Transcript for @Jack: A Conversation with Jack Dorsey
Posted 05/21/2012 09:00AM

Headmaster Nat Conard:

Today, we gather for the culminating event of the 150th Anniversary Lecture Series to hear one of the brightest young minds of our time, Jack Dorsey. As Steve Jobs changed the world of technology, Jack Dorsey, a visionary and an entrepreneur who is still in his thirties, has changed our world of communications. Jack has been recognized by TIME magazine as one of the one hundred most influential people in the world, by MIT’s Technology Review as an outstanding innovator at the age of 35, and, most recently, by the Cannes Lions International Festival of Creativity as the 2012 Media Person of the Year. I had the opportunity to speak with Jack for a few minutes before this afternoon’s presentation, and I can assure you we are very fortunate to have him here today. You’re in for a real treat.

Before we begin, I want to personally thank David Bugliari, Class of ’97, for all of his help in organizing today’s final installment of The Pingry School’s 150th Lecture series, and David’s last name may sound familiar to you. His father is Coach Miller Bugliari, Class of ’52, who is also the Chairman of our 150th Anniversary Celebration. David graduated, as I said, from Pingry in 1997 and went on to Hamilton College. He is currently an agent with Creative Artists Agency (CAA) in California, and I am thrilled to have him here on campus today. At this time, I would like to ask David to introduce his friend, Jack Dorsey.


David Bugliari ’97:

Good afternoon. My name is David Bugliari, Pingry Class of ’97. Being back here is always a humbling experience, and this time it is no different. Upon being on campus for about no more than six minutes, I met up with Dave Fahey ’99, who alerted me to the fact that the keynote presentation I had on my computer was the cheap free trial version, and about five minutes later Jack Dorsey let me know that I am about seven operating systems behind on my MacBook. Always learning!

Thank you so much for having me and Jack. I’m very excited to do this, and, since Nat basically took my entire intro of Jack, we’ll move this along quickly. So, today, we have the honor and privilege to hear from a very close friend of mine, and one of the great minds today—Jack Dorsey.

Jack was born on November 19, 1976, student of Bishop Du Bourg High School of St. Louis. Jack was described by his teachers as determined, motivated, and extremely curious. Jack was so curious that, at the age of 15 years old, Jack taught himself how to code and write programs. Also at the age of 15, Jack wrote, developed, and sold the dispatch software that is still in use in all the taxis, ambulances, and fire engines in all of New York City. In 2006, Jack changed the way the world communicated by co-creating and founding Twitter. By the year of 2010, Twitter became one of the largest social network sites in the world with over 105 million unique users and 55 million tweets a day; and, today, Twitter has over 465 million users and over 175 million tweets a day. Also back in 2010, Jack decided to change the way we interact with our money, our credit cards, and our banks. Jack invented Square. Let’s take a look at how Square is doing now. Square had over $4 billion in annualized payments as of April 2012, $500 million in this month alone, which is over 25 percent growth. They added over one million merchants, and there are only 8 million merchants in all the U.S. And they added 200 employees over the last year for a total of 330. So please join me in giving a warm Pingry welcome to Jack Dorsey.

So, we had a bunch of questions submitted by Pingry students, and we’ll run through a bunch of other questions, some sent to us earlier. And we’ll let the conversation lead us, and, if we have time at the end, we’ll take some questions from the floor.  

Question: How did you come up with the idea of Twitter?

Answer: Great question. As David talked about, I’ve been thinking about this idea for quite some time. My parents were born and raised in St. Louis, Missouri. Actually, I have a funny story that has impacted my life in a pretty significant way. My father, when he was 19 years old, opened a pizza restaurant with his best friend that was called Two Nice Guys. They were two nice guys. My father was from St. Lawrence, so he loves meat of all kinds—so his pizza was the Tim Special, which was all meat. It didn’t even have tomato sauce. So the pizza restaurant started doing very well, and they wanted to make sure they maintained the business and also maintained their friendship as they grew, so they made one rule which was that they would not date the wait staff. They had to hire people. The first person they hired was my mom. The week after she was hired, my dad fell in love with her and went to his best friend and said, “I fell in love with this girl. Marcia. I broke the rule. The business is yours.” I was born ten months later. What I love about this is that my parents have always been true believers of the city. They have always stayed in the city. They never moved out to the suburbs. St. Louis was pretty hard hit over the past 40 years with a very diminished downtown and city life, but they stuck to it. From that desire, I developed a passion for cities and how they work. I became obsessed with maps and what would happen in maps. Take this map of New York City—David is extremely predictive of everything that I’m about to talk about. I would look at maps and I would plaster these maps all over the walls in my bedroom, and my parents thought I was the weirdest thing ever. But I would wonder what was happening in this particular area or on that block or on that particular intersection. So, my parents got a computer in 1984, when I was 8 years old. It was a Macintosh and that’s when Macintosh came out. We also got a hybrid PC Jr. and I just fell in love with them because they were both very practical and they both did a lot of the most amazing things I had never seen before. They could actually alter what they did. I slowly learned how to understand more of the computer and, eventually, I learned how to program it, and the first thing I wanted to program was a map, and so I learned how to draw a map on the screen. I learned how to put some dots on the map and make dots move around, and then I thought what was the most beautiful thing in the world was this map with all these moving dots, but the dots had no meaning whatsoever. So, my parents also had a police scanner, and they also had a CB radio, and these were pretty active in St Louis, Missouri, so I would listen in and I would hear ambulances, and when you listen to these ambulances they are constantly reporting three things: They report where they are; where they are going; what’s going on, so I’m on Fifth and Broadway. I’m going to St. John’s Mercy with a patient with cardiac arrest, and I would take those three dotted points, plug them into my program, and then take a very simple simulation, of constant speed or distance, and I could actually plot the ambulance moving through the city—I could watch it. Then I hooked up more ambulances, I hooked up police cars, taxi cabs, and black cars, and, eventually, I had this living breathing system of the City. I could see the city Live, and I continued to develop this, and I realized there was this entire industry that was pointing to what I saw as dispatch, so I termed this Dispatch software. Then, I found the largest dispatcher in the world. It happened to be in New York City, which I had always wanted to visit and be a part of. I found the website and the website just had a logo. It was a bird with a little packet under it, and it had no other contact information. So I was very curious about technology. I played around a lot and found a hole in the web server. I got through the hole. I found the company’s corporate e-mail list. I found an e-mail address for the chairman and the CEO. Then, I emailed them both. I very simply said, “You have a hole in your computer, in your web server. Anyone can get at your corporate e-mail list, all your private information. Here’s how to fix it, and, by the way, I write dispatch software.”

I was flown out a week later. So I was living my dream. I got to work in the biggest call center in the world, an amazing city, and little by little I had this more and more rich, and more and more beautiful picture of everything that was happening in the city right now, but it was missing one key element, which was the system, the people, so in 2001 I had moved out to San Francisco and I had the first Blackberry. I spoke with RIM about deals for this little pager, and I decided I wanted to write a simple program so I could send an e-mail through the program from anywhere I was, and it would then broadcast out to my friends. I was living in San Francisco at the time. It was a very simple thing. I wrote the whole thing in a weekend. I went immediately out to Golden Gate Park in San Francisco. In Golden Gate Park we have a bison range so there are actually bison who are roaming around the park, which is very odd for San Francisco. But I went there and I sent this e-mail saying I’m at the bison paddock in San Francisco. And it went out to all my friends’ e-mails in real time, and I quickly learned two things. Number one, no one cared, and number two, no one else had a Blackberry, so I was way ahead of the curve. So I put that away and in 2006 I was at this company called Odeo which was a podcasting company. It was my first real job. It was the first time I wrote a résumé. I didn’t have to break into the security system to get a job. And I had no desire to build podcasting. I had no appreciation for podcasts. I didn’t care about them at all. I joined the company, and I learned that no one else in the company did either, so the company didn’t have a strong direction, but it had amazing people, and in 2006, (2006 was the first year that SMS got really big in this country because it was the first time you could send a text message from Verizon to Singular), you could go across carriers. And this had been happening for about ten years prior in Europe, all over the world, so I fell in love with this technology. It was 160 characters. It barely worked back then, but what it allowed was that I could be anywhere, and I could share with anyone what I was doing. I thought that was amazing. Less about communication for me, it was more about broadcasting success.

So I brought this idea up again. This time, I brought it up to my two co-founders who were very familiar with publishing mediums, and communications mediums. And it wasn’t that big of a departure for them to go from audio to podcasting to a little program that did text messaging and broadcast it out to people who were interested, and came up with something that we originally were going to call a Status. This was a very simple drawing back in 2001 around the idea. It took two weeks to develop, and I wrote it with one other programmer, and after the two weeks I sent the first tweet to my other audio co-workers, and we had to name it. It didn’t have a name in the beginning. We wanted something that indicated a physical sensation because when you get these messages, your phone starts buzzing. It twitches. So the original name was Twitch. This doesn’t bring up the best images. It’s not warm or something that people would fall in love with.  So one of our guys got the dictionary out and went down to the letters “tw” and found the word Twitter in the New Oxford English dictionary, and the definition for it was short inconsequential verse of information and chirps for birds, and we’re like “wow, that’s perfect.” So how can we complicate this word more? Let’s take out the vowels and call it “twttr,” and that was the original name that we had gone public with. So that was a really stupid idea. That falls back in, and we made it Twitter so people can actually spell it.

Question: Is there a specific moment in Twitter’s history that you can identify as “The Moment”?

Answer: Yes. The most amazing thing about Twitter is that we had this initial spark of an idea, and the users have constantly redefined it and remade it and made it their own. And when we started, the most amazing moment was, to set this up, we live in San Francisco. We work in San Francisco. There is an earthquake every single day. They range from being very small to very large. When we first launched Twitter, two days afterwards it was the weekend. Everyone was at home or going up to Napa or going down south on a hike or whatever, and my phone starts buzzing and I get this message and it says from Twitter and it says earthquake, and then I actually feel something like that immediately, and that was a huge moment for me because what it indicated was that, with the communication from the technology, it could be much faster than the seismic quake. But also during the earthquake, the first thing you want to know is that you’re not alone and that you’re with other people, and that other people are experiencing the same thing as you are, and, immediately, when I felt the earth shake like that, I knew that other people were out there experiencing the same thing and the world suddenly feels very small, and we saw that again and again.

The first big moment before with Twitter was in the 2008 elections. Barack Obama and Senator McCain were debating. We built this special site for the debates called election .com. What was amazing about this was that they were tweeting during the debates, and people were having conversations around what they were saying. When Senator McCain said “lipstick on a pig,” something blew up all over Twitter. You could see exactly what people thought about that phrase. And in that moment, and it was just a huge, huge moment, that was the catalyst for us in the public eye, and then we had a lot of celebrities join, we had a lot of public figures join, and then we had these major global events like the Iranian election and protests where you know for many people in this country and around the world, Iran is a black box. It’s not something we know or understand. It’s not something we encounter every single day. What was amazing about this moment is that people were taking to the streets and they were using Twitter to share videos, to share pictures, to share thoughts, to share articles, but they were doing so from the ground. They were doing so from their own perspective. They were doing so from their phones and this was coming directly from them. It was not coming from a censored media, it was not coming from a camera just broadcasting. It was coming from a single individual—and anyone around the world that was following that individual could have a conversation in real time with that person on the ground, and what’s amazing about that, to me, is, again, it makes the world feel a lot smaller. It allows you to learn more about how other people are living around the world, and what I hope is that a simple technology like that can enable people to talk about how they live their lives, very simply what they do when they wake up, what happens during my day, what do I think about when I go to bed. If we have more and more people doing that, then we have a greater understanding of how everyone lives. If we have a greater understanding for how everyone lives, we can develop greater empathy. If we have more empathy, we can reduce conflicts. And we’ve seen this again and again and again, and on the surface starting with Iraq and a big part of Arab Spring was also conversed in this way and amplified in this way. So I think to answer the question, there are many, many, defining moments, and that’s the most exciting thing. We’re not building a service that’s just focused on music, or focused on celebrities, or focused on politics, or focused on social. It has a very dynamic range and people come to it every single day, and they define what it is for them in the same way that you approach an outlet, a power outlet. You can plug in a toaster oven. You can plug in a vacuum cleaner. Or, you can plug in an electric guitar. And you can create whatever you want with that. So we see Twitter as a utility that people can come to every day, and define it for themselves, and that’s pretty magical.

Question: How did you come up with the idea of Square? And then one student asks (who is tweeting in the audience as we speak), “I keep trying this on my parents but they don’t get it.”   Can you explain it to us all now?”

Answer: My advice is to download the application from the Square marketplace. We’ll send you a free credit card reader. And then plug that in to your phone, talk to your parents, and ask for their credit card. They’ll save $500 dollars and they’ll get it. Then all of a sudden, they’ll understand what that means in that moment and then you can go celebrate.

So it’s very simple. This is a little credit card reader that we give away for free that plugs into a mobile phone and to an iPad. What’s interesting about this is that there are over 180 million card holders in the United States alone. Less people are carrying cash with them. Less people are carrying their checkbooks. More and more people are carrying plastic cards around. So you know you have this economy where it is going more and more digital, and these are pre-paid cards, gift cards, dental cards, credit cards. You have barely anyone who can accept them because the financial industry has put so much constraint on actually getting in the door. And that’s why there are only 8 million merchants who accept credit cards, total, but there are 26 million small businesses in the U.S. that don’t, and the only reason for this is that it is way too complicated to set up a merchant account.

Typically it takes about one day to four weeks to set up a merchant account to start accepting credit cards. We got the process down to one minute. You download an application for free. We send you one of these readers. If you don’t want to wait for USPS, then you can go to Walgreens or CVS, or Walmart or Target, or the Apple Store and buy one for $10 because there is a $10 rebate inside the box, so it is still free, and you can start accepting credit cards and plug this into your phone. You type in an amount. You take Dave’s credit card, swipe it through, and then the money from his credit card goes into my bank account the next day, and this was revolutionary because of the speed, the velocity. From that, we’ve seen this massive growth because people out there want to accept credit cards—golf instructors, piano teachers, lawn care, people who want to start an ice cream stand, people who want to start a café, people who want to start selling clothes or start selling art. And that’s actually how the company began, because my co-founder, Jim McKelvey, was a glass artist, and he sold his beautiful (some would call them beautiful. I always call them beautiful, but some people would disagree with me) glass fossils, and would sell them for $2,000. He was at an art fair trying to sell these fossils, and a woman came up to him and she said, “I would love to buy that fossil.” He said, “O.k., it’s $2,000,” and she said, “Here’s my Amex.” He didn’t accept credit cards. He had tried to get set up with American Express before, but he was rejected. Only about 10 percent of the people who actually apply for a credit card get accepted. So the woman said she was going to go home and get a check and would be back in about 30 minutes. She never came back. $2,000 for an artist is a month of rent. It’s survival. It’s the option of continuing what you love to do more than a normal job. This is quite meaningful, so he called me up on his iPhone, and we were sitting there. We both have these general purpose computers next to our ears and we begin to think, why is it so hard for a merchant to get set up with a credit card? We took about a month. We built a credit type, we built simple hardware. It was really big. We plugged it into a headphone jack of an iPhone. We hired one person to write front-end software. Then I wrote all the back-end software. In a month it worked. And I was super excited. And then I would go up to people and I would say, “do you want to see my new idea?” And they would say, “yes,” and then I would say, “give me your credit card.” And they would be like, “well why?” and I would say, “trust me. Just give me your credit card.” And some people would give me a credit card, and some people would give me their black American Express, and I had to take $500 from them. I made over $1500 just demoing the new idea, which was amazing, and it really resonated with folks, so we decided to make a company around it, and that was about three years ago, and we since talked about one of our recent stats but we’ve evolved the story a lot.

We started with the individual sole proprietor, the personal trainer, the dog walker, the baby sitter. We built a full register for the iPod. We have the most beautiful register in the world because it’s all software, but then we decided that this wasn’t the full story. The full story was actually the wallet. So we developed this application called Card Case, which was recently rebranded as Pay with Square. This allows you to link your credit card once and set up this really, really unique experience where I can open up the app, link my credit card once, in the same way I would do with Amazon with one click, or iTunes, I start my card, and then hit buttons to pay.

We wanted to bring this concept to every single merchant, so what we did was link your credit card so you can see all the merchants around you, all the businesses around you, and you can see a coffee store, and I can open the card for the coffee store, (a coffee card), and I can see where they are. I can see what they sell, the whole menu in real time. I can see some reviews on the place, but I can also open a tab at that time, and this is very similar to a card tab where I hand over my credit card and I can go all night and just say my name to get another drink, but, depending on where I am, I don’t have to hand over anything. When I am in a particular radius of about 100 feet of that register I can open a tab, put my phone away, leave my wallet at home, go up to the counter, and say, “I’d like a cappuccino, my name is Jack.” They find my name in front of a picture, they touch that. I take the cappuccino and I walk away, so I literally do not have to swipe the card. I don’t have to take my phone out. If it’s my favorite place, I can automatically open the tab when I am next to the counter, so we think there is a real strong future in this technology. The interesting thing about the payments world is that money as a concept has been with us for about 500 years. It started with trading with seashells. And it touches every single person on the planet; and, at some point in your life, every single person on the planet feels bad about it, which is terrible, so we think we can change a lot of this by really focusing on the small details, focusing on the design, taking all the bad practices of the financial industry away, so people can build their businesses and feel really good about the understanding of their money.

Question: So, if you’re a merchant and you apply for a credit card, what does the credit card company take as their percentage from you?

Answer: So, typically, let’s say you’re starting a coffee store, and you go to a bank and you say, ‘I want a credit card terminal,’ and they’ll say, ‘O.K., do you want a mobile terminal?’ and you’ll say, ‘yeah, because I don’t want to install a DSL or a WiFi in my location. So they’ll say, ‘O.k., $900 for a credit card terminal, and then there is a monthly fee of $50 or $30, and there is monthly minimum you have to do, $1500 per month. And there is a setup cost of about $100. There is a break-up fee of about $500. The transaction cost is going to be 1.64 percent, and $.30 or $.50 on every transaction, but there is a little asterisk next to that 1.64 percent, and it says ‘for qualified cards only.’ And the terrible thing about what merchants have to face every day is that there is this thing called the interchange, which means, depending on the card the payer uses, that’s how much the merchant is paying, so, if you use a normal debit card with no rewards on it, the merchant will maybe pay 1.79 percent to accept that. If you use your airline rewards card or your corporate card or your black American Express or something with a lot of awards on it, the merchant may pay anywhere from 4 percent to 5 percent to accept that transaction, and the ridiculous thing about this is they have no idea. They have no idea that they are being charged differently for different types of cards, and they don’t find out until 30 days later when the merchant statement comes, so, for new merchants and small businesses, they run really, really lean, so every single dollar in their bank account is deeply meaningful. So what happens is they get their money in about 2 to 5 days from the credit card processing, and the fees actually come out 30 days later, so the banks come in and take the fees out, and now the terrible thing is the merchant doesn’t know how much they have to pay in credit card fees because it won’t be calculated until the end of the month. The banks come in. They take the fees, and often times the merchant doesn’t have enough money in the bank to cover the fees. So what happens is they get an overdraft and they are charged another $100. Then there is no money in their bank account, and they can’t buy their inventory, and it is just a ridiculous thing. What we wanted to do was simplify all that. There are setup costs. There are no monthly fees. No fees of any sort except for the fee on the transaction, which is 2.75 percent always for any card that comes over the counter, including American Express. It’s 2.75 percent, and you’re going to get the money the next morning, and it’s going to be minus 2.75 percent, so you know everything in your bank account is your money, and no one is going to touch it. So you can face your business off that, and we’re giving you all this data on what is actually selling, what’s not selling, what you should have in your stores that you can actually build your business on. No small business in America really has access to any of this. They have access if they buy a $15,000 point-of-sale system, but, even if they buy a $15,000 point-of-sale system, they don’t know how to figure the business out. To give them very simple information, like how many cappuccinos have I sold today, what percentage of people are buying biscotti, what my busiest hour is, what happens when it rains, we give all that for free and the rest of the industry just does not. So it’s pretty terrible that a lot of the industry is focused on leveraging bad behavior to reap fees—a lot of this is ending, but our goal is to make sure people have information so they can make the right choices. That’s all what really matters.

Question: How and why should all business people in this audience today be using them?

Answer: I think the biggest reason is really running down the information. A lot of the web and a lot of the technology companies have benefits from the fact that we have all these really deep analytics, so there are all these tracking mechanisms, so that if you put the picture over here or the links down here, or the sentence from here, you can really figure out what works and what doesn’t. What people like and what people don’t like. A big part of building any business is understanding how the business is running, and, for a lot of businesses in America, especially small businesses like cafés, they don’t really have any sense because the experience and even for a customer, as you go up to the counter and you order a cappuccino and they have a cash register they bought at Costco for $400, and they have a credit card terminal right next to it which is completely separate, and the customer goes up and orders a cappuccino, they hit the cappuccino button and it says $3.50 on this little receipt. They hand over your credit card, the merchant goes and then takes the credit card, types $3.50 in the credit card terminal, swipes that, takes that receipt, hands it over to you to sign, you sign it, they take it back, they give you your credit card, they take the other receipt, staple that together with a coffee card, give you that back and you throw that away, so it’s a completely missed opportunity for everyone involved. And then, at the end of the day, the merchant has no idea how many cappuccinos were sold. They actually count cups, so they actually look at how many cups are in their dishwasher, or stacked on top of the cappuccino machine, to determine how well cappuccinos are selling, and how to increase that with advertising or other methods. So, simply having access to that data allows you to make decisions based on where you want to go or not, and some businesses want to take over the world. Some businesses want to stay a local corner shop and be happy, but it’s important that the business owner gets to make that choice. So, what we think is really powerful about Square is that it presents that data in real time so you can make your own choices. This is the smallest part of what we do, which is accepting payments. What is really magical about this is the data. Just to put this in perspective, anyone remember the lemonade stand game where you’re given a 60 percent chance of rain, and there is an overstock of lemons so you can price them at whatever you want, and you change all the considerations, it ends up being 97 degrees the next day, so you only have 12 glasses of lemonade. So you could have made a lot more money.

Question: Facebook or Twitter—what is the best social platform for middle schoolers?

Answer: I think, obviously, I’m biased, but the way we think about this is that Twitter is social interest, and social networking is just one aspect of what we do. Twitter is a great social interest medium, but the breadth of interaction is much, much larger.

I think generally what makes Twitter interesting, unlike these other services, is that it is naturally public so the conversation is happening in public. It’s not happening behind the scenes. It’s happening all over the world, so I can follow someone in Iraq. I can follow someone in the middle of Turkey. I can see what’s happening with their day, and I don’t have to be mutual friends with them to figure out what’s happening over there, and it scales all the way from individuals, to public figures, government figures, government leaders, the president of this country, city government, local government. And not only can I follow what they are doing, but I can actually have conversations with them. Mayor Cory Booker is a good example of this, of how he is using the technology in amazing ways. Not only is he constantly sharing his thoughts about the world and about the city of Newark on Twitter, but he is also using Twitter as a conversation medium with his citizens. During the great snowstorm of 2010 in the Northeast, he was tweeting messages to his citizens. One citizen tweeted back to say that he was snowed in and needed diapers, but couldn’t get out. The mayor tweeted back to say that help was on the way, and made arrangements with his staff to deliver the diapers. So I would say Twitter is the best social platform.

Question: So it’s hard enough running one company. You have co-founded and are running two, Twitter and Square, right now. How is your week? How do you balance your time? What does your average week look like?

Answer: First of all, we have an amazing leadership team at both companies. I am CEO of Square, and I have a great COO and a great executive team. At Twitter, I’m Executive Chairman, and we have a great COO. We have great leadership over there. So finding the best people is the first thing, and that’s my number one job—to make sure we have the best people in the roles that really bring the company forward. So that’s number one. Number two is just organizing time. I think in the same way we design products and companies, we can design schedules and be very thoughtful about it. I like a lot of discipline around my schedule because I like setting expectations for the entire company of where I’m going to be and what I’m going to be thinking about, so we can have a very easy conversation when we actually get to that time. So the way I structure my time is that on Sunday I start the week. Sunday is great because it doesn’t have the hustle and bustle of the office. It’s great for strategy thinking, about what’s ahead, thinking about the week ahead. It’s also great for recruiting because you can have a very easy free-flowing conversation, so I do a lot of recruiting and strategy on Sunday. This is in the office or, off site, I go on hikes and walk even to recruit someone and learn about a person, and also to discuss a strategy. I kind of “theme” all my days. Monday is focused on management. We have a kind of management 101. We have our directional strategic meeting for both companies on that day. Tuesday is focused around our products. So all our product meetings are on Tuesday, and product reviews are on Tuesday. Wednesday is for marketing and communications, and growth. I try to arrange all of my external meetings on Thursdays. This includes meetings concerning partnership and anyone we have to meet outside of the company. And then Friday is focused on the company and the culture, and we really focus on how we are building the company. Friday night through Sunday morning is my time to go with friends, have dinner, go hiking, visit schools.

Question: How many hours do you spend a day at each company?

Answer: I spend about 8 hours a day at each company. It’s very fluid now. In some cases, I have to spend a lot of time at Twitter, and then I have to spend a lot of time at Square, so it’s not as firm as it once was, was but it’s working out. I feel overwhelmed when I don’t feel inspired. Not feeling inspired is my checkpoint. If I’m not feeling inspired every morning when I wake up, then I know something is wrong, so I always want to feel inspired. I want to feel inspired with the people I’m working with.  I work very hard because I love what I do. And I love the people I work with, and that’s really what drives me, so when you really love what you do and you love the people you work with, then time fades away.

Question: Students in this room who have ideas for start-ups or have a start-up company, or have a kernel of an idea, what advice would you give them?

Answer: I think the biggest thing is you need to start working on it because an idea is nothing without someone actually executing it and working with it every single day. And I think far too often—and I’ve done this all the time—when you have an idea, you think about it, and you think, well I could work on this idea, but I need Dave who is in a full-time job, and if he was working with me, then we could work on this idea, or if this technology existed, then we could work on this idea, or if I had this money, or if I lived in this particular place, or if I knew this particular person, and you just have excuse after excuse after excuse, and then the idea never gets worked on. And then someone else has the idea, and then they work on it, so I think the most important thing is to get started. It’s the hardest thing to do, but the easiest thing to do is to start drawing it up, or coding it up, or writing it up, talking about it with someone you know and trust and that you want to work with, then you can start iterating on it, and you will get feedback. Dave may say “that is the stupidest thing I ever heard,” and you will dig in on that, and figure out what parts are stupid and you realize this one part, and then you think about it more and think “wow, if I change this, then it’s actually much better.” And now you’ve developed the idea a little bit more and that’s how I think about the concept of building a company.

I don’t really consider myself an entrepreneur or someone who is building a company. I really like working on ideas I want to see in the world. What’s amazing about this is you can have an idea, and then you can get really excited about it, and you start working on it, and then you realize you want other people to help you work on it. I want to have Dave work on it full-time. In order for Dave to leave his full-time job and work on this idea with me, I need to pay him. In order to pay him, I need money, in order to have money, I have to have an investment, so in either of these cases I need a corporate structure to place that money into. So if suddenly you have a company, then once you have a company, you hire more people. Then you need a board. Then you need more investors. Then you need to figure out how you’re approaching the market. Then you need advertising and all these other things, but all of these are in support of the idea.

Mark Zuckerberg, who started Facebook, had a really strong idea and built a company around it to support the idea, and now it has been pretty much everywhere. The same is true of Apple. Steve Jobs wasn’t a business man. I considered him to be an artist, and his medium was technology. His medium was a corporation. But the focus was the idea. The focus was the product. Everything else took care of itself, so a company and a business, and an entrepreneurship, is the most efficient means of spreading the idea around the world right now. In 100 years, it might not be the case, but right now it is. I had to learn everything from scratch on how to build a business to support this idea around the world. So you have to start somewhere, and you have to start small.

If anyone has a question from the audience, we have a little bit of time left. I’ll ask one question while people might be getting up the courage to pick up the microphone: What is now next for you? What area do you look at to get into next? What is the future?

Answer:  Well, what I think is that I’m fortunate to have both Twitter and Square. They represent something foundational, foundational to civilization. Twitter represents communication. Square represents the exchange of value, money and currency, which is another form of communication. When you work on these foundation issues, you can fix a lot things. With Twitter for instance, people are creating support groups for preventative medicine in the country. They are getting active and supporting each other, so they are changing the dynamics in the medical industry.

We have seen the same thing with Square. We have doctors who are using Square to go to people’s houses and taking money directly from the patients. The major part of the damage in the healthcare industry is actually from not being able to pay doctors and nurses in a reasonable time frame. They often get paid six months to a year after a service is performed because it has to go through the insurance industry. And it turns out if it is a direct payment, it’s actually much cheaper for both the patient and for the doctor, so working on something foundational solves a ton of issues and a ton of problems. I think that what’s next—making sure we can apply this platform to every product I’m talking about.

Question from audience: Last year, a number of governments were under threat. I think they tried to shut down Facebook, and I’m not sure if they tried to shut down Twitter, but I wouldn’t be surprised. How would they go about doing that, and what would we do to prevent it?

Answer: That’s a good question. So we know the Egyptian government shut off the net for a few days. They shut everything down, and there were a number of companies who got together to provide easy access to tools to route around that from their mobile phones, and it worked. Three days later, the entire net was turned back on for the country of Egypt, and people started conversing again, so there is no one answer to that. It has to be a case-by-case basis, and it has to be tailored to the government, to the market, but people are always going to find a way to communicate, no matter what barriers are placed in front of them. We see this throughout time. Just look at the Berlin Wall. Throughout history, people will always find a way to break thorough those barriers because people naturally want to talk with each other. They want to communicate. They want to be close with each other, so I’m not worried, so it is just a question of how we can increase the velocity, so they can do that faster and there isn’t going to be a general answer to that.

Question from audience: What were the problems and small challenges you faced with Twitter and Square, and what would you do to overcome them?

Answer: That’s a great question. It’s not really past tense. It’s present tense and future tense as well. We always have problems and issues with both companies, and, to be honest, every day is a roller coaster. You experience the highest highs and the lowest lows. You have a day when everything is looking amazing, and suddenly you hear something about your competition that makes you think oh my god, this whole company is out of business. What are we doing here? Then, 5:00 rolls around, and something amazing happens, and you’re like, “oh, we’re at the top of the world. This can be global. We’re taking over the world.” And this happens every single day, and what’s most amazing about starting something new—experiencing something new gives you a rush and helps you focus. It helps you be creative. It’s really an amazing feeling.

In terms of the bigger system challenges, I worry every single day about Twitter and the fact that it is almost just over 1,200 people right now. Square is 330, and that’s a lot of people working together, working on one thing. It’s like walking together. If two people are walking together, and one is out of sync, it kind of changes the tone of the conversation. It changes how you relate to each other, so, if those 330 people are out of sync with each other or are doing something differently, then we’re going to start tripping over each other. And we’ll actually be competing with ourselves, so I’m not worried about the competition outside the company. Certainly, look at what they are doing and take note, but what I’m really worried about is “can we, as one company, step together cohesively every single day along one path for one purpose,” and that’s my biggest job—to make sure we have a single purpose and that everyone in the company understands the purpose and that we’re coordinated, we’re focused, we’re doing the right things every day because, as we get bigger and bigger and bigger, it’s easy to be distracted. It’s easy to look all over the place, and that is actually what kills companies. That is what kills civilization, in that you’ve lost your purpose and you’ve lost your sense of community and common thread that brought you together in the first place.

Question from a student in the audience: Did you think you’d be lucrative when you were making Twitter? Were you nervous when you were making Twitter?

Answer: No. If you think too far in the future, you’re not going to feel anything in the present, so I think you have to focus on the moment. And in the moment, I was just excited to get to a point where I could actually send a message with my phone and it would buzz someone’s pocket. It was kind of a prankster move, which was to buzz a pocket when least expected, and it sounds ridiculous, but that sort of small action was actually quite meaningful because I could, with this software, actually change something physically, and this was amazing to me.

I could write a line of code, and I could actually buzz someone with this device, so that’s all I was going for, so once you have that, then O.K., what’s the next thing. Well, now, I would buzz six phones at once, and, when I send one message, six phones buzz. Can I do that when we are all in a very serious meeting together, where I send just the words like “ha ha,” and everyone’s phone starts buzzing, and I pull it up and it says “jack calling ha ha.” That’s compelling to me, so then can I do it outside the meeting room? Can I do it in the city? Can I do it in the world? We actually had a programmer in Germany, in Hamburg, where I sent a message and just a second later he got it and that’s amazing because he’s all the way around the world and I’m sitting here in San Francisco just typing in my phone, and it buzzed his pocket when he was in a nightclub dancing, and he thought that was rude. So there are little moments like that you focus on so you don’t have to be nervous, and you get instant feedback or an instant rush. In seconds, you are out in the open.

Question from audience: When did it hit you that you created an amazing enormous catalyst for change, or do you see it that way?

Answer: The original idea was to understand how cities work and how they function, and why make yourself understand a city when you can understand a whole world. And what I think is amazing about Twitter is I can just pull the phone out of my pocket, open the application, and I can see what the world finds most meaningful right now. Whatever the world is talking about, I can see, and then I can limit it down to Iraq or Iran. I can limit it down to Paris. I can limit it down to San Francisco, or I can limit it down to people who like NASCAR, and see what’s important to those people, or what’s happening with baseball with the Yankees, and I can see what’s important in the game right now. So that sort of global vision, that pulse of the planet, then go all the way down to an individual level, is amazing, and it’s never been done before. Then it’s a question of what people can do with that, so I hope what people do with it is that they remain curious and they remain students, and they learn about what’s happening in the world, and they learn what actually they can take to make it better. That’s what impacts change, and you know the greatest change is not building—coming from the technology builders—but the technology users, the folks who are using the technology every single day and redefining this in new ways. We did not create the technology and mandate or have a vision of everything that happened. The users did. The users wanted it to happen, and Twitter in that case was a tool to amplify their voice and to shine a light on something that needed to be seen that was dark in the past.

Question from ’76 Pingry graduate: I am sure you’re aware in the last year that there has been a lot of debate about the value of a college education. What advice can you give about going to college and following your dreams?

Answer: I think what matters most is a desire to learn. I think that’s really what’s important about education, about systems and structures and the amazing institutions that we have set up. From a school’s standpoint, it’s important to tailor that to each individual student because each student will tailor what they learn to themselves in a different way.

I went to New York University (NYU), and I learned some interesting things there, but I learned much faster outside of NYU than I was learning inside. This is partly my fault, but I really was learning a lot from working at the dispatch company. I was learning a lot by teaching myself how to program and refine my skills, and I wanted to focus entirely on that. I wanted to do something non-standard, and really give myself to programming and build something.

I am somewhat impatient, so I dropped out of school, but I’m only a semester shy. Then I moved to San Francisco and that company was a complete and utter failure...