04/07/2026 | News release | Distributed by Public on 04/07/2026 10:52
It had been a long day.
Jim McKelvey - the artist-turned innovator who was the featured speaker at the Rockhurst University Leadership Series event Wednesday - said he fully intended to board a plane to get to Kansas City for that evening's event.
But, because of cloud cover, it was canceled. McKelvey, a pilot himself, decided to fly himself, not knowing exactly where he would be allowed to land.
That crucible served as a fitting metaphor for McKelvey's views on innovation, entrepreneurship and leadership. Sometimes, it pays to be a wildcard, to drive into the storm and hope for the best.
McKelvey founded Square (now Block, Inc.), the revolutionary mobile point-of-sale system, to solve a personal problem - he wanted to be able to accept non-cash payments at his glass art studio. And he wanted people like his friend Bob, a talented but sometimes cash-poor and tech-averse glass artist, to be able to do the same. There's a lesson in that, he said, about the need that proceeds innovation, and the considerations that need to go into the planning stage to take a truly revolutionary product from idea to market.
"We're talking about a few times in your life you'll find some problem that you care about. You say, 'I wish there was a way for Bob to take payments or a way that we can fly planes cheaply,'" he said. "And you'll come up to this edge of what humanity knows how to do. And if you choose to step across that, you think, oh, now I'm being innovative, now I'm being cool. It will feel lonely and scary and horrible. And the odds of success are not great, but it's where progress comes from."
Following his keynote address, McKelvey sat down with Peter Mallouk, president of Creative Planning and majority shareholder of Sporting KC. The two continued talking about the landscape of innovation, including what causes startups to succeed or fail.
"The overwhelming majority fail. And a lot of people think they fail because of lack of capital, and a lot of them do, but it's usually just, it's not a competitive idea," Mallouk said. "It can't compete with the other ideas in the marketplace. So you don't have the right leader, you don't have the right idea, you don't have the right execution, or you don't have enough money. There are so many ways to fail, so few ways to win. And even the winners, most of the time the winners are not big."