It was just one lost sale, but for glassblower Jim McKelvey it was one too many.

“I was trying to sell a piece of glass to a lady who couldn’t pay me because I couldn’t take her credit card,” recalled the 47-year-old Ladue High School grad. “That was a real eye-opener and I decided this problem needed to be fixed.”

So, he put his computer science background to work. Square, the solution he eventually co-created, lets him accept charge cards through a small device attached to his mobile phone. It fixed the problem, allowing him to sell glass more easily.

It also facilitates about $5 billion in transactions annually from small merchants everywhere.

“I believe in designing products that I personally want to use,” said McKelvey, who is now much in demand as a presenter on the local entrepreneurial and innovation circuit. “I’m not really good at abstract thinking in the sense of building for others. I tend to build for myself.”

Fortunately, it turns out a lot of people want to use McKelvey’s products as much as he does. Lately, they seem to like hearing from him as well. The native St. Louisan was a speaker at the Startup Weekend in January and the recent Gateway to Innovation conference this spring.

Friday morning, he’ll keynote the Seeds of Change event at the Donald Danforth Plant Science Center speaking on topics related to innovation in the Gateway City.

In addition to McKelvey’s presentation, the second annual event will also feature panelists Benjamin Akande, dean of Webster University’s George Herbert Walker School of Business and Technology; Spencer Maughan, vice president of venture capital firm Venrock; and Judy Sindecuse, CEO and managing partner of Capital Innovators. Admission is free.

An enterprising life

For those who have seen him in action, McKelvey is an energetic and engaging speaker with a decidedly non-traditional style. He has been known to tell listeners to leave their mobile devices on during his talk. (He said they don’t owe him a “debt of courtesy” if his words aren’t interesting enough to keep them off the phone.) McKelvey also encourages his audience to interrupt him with questions or suggestions, something he took from time he spent in London where presentations are more raucous with heckling and shouting from the crowd.

“I wish we had more of that,” he said. “I think a lot of people just stick to the script and don’t really say anything meaningful. If I’m ever guilty of that, I want someone in the front row to say, ‘I disagree and here’s why.’ Bring it on.”

McKelvey’s own story hasn’t stuck to the script anymore than his talks do. An alumnus of Washington University’s engineering school, where his father had once been dean, he got his start in the computer science field. It was also at Wash U where he learned to blow glass, a happenstance that came to fruition when he was looking for a fun class to take senior year and began flipping through the course catalogue.

“I was just mesmerized by the process,” he said of the unique art. “Glass is extremely difficult to control. Therefore, it’s very challenging. It doesn’t bore you. Since I tend to be fairly easily bored, I was drawn to it and thought that it was something I wanted to do.”

That led him in 2002 to become a co-creator of the Third Degree Glass Factory, a public access glass art education center that offers classes and rental space in a former gas station east of the Delmar Loop. Third Degree wasn’t his only startup either. McKelvey spent 10 years with another enterprise he created, Mira Digital Publishing.

But by late last decade, he was looking for a new challenge. He found it during his fateful interaction with the credit-card wielding customer and soon he reconnected with Jack Dorsey, an associate he’d worked with at Mira who went on to help found Twitter. The pair launched Square in 2009.

It didn’t come without a degree of trepidation. The unique nature of the product catered to tiny merchants who may not even have a physical location, a community traditionally ignored by larger payment companies. Would it actually work commercially?

“We were creating a new market and nobody had done it,” he said. “Nobody had empowered small entrepreneurs and we didn’t know how many there were. These people, because they’d never been served, had never been surveyed.”

There was little hard data, a lot of questions and even a fair share of ridicule.

“A lot of the established players laughed at us,” he said. “They thought we were idiotic going after these people who weren’t in the system.”

They aren’t laughing anymore. Square is now well-established in the market and has more than 300 employees. The company’s rise has been so meteoric McKelvey jokes that he shouldn’t even quote the statistics since they change every day.

Square’s success also came with a big lesson. There are times you just have to jump off the cliff. For some products, the only market research data an entrepreneur is going to get is whether they are still in business a year later.

“You can’t survey innovation,” he said. “You can’t prove the case in advance that innovation is going to work. At least I’ve never seen it done.”

Much of the philosophy McKelvey brought to his new company, he picked up from years spent in entrepreneurial hotbeds from San Francisco to Florida – and even further afield.

“The things I learned in Japan are that the Japanese are fantastic at creating products of extremely high quality down to the smallest detail,” he said. “That ethic is sort of embodied in Apple products in this country but not in a lot of other products. That really stuck with me and the Japanese culture had a tremendous influence over what I built for Square.”

Entrepreneurial St. Louis

Despite his travels, McKelvey is a big booster for his hometown. A multi-generation St. Louisan, he is optimistic about what’s been developing here.

“I see another entrepreneurial revolution,” he said. “The people who built this town were entrepreneurs. At the turn of the last century, the 1900s, this was one of the hottest cities in the world. It was considered much trendier to be in St. Louis than to be in New York. That was because of the entrepreneurial activity.”

But he feels it also sowed the seeds of its own downfall.

“Having been so tremendously successful 110 years ago, that success tends to build great wealth and great wealth tends to build a mentality of preservation as opposed to risk taking,” he said. “Over time guarding what you have impoverishes the future.”

McKelvey has been working to prevent that impoverishment by remaining active in the local entrepreneurial milieu. Among other things he’s now on the board of directors of Emerald Automotive, an alternative fuel vehicle maker setting up operations in Hazelwood.

“They picked St. Louis over all other cities in the world to manufacture this vehicle,” he said. “They are not even based in the U.S. so they could have easily manufactured in Europe or China or anywhere. They picked St. Louis for objective reasons. It has real advantages.”

He’s also involved in Arch Grants, a local group that helps boost startups.

“To the extent that St. Louis is providing support, we’re drawing entrepreneurs from other parts of the world and that’s fantastic,” he said. “That’s very meaningful.”

He said St. Louis still faces big challenges, including problems with a racially segregated social structure and difficulties with the school system.

The entrepreneurial environment also has needs. Often high-growth companies see less depth of talent to draw from than in areas like Silicon Valley or Boston, he said. The region needs to keep working to attract people with skills in demand.

“We also need to remove the stigma of investing in the new,” he said. “People on the West Coast are extremely excited by new ideas and very supportive of them in a way we have not duplicated here.”

He said that’s a key point since the next big thing is likely to come from somewhere unexpected.

“That’s critical because that’s where the giant companies and opportunities come from,” he said. “It’s not from mergers and moving money around, dividing the wealth. It’s creating the wealth. I really think that St. Louis is poised to be an entrepreneurial haven after a hundred year rest.”

Not that rest interests McKelvey much. Constant activity seems to define him and, even for one of St. Louis’s premiere entrepreneurs, old habits die hard. McKelvey still blows glass.

“I had $2,000 in sales last month,” he said with a chuckle. “It was a pretty good month.”