest things, and a lot of these are personal, so I'm not going to read all of them.

Well, my don't list is: don't avoid eye contact, don't be late, don't set expectations for someone and not meet them, don't eat sugar. I'm on the paleo diet, so don't eat wheat, lentils, or dairy.

And then of course, don't drink hard liquor or beer on the weekdays.

So this list, while it sounds very, very simple, has been fundamental in establishing patterns for myself. And it's something that I do check every single morning. I check throughout the day, and I check right before I go to bed, and I make sure that I check everything off and go through it. And I've given it to our companies, I've given it to a number of students that I've talked to as we've gone to schools and recruiting, and people have come back to me and said that this is something that works for me. It's something that's easy to do and something easy to remember. One of the most fundamental things about it that I've learned, that I've taken away from it, is how it gives you focus. How it gives you something that allows you to really ignore everything else that's going on, all the other noise, to allow you to focus on what's most important. So this do and don't list for people and individuals in the company has translated to a do and don't list for our company. For Square, we have a do and don't list. We have, these are the things that we're going to do, these are the core things, these are our bold bets, and these are the things we're saying no to for right now. That's been fundamental in allowing us to move fast, to continue to innovate, and to really push the boundaries and continue to invent and question and reset everything that we think about the organization.

And one of my greatest lessons that I learned in starting and running Twitter and starting and running Square, which is how important it is to instrument all usage. You have to instrument everything. For the first 2 years of Twitter's life, we were flying blind. We had no idea what was going on with the network. We had no idea what was going on with the system, with how people were using it. We were making guesses. We were basing everything on intuition instead of having a good balance between intuition and data, and we were going down all the time because of it, because we could not see what was happening. So the first thing I wrote for Square on the server was an admin dashboard. And we have a very, very strong discipline within the company, which is now 72 people, to log everything, to measure everything, and to test everything. And we treat the dashboard, we treat the analytics, we treat the data as a product, and we call it the inference team. And their job is to instrument all usage and infer all action. And that's something that we need, but it's also something that our users need.

Art, when really understood, is a province of every human being. It is simply a question of doing things, anything, well. It is not an outside extra thing. When the artist is alive in any person, whatever his kind of work may be, he becomes an inventive, searching, daring, self-expressing creature. He becomes interesting to other people. He disturbs, upsets, enlightens, and he opens ways for better understanding. Where those who are not artists are trying to close the book, He opens it. He shows there are still more pages possible. And I think that's so telling for everything that you all are about to do, all the challenges you're about to face. You are going to be the ones that open the book. The world would stagnate without him, and the world would be beautiful with him, for he is interesting to himself and he is interesting to others. He does not have to be a painter or a sculptor to be an artist. He can work in any medium. He simply has to find the gain in the work itself, not outside of it. One of the biggest lessons that I've learned throughout my career is how important the work is, how important not just the end product is, but the actual craft, doing the work, inventing within the work. The work of the art student is no light matter. Few have the courage and stamina to see it through. You have to make up your mind to be alone in many ways. We like sympathy as humans, and we like to be in company. It is easier than going it alone, but alone one gets acquainted with himself, grows up and on, not stopping with the crowd. It costs to do this. If you succeed somewhat, you may have to pay for it as well as enjoy it. For the rest of your life. And that's something— if you do something meaningful, you are going to have to pay for it in all the work, but at the same time, you will also be able to enjoy it for the rest of your life. We are not here to do what has already been done. Everyone in this room feels that we are not here to do what has already been done. Know what the old masters did, know how they composed their pictures, but do not fall into the conventions they established. These conventions were right for them, and they are wonderful. They made their language. You make yours. They can help you. All the past can help you. I think in Silicon Valley, and especially in technology, it's so easy to fall in the footsteps of others, to do what they do because you think it's the right— because the right way because you think they've had the success and you can copy that success. You have to find your own path. You have to find your own footsteps. An art student must be a master from the beginning. That is, he must be the master of such as he has. By being now master of such as he has, there is promise that he will be a master in the future. And what he means by this is purely you have to be a master of your own tools. That mastership is not, uh, it's not a destination, it is a process, and it's constant practice that gets you there. It is not enough to have thought great things before doing the work. We have so many ideas, but what really matters is the work to implement those ideas. Don't worry about the rejections. Everybody, everybody that, that's good has gone through it. Don't let it matter if your works are not accepted at once. The better or more personal you are, the less likely they are of acceptance. Just remember that the object of painting pictures is not simply to get them in exhibition. It is all very fine to have your pictures hung, but you are painting for yourself not for the jury. And what's meaningful about this passage to me is we work so hard to get some sort of acceptance in the world, to get some sort of positive feedback, and we look at others and it seems so fast, their success. It seems like they did it in just a moment, but it takes years and years and years and patience. The bookmarking interface is not easy on this. There's a time and place for all things. The difficulty is to use them only in their proper time and place. There's a time and place for all things. The difficulty is to use them only in the proper time and place. With motive, you will become clairvoyant of means. You will seize and command them. Without motive, you will wobble about. This, in building a team, in building an organization, building a company, is one of the greatest lessons. You cannot do anything without a shared and common sense of purpose. If you don't have motive, if you don't have purpose that is shared between everyone, you will wander about, you will wobble, and you will not do anything of infinite means.

You will not do anything that is timeless.

And lastly, the art student of these days is a pioneer, just like all of you. The art student of today must pioneer beyond the mere matters of fact. I believe the great artists of the future will use fewer words, copy fewer things, essays will be shorter in words and longer in meaning. I love this passage. I believe the great artists of the future will use fewer words, copy fewer things. Essays will be shorter in words and longer in meaning. We must paint only what is important to us, must not respond to outside demands. They do not know what they want or what we have to give. I think one of the most important things about what you all of you do is that you are building what you want to see in the world. You're making the bet that other people want to see the same thing in the world. Sometimes you lose a bet, sometimes you win the bet, but the most important thing is you have that passion to build for yourself because that is what's infectious and that is what brings other people to your cause and to your team.

Thank you guys so much for watching. I hope you enjoyed this video. I made it because Digvijay asked me to, so if there's a famous entrepreneur that you want me to profile next, Leave it in the comments below and I'll see what I can do. I'd also love to know what did Jack say that really inspired you, that motivated you, that made you think or question something. Leave in the comments and I'm gonna join in the discussion. Thank you guys so much for watching. I believe in you. I hope you believe in yourself and whatever your one word is, and I'll see you soon.

How do you go about attracting funding and then managing your investors after you've secured it?

I think the thing that's always worked for me is realizing that your investors are— first and foremost, I always want to go to anyone that I want to work with with something to show. And it was really important to us before we talked to any investors on the Twitter side that we actually had people using the service and in some— at some scale. And on the Square side, that we actually had a working prototype. At Square, we had really 7 merchants when we actually went to raise money. But we had a working prototype that people were actually using. And if people can't see it and feel it, it's very, very hard to sell. And I don't want to just go and tell people this is going to be the biggest thing ever. I want to be able to show that and have them feel it and walk away away feeling that as well. So that's first and foremost, is have something to show so that they can actually feel it and start making it a part of their story as well and feel like they have ownership over it. And then second is a realization. I always kind of approach this as like, if we take money from someone, this is kind of like hiring someone that we can never fire we can never get rid of, right? So that means, do we really want to work with this person? Is this person going to be someone that really pushes us in the way that we need to be pushed? And you can tell that fairly quickly in that first week of pitching Square. Got a lot of people who said, OK, great. We don't have any questions. We'll get back to you in about 30 minutes, probably with a term sheet.

Term sheet.

And I said, I don't want a term sheet, especially if you're not asking any questions, because they asked no questions during the pitch. And that means if they're on our board, that they're actually not going to be all that constructive in terms of really asking the tough questions and making sure that we're, you know, we're not just in our own bubble, but they're looking outside. That is the role of the board, is to look outside and bring all their insight and wisdom to us so that we can help guide the company. And that second week, we got a lot of tough questions. And that's what I love, because I know if I'm getting tough questions in the pitch, I'm going to get tough questions in the boardroom as well. And not just the boardroom, but every week. I mean, Vinod emails me once a week about, have you thought about this? Are you doing this? And I know this person, can I make an introduction here? It's just very, very useful. So I'm looking for someone who I just love working with. And I think you have to set a very, very high bar. It's not just about money or the firm. It's about the individual that you're ultimately going to work with. And people ask me all the time, like, you know, what firms would you suggest I go pitch? And like, find the people that you really want to work with in those firms. And if there's someone that really you know, just really resonates with you and you love the idea of working with them, focus on them. And if it tests out to be the case, great. But I think you have to kind of treat it as like I'm adding this person to my team. One of the biggest things that has helped me is learning how to become a better storyteller. And the power of a story. And by this I mean, if you wanna build a product and you wanna build a product that is relevant to folks, you need to put yourself in their shoes and you need to write a story from their side. So we spend a lot of time writing what's called user narratives of this user, This person is in the middle of Chicago, and they go to a coffee store in the middle of Chicago, and this is the experience they're going to have. It reads like a play. It's really, really beautiful. And if you do that story well, then all of the prioritization, all of the product, all of the design, and all the coordination that you need to do with these products just falls out naturally. Because you can edit the story and everyone can relate to the story from all levels of the organization, engineers to operations to support to designers to the business side of the house. So that story is very, very important for us. And really constantly considering the story and what new twists and elements we need to add to the story are a pretty big deal for us as well. And we want to tell an epic story. We want to solve a really big problem. We don't want to have a bunch of short stories strung together. We want one epic cohesive story that we tell the world. And both Twitter and Square are driving towards this goal. So number 2, good storytelling and writing stories for for the users.

Who's your favorite CEO?

Entrepreneur?

That you would like to— who's your role model?

I always look up to Steve Jobs. I know it's a common one, but I think that's for a reason. I think he's done some amazing things. He has a great pacing about him. You know, there are a lot of horror stories. He is a very opinionated person, but he has a direction and he knows what he wants to do and he does it. And he makes sure that when, you know, he's not so good in the area, he recognizes it and he fills that area. And that's really important for any CEO, I think, is to really recognize your weaknesses and bring amazing people. And bring people in that are much smarter than you.

Smarter than you, yeah.

And, you know, just create a creative work environment.