097: How to Find Your Perfect Problem with Jim McKelvey, author of The Innovation Stack (Part One)
8 Dec 2025 · 32 min
Jim McKelvey, co-founder of Square, discusses how he discovered the innovation stack concept by studying historical companies and interviewing Southwest Airlines founder Herb Kelleher. He explains how Square survived Amazon copying their product in 2014, and introduces the idea of "perfect problems": unsolved-but-solvable problems that compel entrepreneurs.
Questions this episode answers
May 31, 2022
The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time
2014
Two and a half years of working almost every day
Eight full rewrites
Chapters
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This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Hello hello my friends. We have an exciting two part episode coming up for you. This is my interview with Jim McKelvey, the co founder of Square, the author of the Innovation Stack, and just all around fascinating guy. I met him at the TED conference and I was very delighted and surprised when I invited him to the podcast and he offered to record in person. It had been since 2016 when I recorded a Pivot podcast with James Altucher that I had recorded with a guest, someone I didn't know very well in person. I have to say we had so much fun. Jim is the kind of guy you could just put him on a mic. I could have just sat there, not asked any questions at all and still been riveted. So I hope you enjoy. I'm going to release it in two parts. This is part one with Jim McKelvey and be sure to subscribe and tune in next week so that you can listen to part two.
Jim McKelvey is a glassblower, father, entrepreneur, authority, aviator, computer programmer and inventor. We met at TED through our mutual friend John Levy, and today we're talking about fending off an attack from Amazon while he was co founding and building Square. His book where he recounts this tale and his philosophy on finding and solving your perfect problem is called the Innovation Building an Unbeatable Business One Crazy Idea at a Time. As for where to connect, as he puts it on his website, please don't ask me to connect on Facebook, WhatsApp or Instagram. I'm not there. I've got better things to do and frankly so do you.
Yeah, so I actually am. My name is on those things. Like I have a Twitter account, I have a Facebook account, I think I have an Instagram account and it's all run by 26 year old females. It has nothing to do with me. And I'm open about this. I tell people like, that's not me on social media.
And do they sign their tweets from them or from you?
No, they pretend it's me. It drives Jack crazy. Cause Jack was like, you should use Twitter authentically. And I was like, yeah, I know you invented it and I like you, but it would drive me nuts. Cause I'm too obsessive and competitive and weird. And I also say a lot of stuff that gets me in trouble. And I think giving me a microphone like Twitter is just like giving a kid a gun.
But does it ever make you cringe when you see someone writing for you and you go, I would never say that. I would never think that.
Yes. Oh, it totally makes me cringe, which is why I never look at it. So the worst that I get is one of my friends will call me up and say, jim, you used the term happy place in one of your tweets. And they're like, that's not you. And I was like, yeah. The last time I think I officially used the term my happy place, I was in this rural part of Japan trying to use a public toilet that was one of those slot toilets. And I used the term happy place at that point.
And now we have confirmation. Do you in fact have a happy place?
I have many, but I don't use the phrase.
So then what is the benefit of having a team at all? Because I'm not on social media, just like you. I have the accounts. My team did what we call a transparent takeover during my recent book launch, where they signed everything from themselves, not from me. But it's too cringy for me to let somebody write as me ghost social media.
So I tried ghost writing with my book. I really didn't want to write this because it's a chore to write well. And I thought, oh, I'm rich. I could hire somebody to write well for me. This is very few things that I think money's good for, but this is one you can buy your way out of some problems. And I was trying to buy my way out of this massive homework assignment that I had to write this book. And I hired a gross writer. She was fantastic and I read her stuff and it was no good. And then I hired another guy, and he was supposedly phenomenal, and I read his stuff and I was like, this is no good. So we hired a third guy to work with a second Guy. And so I finally just wrote every word myself because I was trying to say something in the first person and it just was so inauthentic. Look, I know my social media is supposed to be me. It's not. Sorry, you want to hear me get the audio tape of the book?
The book is so funny and your personality shines through. I mean, my philosophy on ghost writing is there's a ghost in the book, but I actually think a book is an expression from something deep within. Like it has your own unique fingerprint if you actually sit down and do the work of writing it.
Yeah, mine's like my middle fingerprint in some parts of my book. There's the vitriol buried in there among the platitudes.
But oh gosh, I'm going to have to find some of these excerpts because your humor, it really shines.
Oh God, it was so much fun. Like if you get a good joke that lands. I've never had the balls to be a professional comedian, but it is fun to write something well, but it takes me forever. This book went through eight full on rewrites by me. That was after I fired all the ghostwriters and then started actually doing the actual work myself. I went through eight full revisions before I was happy with something that I.
Could publish over how many years?
Took me two and a half years of working almost every day. Wow. Yeah.
And it's interesting, I mean, you kind of say in the book that you just felt that when you were getting went Square was nascent and basically getting attacked by a large competitor, whether you want to name them or not, not even a competitor. What do we call them? The behemoth. What do you call them?
Amazon. Amazon, the company you probably would least like to be attacked by.
Yes.
Like if you think about, oh, who do I want as a competitor? Amazon is probably the last company you would ever want. Like I would rather have Walmart or Apple or the US government or some other enemy as opposed to Amazon. Because Amazon is wildly successful, super competitive. I mean on every metric they are deadly.
Don't you call them the perfect predator.
They're the perfect predator. They are.
And you said that when this was going on, you had nobody to turn to because nobody had successfully fended off an attack from Amazon.
Not as a startup. So when Amazon copied our product, this was back in 2014, and they released a competitive product to Square, we looked for examples of other companies that had survived an Amazon attack and found none. And that was chilling. Now there were examples of Amazon attacking big companies. You know, Amazon didn't take over Google. You know, Amazon didn't kill ebay, right? But they've certainly wiped out every startup they ever attacked. And we were a startup at the time and we were expecting somewhat to get wiped out, but didn't happen. And then as a result of that, I was very happy, but I'm only happy for brief periods of time. So the happiness was like, oh God, we just survived. And then I was like, why? Like, what happened here? Like, it was almost survivor guilt, Jenny. It was this thing where I was happy it happened, but then the question was, why did it happen? And I don't necessarily believe in luck. Like, I'm a scientist. I don't think the planets orbit the sun randomly. I want to know the math behind it. And so I spent about a year and a half looking for a mathematical reason why Square beat Amazon. And I found it. And that was the amazing thing. I studied and studied and studied and then I finally found it. And it was one of those eureka moments. Like, oh my God, look at this. And then I realized that I'd made this horrible mistake, which is I'd only studied history because I wanted to exclude the tech world, because the tech world is so weird. Like, if you've got a successful tech product and like network effect, you can be just the most drug addicted idiot and run a tech company successfully. Like, if you've got the network effect, you don't need any competence at all. All right? It's been proven half a dozen times at very large scale. So I was like, well, I can't study these companies, so I have to study companies that don't have sort of tech in their DNA. And so I went back in time and found a bunch, but all the protagonists were dead. Like, all the people that I wanted to actually talk to had died, except for one guy, Herb Kelleher, who was legendary, I mean, the founder of Southwest Airlines. And so I went down to talk to Herb, and Herb and I spent a day talking about my ideas and why I thought Southwest was like Square. We were both these little startups that were being besieged by bigger companies and probably should have died. Except that's not what happened. Southwest went on to be the biggest airline in the United States, the most profitable by any measure. Southwest is the best airline in the US and it wasn't a coincidence. The same thing that happened at Southwest Hamilton Square, the same thing happened at ikea. I had a dozen companies that fit this pattern. And I was like, oh my God. And that's how the book Came to be because Herb, at the end of our interview was like, well, how are you going to share this information with the world? And I was like, I don't know, Mr. Kelleher. I don't know what. And he's like, well, you're just going to sit on this yourself? And I was like, oh, God. I just got a homework assignment from one of my idols. It was a very impactful moment when Herbal agreed with me and then told me to get out of the room and go do some work.
I can imagine. So I'm curious. You said you had this eureka moment. How did the thought form in that moment? What dropped into your mind? Because it gets packaged and restated later when it comes to the book. But how did it come to you right in that instant?
The eureka moment happened in a Spanish castle. It was a palace. Technically, it was a palace, I guess.
Fancy.
Yeah. Palace versus castle. Who knows the difference? You know, it was a palace. And I was there looking at all this family's precious heirlooms. And they had this library where they had letters from Christopher Columbus. Right? So, I mean, Columbus is sort of viewed these days as sort of a bad guy. But like him or hate him, what you have to admit about Columbus is that he had a hard pitch, right? Because he was saying, well, we're going to sell this direction where nobody has ever gone before, and, by the way, nobody has ever returned from, and if we go far enough in the wrong way, we'll reach this new land. And that was his thesis, and he had to get people to fund that, and he had to get people to crew with him and sail with him and who would die if he was wrong. That's a tough sell. And I thought about Columbus as I was looking at his letters, and I thought, oh, my God, he was an entrepreneur. He was this person who was trying to do something new. And then I realized that the solution was for me to look back in history was that history was full. Like, if the phenomena that I believed existed, existed, then history has to be full of its instances and tell us.
What that phenomena is.
So the phenomena is this thing I call an innovation stack. It's a very simple idea, and that is innovation. Invention is generally the last resort for a company or anybody. We as individuals don't just choose to do new stuff. We're sort of forced to do it. And when we're forced to do it, it's messy. It's very messy. And messy tends to mean you don't have one or two brilliant solutions. You have probably 20 or 30 little solutions that collectively together make the brilliance. And that collection is what I call an innovation stack. And I found this thing at the core of all these companies. And then I looked at it, and I was like, why hasn't anyone told me this? Like, why hasn't this ever been explained? And I sort of tabled that thought while I was thinking about writing the book, because I wanted to write a graphic novel. So actually, I brought you a copy here.
Oh, thank you.
This is the birth of banking.
Oh, my gosh.
Because the whole thing was supposed to be a cartoon. Because I didn't want to write a business book because they're tortuous and boring.
Yeah, exactly. Oh, God, this is so much more fun.
So I did a graphic novel, and the reason my book is not published as a graphic novel is because of Herb Kelleher. I went through the first two thirds of the book, and I got to Herb's chapter. I had a fantastic chapter that was all ready to do on Herb, and I told him about it, and he said, I don't want to be portrayed as a cartoon. He says, I don't think it's a fair treatment of your subject matter. Herb was taking what I was doing really seriously, which is weird. Well, it's not weird, but it surprised me because he had a great sense.
Of humor, and you had only connected with him this one interview so far, and then he took such an investment in you and this work.
Yeah, I mean, he really thought what I was doing was important work and that it was trivializing it to portray it as a cartoon. And so he said to me, he said, look, I can't stop you from doing it, but I can ask you to leave me out.
Oof.
And I was like, oh, God. So I'm not going to leave Herb Kelleher out of my story, especially since he's the only living human that I've been able to discuss this process. So I scrapped the whole graphic novel and started writing text. Just text, text, text. So if you read my book, it's weird. It kind of reads like an adventure story, but it's text. And I saved one chapter, which is the one that I gave you. Now, that's the birth of banking, because I love it. I couldn't throw that one away. I mean, there's. There's nudity, there's destruction of a major city, there's murder. You know, there's an evil gang. I mean, this is good comic book stuff. You know, fire and clearly explosions, and.
Clearly we are riveted by these entrepreneurial tales of rise and fall and these. I mean, look at all the TV series and the wework stories spawned so much content. Podcasts, video, everything. Oh yeah, we're obsessed with it.
It's fun stuff. Like these are great stories. The problem is that if you take something that basically should be boring and you try to package it up as something that is supposed to be exciting, you end up creating false drama. And in my world, there's a lot of drama because if you're doing something that's never been done before, there's a lot of failure. And failure is interesting. Like stuff blowing up is interesting. Like when the chemical plant just, you know, puts out acetic acid all day, no problem. When the thing blows up and this acidic cloud forms over Cleveland, that's when you crank up the podcasts. So I think there's a lot of false drama in writing and there doesn't need to be. At least if you choose a good subject.
We'll be right back just after this.
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I think also for anybody interested in business, it's this intersection of the hero's journey. So you have Joseph Campbell, you have risk, failure, insecurity, the level of pressure. By the time this was happening at Square, you had hundreds of employees and there was a lot at stake. So I think also people, we want to learn from other people's failures and mistakes. I found it really interesting that you say that if you did in fact have an hour with Giannini or even more time with her, that you wouldn't have asked them how they did it. You would have asked them how it felt.
How does it feel? How does it feel to go through it? And that's the thing that I hope a reader will get from the book. So, look, I'll tell you right now, you don't read the Innovation Stack because it's got some checklist on how to make a billion dollars, right? It does actually have a formula for that, but it's not explicit.
I think of it like a Russian nesting doll. One problem begets another, another and another. So the Innovation Stack, just for listeners, is that it's almost or an onion. You're peeling the layers and layers of the problems until you've solved so many unique problems in a row that it'd be hard for a competitor to come in at that point.
There is somewhat of a formula in there, but it's not explicit. And the reason I wrote the book, this is the reason you read the book, okay, Is because there's this line, and I'll discuss it in detail in the book, but it's an invisible line between what we know how to do and what we don't know how to do. A couple times in your life, or maybe a dozen times in your life, if you're an aggressive sort of person, you will run up against the edge of what humanity knows. Doesn't happen all the time, doesn't even happen once a year. Like, it's an occasional. You will find that mankind just doesn't know how to do this thing. And when you hit that line, most of us will recoil. Most of us will rightly recoil because we'll say, look, I'm not qualified to step across this line because I'm moving into an area where I have no skills, no expertise, no plans. You're a blank slate. The problem is, if all of humanity stops at that line, we never advance. As a species, we're not as good as the pythons we discussed earlier, the invasive species. The whole idea is you get to this line and what I wanted to prepare the reader for. A couple times in your life, you're going to be given the choice of, do I choose to solve this problem that mankind has not solved yet? And look, no's a good answer. You don't have to do it, but if you choose to do it, it's terrifying to be on the other side of that line. It goes against your training, it goes against your DNA. It goes against all of your schooling. Your friends who love you will try to say, jenny, don't do that. Everybody and everything in your world will quickly change to sort of discourage you from doing what brings humanity forward. So what I do in the book is I tell these stories of very normal people who were in this crazy situation, for one reason or another, they got over that line. Sometimes they were forced over it. In some cases, they chose to go. But in every case, they were sort of alone and scared. And these were not heroes. And this is why Herb is such a genius. It shouldn't be told as a comic, because the comic is a hero's tale. Like the protagonist of a comic book. Like, look at the comic book. Like, I got a guy on the front. You know, he's in a storm, in.
A blue trench coat.
Yeah, it looks like a cape for.
God's face with a big bushy mustache.
Oh, yeah, he's a badass. And now that's what Giannini looked like. Right. But I mean, come on, that's a comic book hero. My story is an everyman's story. I talk about very normal people who ended up on that other side of the line and what it's like. And so the reason I wanted to meet these historical figures was to say, how did it feel for you? I can tell you personally how it felt for me. It was like.
I would like to know.
Hand sweating, terror, Just fear, just uncertainty. I mean, I remember once driving with my wife, who at the time was my fiance. We were driving through California, and I had to pull over the side of the road. I thought I was having a heart attack. And I was like, I think I'm having a heart attack. Like, my chest is collapsing. I have to get out of traffic. And then we drove right to a Walgreens, and she bought me some baby aspirin, and she was like, calm down. But that's how terrified I was on a daily basis. It wasn't like there was some event that happened. It was just life.
What phase of your career was that?
That was the first year of square.
The first year of square.
All sorts of stuff. Because 15 things are going wrong at once.
Here's my question about your journey with Square. And then even since you always had a background as a computer programmer, even your dad used to teach, Right? Computer programming.
Dad taught thermodynamics. Thermodynamics. So dad taught chemi.
Okay.
Yeah.
So you have this engineering mind and conversation with your dad, and you were a glassblower. And so I think it's so interesting that what came out of glassblowing was also realizing that smaller merchants, little tiny business owners or service providers didn't have a way to charge their customers and therefore were losing business. So you essentially shifted from glassblower to reaching out to your friend Jack, who was very young at the time and having this idea that became Square. My question for you is, as Square starts to actually grow and get traction and you fend off attacks from Amazon, you're suddenly running enormous business that's in the public eye. It's so different from the life of a glassblower. And I'm just curious how many points along that journey you just thought, this is, I don't know, like, I don't think I would have felt cut out to navigate that, as you describe in the book. And yet you just kept putting one foot in front of the other.
So I never made it into management. So Jack and I decided to start.
Which seems like a saving grace of some kind.
Well, I mean, it's good to have a partner. So Jack had already started Twitter and he called me to see if I'd start a new company with him. So Jack said, hey, you want to start a new company with me? And I was like, yeah, sure, what do you want to do? And he's like, I don't know what you want to do. So we didn't have an idea. So I came up with the idea for Square in my glass studio. But then the question was, well, what kind of company we're going to build and whose company is it going to be? And that was a very quick conversation because Jack wanted to run a big company and I didn't want to run a big company.
That's what I was wondering about.
And so Jack wanted to be CEO. And I was like, okay, you should be CEO. I was like, and I'll be the other guy and I'll work on every problem that you don't want to work on. So Jack wanted to do software. So I dealt with the banks and the contracts and the hardware and customer support and accounting and getting the offices and handling the legal. I mean, I was just like all the crap.
Almost like an operations COO type.
Yeah, I did all the stuff that nobody wanted to do before. We had somebody who was good at it. And as soon as we had somebody who was good at it, I stopped doing it. So it took me about a year and a half to work myself out of a job.
Interesting.
And after that point, well, it coincided with the birth of my son. So I had a little baby and everyone was working 12, 14 hour days. And I was one of the founders, so I was working at least as much as everybody else. And I realized, well, wait a second, I probably won't have a marriage and I certainly won't have a relationship with my family if I worked this Much. So I was like, well, I should work less. And then I thought, well, that's insulting to everybody else to see the founder go home at 6 o' clock when everyone else is going to be there till midnight. I didn't want to be that. So we sort of engineered my retirement from Square, which was great because I wasn't actually any good at the stuff that I was doing compared to the teams that we'd hired to do it. So I can do accounting, I'm not a great accountant. I can do law, I'm not a great lawyer. I can do a lot of stuff. I built all the hardware, right? I designed and built the hardware. But now we have a team of people who are really good at that. So I just was easy to replace.
So it's interesting that you kind of came in as the builder, got these areas from 0 to 1 and then replaced yourself. I mean, I do think that a lot of, at least a lot of people in my audience that that's compelling.
Because, oh, I love it.
When I was working at Google, I looked up the org chart and I thought, I don't want to be a middle manager here someday. Like, I just didn't aspire to. I would rather be on my own. And now I'm going to record an episode on this soon called Minimum Viable Team. Like, I basically want the minimum team structure around me to still enable me to delegate what I don't want to do. And so I've thought about that as thinking about this conversation. Even these new projects that you're working on, like Cash app and some of the nonprofit stuff that you're doing, just how you think about when you have your next perfect problem, which I would love for you to define for listeners as well.
Oh, so perfect problem is a concept I use in the book because I needed a focus. So if you think about the world of problems, the continuum of all the stuff that could go bad or needs to be fixed, right. Something you want to do, you can divide that into problems that have been solved and problems that haven't been solved. Okay. And then the ones that have been solved, that's not too interesting, you just look up the Solution. There's a YouTube video for that. Go find it.
Right.
So look at the unsolved problems, and that's kind of an interesting space. But then the question is, if you look at the unsolved problems, you want to sort of subdivide that into unsolved and unsolvable and unsolved and solvable, but just not solved yet. Right. So let's take a crazy example. Teleportation. Like, it'd be cool to teleport stuff. I spent six hours trying to get back home last night. It would have been nice to teleport. Right? My son would be doing better on his standardized test today if Daddy had gotten home before 2am but it didn't happen. And sorry, kid, you're gonna score low.
He'll have a good story.
Yeah, he'll be humbled. Or maybe he'll just think it's an excuse and never have to say, well, I'm just tired. But if you look at the problems that are unsolved, you have this subset that are unsolved and solvable. And I mean solvable by you. So Jenny Blake, if she chooses and forces herself to be disciplined and work hard and smart and puts the right team together, can write this problem, can fix this thing. That's what I call a perfect problem. And so I devote the focus of the book to these people who are solving perfect problems. It's this idea, it's this catalyst for entrepreneurship. And I don't mean entrepreneurship like start a business. I mean entrepreneurship in its classical definition, which is doing something crazy that's never been done before. And if that's what you want to do, then the perfect problem is your guide. You look in the universe and you say, I'm going to fix this thing that mankind has never fixed before. And I'm going to do it because I believe it can be done, and I believe I can do it. Now. That's the hard part, because you can't prove that in fact, you can do it. You can say, well, it's a solvable problem, but then you're not the person to do it. So I work on a bunch of those, and they're terrifying.
You also say that the problem chooses you. What do you mean by that?
Well, in my case, I have to be grabbed by a problem. I have to care about it, and I don't really control what I care about.
Thanks so much for listening to part one of this interview in person. Person. So Fun with Jim McKelvey. If you're not already, make sure you're subscribed so that you see when part two of this conversation releases next week, and if you enjoyed this episode, please share with a friend. You can visit POD link freetime to get the links so that it can open wherever they listen to podcasts. Thanks so much, everybody. Have a beautiful rest of your day and see you next week for part two.
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Are you aware of the Burmese python?
Yes. Oh, yeah.
Oh, my gosh.
Yeah. So the Burmese pythons all. So this is an invasive species that has sort of taken to the Everglades.
And there's like 100,000 or some insane number of them.
Yeah. And so in a great redneck tradition, we are now, like open season, trying to, you know, have contest who can kill the biggest python.
I know.
So just like, if you really want to hunt with a bow and arrow and just be a total badass, you know, get yourself an airboat and I know, go python hunting.
They have their helper dogs. I'm watching these videos on YouTube. I don't know why. Something about the notion of this invasive species and then these pythons being 18ft long and apparently there is no predator for them other than humans. And then if you catch a pregnant female, they'll have 60 eggs inside.
Yeah.
This seems like an intractable problem. It is not my perfect problem. But to your point about perfect problems, no. How do you even tackle this?
You don't. The python is now native to Florida. I think at some point you just redefine it as native like we did with the tumbleweed.
But I guess the mammal population is down 95%.
Yeah, well, in the Everglades, that's true. I mean, but, you know, we mammals are doing well elsewhere, just not in the Everglades.
That's true. And also, humans are doing no better for the planet by killing species. So it's.
Yeah, I mean, it's sort of like, you know, the tumbleweed is this iconic western invasive species. It came in from Russia or someplace and it just took over the West. And the tumbleweed is like a rolling disaster. It causes fire, it causes traffic jams, it causes, you know, livestock. It's just terrible. But it's old terrible. Like it's been with us for like 100 years. So now it's part of, like, if you picture a Western scene, there's a tumbleweed in it, right?
Yeah.
And we don't think of that as a foreign thing. So I think the Python just needs to sort of wrap itself tightly around the American flag and embrace its new home.
Oh, my gosh.
We're not going to get rid of them, put it that way. I mean, if you've seen one of.
These, it's been that way.
Oh, my goodness. Yeah, you're not gonna do that.
They're gnarly. Oh, my gosh.
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