How Square Cofounder Jim McKelvey Stopped Viewing His Career As A ‘Dumpster Fire’ And Embraced Entrepreneurship

Annoyed that he had to turn away a sale because he wasn’t set up to accept American Express cards, then-glassblower Jim McKelvey teamed up with Jack Dorsey to found Square in 2009.

1. “If you think of the way revolutions happen, they start with the peasantry. The elite does not revolt,” McKelvey recently said last week at the conference “Challenges Met, Opportunities Ahead,” in a conversation with Elizabeth MacBride, editor of the Times of Entrepreneurship, the event organizer.

McKelvey is now on the board of Square (renamed as Block), chairman of the St. Louis Federal Reserve and founder of Invisibly, a startup backed by Peter Thiel’s Founders Fund. He is also the author of The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time. In the book, he chronicles how Square disrupted a financial system that made it hard for many small businesses to accept credit cards, making it cheaper for them than a traditional merchant services provider.

In case you’re wondering what an innovation stack is, he defines it as “the thing that happens when you try to do something new. It’s a mess. It’s an interlocking set of inventions that collectively form this new thing.” 

Here are some takeaways I gathered from their conversation. 

There are no “right” credentials to start a business. “A lot of people think they are not qualified to do the things they are qualified to do,” said McKelvey.

Let go of the idea of a linear career path. McKelvey spent a lot of time seeing his career as a “dumpster fire” because it was non-linear, unlike those of many people he knew.

“It took me a long time to realize I was different,” he said. “It’s the term ‘career,’ I couldn’t handle…Almost implied with the word career is ‘path…’ I didn’t have a career path.”

He came to realize that “the things I was good at were not valued over a long period of time”—but that didn’t mean they weren’t valuable. 

There is only so much planning you can do as an entrepreneur. “Most of the things you do in entrepreneurship haven’t been done before,” he said. “Past that, you haven’t figured it out. 

Watch out for “linguistic gravity.” Existing language can hold you back when you’re inventing something new. “We don’t even have a word in the English language for something that doesn’t exist,” noted McKelvey. That doesn’t mean you can’t make it up. 

There’s always more to be done. At his startup Invisibly, McKelvey and his team will offer a curated content feed that gives users control of their data. It will be released in beta in a few weeks. 

Users of Invisbly will be asked to pay more for the content they like. “If it’s free, you have no control,” he said. “It’s not really free if you are selling your attention to someone else who is making it not free behind the scenes.”