Co-Founder & Director, Square
The Mindset That Builds What Doesn’t Exist Yet | Jim McKelvey
What if the very thing that made you feel like an outsider was actually your greatest advantage? Jim McKelvey, cofounder of ...
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 (12 segments)
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James Mckelvey0:03
It helps to be an outsider if you're doing something different. My name is Jim McKelvey. I was born in the city of St. Louis.
I wasn't a very cool kid. I wasn't very popular. I mean, I had a small group of friends, but we were all sort of the unpopular people. And so I got used to being unpopular, which I think was helpful later.
You know, I guess I embrace my outcast nature now that I recognize its advantage. It's not fun to be an outcast. Like I was trying to fit in. I just didn't. And then at some point I'd failed so many times that I just gave up. You know, it became sour grapes. Like I don't want to be one of the cool kids. I don't want to go to that party. I don't want to do these things that everybody else is doing. And it became a badge of honor. But it wasn't like this moment where I just decided I was going to be a rebel and, you know, dress differently and stuff. It was not so much rebellion, just sort of lack of being able to keep up with the herd.
I got into glass blowing because I needed money. So I took my first job with a startup right out of school. Lasted a couple of months, quit because the boss was a crook. And so I woke up one morning and I was like, 'Well, what can I do to make money?' And I actually knew how to blow glass because I'd taken one class senior year of college. So I became an artist to feed myself. And I was completely unconstrained with artistic integrity. So I wasn't burdened by this need to, you know, sort of prove something. I just wanted to sell stuff. And if pink and blue matched your couch, lady, I would make it for you. No questions asked.
Glass is woven throughout my life. The process of making something, the process of repeating a mechanical operation and being able to try to control something that you can't touch, that's really interesting. And when I'm in the studio, I have different types of thoughts. So I often can go into the studio with a problem in some area of my life and I'll just be working on something and then, you know, it comes to me. And I don't know what it is about my brain that works differently in the studio, but it is profoundly different and I really cherish it.
So Square was funny because Jack came back after he was kicked out of Twitter the first time and asked me if I wanted to start a company with him. And I had worked with Jack back when he was a summer intern at my first company. And Jack and I had a good time. So we decided to get the band back together and we were looking for an idea. I went back to St. Louis to pack up my stuff. And when I was back in my studio, I got a call from a lady who wanted to buy a piece of glass, but she could only pay for it with an Amex card and we don't take Amex at my studio. So I lost the sale. I was really angry. And then I realized that I had my iPhone in my hand and my attitude towards my iPhone was that it should magically turn into this thing that I wanted. Like it turns into a map or a book or a TV, but it wouldn't turn into a credit card machine. And so I called Jack on the iPhone and I was like, 'Man, I know what we got to do. I want to turn my phone into a credit card machine so I don't lose further sales.' And that was it. And we didn't realize it was going to be that hard.
It's tough if you're doing something where there's no model, where you don't get to copy. And you run up against a problem. The first time any human does anything, that person is unqualified. Like the Wright brothers, first pilots in the air. They weren't qualified pilots. Nobody knew how to fly a plane. So don't think that qualification is your excuse for quitting because if you're really doing innovation correctly, meaningful innovation, you will not be qualified.
What in my background allowed me to keep going stubbornly when other people would quit? Part of that's insecurity. So my mother was a dynamic, vibrant, full and in your face New Yorker. Okay. Then Mom got depressed. And I saw this vibrant lady just sort of collapse inside herself. And I always felt like there was something I could do because Mom and I were alike and I could kind of feel it. But I didn't because, you know, at the time I was very young. It didn't occur to me that my mother would be capable of killing herself. But then of course it did occur to me. Like I had these thoughts, 'Well, I wonder if Mom would do that.' But then I brushed them aside, 'Oh, that doesn't happen in our family. That happens, you know, outside.' And then Mom killed herself. And I thought of all the stuff that I would have done to save my mother. Just take her for another walk. Just like talk to her. I didn't do what I could have done to save my mother.
So these days, and I think that was 36 years ago, I still have this annoying drive. If I see something that needs fixing, a lot of my energy comes from a dark place. I lived in St. Louis. I could have been with her. I could have kept her going. I thought I did. You know, maybe I couldn't have. Depression's a big thing. I understand. Like I understand. A lot of people suffer from depression. If she'd held on a couple more years, we would have had antidepressants that are now wonderful and could have cured her. Like if I had just had the tenacity and the arrogance that I have now back then, my mom might still be alive today. She might know her grandkids. So when I see a problem that rises to the level of something that I want to solve, that's where a lot of the energy comes from. It's this idea that my inaction has real consequences.
The other thing about glass is you have to think about everything backwards because your final shape is made by all these antecedent shapes that look nothing like the final shape. So it teaches a different type of thinking. I think being kicked out of my own company was probably the most educational low point in my career. I don't really have a career. But I've been kicked out of everything I've started. Like it just happens. Now in Square's case, it was sort of prearranged. You know, Jack was going to be CEO. I was going to stick around long enough to get stuff working and then probably head out the door. But the first time it happened, you know, I'd started the company and I had this idea that, you know, I was going to be the CEO, whatever that meant, and that I was going to be the boss and the leader. And it turns out I kind of suck at that.
I'm actually pretty good at building new things. But once the things are built and all we have to do is sell them and sort of run the machine, you probably don't want me pushing the buttons because I get bored. And I start pushing the buttons in different orders. Or I say, 'Well, we need to put some more buttons here or change the color or I think we should rearrange, you know, the way this machine works.' One of the reasons I got kicked out of companies is that I would, I think subconsciously, create situations that I knew I could handle, but they would be crazy and I would have to handle it. The problem is that I became dependent on the chaos. That I became used to getting my energy up sort of artificially through this level of problem and emergency that was necessary for me to get into my, you know, sort of top performing state. And that led me to create chaos unnecessarily. So that's not good. You don't want to absolutely, you know, I'll put out fires, but I shouldn't be setting them as well. I just have too many new ideas. Sometimes those new ideas, like if you've got something that works, give it to somebody else. Get me out.
The fact that I was doing something that was odd or considered odd didn't bother me. You know, after 25 years or 30 years of being the oddball, well, I'm kind of used to it. You know, it doesn't, it just kind of bounces off me now. And people call me crazy, call the ideas crazy. I'm like, 'Yeah, I might be, you know, whatever.' Like I just, I don't take that much weight from those statements anymore and that helps.