CEOInterviews.AI
Start App
James Mckelvey
Co-Founder & Director, Square

Jim McKelvey: Disruptive By Design

📅 Aug 08, 2025 mossappeal 23 MIN 21 VIEWS 59 SEGMENTS · 2 SPEAKERS
What do glassblowing, fintech, and plastic-free diapers have in common? One brilliant disruptor: Jim McKelvey. I had the privilege of interviewing Jim McKelvey, the award-winning, Amazon-beating polymath who co-founded Square (now Block) with Jack Dorsey. But calling him just a fintech entrepreneur or a computer scientist would be like calling Leonardo da Vinci just a painter. This man defies categorization in the most fascinating way possible. “I’m a guy that’s had no focus for 30 years,” Jim told me with characteristic humility. “I am a transport category pilot. I’m a professional glass...

Questions asked in this interview

10
  1. 0:31You know what else Jim predicted?
  2. 2:01You've done a bunch of stuff, but how do you summarize it for us?
  3. 4:12Like, is this a time when we do a screen share and I just show you this?
  4. 8:04How do you think brands should embrace brand purpose? And what are you doing?
  5. 11:17Do you know what I'm trying to ask?
  6. 14:04But isn't that the definition of a problem that it's unsolved?
  7. 14:44Since you won your award in 2018, what's changed in the industry?
  8. 16:25What does being inducted into the Hall of Fame mean to you personally?
  9. 16:58What's your go-to hobby or ritual that helps you recharge?
  10. 17:55Is there a mentor who changed the course of your career?
James Mckelvey 0:00 ↗
Herb Kelleher sitting in his office told me exactly what was happening, and based on the research that I'd done for the book, I was like, 'Well, then if this is happening now, then this will happen to your company.' And Herb was like, 'Yeah.' I was like, 'That's going to be a disaster.' We called it. I put it in print. It was typeset in 2019 and has been eerily accurate.
Eie Moss 0:31 ↗
You got a horse in the fifth race for me? Hey, it's Eie Moss, and that was author and inventor Jim McKelvey explaining how a conversation with the late Herb Kelleher, founder of Southwest, predicted challenges that the airline is having today. You know what else Jim predicted? The success of his little invention called Square with co-founder Jack Dorsey, now called Block. It transformed the world of mobile payments. Now, this is the first of several interviews that I had the chance to do with past winners of the prestigious Folio Awards for publishing. These folks will be inducted into the Hall of Fame in October, and they've since reinvented their work or their place in the world. So, here's a little more with Jim McKelvey in episode 41 of Insider Interviews, where you get the insider scoop on the business of media, marketing, and advertising. I've never really researched Jim McKelvey before. I found out I'd have the opportunity to interview him about 7 minutes before I hit record in my Descript studio. And from what I know so far, he is one of the most interesting guys I've ever had on Insider Interviews. Welcome, Jim. Thanks for doing this.
James Mckelvey 1:55 ↗
Thanks, Eie.
Eie Moss 1:56 ↗
Okay, so you can say that because you don't know who I am.
James Mckelvey 1:59 ↗
That's true.
Eie Moss 2:01 ↗
Now, in a little bit of my research, I am going to make you do the thing you hate most, which is please just share a little bit of what would be on a Wikipedia page. You've done a bunch of stuff, but how do you summarize it for us?
James Mckelvey 2:15 ↗
I'm a guy that's had no focus for 30 years. I was a professional glass artist. I am a transport category pilot. I am a glass artist. I've got industrial designs in MoMA and the Smithsonian. I'm a computer scientist. I was on the Federal Reserve. I used to vote on interest rates. That was fun. Started Square, which we now call Block. Built the hardware for it, have started a bunch of other companies. But look, yeah, it's a mess. Basically, what I do is I build tools.
Eie Moss 2:55 ↗
Yeah.
James Mckelvey 2:56 ↗
And I build things. And right now, I'm working on a plastic-free diaper, which may or may not work.
Eie Moss 3:02 ↗
Plastic-free diaper.
James Mckelvey 3:04 ↗
Plastic-free diaper.
Eie Moss 3:05 ↗
Tell us.
James Mckelvey 3:06 ↗
A diaper with zero plastic in it. It's very, very difficult to do this, but diapers last for a thousand years. Yes. And they become these horrible microplastics that are sort of bad for the world. And I just thought it could be possible to do it without plastic. And so I've been working on it for 5 years with the team. We're this close to a breakthrough. That said, we also had an explosion in the lab the other day. So, you know, like, yeah, a little explosion. Not a diaper explosion.
Eie Moss 3:34 ↗
Well, that's good. That could be messy.
James Mckelvey 3:37 ↗
Something blew up. Look, I work on projects that are right now sort of long shots because I'm in a position where I can take a long shot. I've, you know, made way more money than I ever expected. My wife and I have taken the giving pledge, so we're going to give all the money away. But in the time I can take crazy risks. So, the diapers, I'm working on FDA trials. And I also just built this product that I don't know what to do with. It's amazing. It allows you to accurately manage or measure any brand or person. So anything, if and I should URL...
Eie Moss 4:12 ↗
Yeah, measure in terms of what? It's... so... brand screen share here? Like, is this a time when we do a screen share and I just show you this?
James Mckelvey 4:23 ↗
Sure. Let's try it. So I just happened to be talking to one of the guys at Pepsi. So this is what Pepsi had on here. So this center is every quality that any person or product can have. And I'm going to read a few of them out. It says like trendiness and flexibility and authenticity. Yes. So and under each of these are things that covary. So for instance, trust. Here's I've got the tab open for trust. Trust and honesty are not exactly the same thing, but if you measure them together, they will tend to rise and fall at the same time. Security is not the same as trust, but again, security and trust tend to have high covariance. So, what we did was we basically took every quality in the world. And we measured their covariance and then collapsed it into these 15 different qualities which can be measured for any product or person. So for instance, I can say Pepsi and this is Pepsi's graph. Well, what does Pepsi care about? Well, Pepsi probably cares about Coke, right? So you can see how, you know, Coke maps a little bit differently. You can also see something called the power score, which is Coke has a much larger following and much larger impact on the world than Pepsi does. They're a much bigger brand. But you don't have to just do it between product to product. You can also do people. So, for instance, if we have Pepsi set up here, it turns out that, you know, Rihanna is actually the best brand fit for Pepsi. But, you know, down here at number three, which is kind of cool, is Billy Idol. You will see Billy Idol actually fits the Pepsi brand really well. It's super fun. And here's the thing. We're giving this away right now. You can go to www.powerscore.ai, AI, but it's spelled PWR score. PWRs.ai.
Eie Moss 6:17 ↗
Okay.
James Mckelvey 6:18 ↗
You can use the tool for free. I wish somebody would tell me what to do with this thing. I show it to marketing managers. They all love it, but then I don't know how to charge. I mean, I never planned to build this, but it was this tool that I needed to do some work that I was doing and I had to eliminate bias because what I realized was that there was a lot of bias in my work that I couldn't control. So this mathematically eliminates bias. It is so beautiful and it can do it for any product or anything. So we can take Chanel here. We can take cocaine. You know, cocaine. There's cocaine, right? But you know, and you can have fun with it. Like so for instance, if we... this is one of my favorites. If you take the physical attributes of cocaine, yes, and then you want to find people who fit that brand. The best brand fit for cocaine, let's see, is Marlboro cigarettes. But the best person is Donald Trump. Look at Trump's scores versus cocaine. Okay.
Eie Moss 7:27 ↗
I don't know what this means.
James Mckelvey 7:28 ↗
I don't either. But it is... and we got the charm point on that is a little low but the independence line is pretty high. So that's interesting. It's crazy. It's crazy. And this is all... this is not my opinions. This is just math, right? This is just how math covaries qualities between people. So anyway, that's powerful. If someone could figure out a way to make money with it, I will, you know, be... well, I'll just give the money to a good charity because we're giving it away.
Eie Moss 8:04 ↗
I love that. Well, that actually brings me to another question. A lot of what I ask my guests is their definition of or use of pro-social activities or brand purpose. How do you think brands should embrace brand purpose? And what are you doing? You're giving your money away.
James Mckelvey 8:24 ↗
So, first of all, you want to watch the brand, okay? Which is to say, associate with people who enhance what you're doing, not who do what they did with Bud Light, right? So, Bud Light was one of the strongest brands in the world and was literally destroyed by a bad association. You know, they zigged when they should have zagged on trans rights and literally destroyed the top beer brand in the world and it has not recovered. The company was damaged and it was completely knowable. Like if they'd had my tool, it would have shown in stark graphics how much of a risk that association was and how potentially negative and destructive it was. And you know, and I'm from St. Louis, so I see this happen. I like, well, how could I prevent this from happening? Well, this is what was the inspiration behind this because I like... it wiped out part of my city. Like Anheuser-Busch used to give generously around town. Well, they can't do that unless they're selling you beer, you know? They're not selling beer anymore. So, I've got, you know, hospitals that are... you know, I mean, it's a tragedy in St. Louis.
Eie Moss 9:35 ↗
Yeah.
James Mckelvey 9:36 ↗
And the question is how do you prevent this without introducing your own bias? Which is why we did all this math. And I won't go into the math because it'd put all your listeners to sleep. But you know, the point here is, Eie, that we should... if you are being responsible for a brand, which can be a personal brand or it can be something that you're selling a product, you don't know how the world perceives you and you really have no way to in real time measure that. Now, the LLMs actually know a lot about this, but there's no way to quickly synthesize it. So, we came up with this LLM-based visualization that allows you to, you know, as somebody who's managing a brand, to know what you represent and then know what others represent.
Eie Moss 10:25 ↗
Yeah. I see. That is so important because who you associate with and what you associate with is either going to enhance or detract from your brand and you should make those decisions positively. You don't want to do what Bud Light did. Brilliant. One of the things that you've said is that you want to be a conduit to ideas. You want to help people be inspired and innovate. You want to solve problems and inspire others how to do that and you've clearly solved a few problems and you're on your path to a few more. God bless if you can get plastics out of diapers for example because that's in all our bodies.
James Mckelvey 11:13 ↗
We'll have that in a year. It won't be commercially available but it'll be in prototype.
Eie Moss 11:17 ↗
All right. It's a start. So in the meantime, how do you like approach a problem? What sparks your ideas and how do you advise others how to get out of their own way and identify the problem for and the inspiration? Do you know what I'm trying to ask?
James Mckelvey 11:38 ↗
Yeah. Yeah. I know. And there's a whole chapter on this in The Innovation Stack. Look, I believe...

29 more exchanges in this transcript

Sign in free to read the rest of this interview. No card required.

Sign in to read the full transcript

Cite this transcript

APA, MLA, BibTeX
APA

Mckelvey, J. (2025, August 8). Jim McKelvey: Disruptive By Design [Interview transcript]. mossappeal. CEOInterviews.AI. https://ceointerviews.ai/interview/805497/

MLA

James Mckelvey. "Jim McKelvey: Disruptive By Design." mossappeal, 8 Aug. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/805497/.

BibTeX
@misc{mckelvey2025_805497,
  author       = {James Mckelvey},
  title        = {Jim McKelvey: Disruptive By Design},
  howpublished = {Interview transcript, mossappeal. CEOInterviews.AI},
  year         = {2025},
  month        = {aug},
  url          = {https://ceointerviews.ai/interview/805497/},
  note         = {Speaker-attributed transcript with timestamps}
}