Appian’s CEO abandoned millions — twice. Now he is worth more than $4 billion

Calkins was the youngest director at MicroStrategy when he left the company to found Appian in 1999 with three of his friends, Michael Beckley, Robert Kramer and Marc Wilson. That meant giving up his shares, which had just skyrocketed thanks to the company’s IPO a year ago.

“When I was in my 20s, it seemed like you could walk away from one asset to find another,” he recalls. Luck.

“The reason I left was because I wanted to make a social impact instead of a financial impact,” the now 51-year-old added. “Money is not the most important thing to me. I really wanted the opportunity to show what I could do, and I felt like I could make a bigger cultural impact, beyond just the financial impact, if I started my own company and that extremely important to me.”

Just like that, Calkins founded a software company called Appian.

Back then, they worked primarily with government agencies: In 2001, the company developed the U.S. Army Intranet—considered the world’s largest intranet at the time—before expanded into the corporate world in 2005.

Today, Appian has evolved into a platform that helps leaders with little to no knowledge of app building do exactly that. It currently has more than 2,500 customers worldwide, incl Aviva, Deloitte, GSKAnd KPMG.

Unusually for a technology company, Calkins and his friends are still running the company after 25 years.

“It’s not easy, especially when the stakes are high and people’s greed or jealousy are getting in the way,” he beams. “And the great thing is that 25 years later we still have complete autonomy. I still have control of the business.”

That means Appian has always followed Calkins’s vision of putting value above money—even if that sometimes goes against the better (or maybe in this case, worse) judgment of the guild board of directors.

He even convinced his co-founders not to sell for millions of dollars

It’s probably easier to make a splash with millions when you’re ambitious, young, and have fewer responsibilities—but the founder says as he and the business grow, there will be more opportunity to make money. Even outside investors and the board wanted him to sell.

However, Calkins firmly maintained his stance. “Because I have the majority of votes, they can’t do it,” he boasted.

“It was never about money,” he said. “The goal of this company is to touch as many people’s lives in a positive way as possible… I have enough money to live on and I don’t need more.”

Calkins put his money where his mouth was a second time in 2011 when, at the age of nearly 40, he again walked away from the opportunity to sell Appian for $200 million.

With the bulk of the steak in the company, the deal could have made Calkins and his co-founder millionaires overnight.

“I had to convince them to participate,” he laughed, adding that he took them out for burgers while presenting his case.

“They haven’t decided yet and actually I have a vote, but in the end they all agreed with me.”

In the end, valuing his worth over the money in his pocket actually made Calkins richer.

In 2017, just a few years after rejecting the acquisition the board had pressed Calkins to approve, Appian went public. Nasdaq. Its stocks skyrocketed more than 25% overnight and the company is now valued at about $2.7 billion.

Meanwhile, Calkins’ net worth has been trending upward since then and in 2021 stood at aroundd 4.1 billion USD, according to by Bloomberg estimated.

Looking back on the moment he went back to the board and said “no” to sales, he says confidence in himself was “the most important thing.”

“I’m not saying the business is necessarily worth more than the money being offered,” he explains. “I just felt like I could get more than what was offered. I feel like I still have a lot of work to do here.”

“Maybe it’s a superpower, ignoring people,” he laughed. “I always felt like I could hear people without watching them…. I absolutely didn’t want to do it and so I didn’t.”

Advice for Gen Z with a purpose

Many of today’s Gen Z think like Calkins—and are even willing quit your job not consistent with their values. However, they are also facing record high costs of living, a housing crisis and a job market that is tougher than ever.

They don’t need to stress, Calkins said. In his eyes, there is no trade-off between making money, being successful, and doing work with purpose.

“We mistakenly believe that the good things we do are done for free—like the days we work, we may not do anything good, but then we take a day off and helping at homeless shelters, we’re doing that. something good,” he said.

“I think I get more done in a day at the office than walking to a charity and spending the whole day there because what I’m doing here, I’m really good at. I don’t know if I can do anything else.”

Fundamentally, you may need to reframe your thinking about what “doing good” looks like, beyond working for charities or companies working specifically in the sustainability sector .

If you’re helping customers—even if it’s simply helping them build an Appian-like app—Calkins says you’re working with a “force for good.”

“I think people should realize that in many cases, commercial enterprises are a force for good in their own right – and doing them well is actually contributing a lot to our society .”