R. Gore Bolton

The Basics

When six-year-old Gore Bolton stepped off the school bus each day, he knew his grandfather would be there to meet him. He knew they’d walk home together, and he knew they’d sit down to examine the large piece of cloth his grandfather had fashioned into a trading board. The old man had graduated in finance from Yale University in 1915, advanced on to a successful career at the Pentagon as a military officer, and become a skilled entrepreneur and business owner. Now, he was committed to teaching his grandson how to play chess, read the Wall Street Journal, and trade the markets, from futures to penny stocks to blue chips.

“He would stack pennies on each ticker symbol I selected,” Gore remembers now. “The next day, we’d read the prices in the paper and add or remove pennies based on the trades I had made. It was an exercise in financial planning and strategy that went on for several years, cementing the business basics that would sustain me my whole life.” Now the co-founder and CEO of Diversified Advantage Group, Inc. (daGROUP), a firm providing private equity to Main Street businesses to help them reach the next level of success, Gore has built a business around these core principles, setting his sights on revitalizing the economic fiber of American society.

Small businesses are America’s most powerful job creators, yet they have comparatively scant access to capital and expansion opportunities. Gore wanted to change all this, providing avenues for accessing cash and expertise. After launching an engineering consulting firm from scratch and investing in dozens of businesses throughout his career, he has a keen sense of just how expansive the possibilities are, and thrives off of opening these doors for clients. Operating in a climate of baby boomers who want to retire but don’t have a succession plan, paired with millenials who have limited access to capital to fund business ventures, Gore wanted to invest in good, solid businesses while leveraging relationships to cross-pollinate ideas and best practices, helping the middle market thrive to revitalize the very structure of American society.

Since the launch of daGROUP in the beginning of 2015, the firm has invested in eight companies. daGROUP invests in small businesses and startups, especially those with the diversity advantage of being of women, minority, or veteran-owned services companies with existing staff and resources that need a modest investment—generally under $200,000—to take that next step. The firm is keenly interested in Benefit Corporations and other types of structures that create and strive to reach a higher purpose. “Businesses often reach their limit and then don’t know how to partner, ask for help, or reach across the aisle,” Gore explains. “We’re all about figuring out, what’s next? What needs to happen now to make you successful three months from now? As Economic Development Advisors, we’re able to help these businesses actually identify, implement, and execute approaches garnered from our multi-billion dollar project histories, extensive experience, licenses, and certifications.”

Today, one of daGROUP’s most exciting projects is the Piranha Tank (PiranhaTank.com), a direct competitor to Shark Tank. The series, now in its pilot stages, films and broadcasts live at the U.S. Patent and Trademark Office. “We see this as a sustainability model in business and finance because it’s pushing the triple bottom line value proposition via branding, event planning, and a TV show wrapped into one venture,” Gore explains. Piranha Tank had dozens of applications for only six slots on its first show, and two of the companies that pitched have already received funding. “The goal is to build a network of promotable investors in each community that can build their track record and then facilitate their own deals, reaching into their networks to bring more people to the table,” he says. “And it establishes daGROUP’s prominence in the conversation of capital, assessing who’s raising, who’s looking, who’s making deals, who’s applying, and how those trends and ideas are evolving.”

In many ways, daGROUP aims to celebrate geographic and cultural uniqueness to help it thrive. It’s founded on the principle that Washington, DC is no New York City or Silicon Valley. Rather, it’s a force all its own, with unique needs that provide geographic-specific yet fertile soil for businesses to flourish. Of all people, Gore should know. Born in Washington, DC, and having grown up on a small farm in Maryland, he considers himself “an original DMV.”

Gore’s family has always been the kind to be revolutionary. His eighth-great grandfather, Thomas Marshall, had a colonial mansion on the Potomac River called Marshall Hall (www.marshallhall.org/history.html) across from Mount Vernon, and his seven-great grandfather John Dent was a General in the American Revolution, a contemporary of George Washington.   “My mother still has letters between Marshall and George Washington, politely sparring over real estate,” Gore laughs. “There is a legend in our family of a letter from Washington describing the lighthouses that were set up along the Potomac to signal a British invasion, and explaining that they didn’t think it was worth it to worry about the Patuxent River because they couldn’t imagine the British marching through the marshy bogs of the Upper Marlboro. Of course, that was the route the British used to succeed in the burning of Washington in 1814.” Several hundred acres of the land remain in the family today, including a small house built in 1752 before America was even a country.

Growing up on the farm as the youngest of four children, Gore remembers an active agricultural lifestyle where he learned early on how to drive tractors and fix machines. His father was also a serial entrepreneur who wielded his talent for business across a number of industries, including excavation and construction, automotive repair, and real estate. His most pervasive venture, however, was the general contracting and earth moving company that would build much of the Beltway and early foundations of Washington, thanks to relationships with Congressmen fostered in an underground Capitol Hill bar that his great uncles ran during Prohibition. Gore’s mother, a very traditional lady with finely-tuned manners and sensibilities, took care of the books while his father ran the businesses. She taught her children etiquette and simple civility, and was the picture of industriousness, always making sure that the laundry was done, the house clean, and dinner ready on time.

As a boy, Gore would help neighbors and family to earn pocket money, but the real work was done on his family’s own farm, where he earned wages for bailing hay, tending chickens, and selling eggs. When he started fifth grade, his father began paying him a dollar a week to move tires at his auto garage. Then, for Christmas when he was in sixth grade, his parents relented to his persistent pleading and got him one of the first home Commodore 64 computers, which came with a dot-matrix printer and Print Shop Deluxe software. He spent the rest of his holiday break pouring through the software manual, teaching himself how to make greeting cards, calendars, and custom book covers. When he returned to school with his new wares, his friends wanted in on the action, and by Valentine’s Day, he had set up a rudimentary business making custom cards for his classmates. His teachers began hiring him to make classroom decorations, and in no time, Gore had taught himself to buy low, sell high, and account for his production costs in his pricing. “I had goals,” he recalls. “I wanted a new bike, and I knew exactly how much I’d need to sell to get it.”

Gore always performed well academically, but he was a troublemaker. He finished assignments quickly and would then look for fun things to do, often distracting other students. Teachers would give him extra assignments or even have him fill in as a substitute teacher when they were absent, just to keep him occupied. Always one to see the opportunity in every situation, he began negotiating deals between teachers’ aides and students looking for advanced notice on quiz and test information, and was soon brokering valuable information. “When the dealings were discovered, thankfully the teachers and administrators saw the creativity, ingenuity, and humor in it,” Gore recalls. Though he was ultimately given the “Ivan Boesky” award for those innovative antics, he quickly learned that one shouldn’t necessarily pursue ways to make money, even if the opportunity is there. “I didn’t want another award like that,” he laughs.

While he was in ninth grade attending boarding school at Episcopal High School in Alexandria, Virginia, Gore’s beloved grandfather passed away. It was a sad time in his life and he looked for new creative habits to fill the void.  It was that winter that he fell in love with all manner of sports and remote controlled airplanes, a hobby that led him to engineering. When he returned to public school, he lettered in varsity football, basketball and track, and still managed to plow through all the math classes available by the time he was 16. He enrolled at the local community college during his junior year, and by the time he graduated from high school, he had already finished his first semester of college. In search of an athletic scholarship that might lead to a future in the NBA, Gore applied far and wide, accumulating a shoebox full of letters from coaches across the country recruiting him to play basketball. During the last week of football season during his senior year of high school, however, Gore suffered an ankle injury he never fully recovered from. “An injury report like that really dings your stock, and a lot of my prospects dried up,” he remembers.

Gore ended up accepting a risky walk-on spot at the University of Maryland to play for Coach Bob Wade. He enrolled in a summer engineering class and began his tenure on the team, only to be kicked off when Wade was fired two weeks before the summer started. Thanks to his accrued credit, Gore was already considered a sophomore. “I had four years of engineering school to finish and only two years of eligibility left, so I decided to stay put,” he recalls. “But I wouldn’t be kept off the court. Joining forces with some of the other guys who were cut, we started an intramural team and had a ball clobbering every other team in the league. One fraternity had won the championship every year, and we beat them 96 to 6.”

Meanwhile, Gore worked studiously on his engineering degree—something he likely would have given up if his schedule had been subject to the rigor of playing on the official basketball team. Having cultivated an innate understanding of the built environment through growing up on the farm and observing his father’s construction business, Civil Engineering was a perfect fit, and he got a job early in his college career with the State Highway Administration. During his last semester of engineering school, he was a member of the Chi Epsilon Honor Society and President of the Student Chapter of the American Society of Civil Engineers, mastering the art of establishing a work/life balance that accepted wins and losses in stride.

Gore graduated from college in 1993, and by the time he was 26, he had accumulated a multitude of experiences that included work at a small consulting firm in Baltimore, as well as a larger firm. In 1999, he decided to partner with Tony Latham to launch his first LLC, raising $50,000 from local investors to get started. “I went down my list of relationships, and 18 of my top twenty clients decided to come to our new company,” he remembers. “In hindsight, I was an irrationally-exuberant 26-year-old, and some of those clients were eager to capitalize on that inexperience.”

Gore and Tony had planned to bring on only a couple support staff, but by the end of their first year, they had accumulated so much work that their team had grown to 24 employees. The challenges they faced were fairly common for new business owners, until tragedy struck: Tony was almost killed in a car accident in 2001, transforming Gore’s concept of responsibility and commitment virtually overnight. “He was in a coma,” Gore recounts. “His wife was our CFO, and his father-in-law was our VP of Sales, so they were out of the game. Suddenly, everyone was depending on me to keep the ship moving and the paychecks coming. In a small business setting, those moments of disaster, trauma, and organizational upheaval become extremely defining as you decide if you’ll go into hiding or really put your nose to the grindstone. You realize what you stand for, and you show others they can count on you. I worked harder than I had ever worked in my life, and I was surprised at who I had become: a loyal, dedicated, persevering leader who did everything I could to take care of the people depending on me.”

Fortunately, Tony recovered with time, and the team came back stronger than before. Gore went on to launch his first investment LLC, calling all his friends to see who would sign on as a member. They reached out through their network to find people looking to launch new ventures, advance their business, or flip a house, and they started private lending. “We found people tired of a commute who wanted to work locally by starting a roofing business,” he reflects. “We found people who wanted to open a retail store. We trusted them and knew them in their community, so we learned how to use convertible notes and fixed income payments to help them follow their passions.” Through this time, Gore evolved not into a serial entrepreneur, but a parallel entrepreneur. Eager to be engaged in multiple pursuits simultaneously, he would become involved in hundreds of ventures over the years, adding value through his ability to examine deals from a range of perspectives garnered over time and with experience.

By the fall of 2014, Gore and his partners decided to take their impact a step further by pursuing their belief that the small businesses of Main Street deserved access to the same resources and firepower that larger entities enjoy. In daGROUP, they envisioned a partnership firm distinguished by the honed entrepreneurial thinking they bring to the table. “Our partners love that we look at their businesses not just as service providers, but also as business owners,” Gore says. “I’m an engineer by training, and now I see myself as an engineer of businesses, aiming for excellence through establishing the appropriate formula of strategy, finance, business development, and organizational deal making.”

Engineering school didn’t prepare him for the human aspects of management and leadership, nor did Gore’s earlier upbringing. Indeed, his greatest challenge in business has been overcoming the independence deeply ingrained in him during his childhood on the farm, which was reinforced by the engineer’s process of working through problems in a sterile laboratory instead of in the colorful, emotional world of interpersonal connections. But his grandfather and father had a natural emotional intelligence, and Gore cultivated that same strain in his own character—a defining factor that allowed him to lead teams through the inevitable ups and downs of business. “As leaders, we have to manage change through strategic planning,” he says. “Change is inevitable, so you can either be subject to it or part of it. I firmly believe that success is the product of a thousand failures, so it’s important to show your team that a failure does not define you or negate one’s future. In some ways, it’s even wonderful to fail, because success can be the enemy of future success by breeding overconfidence and a skewed perspective of reality.” These impassioned, transformative leadership principles have won Gore a CEO of the Year Award, a SmartCEO Future 50 recognition, a National Innovation Award from Chief Executive Network, and several designations as a Best Firm to Work For.

Gore’s leadership also radiates a sense of integrity which stems directly to the influence of his loving wife, Sunny. The pair married in December of 2014, and Gore never ceases to be amazed by her kindness, reliability, and life choices. “She has more integrity than anyone else I’ve ever met,” he remarks. “She’s carried this into her work to reform the largest child development center in the Department of Defense, where our military leaders entrust their children. She poured her heart and soul into that mission, and last year was honored to receive the highest civilian award from the Army at Joint Base Myer-Henderson Hall.  “Considering my grandfather was in the Army, it’s fitting that my wife works to serve the needs of the children of our nation’s heroes,” Gore says. “I get to live with that level of integrity and caring everyday through her, and it definitely creates a standard I carry into the workday.”

In advising young people entering the working world today, Gore underscores the advice he would have given himself. “Don’t be afraid to try what you want to try,” he says. “It’s important to do this when you’re young, and to really take ownership of those early successes and failures. Figure out your comfort level, how much of yourself you can invest in something, and whether it makes sense to pivot to a new approach at some point. Be mindful of your own expectations, and set milestones and goals to assess whether you’re moving in the right direction. Don’t underestimate the power of positive thinking, and envision in your mind’s eye how you want your life to look.”

Beyond that, Gore reminds us that business is a marathon, not a sprint. His professional accomplishments are a testament to the pursuit of perfect form, learning the lessons of longevity to hopefully make the road a little easier for the businesses to come. As a person, he remains committed to mindfulness and continual self-improvement—cognizant that leadership is something that, by definition, is never truly mastered. “Over the course of my career, the mind-body-spirit connection has been the most influential thing,” he affirms. “Whether you’re a solo artist, a member of a team, or a leader of your organization, psychological health and awareness are absolutely key to being able to engage effectively in your work and achieve success. This mental agility allows you to pivot in your worst days and make them your best days. It’s what allows you to expand your own limits every day and inspire others to do the same, stretching beyond what you thought was possible or imaginable. From every company I’ve worked with, I’ve come to know that it’s a process to get people to see their own potential. It’s a process well worth the work, and it all starts with the basics.”

R. Gore Bolton

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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