How This CEO Walked Away from Millions—Twice—and Became a Billionaire

Meet Matt Calkins, the CEO of Appian, who turned down multimillion-dollar deals not once, but twice! His journey from being a young director at MicroStrategy to founding a successful software company is a testament to his commitment to purpose over profit.

Choosing Purpose Over Profit

At just 26 years old, Calkins was the youngest director at MicroStrategy. After the company’s IPO, he had the chance to cash out big but chose to launch Appian in 1999 with friends Michael Beckley, Robert Kramer, and Marc Wilson instead. “Money wasn’t the most important thing to me,” he recalls. “I wanted to have a social impact.”

Calkins’ vision led Appian to work with government agencies, including developing the U.S. Army’s Intranet—the largest in the world at that time. By 2005, they expanded into the corporate sector, and today, Appian serves over 2,500 clients, including big names like Deloitte and KPMG.

Staying True to His Vision

What sets Calkins apart is his unwavering commitment to his values. Even when the board and outside investors pushed for lucrative buyouts, he stood firm. “It’s never been about the money,” he insists. Instead, he focused on making a positive impact on people’s lives.

In 2011, he faced another opportunity to sell Appian for $200 million. After a casual burger outing to discuss it with his co-founders, they all agreed to reject the deal. “I had the votes either way, but they ended up all agreeing with me,” he laughs.

The Payoff: A Billion-Dollar Company

Calkins’ decision to prioritize his vision paid off. In 2017, Appian went public on Nasdaq, and its shares skyrocketed by over 25% overnight. Today, the company is valued at around $2.7 billion, and Calkins’ net worth has soared to approximately $4.1 billion.

Reflecting on his choices, he emphasizes confidence in himself: “I just felt that I could make more of it than was being offered. I had more to do here.”

Advice for Gen Z: Follow Your Values

Calkins’ journey resonates with many Gen Zers who prioritize purpose over paycheck. While they face high living costs and a tough job market, he encourages them to seek fulfilling work without sacrificing financial success. “We falsely assume that good things are done for free,” he says, highlighting that purpose-driven work can also be financially rewarding.