Board Games, Hiking, & Bootstrapping: How a Nasdaq-listed Company Founder & CEO Finds Higher Ground

Appian CEO

Matt Calkins, Founder & CEO at Appian, a leading provider of low-code and business process management solutions.

Mike Rohner: Matt, can you tell us what Appian does?

Matt Calkins: There is a great deal of demand right now around the world for unique software and not a lot of expertise or patience or budget in order to make it. So the world’s asking for an easier way to make unique software. And Appian is offering that easier way. These applications run some of the most important functions for some of the world’s most important organizations. Whether that’s government or major retail or airports or pharmaceutical companies or banks. We run some exceptionally important processes and applications at some of the world’s biggest institutions.

I think digital transformation is using technology to offer a better product, a better customer experience, and to make a better relationship with your customer than you had in the past. Appian is very good at creating a relationship by remembering what’s been true with that customer in the past and streamlining each interaction so that the customer feels very well served.

Mike Rohner: You have a unique background. You left behind $2 million in stock options as the youngest board member at Microstrategy, another Nasdaq-listed company, to start Appian back in 1999.

Matt Calkins: The decision probably wasn’t difficult enough. I think it was made with a degree of overconfidence. I think at the time it was the late 90s and everybody’s business was taking off so it was all too easy to make the leap. I think we’re fortunate that it worked out so well.

Mike Rohner: You started Appian in 1999. It’s one thing to start a company and get it off the ground but to navigate through the tech bubble and burst in 2001 and the market correction in 2008 without seeking outside funding…

Matt Calkins: We essentially broke even on a cash flow basis from the day we were founded until the day we did our IPO on Nasdaq in 2017. So that’s an unusual story, particularly for a firm who was growing at the rate that we were growing, and that did as well as we did in the markets. It’s not often you see that from a bootstrapped company.

Mike Rohner: What hasn’t changed for the company over the years?

Matt Calkins: The culture hasn’t changed. The people haven’t changed. I still do the interviews. We still look for people who are good team members, good communicators, high talent. That’s still a hallmark. You can still spot an Appian person.

Everyone’s voice matters here. We hire people who think of good ideas and it would be a shame not to listen to them. We have a culture here where everyone is respected when they speak up and they are expected to speak up and that stems from our early heritage as a debating culture. Two of the four founders here were big time debaters in school, and so we started out arguing everything and it turned out to be a good way to run a company.

Mike Rohner: What have you learned about negotiating from your co-founders who have a great deal of experience in that area?

Matt Calkins: You’ve got to know what you think and say it in a smart way and defend your ideas. That’s exactly how work should be. So it just keeps you sharp. Being challenged all the time. Being contradicted all the time. Being offered variations and alternatives to your thoughts and strategies is just a great way to run a company.

Mike Rohner: In addition to starting your own company, you designed a few board games and have been competitive as a gamer yourself.

Matt Calkins: There’s a parallel to designing a game and designing a company. Or, for that matter, spotting a market opportunity. In both cases you start with something complicated like, say, the history of Japan in the year 1600 and you figure out what are the essential causal relationships that make history move in one direction or another and that kind of thought is a good way also to approach a market. What does the market need right now? What would move the business equilibrium at this moment? That’s a good way to think and that’s an economic way to think and I’m originally an economist. Beginning with a very complicated situation and boiling it down to essential causal relationships whether that’s to make a model as you do in economics or a game or a business proposition is a relatively similar exercise.

Mike Rohner: You were actually the #1 economic graduate at Dartmouth in 1994. I’ve heard you talk about the value of having the right systems in place in the past. Can you elaborate on that?

Matt Calkins: It’s a funny thing about how I design games. I always feel like I’m about 90% finished. On day one when I come out of the shower and scribble down my ideas I think I’ve got it or back from a walk I feel like I got it and it’s about 90% of the idea done right there. In designing a game—in order to be good at it—you have to be really good at confronting the fact that it’s not 90. It’s a process of understanding what’s really great about the game and then ripping down the rest of it and rebuilding with another candidate for greatness. That persistence and that honesty and that sort of humility to realize that what you thought of wasn’t good enough yet…that is a really important quality to have in building an organization or a game.

Mike Rohner: Can you talk a bit more about your collection of board games? I’ve heard that you really don’t play the games but enjoy going through the rules and designs of different games.

Matt Calkins: Sometimes I buy a game and look at just to see if they thought of any new ideas. I want to know if there is a new mechanism. And so I investigate in order to find out whether the authors thought about anything elegant that goes into that game and those become...there’s an ever advancing art in gaming….how do you deal with a random event? How do you represent progress on the board? How do you create all these experiences that you want to create in a game? How do players get better at it? How to use dice, cards…other things? New innovations are always happening and those innovations interest me. So yeah, I do buy games just to see if there’s a new idea.

Mike Rohner: Are the concepts the same between games and business? What are the rules and commonalities?

Matt Calkins: We have new problems. How do we do digital transformation? How do we make it easy for companies to build their own software? Well we certainly don’t want to do it like 20 years ago and nor would we want to make a game today that looked like it did 20 years ago. We’ve got new ideas. Better ideas. We have tested new approaches and now today’s answer should be the heir to all those new ideas.

We found our way opportunistically. That’s part of what you have to do if you’re a boot-strapper. When the demand dries up you just have to move on. And so we’ve moved on a few times. We moved on after the tech bubble burst for example…we had to. The old business didn’t work anymore. And then we moved on again because margins were dropping and we wanted to create something more valuable. And now we’ve transformed our market again over the past five years.

Mike Rohner: How do you destress and manage your time? I know you grew up on the West Coast and have enjoyed back packing from an early age.

Matt Calkins: Backpacking is not a de-stress it’s a different kind of stress and I just like to alternate. It’s very different. It can be less comfortable than a day at the office. Its grueling…it’s uncomfortable. It’s a great different experience. It’s easy to live at the very top of the stack, by which I mean all these layers of technology and infrastructure supporting us, and then we live at the top and we don’t even notice the day cycle, the weather cycle. Right? We’re unbound by distance. We’ve almost exempted ourselves from nature. It’s nice to get back into nature not as a way to unwind but really as a way to reconnect with natural factors. So I like that. I don’t spend a lot of time at the beach or really relaxing at anything but I do love hiking. I feel better and stronger afterwards.

Mike Rohner: Can you talk about your decision to go public and why Nasdaq?

Matt Calkins: First of all I wanted to say that I’ve really enjoyed working with Nasdaq. Nasdaq has been a good partner for us. From before our IPO to during it, to after it. It’s been a really positive partnership. The reason we did the public offering in the first place is because we wanted the profile. As a bootstrapped company we didn’t need the cash. But we did want more attention on what we felt was great technological innovation that wasn’t getting enough play.

Mike Rohner: What’s your approach to project management?

Matt Calkins: We make it so much faster to do these things. Our goal internally is to cut in half the amount of time it takes to build a new application every two years. Like Moore’s law, right? We’ve got our own version of Moore’s law and we’re going to reduce not the size of a transistor but the total number of person hours it takes to write an app in half every two years. It’s a matter of just executing and how far can we push this barrier, this frontier. I believe that pushing this frontier is a really valuable thing to do. Time will tell if this is the best standard but I believe we have found a really meaningful thing to improve on.

Appian provides a leading low-code software development platform that enables organizations to rapidly develop powerful and unique applications. The applications created on Appian's platform help companies drive digital transformation and competitive differentiation. For more information, visit

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