Billionaire Matt Calkins is a board game whiz. That has something to do with being a business success
feel like I should apologize,” Matt Calkins tells his opponent as they shake hands. It’s mid-evening in the log-lined cafeteria at the Seven Springs Mountain Resort, and Calkins, from a trailing position, has just played a decisive move in the board game Sekigahara. His opponent shakes his head at the suggestion Calkins prevailed through luck. “You sprung a trap on me,” he says.
And then there’s his other life. Calkins, 46, cofounded Appian 20 years ago; it initially built software tools, such as an intranet portal for the U.S. Army. Since 2004 the company has been tackling the bigger problem of making digitization less coding-intensive for programmers. With Appian software, a corporate client can create its own applications at a lower cost than it could on its own.
By 1999, Calkins and three friends were meeting to teach each other coding languages. He left MicroStrategy that year to launch Appian with them. “I thought, I can do this,” Calkins said. “Overconfidence helped.” Demand for Appian grew as more companies realized that customers expected the same streamlined experience they knew from their favorite smartphone apps. Sales and its stock, nearly triple its IPO price, soared—though not profits. Like many software-as-a-service companies, it still runs at a loss to support increased marketing and R&D.
One of Appian’s competitors is the Boston firm Pegasystems. That outfit is run by Alan Trefler, also a billionaire Dartmouth grad and, not so surprisingly, cochampion of the 1975 World Open in chess. Playing games requires you to hone your pattern recognition and deep evaluation skills and develop a sixth sense for mistakes, says Trefler. “If you lose concentration, you die. And that’s true in business,” he says.
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