Brian Roberts

The Five People You Meet in Business Heaven

In the spirit of Mitch Albom’s The Five People You Meet in Heaven, Brian Roberts has conceived of the professional world’s analogue, outlining the five people you meet in Heaven based on the impact they have on your professional life. This host of game-changers might include the stranger whose advice came at the perfect place and time, so serendipitous as to seem divinely inspired. It might include the superiors whose encouragement led to higher aim and higher achievement. It might include the individual who offered you that incredible opportunity or solution you had hoped for. And it should certainly include the people who connected you to that individual.

Now the founder and CEO of Croix Connect, Inc., a management and technology consulting firm with both commercial and government clients, Brian has dedicated his life to being that connecting force. Thanks to the eloquent sequence of people, ideas, and experiences that make up his own life, he’s developed a skill set and network ideal for the solutions-driven work he does today, but he couldn’t have gotten here without confronting the very questions he helps his clients face now.

After working for a telecom company at the center of the internet explosion and witnessing the rise and burst of the dotcom bubble, Brian felt the urge to start his own business, but fear of the unknown and contentment with the status quo kept him from action. All that changed, however, when he was outside walking in downtown DC on the morning of September 11, 2001. Seeing the smoke from the Pentagon curling toward the sky, he knew inaction was no longer an option. “As a former service member, it really hit home, and I realized I wasn’t doing what I wanted to do in my life,” he remembers. “I wasn’t seeing the Golden Rule followed in the way we treated clients, and that’s just not me. I had some ownership and was making six figures, but I wasn’t happy. I stopped to think, what do I want to do? Who do I want to be?”

A month later, Brian and his wife, Donna, found themselves chatting in a swimming pool on vacation in St. Croix, when the epiphany was realized in full. Brian had always been a connector—the person others came to when they needed a particular company or person to help them with a given problem. He would make the introduction, step aside, and watch the new combination of skill sets create powerful solutions. He envisioned a company that formalized this service and embraced a culture of ultimate integrity. And though Donna, an entrepreneur herself who had just experienced a 75 percent decline in business, was hesitant at first to encourage Brian to give up a steady income amidst a recession, the couple realized it was worth the risk.

With that, Brian hung the shingle and launched Croix Connect. Originally intending to put his service experience and security clearances to good use, he focused on government work despite the heavy saturation of the market. After securing a steady stream of revenue, he began shifting his sights to the commercial realm and interviewed friends in various companies about the problems they faced related to people, processes, and technology. He readily identified individuals and companies that could help with those problems, but he quickly found that people were more interested in putting their trust in him. He would then subcontract out the work and manage the projects, handling any issues that arose.

Croix Connect’s first big client was AOL, and their work began trending toward technology, picking up big data analytics solutions projects for Comcast and Time Warner Cable. After determining that his time was better spent in the private sector, which boasted quicker sales and higher margins than his government work, Brian began focusing wholly on commercial business starting in 2007. Then the Great Recession hit, drying up the majority of his large commercial technology deals and driving him back into problem solving mode.

Around that time, he got a call from Vistage International, a professional development organization for CEOs and executives, asking if he would chair and head one of their executive peer groups. “Croix Connect had already made the leap from government contracting to big technology solutions,” Brian points out. “I wondered, could we make that leap to becoming an executive facilitator, coach, and advisor? Aside from my enthusiasm and appreciation for the Vistage program itself, I saw it as an opportunity to develop my focus and branding message.”

Thus, in 2010, Croix Connect evolved into professional development services for interim executives, and Brian became known for the advisor and coaching program he designed, Executive Whisperer. In that capacity, he focuses on being the “angel” on the shoulder of his clients, whispering advice, vetting ideas, and helping them build the courage to take action. On the side, he leads Vistage groups at the CEO and Key Executive levels. “Right now, my work primarily revolves around coaching and advising the CEOs of small and medium-sized businesses,” he says. “It’s some of the most powerful, exciting, fun, and rewarding work I’ve ever done. I work with hard-charging executives who are putting the livelihoods of their families on the line to do what they believe is right, making tough business decisions on a daily basis and always pursuing betterment. To help them on that journey, connecting them to insight and solutions, is an incredible experience, and seeing the changes in people is truly powerful.”

Today, Brian is working with eight companies through his Executive Whisperer program, touching around 400 employees. Including the companies touched through his Vistage groups, hundreds of additional families are impacted. “I’ve always loved the proverb, ‘He who influences few influences the many,’” Brian affirms. “Helping people solve their problems, achieve their dreams, and help others do the same is why I do what I do.”

Having this impact on business leaders and the families their companies touch mirrors the opportunities he would have wanted for his own family when he was a kid. Brian grew up in a blue-collar, hard-working, values-driven Midwestern family in a town 15 miles west of Detroit, Michigan. His father, a heavy equipment operator for a construction company, and his mother, a homemaker during Brian’s childhood, raised their children believing in the power of an unyielding work ethic and the Golden Rule. Doing unto others as he’d have others do unto him became the litmus test for every decision he made, and would become the cornerstone of his business philosophy later on.

As a child, Brian earned strong grades and loved sports of all kinds. Demonstrating an early aptitude for numbers and memorization, he bought the record books for basketball, baseball, hockey, and football, memorizing countless bits of trivia. He thought he might become an accountant or a sportscaster, though he hadn’t yet come out of his shell and expressed the off-the-charts extroversion that would characterize his personality later on.

At his parents’ suggestion, Brian began mowing his neighbors’ lawns when he was 12. He charged only $3 per lawn, so he was shocked into silence one day when a neighbor gave him a $7 tip. “I was so dumbfounded I couldn’t speak,” he recalls. “Later, my father took me aside and said, ‘You know, son, when someone does something really nice for you, it’s important to say thank you in a big way.’ I remember that as a trigger point in life. I really understood the value of taking other peoples’ feelings into consideration and always doing the right thing. Now, I go above and beyond in saying thank you to people, and I appreciate anything anyone does for me.”

No one in Brian’s family had gone to college. They didn’t have money set aside for higher education, and they didn’t know about grants or scholarships. Brian had worked at the corner donut shop since eighth grade, but hadn’t saved up enough to cover the cost of tuition. Despite the odds, he became the first Roberts to set his sights on advanced education, gaining admission to both the University of Michigan and Michigan State. For cost reasons, when he received an Air Force recruiting card in the mail, he decided to relieve the pressure put on his parents to help pay for school by enlisting.

When Brian took the Armed Services Vocational Aptitude and Battery test, computers were just hitting the market, and though he had no idea what the phenomenon was all about, his scores indicated a proclivity for the new technology. Thus, when he entered the Air Force on July 11th, 1977 he quickly became immersed in tech. Based in Northern Michigan, he worked on computers manufactured by Burroughs Corporation, a competitor of IBM, and planned to leave the military and enter the field after his four years were up. In anticipation of his discharge, Brian called the Burroughs headquarters in Detroit to discuss his impending job options.

The year was 1980, and the voice on the other end of the line mentioned that the job market was competitive and he’d do well to take another hitch. “I didn’t know the guy on the phone, but I took his advice, and it had a huge impact on my life,” Brian recounts. “Because of him, I chose to stay in the military and relocate to Colorado, where I diversified my skills through working on IBM equipment.” In that capacity, Brian found himself working on Space Command, tracking missile launches and global events. As he got to know the officers he worked with, he began to see that there was nothing holding him back from becoming an officer himself. “They pushed me to pursue an officer program,” he says. “I had to take algebra, trigonometry, and calculus before I could even apply, but with their urging, I did it. If they weren’t there encouraging me, I’m not sure it would have happened.”

With one course left in the program, Brian was burned out, so he took a 30-day vacation to road trip to California and back. If he hadn’t gotten bored early and returned to Colorado on the 27th day, he would have missed the White House Communications Agency (WHCA), which happened to be in town conducting interviews for one of their esteemed slots. Brian had perfect performance records, a clean background, and the specialized skill set they were looking for, landing him the opportunity of a lifetime. “I packed my bags, moved to DC, and spent two years working on the Presidential Advance Team,” he says. “We traveled ahead of President Reagan everywhere he went to set up communication centers for his time away from the White House. I worked with top-notch people in a perfect team dynamic, and in a climate where the job had to be done without ifs, ands, or buts. I traveled to Geneva and Reykjavik for the Reagan-Gorbachev summits and took great honor in the significance of what we were doing.”

At the end of the two-year WHCA appointment, Brian finished his officer program. Three years later, in 1992, a wave of base closures and a climate of general military drawdown left him faced with a decision: he could end his military career and accept a nice volunteer package, or stay and face possible termination without the benefits. He had been in the Air Force for 15 years, but planned to stay 25 or 30 and return to the White House Communications Agency as an officer. “I had to take all the emotion out of the decision and do a pros-and-cons list,” he remembers. “In the end, it just didn’t make sense to stay, but I treasure my time in the military. On so many levels, joining the service was one of the best things to that ever happened to me. It exposed me to tremendous diversity and incredible people. Also, seeing that even the military can lay you off, I realized I never wanted to work for a large company where I didn’t have control over my destiny. It lit an entrepreneurial flame in me, though I didn’t realize it at the time.”

That flame was cultivated in the commercial technology sphere, when he landed in a data communications startup called MFS Datanet. The company was operating at ground zero for the internet, and was the first to offer high-speed connections to major companies like Merrill Lynch, JP Morgan, and Goldman Sachs. Brian worked on the team that facilitated the first big interconnection point that connected the various internet providers to one another, creating the Metropolitan Area Ethernet (MAE). “For the first time, the world’s top six or seven internet providers were connected,” he remembers. “We were working until all hours of the night, but we were having a lot of fun doing something no one else had done.”

As the company grew, however, Brian realized he was much more interested in being a starter and a builder. As it plateaued, the daily grind began to set in, and he grew less satisfied. When the company was bought by WorldCom, he knew it was time to leave. Brian landed at another telecom company and then transitioned over to a professional services company, learning the right ways and the wrong ways to do business and treat people.

Those lessons continued after he launched Croix Connect, augmented when he launched a radio show in 2004 called “Taking Care of Business with Brian Roberts.” An acquaintance, David Bird, had a weekend morning slot, and when Brian asked to be on his program, he told Brian he should consider hosting his OWN weekly show where he interviewed government and business leaders. “Business is all about relationships, and that show afforded me incredible access and solid relationships,” he says. “I could write a book about the stories from the studio and the advice I got from those leaders. It was a great way to connect with people and to then connect them to opportunities, so it was perfectly aligned with the mission of Croix Connect.”

In advising young people entering the working world today, Brian highlights the importance of networking and the dangers of living in the past. “I can’t stand it when people dwell on ‘shoulda, coulda, woulda,’” he says. “You can’t drive forward with your eyes stuck on the rearview mirror. Things happen for good reasons, so be content in that knowledge and focus on the opportunities of today with optimism and enthusiasm.”

Though Brian never adopted the risk-averse, often pessimistic attitudes of his parents, who, like many people disliked change and often forecasted worst-case scenarios, his worldview has certainly been advanced by the risk-taking and optimistic nature of his wife, Donna. Married almost thirty years now, she’s been with him every step of the way, a perfect partner in making choices and living life. “I’m so fortunate to have met someone as special as Donna,” he remarks. “She’s amazing. Everything I do now comes through and out of that, including my faith as a Catholic. We were married in 1986 at Bolling Air Force Base by their auxiliary priest, and the same priest presided over the ceremony initiating me into the faith in 1991.”

As the Vice Chairman of the Board of Catholic Charities for the Arlington Diocese, and as a member of its Executive and Advancement & Communications Committees, Brian focuses his volunteer efforts on growing that agency. He and Donna also work monthly shifts at the United Service Organization’s (USO) lounge at Dulles Airport, where military personnel and their families find a home away from home. They’ve recently become Eucharist Ministers, and in the past, Brian worked with inmates at the Fairfax County Jail, giving spiritual and community support through the transition back to society. “I’ve always wanted to be a helper,” he says. “It’s important to me to have a positive impact on everyone I touch, whether it’s on the personal side or the business side.”

And, in reflecting back over his personal and professional journeys, the division between the two grows less defined. The compassion and care he exudes as an advisor and coach today, for instance, is in part an echo of the kindness showed to him by a student teacher many years ago. “I was being picked on during a middle school softball game, so Mr. Kobelars threw me two of the fattest pitches,” he recalls. “I slugged the heck out of both of them, winning the admiration of my peers. That’s something I’ll never forget. Don’t underestimate the impact you have on people. Help others along the way, because you can’t imagine what it might mean to them. Look for ways to be the reason they hit it out of the park. You never know—maybe you’ll become one of the five people they meet in Heaven, in the end.”

Brian Roberts

Gordon J Bernhardt


President and founder of Bernhardt Wealth Management and author of Profiles in Success: Inspiration from Executive Leaders in the Washington D.C. Area. Gordon provides financial planning and wealth management services to affluent individuals, families and business owners throughout the Washington, DC area. Since establishing his firm in 1994, he and his team have been focused on providing high quality service and independent financial advice to help clients make informed decisions about their money.

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