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Square's Jim McKelvey Explains How To Build A Business, 'One Crazy Idea At A Time'

Jim McKelvey is the co-founder of LaunchCode, a St. Louis-based company celebrating its fifth anniversary this October.
Jim McKelvey is the co-founder of LaunchCode, a St. Louis-based company celebrating its fifth anniversary this October.
Jim McKelvey is the co-founder of LaunchCode, a St. Louis-based company celebrating its fifth anniversary this October.
Credit LaunchCode
Jim McKelvey's new book has advice for entrepreneurs, and some good stories, too.

The mobile payment company Square was a game-changer. It slashed the costs of taking credit card payments — allowing small businesses and artisans to get into the game without having to pay sizable percentages of their transactions to processors. In retrospect, it seems like a no-brainer.

But in 2009, it was just an idea — one born of frustration when St. Louis glass blower Jim McKelvey lost a sale after being unable to take a credit card payment. After McKelvey shared his idea of a better way with his former intern, Square was born. (It helped, of course, that the intern in question was Twitter co-founder Jack Dorsey.) 

How Square went from an inkling to an industry disrupter is the subject of McKelvey’s compulsively readable new book, “The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time.”    

On Friday’s St. Louis on the Air, McKelvey discussed the book — which, he acknowledged, he’d conceived as a graphic novel. It took pushback from the late Herb Kelleher, the iconoclastic Southwest Airlines founder, for McKelvey to drop the idea and resort to a more traditional narrative. (Still, one chapter can be found in comic book form online; check it out at jimmckelvey.com.) 


McKelvey explained a metaphor he uses in the book: the ordinary business world as a walled city. Entrepreneurs, he said, venture outside the safety of that walled city for a place where no rules apply.

That said, McKelvey pushed back on the idea that he deserves credit for leaving the walled city. 

“Let’s dispel a myth,” he said. “I am not some bold person who ventures out. I am a guy who tends to get kicked out of stuff. I’m the guy that gets tossed over the wall by some angry crowd or something. And whatever gets you outside, you’re still there.”

In that lawless world outside the walls lies great opportunity for those bold enough to seize it, McKelvey said. Those are the stories he tells in his book.

“If you trace back the history of some of our greatest inventions, the people at the founding moment were not qualified to do what they did,” he said. “The Wright brothers — they were not qualified to be the first people in the air. IKEA was founded by a 17-year-old kid. It’s the biggest furniture company in the world right now. What does a 17-year-old kid know? The biggest bank in the world was started by a kid who dropped out of school at age 15 and became a produce vendor. Think about the world of banking being totally upended by a guy who sold lettuce. These are fantastic stories.”

St. Louis on the Air” brings you the stories of St. Louis and the people who live, work and create in our region. The show is hosted by Sarah Fenske and produced by Alex Heuer, Emily Woodbury, Evie Hemphill, Lara Hamdan and Joshua Phelps. The engineer is Aaron Doerr, and production assistance is provided by Charlie McDonald.

Send questions and comments about this story to feedback@stlpublicradio.org.

Copyright 2021 St. Louis Public Radio. To see more, visit St. Louis Public Radio.

Sarah Fenske joined St. Louis Public Radio as host of St. Louis on the Air in July 2019. Before that, she spent twenty years in newspapers, working as a reporter, columnist and editor in Cleveland, Houston, Phoenix, Los Angeles and St. Louis. She won the Livingston Award for Young Journalists for her work in Phoenix exposing corruption at the local housing authority. She also won numerous awards for column writing, including multiple first place wins from the Arizona Press Club, the Association of Women in Journalism (the Clarion Awards) and the National Society of Newspaper Columnists. From 2015 to July 2019, Sarah was editor in chief of St. Louis' alt-weekly, the Riverfront Times. She and her husband, John, are raising their two young daughters and ill-behaved border terrier in Lafayette Square.