Rick Higgins feels equally comfortable in a cowboy hat at a rodeo, in black tie at an awards dinner or gathered with a group of nerds designing portfolio performance software for financial advisors. When I ask him to describe himself, he says: “My mission in life is to simplify complexity.”

At 41, he’s got a good start. He co-founded myCFO. He’s built and sold four portfolio performance software companies. He designed Risclarity, a software program that measures the risk in an investor’s portfolio, dividing that risk into 18 different categories. And he’s hosted and produced The Rocky Mountain Experience, a TV reality series with features on bull riding, ice climbing, mountain biking, dogsledding and snowkiting in the Colorado wilds.

Higgins comes from a family of entrepreneurs. Along with his parents Rick Sr. and Gloria and his brother Brian, Higgins has created a number of companies in technology, finance and entertainment, most notably WealthTouch, a portfolio performance software company that he and his mother sold in 2009. His parents, both CPAs, formed a practice together in 1976. In 1980, his mother’s biggest client, Frederick R. Mayer, founder of Exeter Drilling Co., hired Gloria to run the Frederick R. Mayer family office. Rick Sr. revamped the firm as Higgins, Meritt & Burdick and was managing partner until he left to roll some of his clients into WealthTouch. At the same time, Rick Sr. created a new accounting firm, RT Higgins & Associates P.C., his third start-up company.

Rick Jr.’s grandfather worked as a cowboy; his grandmother was a seamstress. His mother’s dad worked as a sheriff and later developed a courier business.

Still, Higgins didn’t plan to become an entrepreneur. When he graduated from Penn State with a bachelor’s degree in finance, he figured he would become a Wall Street trader. By the time he finished his master’s degree in management information systems at George Washington University, he thought otherwise. He worked for two years as a systems administrator in Virginia for Cigna Financial Services. Then it was time to move back to Denver, where he grew up, and start solving problems. “I always felt I had enough ideas to pursue on my own without working for someone,” Higgins says.

When he returned to Denver in 1997, he went to work for his mother’s multifamily office, Synectics, developing software to solve reporting problems. “As her business was growing, she had to keep hiring consultants,” Higgins says. The two formed a partnership called Digital Partner, a firm that made data aggregation and portfolio reporting software. In 1999, they sold it to myCFO, which Rick joined.

Then in 2001, he and his mother began working on WealthTouch. At the time, they didn’t realize that many other groups, such as the Rockefeller family office, which developed Rockit, were also working on portfolio reporting software. “We thought we were competing with Advent,” he says. They sold WealthTouch in 2009; Higgins began the development of Risclarity and at the same time pursued a career in television. “When I left WealthTouch, I thought I was at the top of my game,” he says. “When I came into the TV business, I was entry level. It was very awkward.” Higgins partners with his brother, Brian, an architect in Denver, in the film work they do. “We both have a passion for video,” Higgins says. “Brian is an aspiring documentary filmmaker. I like TV episodes.”

Higgins was introduced to computer programming in the fourth grade, when he had the opportunity to take a programming class at the high school. “That was before the elementary school even had computers,” he says. “Now, the family wealth reporting space is my passion. I’m the guy that, once the idea has been identified, I can get going. I just love it.” Higgins says he also does some consulting. “If it’s presented to me, I accept it. I enjoy it because these are additional problems to solve. Unlike traditional consultants, I like to solve problems.”

Throughout his career, Higgins has worked with his college roommate, Carl Knecht. The two founded Higgins-Knecht, a technology consulting company, in 1997. “Part of the secret of my success is that I have worked with my college roommate at every company since Digital Partner,” Higgins says. “He was a co-founder of Digital Partner and WealthTouch. He is also a cinematographer on our TV series. My mom presents the problems, I see the solutions and Carl brings them to life.”

In 2010, Higgins joined Ron Surz, president of Target Date Solutions in San Clemente, Calif., at StokTrib, a software program that evaluates portfolio managers. Surz founded the company with a partner who wanted to sell his 50% share. Higgins bought it and the two worked to enhance it. “It was just the two of us,” Higgins says. “He was the academic. I was the nerd.” The two sold StokTrib to eVestment, an Atlanta company that works with RIAs to build portfolio tools.

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