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 artist with industrial designs in MoMA and the Smithsonian. I’m a computer scientist. I was on the Federal Reserve and used to vote on interest rates. That was fun. I built the hardware for Square, which we now call Block. I’ve started a bunch of other companies…Ugh. Look, basically, what I do is I build tools.”

His “lack of focus” has actually been his superpower, creating a truly unique lens on innovation, branding, and problem-solving that most specialists simply can’t achieve.

From Frustration to Billion-Dollar Solutions

Our conversation revealed how Jim transforms everyday frustrations into industry-changing innovations. The Square story began with something as mundane as being unable to accept American Express at his glass studio. That simple pain point sparked a billion-dollar disruption that fundamentally changed mobile payments forever. 

Jim shared his methodology for spotting opportunities hiding in plain sight and building products that resonate deeply with audiences. More importantly, he explained how he predicts business disasters before they happen – and his track record is impressive! Hint: his accurate predictions about Southwest Airlines and other major corporate meltdowns, made it into his book “The Innovation Stack” years before its current challenges. Then he shares how and why brand associations can make or break a company (hello, Bud Light disaster. Listen for how that motivated his current project, PwrScore.ai.)

The Art of Taking Calculated Risks

What struck me most about Jim was his fearless approach to high-risk, high-impact projects. “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,” he explained. “I’ve made way, way more money than I ever expected. My wife and I have taken the giving pledge, so we’re gonna give all the money away, but in the meantime, I can take crazy risks.”

That’s not just talk – Jim and his wife have literally committed to giving away their entire fortune for the betterment of the world. It’s a level of commitment to pro-social behavior that’s both inspiring and rare in today’s business landscape.

Two Game-Changing Projects You Need to Know About

Jim pulled back the curtain on his current ventures, and they’re both fascinating for completely different reasons.

First is PwrScore, a that tool that measures and assesses brand resonance and compatibility using AI to minimize research bias and enhance brand capabilities through better data. The kicker? He’s giving it away for free. Yes, really. This isn’t some limited trial – it’s a genuinely useful tool that most companies would charge thousands for, and Jim is just handing it out because he believes it can help businesses make better decisions.

PwrScore.ai

The second project might sound unusual, but it could change the world: plastic-free diapers.

“Diapers last for a thousand years and they become these horrible microplastics that are bad for the world, and I just thought it could be possible to do it without plastic. So I’ve been working on it for five years with a team. We’re this close to a breakthrough…”

Think about it – billions of diapers end up in landfills every year, taking centuries to decompose and creating environmental havoc. If Jim cracks this code, the sustainability impact could be massive. (Hint #2: Catch my previous episode with the founder of Sustainable Brands for more.)

The Renaissance Entrepreneur

What makes Jim truly special isn’t just his business acumen – it’s his genuine curiosity about everything. He flies “small, crappy airplanes” for fun, creates glass art displayed in world-renowned museums, and casually mentions voting on Federal Reserve interest rates like it’s a weekend hobby.

This broad range of experiences gives him perspectives that pure business specialists simply can’t match. When he talks about innovation, he’s not just drawing from MBA case studies – he’s pulling from art, aviation, monetary policy, and manufacturing.

Why This Conversation Matters

Whether you’re in media, marketing, or building the next big thing, Jim’s approach to problem-solving offers a masterclass in thinking differently. He doesn’t just spot trends – he creates them by identifying problems everyone else has accepted as unsolvable.

His insights on brand compatibility, disaster prediction, and sustainable innovation are particularly relevant right now. Plus, his commitment to giving away his wealth while still actively building and creating is a refreshing take on success and legacy.

This episode is packed with inspiring stories, clever insights, and tactical wisdom that will help you rethink what’s possible in your own work. Jim McKelvey proves that true innovation comes from embracing diverse interests, taking calculated risks, and always asking “what if we could do this better?”

A Series of Legends This interview is one of several featuring winners of the Eddie & Ozzie Award who are being inducted into the Folio: Legends Hall of Fame this October. What’s the common thread among these industry legends? Each has reinvented themselves or their company in remarkable ways.Be sure to watch for upcoming episodes with Neil Vogel, David Adler, and other Hall of Fame inductees. You won’t want to miss this any of these legends! For all their brief profile award interviews, visit the award site. Key Moments:

00:00 Jim McKelvey’s Eerily Accurate Business Predictions

02:15 Hall of Famer but a Career with No Focus — On Purpose

03:02 The Plastic-Free Diaper Project

03:36 Giving Away his Fortune

05:55 Giving Away his Power (Score).ai Tool

08:05 What Makes for Dangerous Brand Associations

11:17 Writing the Book on Innovation

14:17 Why McKelvey Only Solves Unsolved Problems

15:12 Trading News Consumption for Data Capture

16:30 Humble Pie, Hobbies and Heroes

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