In 1999, Calkins co-founded Appian and began building software tools such as an
intranet portal for the
U.S. Army.[1] In 2008, the company raised $8 million, and in 2014, raised $36 million in a secondary offering led by venture capital firm
New Enterprise Associates.[1] Appian later went public in May 2017.[1][6][7] As of 2019, Calkins owns just under half of the company which is valued at $2.1 billion.[1][8][9] Calkins believes there are different dimensions of
AI.[10][11]
Appian
Calkins left
MicroStrategy in 1999 in order to launch Appian Corporation.[1][2] He was 26 years old.[2][1] Appian creates low-code software that helps businesses build apps more quickly.[1][2][3] It is used by government agencies including the United States Food and Drug Administration, and private companies such as
T-Mobile,
Bayer, and
Exelon Corp.[12] The company went public in 2017 and Calkins owns just under half of it.[1]
Board gamer
Calkins is well known for designing board games and playing competitively.[13] He has collected 1,000 games,[13] and has won a number of events at the
World Boardgaming Championships.[1][2][14][15] His philosophy is that business and gaming have a lot of similarities: business skills can make someone a better game player, and playing games helps to make him a better CEO.[13][16]
Calkins created the board games Sekigahara, Tin Goose, Charioteer, and Magnet.[1][2][17]
Tin Goose: players build one of the first commercial airlines[1][2]
Charioteer: a strategic racing game set in ancient Rome[18]
Magnet: an “abstract game where players try to get their king to the middle of the board” [8] (runner-up for Games Magazine's Abstract Game of the Year, 2010[13])
Calkins has contributed to The New York Times about the value of board games in business.[19]
Other involvement
In 2017, Calkins was named to the Northern Virginia Technology Council (NVTC) board of directors.[20] He also serves on the leadership council of the Virginia Public Access Project and the board of the Sorensen Institute.[21] He was previously on the board for the NVTC TechPAC.[20] Calkins was named to the 2022 Virginia 500: Federal Contractors - Technology.[22]
War against Ukraine
Calkins helped the Renew Democracy Initiative to create fight4ukraine.com, a website that tracks the world's response to Russia's February 2022 invasion of Ukraine.[23] This initiative included banning the sale of software to Russia.[24][25][26]