Paul Boudrye

Asking the Right Questions

“Somewhere between your mind and your heart lies who you are, and that’s what I want to know about,” Paul Boudrye says boldly.

In a culture that often settles for the ease of surface-level exchanges and shamelessly self-interested networking, his words have a weight to them—the kind of weight that causes a conversation to sink deeper, past the formalities and how’s-the-weather discourse so many of us have come to expect, to a place that is real.

“From as far back as I can remember, I’ve wanted to help people,” he says. “If someone has a problem, a dream, or a goal, getting to the right place is about asking the right questions, but so often, people are taught to ask the wrong ones. That’s why, when I meet people, I focus on getting to know the real them. I ask questions and listen to understand what their dream is and why, and then I think about people and opportunities I can connect them with to help achieve that dream. The question I enjoy asking the most is the Wizard of Oz question—if I was the Wizard of Oz and I could grant you one wish to solve a social problem that’s important to you, what would it be and why? The responses to these questions are amazing.”

As founder of HowToBe.Me™ and owner of ConnectorHub, a business development consulting firm serving the Washington, DC metropolitan area, Paul’s success stems from the fact that he won’t settle for the traditional networking styles pursued by so many of his peers. His approach is about getting to the soul of the matter—helping people improve their lives, further their businesses, and see in themselves the potential they couldn’t see before. “People need to be asking themselves questions like, how can I change and do something better?” he says. “Or, how can I connect two things that have nothing to do with each other and create something new to solve a problem? I’m there to connect people—to the right questions, the right answers, the right people, and the right situations. Making these connections and watching people reach their potential is the why behind everything I do, and it’s extremely gratifying.”

Paul is passionate about seeing people take control of their destinies and success because he knows firsthand how difficult it can be when situations are at the whim of forces beyond one’s control. When he was in sixth grade, the company his father worked for went under because the owner’s father had been embezzling money. Paul’s father, a chemical engineer and linear programmer by trade, was left struggling to find a new job, forced to uproot his family from Rockville, Maryland, to move to Blacksburg, Virginia. Paul had to leave the friends he had known since preschool, and it was a defining moment for him. “I saw my dad struggling due to something outside of his control,” he remembers. “It led me to realize that you have to be in charge of your own destiny, and a great way to do that is to be your own boss. If you’re not relying on someone else for a paycheck, no one can surprise you. In that sense, being an entrepreneur is one of the most secure jobs you can have. In my young mind, a seed was planted.”

That seed would first sprout when he was in eighth grade. The family had moved back to Maryland, and Paul saw an opportunity to market candy in his mid-afternoon shop class. His mother would drive him to the store to buy bulk candy, and he would then sell it at retail, until the Vice Principle decided his venture was diverting too much business from the school store. “The Man came in and shut me down,” he laughs. “But from that moment on, I was hooked on connecting a person with a need with a person with a solution, regardless of the product or service.”

Beyond his entrepreneurial drive, Paul connected with the community around him through his humor. “The feeling I get when I make someone laugh is unlike anything else, and I really appreciate that as a way to get to know people and establish trust. The shortest distance between two people is through humor.”

With diverse interests as a child that included piano, saxophone, psychology, baseball, football, soccer, and karate, Paul’s focus settled into tennis in ninth grade and rooted itself as a lifelong passion. He played varsity tennis all four years of high school, and today, his game lends new meaning to the mantra, Be the ball. “When I play now, I’m in a state of Zen,” he affirms. “There’s a kinesthetic connection between the ball and me, and nothing else exists. I have no expectations, and I don’t think, or my mind interferes with the natural flow of things. I just relax and let my mind and body work—I’m just along for the ride.”

Aside from sports and his equally strong performance in academics, Paul launched a lawn and landscaping business in ninth grade after the sting of his thwarted candy operation had subsided. From the time he was 13, each summer found Paul hard at work. “I saw my father struggling to get his feet back on the ground, and I felt that if I didn’t have to ask for money, that was my way of helping,” he recalls. “The business grew to 20 lawns, and I’d employ my friends, paying them more than what they could earn in a store.”

It was the early 1980s, and the computer was just becoming a household item. As Paul looked to expand, his father helped him use an electronic spreadsheet to build an optimization model that would show the right amount and type of equipment to invest in. His father financed him, and he bought the additional equipment that allowed him to expand from 20 to 40 lawns. “When he lost his job and went into consulting, my father became a reluctant entrepreneur,” Paul remembers. “He was very smart to marry technology with entrepreneurship, and that rubbed off on me in some ways.”

Paul continued running his lawn business on the side when he enrolled at the University of Maryland at College Park. But after four years of taking a full load of classes, managing his business, and commuting to school since he couldn’t afford to live on campus, things began to take their toll.

Disillusionment was overwhelming. The lawn business was backbreaking work, and when Paul decided he instead wanted to make a living with his mind, he dismantled the company and took a year off to explore other opportunities. He also produced an entrepreneurship training video based on a class taught at the old Learning Annex by a local entrepreneur. He teamed up with graduate students from Maryland and interviewed entrepreneurs on camera to tell their story.

Inspired by this work, Paul decided to launch a traveling car detailing business to serve people who didn’t want to spend time waiting in line at car washes. It wasn’t long before he partnered with another local entrepreneur who did detail on cars in dealerships, and while doing that, the general manager of a Manhattan Subaru noticed his work ethic and offered him a position.

Paul had never sold cars before, but in his first month on the job, he sold 21 vehicles and made $10,000. “I didn’t know what the hell I was doing,” he laughs. “But I had the same success again the next month, so by the third month, I thought I was a star. That’s when I began over-thinking things, and I tanked. I learned I didn’t want to do that for the rest of my life, and when I married, bought a home, and decided to have children, I realized I needed to build something stable and long-term.”

At the advice of one of his clients, Paul left the car business and was recruited into the life insurance industry. It was hard to make ends meet, and the pressures of fatherhood revolutionized his sense of responsibility, but he was a leader amongst his peers in number of policies sold and in the creative caliber of his ideas. He even came up with the concept of helping his clients leverage the cash value of their life insurance policies to help offset bankruptcy issues, and was commended by New England Mutual Life for his creative sales strategies. “People always say you should think outside the box, but for me, there is no box,” he says. “When someone lays rules out for me and tries to put me in a box by saying I can’t do something, I’m compelled to say, why not? You always have to turn things inside out and look at them differently.”

It was this kind of thinking that compelled him to resign his position and launch an internet company just before his thirty-first birthday. His vision was a simple directory system that would serve as a virtual Yellow Pages for Delaware businesses. Companies would pay to have their websites posted in the directory, and Paul would cross-promote each company on radio, in print, and on billboards as well. His father loaned him $5,000 to get him rolling, and he then bartered over $200,000 in advertising with his vendors to make his vision a reality, promising to refer all companies that entered into the directory to the companies that helped him out free of charge.

Paul was then recruited by an accounting firm in DC to build an internet consulting practice, and it was here he taught himself web design and development. Three months later, however, the company decided to cancel the project, which led Paul to launch his own web site design and management business called ClikIt Web Solutions.

He grew ClikIt Web Solutions to 30 clients. When 2000 came and went, however, Paul saw the writing on the wall and knew web businesses were starting to become commodities. With that, he sold his business to an IT staffing company that wanted to develop its own web content management business, staying on to build that up until the dotcom bust of 2001 cut his salary in half and led him to walk away.

In 2009, he decided to explore and create another internet business, called BizConnect. “It was kind of like LinkedIn meets EHarmony,” he says. “I wrote a business plan, got funded for $50,000, and worked on that for several months before turning it over to my partner.” Then Bond Beebe CPA and Advisors reached out to him over LinkedIn, ultimately offering him a position as Director of Business Development.

After a professional career of sampling different opportunities and work environments and getting to know his own strengths better in the process, Paul has an acute sense of what those strengths are, and he focuses every day on using them to further the success of his clients. With this in mind, he would advise young people entering the working world today to take the time to identify their own strengths early on. “Take the Predictive Index or StrengthsFinder tests,” he encourages. “So much emphasis is placed on transcripts, test scores, and resumes, but we should be focusing on a child’s strengths, motivations, talents, personality, interests, vocations, and passions. We should look at their natural strengths and then support those with all we’ve got. That’s how we help young people reach their potential and live happy, purpose-driven lives.”

Key in this equation of finding one’s true strengths is the role of a mentor—something Paul never really had in his own life. Instead, he read the books of Ted Leonsis, Daniel Pink, Jim Collins, Mario Morino, Gerald Chertavian, Tom Rath, Jim Clifton, Richard Branson, Donald Trump, and Ross Perot, lining his bookshelves twice over with the thoughts of brilliant minds put to paper. “Soaking in these ideas through reading is important, but having a mentor is unparalleled,” he remarks. “If you can reach out to people you trust and like, they can be invaluable in helping you mitigate errors you might make down the road.”

Paul isn’t just interested in studies and theories about youth, entrepreneurship, and education—they’re his ways of paying forward his own success. He also works with the Network for Teaching Entrepreneurship, BuildDC, and with Year Up, a program that helps at-risk youth transition into the business community. He supports Cornerstone Montgomery as a business mentor and the National Center for Children and Families in their mission to help foster kids, homeless families, battered women, and single mothers, as well as the Duke Ellington School of the Arts and various other organizations committed to helping children—whether through equipping them with marketable skills or simply making sure they have food to eat.

Paul’s professional and personal journey is the aggregate of diverse steps that may seem, at first glance, to lead in a number of different directions. Yet every single step, and each choice that guided it, was streamlined by the understated style of leadership that focuses on raising people up with new solutions and new success. “Faith is the ability to believe in yourself and the choices you make, however hard they may be,” he affirms. Learning to ask the right questions of life, and of yourself, is a way to take control of that story and guide it the way you want, and that’s the kind of change I’m committed to bringing people. It’s about writing the story you want with each word, each step, and each decision you make. It’s like traveling down the yellow brick road of life—equipped with your brain, your heart and your courage—and ultimately reaching your personal Oz.”

Paul Boudrye

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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