Jack Dorsey is a co-founder of Twitter, as well as the founder and CEO of Square. In this interview, he sits down with Detroit’s Chief Information Officer Beth Niblock to talk about how technology can impact commerce—which he likens to communication—and ultimately bring economic growth to cities like Detroit.

Kirkpatrick: Now, I will say, I actually believe Jack Dorsey, who is about to join us, who is of course the CEO of a for-profit company, but I also—and one with a very high valuation, I might add—but I actually do believe that a lot of reasons he’s doing it are because he’s trying to do something that really improves the world. So you can judge for yourself, because he’s gonna be up here—you don’t need to be told what he did—he really invented Twitter, he’s started Square, which he’s now running, and he’s still deeply involved with Twitter as well.

He’s going to be interviewed by Beth Niblock, who’s the CIO of the City of Detroit, and I’m very excited to hear that interaction, Jack being such a deep believer in city technology as a transformative force. So Jack and Beth, please join us onstage; I can’t wait to hear what you have to say, so thank you.

Welcome, Jack.

Niblock: Well, I can’t tell you how great it is to be here today, because this time last week I was on the witness stand for the bankruptcy trial for three hours, so this is way more fun, and it reminds me that I have probably the coolest job in the universe, so thanks for having me. And we are so glad, Jack, to have you here again.

So I thought we’d—we’ve got a compressed amount of time, so I thought what we’d do is break this into three sections and then leave about 10 minutes for questions and answers. So first, we want to talk a little bit about Square, your new venture. Square’s whole motto is, “Making Commerce Easy.” Can you talk a little bit about your vision of the whole commerce ecosystem?

Dorsey: Absolutely. And first of all, thanks for having me back. This is my third year in a row; my parents come all the time as well. Where are my parents? My parents are right there.

Niblock: Hi, Mom and Dad.

Dorsey: I’m from St. Louis, Missouri, and the reason this is so important to me is I see a lot of parallels between Detroit and St. Louis, in all the best ways and some of the ways that we need to address and fix, and my dad would come up to Detroit all the time to work—drive from St. Louis, fly from St. Louis—so it’s definitely a city that’s important to our family in many ways.

But no matter what size of business you are, whether you’re just getting started and you’re a piano teacher, or you have your first brick-and-mortar location just opened up on Cass Street, for instance, or you’re a Facebook or you’re a Twitter, there are only three things that you need and only three things you need to address. And they are, number one, access to capital, number two, new customers, and number three, tools to retain those customers. And when we started out, we built a reader that enabled people to accept credit cards. And a lot of people said, “Well, they’re a payments company. They’re really driving around payments and accepting credit cards, and whatnot,” but actually what that was about was hitting point number two, which is making sure that you have new customers and you can make every sale. And what we found was all these buyers were using plastic cards—debit cards, credit cards, pre-paid cards—and they wanted to use them everywhere, because they were convenient, but not a lot of sellers could actually accept them because they just didn’t have the tools. They had to go to a bank, it would take a month, they had all these fees, they would have to buy equipment, lease the equipment, pay all these service charges, and it was just—it ended up being really criminal, in ways that were obtuse and took a lot of time away from them. So our first manifestation of us as a company and us as a product was to make sure that we’re building the smallest amount of hardware possible, so that a seller can always make the sale, and that hits point number two. Point number one, of access to capital, was making sure that they had—after that swipe—they had those funds in their bank account the very next business day, instead of a week or two weeks, which is what typically merchants have to wait for. And number three is really building a register around it, which allows them to retain their customers and build loyalty.

So what we saw when we came onto the scene five years ago, was there was a lot of fragmentation. There were a lot of people doing one tiny little part—someone doing payments, someone doing credit cards, someone doing the bank, someone doing the point-of-sale. And they, none of them were connected together at all, so our simple thing was to solve the most critical thing first, which is enabling people to make every sale by accepting that credit card, and then building more and more towards commerce. And commerce is very different from payments, because payments is just a tiny little aspect of everything that happens in a commercial transaction. The definition of commerce is the activity between a buyer and a seller, and it’s a very simple, human interaction that’s been around for over 5,000 years. We were actually trading goods and services before we were using language to trade stories, but for whatever reason, it’s become more obtuse and more abstract and harder to get into, whereas communication always becomes freer and simpler and more straightforward. So our mission is to make that as easy as communication, to make it as free as communication, so that anyone can get into it, it’s accessible, and they can really use the tools to build their businesses up.

Niblock: And I know that you all packaged a lot of new data analytics into software for the merchants, so that they can really understand their business and what’s driving it. I know that you had a visit this morning with a Square merchant called Human here in Detroit. How was that, and what’d you think?

Dorsey: Well, I always love visiting our merchants. You know, one of the reasons we do this is because we love local commerce. We love local merchants, and there’s a trend of going to more and more folks who are local businesses with local character, and are able to maintain their character. And I think one of the biggest trends you see with technology is that small businesses and small teams now have the freedom to stay small and still interact on a global canvas. So a team of six can build a technology and can build an application that can actually impact the entire world, and that really leverages everything that we have. So the reason we visited Human today, on Cass Street, was because they were using a product and a service we have called Square Capital, which really addresses point number one, back to access to capital. And what this is, is we have such a deep understanding of all of our sellers, because they’re running and accounting for their entire business on our register that we can eventually, with an extreme amount of confidence, send them an email saying, “We’d like to give you, we’d like to advance you some capital. Here is exactly how much it’s going to cost. Touch this button if you want it.” You can go out and you can try to get a small business loan or whatever other ways to get capital that you have before you. But we send you that email, you touch that button, and the money is in your bank account the very next business morning, right?

So we have salons who get an advance of funds and they buy new salon chairs, which means they can have more customers. Human actually used those funds to hire a new employee and buy mannequins, because they wanted to take pictures for more of their online sales as well. And the way that money is actually paid back is by actually selling, actually running your business. So every swipe of a customer’s credit card that comes through Human, they’re actually paying the advance back automatically. And we intend to have the lowest rate and the easiest access so that, typically if you go out for a small business loan, it takes about one to three months and there’s a very low chance that you get it. They need a lot of collateral and they need a lot of assurance. We don’t need any of that, because we have so much confidence in our businesses, because we see the business and, you know, they have, they continue to build trust in us as we extend that, and then they pay it back. And, you know, the folks who actually engage in a capital advance end up doing more and more of it to build their business. And if they grow their business, our business grows as well.

And yes, we are a for-profit company, and the way we look at this is, you know, we, we need capital, we need revenue, and we need profits, so that we can invest back into growing our business. Revenue and money is like oxygen. It’s not something that you want to live for, it’s something that you absolutely need to live. And we want to serve more people around the world, and to do that we need investment, we need capital, just like all of our small merchants need capital to grow their businesses and to serve their customers.

Niblock: Well, I want to shift for a second to Square and your support for science, technology, and math, and talk about your support of coding, because that’s something that’s near and dear to our hearts here in Detroit.

Dorsey: Yeah, so we have a specific focus on getting more women into engineering, and we have a lot of this energy at Square. Over 52 percent of the company is actually led by women. We have three women on my team, my executive team, who lead engineering, who lead finance, and who lead the business team. So our CFO, our VP of Engineering, and our VP of Business are all very, very strong female leaders, directly on my team.

Over 60 percent of all Square sellers are actually women-led and run and owned, and the national average in the States is 30 percent. So we want to build technologies that are accessible to everyone, that everyone can pick up and use and really do whatever they want to do with it, wherever their passion leads them. But what’s really important for us is that we have a diversity of perspective inside of our company, and where there’s a lot of lack of diversity of perspective, specifically in engineering, is women leadership and women engineering. And we have invested pretty significantly in two specific programs around this, to help address and to seed more of the engineering attitude and the skill within our company and abroad. One is Girls Who Code, which is actually a national program started by a woman named Reshma who—all of the, my Twitter co-founders and myself invested pretty heavily in and supported, but also holds an intensive class for about seven weeks. There’s about 20 to 30 senior high school girls to entering-college girls, that spend seven to eight weeks within our companies, within Twitter, within Square, learning how to program. And not just learning the abstractions and the academic parts of programming, but the actual practicalities of programming, so they can leave that and actually know how to build something. And the goal for all of them is to build a product that they can show off at the end, and all of them do.

That’s number one, and then Square has a program called Code Camp, which invites people for an intensive weekend—invites women from, who are just starting college or juniors in college, and we just started one that’s focused around purely high school, to get younger and younger and younger—to do the same thing. We take time from all of our staff, from our employees, during the workweek and also on the weekend, to teach them how to program. And these are all women who want to learn how to program, who want to make something. And that’s one of the most amazing things about engineering, is you can start with a very, very simple tool, and you can build something and you can see the results of it almost immediately and almost instantly, and it feels amazing. And then when you share with someone else, and you get to see them feel it and see them interact with it, it just emboldens you even more and if gives you confidence. And that was my own experience when I taught myself how to program, is it just gave me confidence, because you see the results of it constantly. And I think that’s what’s really missing, is these tools that inspire a confidence in people to really go out on their own and do their thing, and to build something that is really relevant, not just to them, but hopefully resonates with a much larger audience. So we invest a lot of time and a lot of money in it, and we think it’s definitely worth it.

Niblock: That’s fantastic. I want to shift really quickly to two quick things. Cities—your love of cities is well-known, and you have chosen to come back, of all the offers that you get, which I’m sure I can’t even imagine, you have come back to Detroit for the past three years, three years in a row. What is it about Detroit that kind of draws you here, and what do you see for Detroit in the next couple of years?

Dorsey: Well, I mean, I’m always attracted to places with really, really deep soul and deep passion, and Detroit is one of those places. I mean, you walk around the streets and you feel—you feel the energy, you feel the soul, you feel the fight, and it’s similar to what I feel in St. Louis, it’s similar to what I feel in one of my other favorite cities, which is New Orleans. You know, these are cities that just have a lot of character, a lot of fight, and a lot of soul, and I love that. So I want to help in whatever way possible, and you know, I come from a technology background, we do intend to use those technologies to have positive impact on the world, and it’s not really a factor of what we intend, but it’s a factor of what people use the tools for. And I think we often get trapped in this word, this word “technology” because it becomes this, like, overwhelming thing that has this abstract notion of what it is, and all of you have probably heard or maybe even said, you know, “I don’t understand technology. I’m not good with technology,” and this is one of those phrases that becomes this very abstract concept that people just get a little bit afraid of. But at the end of the day, technology is really just a tool. That’s all it is, and great tools get used, and great tools save time for people and they create efficiencies and they allow us to focus on things that are more meaningful to us. Bad tools take attention away and they actually take time.

So we want to build great tools, and I think the role of the city in that is to first vocalize support, vocalize support that we want better tools to make the running of our government, to make the balance of our city, that make the balance of the public sector and the private sector more efficient. And there are a lot of cities around the country who are giving up a lot more of their data so people can come in—and specifically college kids who really want to build something and really want to build something to scale, and can take all that data and feed the data back to the city in an insightful way, in a way that allows them to make a better decision. So I think the more we surface what’s actually happening in a city in real-time and we build technologies to take insights from those, we can make better decisions about how to grow the city, what the city needs, and we can build, you know, a stronger economy, ultimately, and a stronger civic society. So again, these are concepts, and concepts and ideals we have to make real. And it’s not just companies that have to do it, it’s not just city governments, it’s people who want this and want to use it, and are demanding that this data and this technology is available to them to make their lives better. And it’s definitely possible, as long as we’re having the conversation and we have the desire, which I think this conference represents.

Niblock: That’s great to hear. I know Mayor Duggin, the mayor of Detroit, is very committed to transparency, and you will start to see from the city of Detroit a whole new level of open data. So we’re really excited about showing the citizens of Detroit that we’re trying to do business differently, because we have a history that maybe doesn’t make us so proud in that area, so that’s coming. So that’s exciting.

I wanted to ask you, and then if folks—I know folks have questions, if you want to start queuing up, we’ll get to questions. But, you’re widely regarded as a polymath, and what new ideas or technologies or things have caught your imagination?

Dorsey: I’m very interested in any technology that we don’t have to see, at all. I think the best technology reminds us that we have everything we need, and that encourages more human interactions, and a lot of that has to do with saving time. So you know, a great tool, a great technology is, we believe, giving time back to people so they can focus on what’s more meaningful to them. So if we’re building technology for technology’s sake, I think we’re doing something that ultimately is a negative action. If we’re building technology that gets out of the way and allows us to focus on things that are actually meaningful, creates efficiencies, so that we can really be more creative, those are things that I love to see. So those are the things that always inspire me, is taking something that’s traditionally very obtuse and very difficult or very time-consuming and bringing it down to a second or bringing it down to a minute. And we tried to do this with Square, in that we saw just to participate in the economy, more and more, which was moving to a credit card, you had to go to this bank and you had to spend a month trying to apply to accept it. How do we get that down to three minutes? If we get it down to three minutes, then you can spend that entire month thinking about building your business, instead of thinking about what you have to do, and all the paperwork you have to collect for the bank, just to prove that you should be able to be allowed to be on their rails. And those are the terms, you know, they use. So, you know, any technologies that really give time back to people is something that—and makes us more human and enables more of that.

And I know that sounds counter to everything that we read about technology, and everything we see about technology, but ultimately I do believe that we’re heading to a future where the technology is very, very much in the background and it really reminds us that we’re born with pretty much everything that we need…and this is a reflection of that.

Niblock: So one of the things that we know about you is that you really like simplicity and form and function. Where did that come from?

Dorsey: Well, I guess originally from my parents, but I don’t know—I mean, my dad will tell you, I’ve always—he tells this story all the time, but like, whenever we moved into a house, I would try to find the smallest room, because I just don’t like having a lot of stuff. And it just, it takes time away, and it’s not stuff that I’m really interested in. I like very straightforward things that allow me to focus on what I find most meaningful, and anything that makes me think about it is taking time away from what I want to think about. So, you know, we find, and I find that if you interact with something that’s simple, that’s straightforward, you have more control and you have more ownership, and you have more drive to whatever it is you’re passionate about, and whatever your destiny is, so you know, it’s a matter of not—I guess it’s laziness, you know, ultimately. But it’s just seeking out the simple things, because I don’t want to deal with all the complexities.

Niblock: Well, and I think something my grandmother used to say, she had a very simple silver pattern, and I was like, she’s like, “Well, you can hide the flaws underneath all that other fluff, but if you have it very simple and elegant, you see everything in its purest, more true form.”

Dorsey: Straightforward, yeah.

Niblock: One quick thing before we get some questions. What was the most surprising use of Twitter that you had seen?

Dorsey: It—I mean, it never ends, really. The first surprising thing was probably—we live in San Francisco, so I was working in the office one day on a Saturday, and there was an earthquake and my phone was right next to me, it was a cheap little Nokia device, and it started vibrating, and I looked at it and it said, “Earthquake,” and then I felt the tremor. So what was amazing was the technology actually moved faster than the earth. And then these tweets kept coming in, “Earthquake. Earthquake. Earthquake.” “I think it’s a 5.7 out of Richmond.” “I think it was up centered out of Berkeley.” “I think it was up in Napa.” Whatever it is. And it was amazing, and then the USGS was actually on Twitter at the time, and they stated, “Nope, it was a 4.3 out of North Richmond, and here’s a link to see everything about it.” And what was amazing to me about that moment was how it went from speculation to fact in a matter of minutes, and you got to see every single point of view instantly, and I think that is important. I think it’s important to hear every perspective and every point of view, so we can really find common ground in what we’re trying to do.

And the other thing I notice is, like, this is an earthquake. I mean, I grew up in St. Louis, there are tornados, you can see the tornados coming, and then you go down into the shelter. Earthquake, it’s completely unpredictable, you don’t know what’s going to happen. You don’t know when it’s going to happen, and they happen a lot, you know, they happen every single day. So what was amazing about that, is that you’re in this event and it could be nothing and it could be life-changing, but you actually have people with you, and they’re going through the same experience, and they’re just stating they’re in the same experience, and that makes the world feel very, very, very small. And it makes it feel like you’re with people even though you might be alone, right? So that I think is the most impactful thing to me about the technology, is that it makes the world feel very small. It makes it feel like we are, you know, we’re all connected in ways. And we see it not just with an initial earthquake, but every natural disaster around the world, with what was happening in Iran during the protests, what’s happening today with Scotland, with ISIS, with Ferguson, with, with everything—with Robin Williams passing away—everything—the world comes together and has a conversation. And they have every single point of view and it’s all laid out instantly and you actually get to see all of it and also share your own opinion, which is equally valuable.

Niblock: So, we’ve got a question over here. Can you identify yourself?

Leland: Max Leland in the high-tech business, running various companies. Two questions, one that relates to the topic and one that’s slightly off-topic. One, your companies are global, so are there things from your international travels in other cities where you’ve seen either sustainable building or other type of transformations that we could bring back into Detroit that could be used to revitalize Detroit? And then the second question, which is kind of a little bit off-topic, as somebody who is running high-tech companies, I was very curious about your feedback on yourself, that you put it online and had all the employees give you the feedback on your 360 reviews. How did that go?

Dorsey: Really well. I passed. But yeah, so I did—there was an article that, you know, said I’m a glutton for pain, I guess, but we have over 1,000 people at Square, and you know, I think people—and I know this because I grew up very, very shy. I’m still fairly shy. It gets very hard to talk to people and you know, tell them how you really feel, so I created a spreadsheet and I gave it out to the entire company, and I said, you can be anonymous, tell me what is going really well, tell me what we need to fix, and give me any advice you want me to take. And be frank, be honest, be direct, but also be respectful in moving the company forward and moving it forward for our customers. And you know, I almost got 100 percent participation in that, and I heard everything. And I read through every single one of those comments, and I’m a believer that the most important things keep coming up and surfacing, so I really tried to figure out what the patterns were, what were the commonalities, and what really resonated with people, and acted on that.

If you go line-by-line and you simply react to each one of those, it becomes very hard, and you’re actually going to do the wrong things. You have to take all this as input, and then you have to make a decision based on the input, and that’s exactly what I did. So it was a great exercise and I’ll do it again. I’m going to do it every six months, because I want barometers around the company of how things are going. Like, are they going well? Are they going poorly? If they’re going poorly, tell us what we have to fix, because we’re all owners in this business, and I don’t want you to sit back there and just complain about, “Hey, I really can’t stand that guy over there, and I’m not going to tell him.” Because that doesn’t do anything for anyone and actually makes us go backwards a bit. So I appreciate people being very vocal and telling us what we’re doing right, what we’re doing wrong, because we need to know.

And in terms of global businesses and bringing things back to Detroit, I think it all comes back to confidence, really. I think you look at entrepreneurs in Europe, for instance, and entrepreneurs in Europe are—have had in the past a tough time about getting their companies out of Europe. A lot of them have, but some of the younger ones really want to play more in a global market, and the U.S.—not just technology companies—but the U.S. has always had this, like, extreme amount of confidence in taking massive, massive risks, and the culture really supporting it, and that’s allowed them to go global faster. And the support network around some of these European entrepreneurs is just not there. In fact, a lot of these cultures—and I don’t mean to just pick on Europe—but a lot of these cultures actually really look down upon any mistakes whatsoever, any failures whatsoever, and if you make one failure, you’re kind of cast out of society, so there’s less of a desire to try something new, because you’re so worried about failing. And I see that in a lot of cities in this country as well.

So anything that we can do to give more support to our younger folks who are trying to start something, who are doing something new for themselves—not just starting a business, but doing something new and taking on a risk—and just saying, hey, it’s okay to fail. You’re going to make some mistakes, you’re going to get back up and you’re going to do it again, and you’re going to find whatever you’re passionate about, and we support you. And that’s been one of the most interesting things that we don’t talk a lot about in Silicon Valley, that’s really driven it, which is this culture of mentorship and accessibility. So you can walk up to anyone and ask them a question about their business, about what’s going on, about what their biggest failure was, about their biggest success. Like, hey, how do you hire people? Hey, I’m really having a tough time firing this person. I know I need to, but I can’t do it. And these are commonalities in every organization, not just businesses. And I’ve always found that, you know, that support network is so critical to success and when kids are in college you have it because of all the students around you and hopefully your professors as well, but when they get out, it really is a function of the community supporting them and it’s really a function of the government supporting them. So just the government saying, “We support entrepreneurship. We support taking risks. We support you making mistakes, because we’re going to be there to support you to get back up,” we’ll see a lot more of this energy, and we’ll move the city forward much faster. But people need to feel that support network, and when it’s not felt, nothing changes.

Niblock: I know we’re at time, but we have one last question.

Oyewole: How’s it going, Jack and Beth? I’m Seun Oyewole from Invest Detroit, and I have I guess two questions. My first question relates to the convergence of social media and mobile payments in e-commerce. So there’s been an advent of the use Venmo, GroupMe for mobile payments. We see Twitter’s rolling out the Buy Now, Facebook’s also trying to use the platform for easier e-commerce purchases. So what are the big obstacles or thoughts for, I guess, the convergence of social media and mobile payments?

And then second, as relates to tech and cities, there are large markets—especially in urbanized cities—large markets that don’t necessarily use credit cards or debit cards. Do you see that as potential market for mobile payment growth at all?

Dorsey: Yeah, great questions. So I mean, I believe that commerce is inherently social, and it’s something that we do, but there’s just been a lot of abstractions placed upon it, and a lot of mechanical things. So really excited to merge those two even more, and see, you know, that just the intent of sending someone money is—and communicating that intent, actually sends them money, in the peer-to-peer case. And then on the Twitter side, you know, we have tons of small merchants and larger businesses who are tweeting about their products, and being able to meet the intent and instantly buy into it is important. So it’s just a matter of time.

And then in terms of credit card usage, and how that interacts with a community like this, it’s—I don’t know if it matters as much as the seller having the tools to always make the sale, right? So even if you use cash, or you use a check, or you use Bitcoin, or ApplePay, we should enable the seller to always accept every single device, and that’s exactly what we’re building with Register. We have merchants accepting cash—only cash—we have merchants who are accepting pre-paid cards and debit cards and credit cards. We have folks who are accepting checks, we have folks who are accepting Bitcoin online, and we’ll have people accepting ApplePay as well. So it’s really just making sure that that seller always makes a sale and the buyer gets to use what they want. So it’s not about one payment device versus another payment device, it’s about having choice and having the freedom to use the tools that feel most comfortable to you. And as long as you’re making that sale, you’re building the economy, and the buyer is getting whatever they want, and that’s what we’re focused on. So to us, like, we’re not building a payment device, we’re just enabling the usage of them, and that is our focus.