Jack Dorsey On The Books That Helped Him Succeed

by Y Combinator8/25/2017

Jack Dorsey is the CEO of Twitter and Square. This is his talk from Startup School 2013.

The books he mentions are:
The Art Spirit by Robert Henri
The Score Takes Care of Itself: My Philosophy of Leadership by Bill Walsh

And the song is:
Angoisse by Serge Gainsbourg


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Craig Cannon [00:00] – Hey this is Craig Cannon and you’re listening to Y Combinator’s podcast. Today’s episode is with Jack Dorsey and it’s from our 2013 Startup School. This is my favorite Startup School talk ever. If you haven’t read The Art Spirit, which is one of the books Jack mentions, I highly recommend it. So quick note on the audio, it is a little bit rough on this one. I think it’s still worthwhile to listen to, but if you’d prefer to read the transcript. That’s at blog.ycombinator.com. Alright, here we go.

Jack Dorsey [00:28] – Wow, this is a huge, huge crowd. Well, thank you all for having me, thank you for your time. I’m going to do something a little bit different, something I’ve never really done before, which is simply read to you from some books that have helped me along the way, helped me along the transition, helped me get started, but also help me through many things. There’re so many lessons in these books and please if you get a chance, buy them yourselves and read through the entire things, but I’m going to give you some highlights and some of my experience with the passages.

The first book is a book called The Art Spirit by Robert Henri, who was a painter and I know there’s a lot of affinity for painters in these parts. This is about creativity through the lens of an art student. I’m going to read it through my phone because I could not find a book store that would sell me a paperback version of this today. We’re going to bring up iBooks.

It starts off, “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. When those who are not artists are trying to close the book, he opens it. He shows there are still more pages possible.”

I think that’s so telling for everything that you all are about to do, all the challenges you’re about to face. You’re 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. A cost 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.”

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 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’s promise that he will be a master in the future.”

What he means by this is purely you have to be a master of your own tools. That mastership is 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. Now, don’t worry about the rejections. Everybody 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 objective of panting 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.”

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. 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. Bookmarking interface is not easy on this. “There’s a time and place for all things, the difficulty is to use them only in the 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 cease and command them. Without motive, you will wobble about.”

This in building a team, in building an organization, in 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.

“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 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 a 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.

The second book is by a local favorite, his name is Bill Walsh who is the coach of the 49ers, the San Francisco 49ers. He took a team that was at the very, very bottom and he brought them to the top. He focused entirely on the details. He didn’t come in and just say, “You all need to win games.” He said, “You need to tuck in your shirts, you need to clean your lockers, this is how we answer the phones here.” He set a new standard of performance. One of the hardest transitions anyone has to make and especially anyone in this room has to make is going from individual creation to actually leading a team. It’s something that I certainly fumbled with along the way.

I was not really excited about reading any leadership books or management books and this was actually the first one that I ever read. It was given to me by Keith Rabois when I hired him as our GM at Square and our 23rd employee. I want to read a few passages from his book to you. He starts off the book by saying, “Running a football franchise is not unlike running any other business. You start first with a structural format and basic philosophy and then find people who can implement it. You start first with an idea and a philosophy of purpose, a mission and then you go and you find people to help you implement it.”

The book, if you read it and I definitely encourage you to read this book if you’re thinking about leading teams or building a company or leading a team within an organization, is a series of lists, series of lists of what to do and a series of lists of what not to do. He starts off by establishing a standard of performance and builds standard of performance as thus, “First when you establish a standard performance with your team, you start with a comprehensive recognition of reverence for an identification of the specific actions and attitudes relevant to your team’s performance and production. Number two, you be clearer and clearer in communicating your expectation of high effort and execution of your standard performance. Number three, let all know that you expect them to possess the highest level of expertise in their area and responsibility. Number four, beyond standards and methodology, you teach your beliefs, your values and your philosophy. Number five, teach connection and extension. You don’t want a group of independent contractors. You want people who feel connected that can actually expand the organization. Number six, make the expectations and metrics of competence. They demand in action and attitudes from personal, the new reality of your organization.”

Now what’s important about this is as you start building a team, you need to set expectations around how people need to perform in the company, how people need to act in the company. These can be very, very simple things, but without that you are rudderless, you will react to the outside. If you react to the outside, you’re building someone else’s roadmap and you’re building someone else’s dream instead of your own. As you grow, your collective… Bill goes on to write about being a leader, 12 habits of what to be in a leader and Bill has a lot of again what to do, what not to do and this is the best example of that.

“Number one, be yourself. Number two, be committed to excellence. Number three, be positive,” just probably one of the hardest things to do as you start building technology or as you start building a company. “Number four, be prepared. Good luck is a product of good planning. It’s not so much that people are lucky, it’s that they’re prepared to recognize fortunate situations and act on them immediately when they occur. Number five, be detail-oriented.”

In Bill’s way, he came into an organization that lost every single season that had no chance of getting to the Super Bowl and he talked about those small details that no one pays attention to, pushing our chairs, tuck in our shirts, act professional because if you build an organization that does that you build an organization that cares about itself. It cares about doing great and setting its own standard of performance and constantly raising the bar on that.

“Number six, be organized. Number seven, be accountable. Number eight, be near-sighted and far-sighted. Nearsighted is very very easy for us to do. Farsighted is not so much. Number nine, be fair. Number 10, be firm. Number 11, be flexible. Number 12, believe in yourself. An extra number 13, be a leader” and what that means is actually getting up there and showing and not telling.

Then, he talks about what not to do. “Exhibit patience, paralyzing patience, number one. Number two, engage in delegating, massive delegating or conversely engage in too little delegating. Number three, act in a tedious, overly cautious manner. Number four, become best buddies with certain employees, playing favoritism. Number five, spend excessive amounts of time socializing with superiors or subordinates. Number six, fail to continue hard-nosed performance evaluations of long time or tenured staff members, the ones most likely to go on cruise control or to relax.” This, I see in so many startups is the folks that start early have the least pressure in the company when they should actually have the most pressure in the company.

“Number seven fail to actively participate in efforts to praise and acquire new hires. Number eight, trust others to carry out your fundamental duties. Number nine, find ways to get out from under the responsibilities of your position to move accountability from yourself to others in the blame game. Number 10, promote an organizational environment that is comfortable and laid back in the misbelief that the workplace should be fun, light-hearted and free from appropriate levels of tension and urgency.” You want both, you want a contrast between fun and also having a good amount of tension.

One of the things that he references is General Patton and General Patton’s list during World War I. He had six points, which was how General Patton ran his army. “Number one remember that praise is more valuable than blame. Number two, use every means before and after comment to tell troops what they’re going to do and what they have done. This goes back to setting expectations and making sure everyone knows what’s expected of them and what to prepare for. Number three, discipline is based on pride in the profession, of arms, on meticulous attention to details and on mutual respect and confidence. Number four, officers must assert themselves by example and by voice. Number five, general officers must be seen in the front line during action.” Again show, don’t talk. “Number six, there’s a tendency for the chain of command to overload junior officers by excessive requirements in the way of training and reports.”

Finally, as you continue to build, as you succeed, there develops what Bill Walsh calls a disease, which is the success disease. What happens when you really start winning, what happens to an organization when you start winning, what happens when you start having minor wins that turn into major wins? He wanted to protect against this as well, so he created yet another list. “Number one, formally celebrate and observe the momentous achievement, the victory and make sure that everyone feels ownership of it. Number two, allow pats on the back for a limited time. Number three, be apprehensive about applause. Number four, develop a plan for your staff that gets them back into the mode of operation that produced success in the first place. Number five, address specific situations that need shoring up. Focus on the mistakes that were made and things that were not up to snuff in the success. Number six, be demanding, do not relax. Number seven, don’t fall prey to overconfidence so that you can feel you can or should make change for the sake of change. Number eight, use the time immediately following success as an opportunity to make hard decisions.” This one stuck with me the most.

There is never a better time to do the hard things when things are going extremely well and that can be as an individual that can be as a team as well. “Number nine, never fall prey to the belief that getting to the top makes everything easy.” It doesn’t, it makes it harder. “Number 10, recognize that mastery is a process, not a destination.” That’s what Bill Walsh had to say. The book is The Score Takes Care of Itself, a fantastic, fantastic tome of lists and everything that he’s learned in managing some very, very hard and ego-driven people, football players through the most losing team in the world to winning four Super Bowls in a row, amazing turnaround that he did by building a team and focusing on those details.

Bill inspired me to create a number of lists of my own and I wanted to share a tool that I use on a daily basis that has been most fundamental in my own growth and my own establishment of practices. This is participatory, I’d ask you to bring out your phone right now or your computer and bring something out that you’re going to view on a daily basis, on my dock, on my iPhone, I have notes. Notes is something that I check every single day. I have a note for every single person that I encounter in the company. I have a note for every single thing that I’m doing, every person that I talk with in the company such as Sarah Friar, our CFO at Square has one specific note in my Notepad and anytime I need to talk to her about something, I write it down. Then, whenever, I see her, I go through my entire list, very, very simple memory device.

What I want to talk to you about today is a note, which I call Daily. If you create a new notes in your Notepad or something that you check on a daily basis, this is the most important thing, name it Daily. Then, write the word do: and then go down a few lines and write the word don’t: 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. 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. The easiest way to add to the don’ts is to notice something that 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 one 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 two 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 three, 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 three is six sets of twenty squats and push-ups throughout the day. I just have to do them every day. Six sets of thirty-second planks, run for three miles, meditate on this list, stand up to 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 the heavy bag every day. I want to do a video journal every single day and I want to get seven 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, one of 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. Then, of course don’t drink hard liquor or beer on the week days.

This list, while it sounds very simple has been fundamental in establishing patterns for myself. 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. 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. 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. 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,” has 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.

Normally, I talk about entrepreneurship and I talk about founding a team and I talk about design and product. I didn’t want to do any of that today. I just wanted to share some of the books that have kept me going, the books that I’ve learned so much from, read so much from and I didn’t want to leave on a sour note of just giving you a list of 10 or 12 things from a football coach. I wanted to share and listen with you what we end up doing when everything goes right.

When we move from creation, individual creation and we find something that resonates with other people and we organize a team to build something together, what’s the end product? It’s something that delights people, it’s something that they want to listen to again and again. It’s something that they can’t help, but engage in, they can’t help, but tap their feet to. I want to leave you with one of my favorite songs.

How many of you heard this song or recognize it at all? No one? Okay, this will be excellent then. This is a very simple, but lively song and I find myself listening to it non-stop, but what it reminds me of is just how simple creation can be, but also how complex it can be, how strong you have to be to get to something this deep to get to something this essential, to get to something that actually strikes a chord with so many people and potentially strikes a chord with everyone on the planet. That is why we’re all here in this room. We want to build something, we want to create something that resonates with every single person on the planet.

Music does that in a very easy way, but it’s very hard to get to. I’d like to play this for you and just listen for a minute. This song goes really well with red wine, great red wine.

If you take away anything from this day, it’s that you are the future. You are the ones that have the ideas in your head. You’re the only ones that can actually build it for yourself. That is your task. You are building what you want to see in the world. You are making a bet with the world that it resonates with other people. Sometimes you’re going to win the bet. Sometimes you’re going to lose the bet. You put that loss on the shelf and you bring it back another day. It’s up to you to make that interpretation, to make that creation, and to paint what you want to see in the world. Thank you very much for your time and great luck in all of your work. Thank you.

Craig Cannon [28:58] – Okay, thanks for listening. So as always, please rate and subscribe to the show and if you’d like to read the transcript or watch the video those are at blog.ycombinator.com. Okay, see you next week.


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