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.

Risclarity, his new program, does what other programs doing risk analysis have done but takes it much farther, evaluating risk according to 18 categories, such as valuation risk, liquidity risk and counterparty risk, etc.

When he presents his first round of reports for Risclarity in July, he hopes to have three clients on board. “Part of the reason I’m getting into this space is because most of the stuff out there is too expensive,” Higgins says. “I’m starting in the family office space but my ambition is to take it all the way to the consumer to analyze IRA portfolios."

He is talking with Andrea Bornstein, a colleague from myCFO, about combining Risclarity with InProfile, her program that combines everything from details about clients’ investment appetite to details about their family that can help form an investment advisor profile. The merged companies would provide a client profiling and risk management tool. Higgins’ mother, Gloria, is providing input on what a CPA would like to see included, such as information on taxes. His father introduced him to forensic accounting so he could consider the risk of fraud.

Rick Sr. closed RT Higgins & Associates in 2010. He continues to work as a partner with Eide Bailly, an accounting firm. Gloria sold her multi-family office to GenSpring in 2009. She left at the end of 2011. The GenSpring office in Denver closed at the end of January 2013. Gloria Higgins is now consulting to multi-family offices and serving as the executive director of EPIC, a nonprofit that promotes and supports preschool education. She also works with Higgins on the design of Risclarity.

Not surprising that Higgins is into binary numbers. He married his wife, Lesley, on 10-10-10. They live with their 16-month-old son, Will, at 101 Enchanted Road in Golden, Colo. Higgins doesn’t mind being called a nerd. In fact, he likes it. “I love being a nerd and a geek,” he says. He also likes the fact that he can fit in anywhere: at a black-tie dinner, wearing his cowboy hat at a rodeo, or just hanging out with other nerds. His LinkedIn profile says that Higgins’ work on Digital Partner “firmly placed him at the heart of what became known as the technological renaissance in wealth management.” But he’s only gotten started solving problems. Stay tuned.