When he’s not designing or playing games, he runs Appian Corp., a Reston, Virginia, firm that sells software to help businesses build apps more quickly. Appian, which went public in 2017, is worth $2.1 billion; Calkins owns just under half. 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 (say, for a bank’s users to check their balances or for a government agency to handle payments) at a lower cost than it could on its own. Growing up just north of San Francisco, the son of a real estate developer and a math teacher, Calkins spent his time camping, studying music and playing games. At Dartmouth he graduated in 1994 as the top economics student in his class. By 1999, Calkins and three friends were meeting to teach each other coding languages. He left MicroStrategy that year to launch Appian with them.