At this year’s Strategic Summit, attendees were treated to an inspiring and candid conversation with Jim McKelvey, co-founder of Square (now Block, Inc.) and author of The Innovation Stack. Drawing from his own entrepreneurial journey, McKelvey shared insights on what it takes to build enduring companies, overcome industry giants and innovate in ways that truly matter.
From a missed sale to a billion-dollar idea
McKelvey opened with the story that sparked Square’s creation: losing a sale for his personal glass blowing business because he couldn’t accept an American Express card. Frustrated but motivated, he joined forces with Jack Dorsey to create a simple tool that would let anyone process card payments from a mobile device.
That problem, one faced daily by small merchants, set the stage for a company that would go on to revolutionize how millions of businesses handle payments. But McKelvey made clear that Square’s success wasn’t born from a single idea; it came from a relentless process of copying what worked and innovating only when forced to.
“Innovation,” McKelvey said, “is what you do when you can’t copy.”
The power and pain of innovation
Square’s early journey was anything but easy. McKelvey described the obstacles his team encountered while trying to operate within the highly regulated financial system. From legal hurdles to banks unwilling to support their model, each barrier forced Square to invent a new solution. The result was what McKelvey calls the “innovation stack” – a series of interdependent innovations that, together, made Square impossible to replicate.
When Amazon later tried (and failed) to launch a competing product, it proved the strength of that stack. “Amazon quit,” McKelvey noted, “because they couldn’t copy it.”
But he also emphasized that true innovation is rarely glamorous. It’s messy, uncertain and often painful. Yet, it’s precisely that discomfort that creates breakthroughs. “Innovation,” he reminded the audience, “is not fun but it’s powerful.”
Serving the underserved
McKelvey’s insights extended beyond technology to a core business principle: serve the underserved. He pointed to companies like Southwest Airlines, which disrupted air travel by focusing on price-conscious travelers that major airlines ignored. Similarly, Square succeeded by empowering small businesses who had been overlooked by traditional financial institutions.
“Big companies chase big markets,” McKelvey said, “but opportunity lives in the gaps.”
For financial institutions and credit unions, he argued, the lesson is clear, innovation doesn’t have to start with cutting-edge technology. It begins with empathy: understanding who isn’t being served and finding creative ways to meet their needs.
Risk, regulation and the courage to build
Throughout his session, McKelvey reflected on the delicate balance between regulation and risk-taking. Rules are essential, he acknowledged, but when systems are too rigid, they choke innovation. The key is to allow space for experimentation, especially for smaller, more agile organizations that can move faster than large incumbents.
He urged leaders to create environments where calculated risk is encouraged, and where “unqualified” individuals, those who don’t fit the traditional mold, are empowered to try new things. “Meaningful progress,” McKelvey concluded, “often comes from people who have no idea what they’re doing but do it anyway.”
A call to action for CU leaders
McKelvey’s message resonated deeply with Summit attendees, many of whom face the same challenge of balancing stability with innovation. His talk served as a reminder that strategic growth doesn’t come from playing it safe, it comes from rethinking how we serve, whom we serve and what barriers we’re willing to challenge.
In a world where technology evolves daily, McKelvey’s perspective offers a timeless takeaway: innovation isn’t about disruption for its own sake, it’s about solving real problems for real people.
As organizations look to the year ahead, his call to action is simple yet profound:
Copy what works. Innovate where you must. And never forget the people who’ve been left behind.
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