An army can look impressive and still decline to fight. In Sekigahara, the historical board game designed by Matthew Calkins, wooden blocks represent forces in seventeenth-century Japan. To make them act, a player needs the right cards. Position matters. So does allegiance. A commander can discover, at a deeply inconvenient moment, that the troops have other plans.
It is an absorbing problem for someone whose other occupation involves getting large organizations to work. Calkins is the co-founder, chairman and CEO of Appian, the enterprise software company he started with three friends in 1999. He builds systems for business processes. He also builds games in which people must decide what to do with incomplete information.
The two pursuits offer an unusually concrete way to understand him. A corporate title tells you where a person sits. A game makes you live with the consequences of the rules that person chose. Calkins has supplied both, over a career long enough to outlast several changes in the technology industry's preferred vocabulary.
The army that might refuse
Published by GMT Games in 2011, Sekigahara: The Unification of Japan asks two players to contest the campaign of 1600. Its armies remain partly hidden. Its combat uses cards rather than dice. A matching card lets a force participate; an impressive collection of blocks without the necessary support can be an elaborate disappointment.
That arrangement reflects a decision about what history should feel like to the person playing it. In his designer notes, Calkins explains his preference for uncertainty that allows planning and bluffing. A dice roll surprises both sides. Hidden information lets each player know something the other does not. The distinction changes the kind of decision the game rewards.
His objective was to recreate the commander's experience, including doubt about supporters, within a game that could finish in an evening. The design leaves room for calculation while denying the comfort of complete knowledge. It is a rather efficient way to spoil an overconfident plan.
“Designing games is like designing organizations”
Matthew Calkins, in a 2021 interview
Calkins made that connection explicitly when asked about his software and game work. The relationship, he explained, concerns mechanisms for making decisions and recognizing what matters in a complex situation. That is a more useful claim than the familiar idea that every business encounter is a contest somebody must lose.
Four friends, before the flowchart
Calkins graduated from Dartmouth College in 1994 with a degree in economics. His official biography identifies him as his class's top economics graduate. He then worked at MicroStrategy, where he became director of the Enterprise Product Group. By 1999, at 26, he was ready to leave and start something with people he knew.
The other founders were Michael Beckley, Robert Kramer and Marc Wilson. Dartmouth supplied more than one connection: Beckley and Wilson were alumni too. The company began in Calkins's basement. Its public listing arrived in May 2017, eighteen years after the founding. That interval is worth keeping in view whenever a business history threatens to hurry directly from inspiration to the stock exchange.
In recounting the beginning, Calkins has emphasized the culture he wanted to create before a fully formed product or market plan. The early ambition concerned the sort of organization the friends could build together. His advice to founders has consequently been practical: find a customer, understand a problem and create value early enough to earn some independence.
Appian became associated with low-code development, allowing people to construct applications through visual tools rather than writing every instruction line by line. In a 2022 explanation, Calkins described drawing a flowchart with boxes, arrows and a beginning and end. A business process becomes something a person can see, discuss and change.
The appeal is easy to grasp without pretending that complicated work has disappeared. Organizations still have exceptions, permissions and awkward handoffs. Making the process visible gives people a way to reason about those details. It also makes the software conversation available to someone whose expertise lies in the work rather than in programming syntax.
The interview as an open door
For years, Calkins personally interviewed Appian's job candidates. He has described those conversations as a way to establish a consistent culture and to show respect to the people considering joining it. The meeting carried a second message: the chief executive was a person a new employee had already spoken with.
That is a small organizational mechanism with a recognizable purpose. An invitation to speak openly sounds different when the person issuing it has previously given you time. Calkins wanted employees to feel able to approach him, offer comments and disagree. He regarded the early hiring decisions as choices that would be multiplied as the company grew.
There is an obvious tension in the approach. Personal involvement helps define a young organization, but the number of candidates eventually outruns the founder's calendar. In discussing the practice, he acknowledged that he could no longer conduct as many interviews as before. The useful detail is the effort to make accessibility a habit before scale made it harder.
An airline, a chariot, a change of dice
His published games make a varied shelf. Tin Goose, released by Rio Grande Games, puts players in the early airline business. They acquire aircraft, develop networks and respond to disruptive events. An expansion plan has to coexist with the possibility that somebody else's cards contain a distinctly unwelcome development.
Much of its information begins in players' hands. Watching what rivals bid can therefore tell you something about what they expect. A price becomes evidence. An apparently generous offer may deserve a second look. The game's economic setting gives Calkins another way to explore decisions whose consequences depend on other people's knowledge and incentives.
Charioteer moves the action to ancient Roman racing. GMT describes a game built around accessible rules, quick play and distinct mechanisms. The change of scenery matters: Calkins's interest reaches beyond a single historical period or type of competition. A chariot race and an airline business demand different models, even when both can punish a badly timed commitment.
His later Racket Dice, listed by GMT as published in 2026, makes skills upgradeable through dice with different numbers of sides. Players weigh improvement against its immediate cost. The design also looks back to family camping trips when Calkins played dice games after sunset. A new set of mechanisms carries an old memory of being around a table.
The personal detail is useful because a founder's hobby can otherwise become a convenient management parable. These are also games he wants to play. The subjects arise from curiosity, experience and the pleasure of making something that gives another person an interesting choice.
A machine needs rules, too
Appian's present work places Calkins in the debate about how companies should use AI. His position starts with the operations surrounding the model: information, permissions, supervision and the allocation of tasks. In an August 2026 interview, he argued that probabilistic systems need a dependable software framework when the work cannot casually accommodate mistakes.
It is a commercial argument from someone selling enterprise software, and its practical questions remain worth asking. Which information may the system use? Where does a human review an action? How will an organization understand what happened afterward? A convincing demonstration still leaves those choices to be made.
An editorial diagram of his stated priorities, not a product architecture.
The concern extends to the rules under which AI gets its information. In a 2023 essay, Calkins called for a public debate that included entrepreneurs, artists, musicians and writers. He objected to leaving the discussion inside a private meeting of prominent industry figures and lawmakers. The people whose work supplies the material deserved a place in the conversation.
In 2024, he developed the case for privacy and property rights, arguing that trust would make people more willing to participate. His proposals included consent and compensation for copyrighted information used by AI. Those are policy preferences, with consequences for providers and creators, rather than settled descriptions of how every system operates.
The continuity with his other work is a matter of emphasis: who has information, who has permission, and what makes participation worthwhile. That reading does not require turning every game rule into a prediction about technology. It simply follows the questions he has chosen to discuss in public.
The promise with a condition attached
One revealing document sits outside the interviews. In June 2022, Calkins wrote to Appian's compensation committee about a proposed option award covering 700,000 shares. Full vesting required the share price to average $250 over a year within an eight-year period. He said he would donate all income from the award to charity.
The conditions matter. The letter records a promise about potential future compensation. It does not establish that the award produced income or that the corresponding donation has occurred. Its interest lies in how explicitly the executive connected an incentive for himself to a benefit he intended for others.
Meanwhile, the founding group remains visible in Appian's leadership directory. Beckley is chief technology officer, Kramer is founder and general manager, and Wilson is founder and chief executive ambassador. Calkins still leads the company. The four names give the long history some human continuity.
At the game table, he has spent years deciding which uncertainties make a contest interesting and which rules make a decision meaningful. At Appian, the consequences leave the table and enter somebody's working day. His career keeps returning to that uncomfortable, productive space between a plan on paper and the people expected to carry it out.
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Conversations, games and more from Calkins.