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Jim McKelvey is one of America’s most successful entrepreneurs. Not that you would know it by talking to him. “I always feel unqualified,” insists the 54-year-old billionaire, who has started six businesses including $33 billion (market cap) payments firm Square, which he cofounded with Twitter CEO Jack Dorsey. Seated at a crowded midtown Manhattan Le Pain Quotidien, the billionaire is explaining how his lack of experience or expertise is the reason for his success. “So often when I do something that’s never been done before, I feel like I’m not qualified,” says McKelvey, casually dressed in a leather jacket and jeans.
But sometimes unqualified people like him are the best at coming up with solutions to new problems. That’s how he came up with the idea for payments firm Square, the source of his $1.5 billion fortune. McKelvey, who has been a glassblower on and off for more than 30 years and still sells his works, including today 44 sink spouts, opened an 8,000 square foot glass facility with a friend in a converted former 1930s car dealership and service station in St. Louis in 2002. A few years later he became frustrated that he was losing glassblowing sales because he couldn’t accept American Express cards, whose fees were too high. He called up his friend, Twitter cofounder Jack Dorsey, who’d interned for him as a teen. In 2009, they started Square, which made it possible for anyone to accept card payments with a smartphone or tablet; it now processes payments for 2 million businesses. He left daily operations a year later when his son was born but still sits on the board.
Nowadays McKelvey is applying his creative inexperience and liberating lack of expertise to the publishing industry. Tired of fake news, clickbait and the overload of online ads, McKelvey says he began thinking of ways to help readers take back control of their online identities. He started Invisibly, which powers micropayments for online content, in 2016 in St. Louis. So far he’s invested $11 million of his own cash and raised an additional $20 million from investors including Peter Thiel and Founders Fund. The startup’s tools are designed to give consumers, not advertisers or publishers, the power to decide what ads they see, stories they read and data they share. “We will tell you how your eyeballs are being bought and sold, what information the world has about you and how it’s being monetized,” McKelvey explains.
Currently most websites make money in two ways: subscription (like the New York Times and Washington Post) or ads (like Forbes). McKelvey wants instead to give readers free digital wallets, to be funded every time they watch an Invisibly-served ad. They could then spend that “money” to access content. Hypothetically, each article would cost a certain amount – set by an algorithm factoring in quality and demand. As readers share more personal data that, in turn, lets advertisers tailor ads to them, their costs go down.
Right now this idea is still something of an eccentric billionaire’s pipe dream. “I don’t know if it’s going to work,” McKelvey cheerfully admits, as he rips off a piece of croissant. “We have a couple of private investors who are highly risk tolerant, and they know it could go to zero,” he says. “We burned through 20 million bucks already. We don’t even have a product,” he says, jovially. “I just want to live in a world where quality earns more money.”
What Invisibly does have is a beta test that it launched on its site in February, which allows users to see the digital price they are paid to engage with ads. The more they earn, the more content they can read on participating websites. (Theoretically, a user could also add their own money to their wallet to avoid ads altogether.) The startup says it has already signed up more than 30% of publishers in the U.S. including the Associated Press, Scripps and McClatchy for its test.
While McKelvey is still involved in the business as founder, he has brought on his longtime friend, Matthew Porter, formerly CEO of CMS platform and IT support provider Contegix, to run the show. According to Porter, McKelvey showed up at his house in St. Louis one night last summer and refused to leave until Porter agreed to join Invisibly; he is now CEO of the firm, which has offices in St. Louis, New York and Palo Alto.
Jim McKelvey wrote the first textbook for glassblowing, called Art of Fire, in 2006. He still sells his work, he says, “because if I don’t sell it, I can’t tell if it’s any good.”
“Jim is wicked smart. His intensity when he is passionate about something is off the scales. He will bounce between the 30,000-foot-view and the 3-foot-view,” Porter says.
That’s been true throughout his peripatetic career as a serial entrepreneur. Over the years he’s started a handful of businesses, in addition to Square, in such fields as software, book printing and roofing. One of his early companies was the first, according to McKelvey, to publish trade show literature on CDs. His non-profit was set up to help solve the national shortage of programmers.
All of these disparate ventures are tied together by one thing: at the core of them all, McKelvey was trying to solve a problem. In most cases, that has meant jumping into new industries about which he knows little. That realization is part of what prompted him to write his new book, “The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time,” which goes on sale next week.
“Maybe my calluses are a little bit thicker. I still feel confused and scared. I still feel like I don’t know what I’m doing. I still feel all the ways I felt when I was starting Square,” McKelvey says. “The fact that I’ve written the book for the last three years has helped me understand that at this moment, I should be uncomfortable…But I have a little better understanding, and it’s a small improvement.”
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