Co-Founder & Director, Square
Where Is AI Going? Square co-founder Jim McKelvey
Jim McKelvey talks about how AI will keep growing but says engineering and actually building things still matter a lot. He also ...
About James Mckelvey
Jim McKelvey, co-founder of Square (now Block, Inc.), has been speaking publicly about his concept of the "Innovation Stack" and the early challenges of building Square. In a March 2026 podcast, he recounted that Square started after he lost a sale at his glass studio because he could not accept an American Express card, and that in the first week of operation he found 17 laws or rules Square was violating. He described Amazon's later attempt to copy Square with Amazon Register and said the threat led him to write a book about how innovation forces a company to invent rather than copy. McKelvey also discussed the emotional difficulty of innovation, noting that "the first time any human does anything, that person is unqualified" and that meaningful innovation is rarely comfortable or cool. In April and May 2026 appearances, McKelvey reflected on his personal history, including his mother's suicide and his experience as an outsider. He said that being unpopular as a child gave him an advantage in not caring what others think, and that he has "been kicked out of everything I've started" because he gets bored once a venture is built. He also described his approach to layoffs at Square, stating that the company avoided small, repeated cuts and instead conducted a single org-wide reduction with six months' severance plus a week per year of service. McKelvey continues to promote the idea that true innovation arises when copying is impossible, and that entrepreneurs should embrace the demoralizing, failure-laden process that comes with building something new.
Transcript (20 segments)
I
Interviewer0:05
I am so happy to have Jim on the podcast today, who is a wonderful person when it comes to tech and AI, I would say, but more so tech with Square as well as Glass. You've lived in St. Louis your entire life. So tell me a little bit about what it was like growing up in St. Louis, going to college, and then getting involved in the tech world.
J
James Mckelvey0:34
I mean, so I was born and raised in St. Louis. I no longer live there. My wife couldn't stand it anymore and we moved five years ago to New York City. And I tried to make an argument for my hometown and lost. But I am from the Midwest. I still have a home in St. Louis. My heart's still there, but I live in Manhattan right now. Look, St. Louis was a phenomenal city a hundred years ago. It's been in decline my entire life. It gets worse every year. And there are a bunch of reasons for that, but primarily because we never learned how to integrate. And I'm sitting here in Atlanta right now, which is one of the more prosperous and I think probably better integrated cities we have in the country. St. Louis didn't deal with racism very well and we ended up going the segregation route and it was a disaster and is a disaster. We're still one of the top segregated cities. So there are a bunch of us working on trying to fix this, but so far those efforts have been dwarfed by the enormity of the challenge.
I
Interviewer1:51
And for you, of course, you obviously have a glass factory, if I'm correct, and you were struggling to make a payment and Jack Dorsey worked for you or was an intern for you, if I'm correct. And in 2008, 2010, somewhere in between there, you were trying to sell something to somebody and that's how Square came about. What was it kind of like being from the Midwest and then obviously having a big tech product like that, go somewhere and be part of innovation?
J
James Mckelvey2:26
So, Jack and I are both from St. Louis. You know, we worked together many years ago at another company that I actually still have and have been, you know, sort of friends and colleagues for many, many years now. He called me when his time at Twitter ended the first time, like kicked him out. They've kicked him out several times, but the first time they kicked him out, he called me. And we decided to work together. We didn't know what we were going to do. But I happened to be a glass blower, as you say. I was trying to sell a piece of glass. I lost a sale and I was very frustrated and I knew how abused I felt as a small merchant. So that was the impetus for Square. In other words, I wanted to build something for myself so that I could get paid. And that was the founding spark behind that company.
I
Interviewer3:23
And it's incredible. I see so many people use it still today. And obviously you do some work with Cash App and things like that. And Cash App is big with college students as well as things like Venmo. Where do you see, I guess, fintech moving forward? Not just from an AI standpoint, but where do you see it going? Do you think we're going to have something better one day than Cash App or even PayPal and Venmo? Or do you think as far as credit card processing that this is as advanced as it'll get from a technical standpoint?
J
James Mckelvey3:52
No, it's absolutely getting better and continues to. I was just at a payments conference, as a matter of fact, that's what I'm leaving now. Look, it's generally true that things get better over time. Margins got lower. Now, in some very limited areas, that's not the case when you've got monopolies, but there really aren't too many monopolies in payments right now. So, it's going to keep getting better and people are going to get more access, more products, and the AI is going to make it possible for you to get the advice that a rich person used to be able to only get and now everybody can get it. So, hopefully it will lead to a greater democratization of access to financial tools.
I
Interviewer4:40
Amazing. I'm young, so I'll get to see a lot of it. And from a college aspect, what would you say are careers people should go into? Not just if they're obviously trying to get into the tech world today, but what would you say are maybe some of the underrated programs in college that you think people should take or courses they should take or anything like that in their free time?
J
James Mckelvey5:04
I mean, I'm a big believer in engineering. I think Purdue is probably the top school in that regard. Even though there is a school called the James McKelvey School of Engineering at Washington University, I would put Purdue ahead of my own namesake because of your attitude towards letting everybody in, kicking their ass. If you can afford it, if you can handle it, Purdue's going to let you get a world-class education. And I'm particularly interested in engineering because it's a very durable skill set. Like you might not use these specific engineering tools that you learn in school, but you will learn how to learn and you will learn how to work on hard problems and you'll learn how to work on teams and that's taught better in engineering school than in anything else. And though I would say, you know, programs like MIT would also qualify. You know, my favorite statistic, which I learned from Jim Bullard, who runs your business school, is, you know, MIT, Stanford, and Caltech are ranked above Purdue in engineering, but Purdue produces more engineers than all three of them combined. So, like if I was a student right now and I actually ran into a student 20 minutes ago and told him this, like go take some engineering classes. Go get your ass kicked. Go see what you can handle because believe me, it's easier to learn it in school than to learn it out in the real world.
I
Interviewer6:47
Wow. Wise words of advice. And a couple other questions. What is something that has always inspired you? No matter if it's in the glass factory, in the tech world, or anything else, what's something that always inspires you? Is it family? Is it religion? Is it doing good in your opinion? What is it for yourself?
J
James Mckelvey7:12
I mean, obviously I'm devoted to my family. But if I had to talk about motivation, usually it's problems. Usually it's things that I see that I think are wrong that need to be fixed. It's generally the case that I see a lot of problems and I let them go and then some problems I try to fix. Like I was really, really heartbroken. You know, one of my workers' son was shot and murdered in St. Louis. And so I spent, you know, 10 years trying to build up part of the town where the murder happened. You know, trying to go there and say, well, if I grew up in this world, what would my life be like? And I tried to build things. So, you know, those are sort of dark forces, but they're very powerful and I listen to them. So I just wait until the problem, I won't say appeals to me, like a problem grabs me. There's something I think needs to be fixed and then I just work on that.
I
Interviewer8:27
Great to hear and so sorry to hear about what happened to a colleague of yours, that's horrible.
J
James Mckelvey8:32
Yeah, it was terrible. Kid was shot delivering a pizza.
I
Interviewer8:38
Just horrible to hear. Wow. And do you think that, do you kind of feel like, I guess, do you think technology is going to wipe out 80% of jobs, 90% of jobs like they're saying or do you think that Gen Z and millennials have a little bit more time?
J
James Mckelvey9:03
It's definitely going to wipe out a certain type of job. If your job is compiling information, it's already gone or very soon will be. If your job is using information and building new things, it's probably safe.
I
Interviewer9:21
Wow. And kind of one last question I want to close on is, do you think that Silicon Valley, obviously you've kind of stayed on this side of the Mississippi River, but do you think Silicon Valley is going to be broken up more and that there'll be other tech spots and there are other tech spots or do you think Silicon Valley with the AI revolution is still going to be the capital of the world for technology for, say, the next 20 years?
J
James Mckelvey9:51
I mean, despite everything California does to try to drive creativity out of its jurisdiction, they've got this magic formula out there and I think it's sort of like Shenzhen, China, like you're not manufacturing stuff unless you're manufacturing it in Shenzhen for certain components. There's just not the ecosystem. Silicon Valley has this weird ecosystem and also this sort of magical acceptance of new things that is not prevalent in other parts of the country. So unless you can get an entire system to feel as welcoming in Silicon Valley to new ideas, you will still see the greatest new ideas birth and grow in Silicon Valley.
I
Interviewer10:38
That's very nicely said. And I got to sneak in one last question. Is there a specific team that you root for or maybe a hobby you have outside of glass and obviously solving problems as you mentioned that you do to kind of relax or keep your mind off since you're a busy type of guy? I'm just curious if there's anything like meditation or something you do if it's not sports.
J
James Mckelvey10:59
I mean, I'm trying to learn how to meditate. I'm not very good at it, but I root for the Cardinals under all circumstances.
I
Interviewer11:06
Wow. Well, thank you so much for coming on the show. I really appreciate it and good luck to the Cardinals this season.
J
James Mckelvey11:14
And thank you, Jacob. I'm sorry it took so long to schedule this and I appreciate you taking my commute time as your podcast, but good luck with you.