Guy Timberlake

Born to Win

Guy Timberlake was a jock in school. He played soccer growing up, he transitioned to football, he studied martial arts from the age of five and he did well in wrestling and indoor track. But as far as athletics went, there was one sport nearest and dearest to Guy’s heart, and it was lacrosse. At Howard High, lacrosse was “almost a religious thing,” says Guy. The school was known for its winning record, and Guy became an important contributor to that winning tradition.

During his years playing lacrosse for Howard, the team won championships two years out of four. Guy particularly remembers his JV coach, Kevin Riley, who was not only a fantastic coach but was also a friend and mentor. “Coach Riley may have been like any other coach on the surface, but he went above and beyond to make us believe in ourselves,” Guy reflects. “It didn’t mean as much to me then, but it does today. Now I appreciate it. Before a big game, he would leave us all notes taped to our lockers. He hand-wrote every single one. But there was one note I kept. The three words on the front were: ‘Born to Win’. Every time I think about it, it fires me up. I work every day to live up to that.”

After high school, Guy went through some rocky years, but with hard work, talent, and commitment, he clawed his way up from warehouse worker to a successful salesman pulling in million-dollar deals for established and start-up companies in the defense and intelligence sectors. From there, he joined his wife in launching and building their own business. All was going smoothly until a freak infection nearly derailed Guy’s hard-won career.

“There was one note I kept. The three words on the front were: ‘Born to Win’. Every time I think about it, it fires me up. I work every day to live up to that.”

The infection in his leg started as a pimple and was something he initially didn’t worry about. It began to become more painful, and his doctor put him on antibiotics as a precaution. A couple weeks later, he was rushed to the ER with a fever of 103 and a baseball sized-growth on the back of his leg. “The thing had abscessed,” he explains. “They lanced it, but nothing came out. It was necrotizing fasciitis, flesh-eating disease. Because my doctor had put me on those antibiotics previously, the bad news was that they couldn’t determine the specifics of the infection. The good news was that I may have lost my leg if he hadn’t done that.”

Guy was in the hospital nearly two weeks working with the soft-tissue team of specialists and underwent five surgeries. At the time, his company was five years old and on the upswing. His baby daughter was only six months old and suddenly his wife, Margaret, was juggling the new baby and the business, with her partner down for the count. “By all rights we should’ve been done,” nods Guy. “Our business should’ve just gone under. But members of our organization, people who paid to participate in the membership program we developed and offered, stepped up, supported us and ran the company until I was back. It didn’t miss a beat. We were told that we were too important to die. I owe it to them to never give up, because they would not give up on us. It’s the kind of thing that gives you absolute hope and faith in humanity.”

Thanks to the wonderful relationships Guy had built over the decades, the business—then called The American Small Business Coalition (ASBC)—survived and thrived. Over time, it developed and evolved into the booming organization it is today: GovCon Club is the “back by popular demand” rebirth of The American Small Business Coalition. “After shutting down the membership operation and pivoting to a services model for two years as SCIIF, or Skunkworks for Competitive Intelligence Innovation in Federal Contracting, we were called back to the membership community approach and launched GovCon Club. To that end, several of the GovCon Club’s founding members were founding or long-time members of The American Small Business Coalition. “The members of The ASBC saw much more in the organization than Margaret and I ever did. It was they who convinced us how much the community meant to them, so here we are again, and it’s great!”

Though Guy and Margaret consider themselves co-founders of their business, Margaret was the one who initially launched the seed that is now GovCon Club. She had started a business intending to provide virtual admin services under the name One-Click Office Solutions, and Guy decided to begin helping out. He put his name on the website and, with his large network of connections in the business and contracting world, they began getting phone calls. As interest grew and clients multiplied, Guy and Margaret began to focus on providing knowledge and best practices to companies in the federal sector.

Thus, the ASBC was born in 2004. It was a membership program that small businesses could join, and in return receive guidance, advice, trainings, networking opportunities, and access to education. The model was successful, but difficult to maintain over time. Additionally, Guy saw that their audience had begun to expand beyond the small business world, and, therefore, the business pivoted to become GovCon Club. “Our pillars are training, education and advisory,” says Guy. “We have a brand for each one, and people know us all over the country. Our Ethical Stalking for Government Contractors® program essentially began as education about how to use open-source information and tools to make good decisions as a federal contractor. It’s become incredibly popular. Plus, people in government know who we are.”

With only four employees including Guy and his wife, GovCon Club stays lean by relying on volunteers to help administer some of their programs. The company also leans heavily on Guy as the Chief Visionary and CEO. He has been known to facilitate and teach many of the programs he developed, although he is working to step back from these day-to-day responsibilities over time.

As far as clients go, GovCon Club is no longer limited to just small business and attracts representatives from mega-contractors like Lockheed and even government workers themselves. “From a target audience standpoint, I’d be lying if I gave you any one answer,” acknowledges Guy. “We have large and small companies as members.” GovCon Club offers a six-month subscription that includes a 2-day long bootcamp, a program that launched about four years ago out of a much shorter, hour-long bootcamp that the company spearheaded a decade earlier. After bootcamp, companies participate in coaching calls and continued learning to help them apply their new knowledge and skills. “Everyone who attends bootcamp receives new content every week,” explains Guy. “That could be a new piece about a tool they use, a process, a tactic, or whatever. Our goal is simply to make people smarter and more effective at what they do.”

“If I could talk to myself at 22, I’d probably say, ‘Shut up and listen more. Learn what your gift is and use it.’”

Guy comes by his work ethic honestly, noting that his parents “worked their tails off” throughout his childhood in Columbia, Maryland. His father had been in the military before going to work for the government, first in the postal service and later in the FDA. His mother was a schoolteacher. Both parents were from Richmond, Virginia, where Guy was born and lived the first couple years of his life. The family often returned to the area to visit Guy’s grandparents, aunts, and uncles. “I grew up hanging around Byrd Park in Richmond,” recalls Guy. “The neighborhood my grandparents’ lived in was like the Jeffersons. Mixed, upscale neighborhood for folks who were a part of the community.”

The family briefly moved into DC before settling in Columbia when Guy was entering second grade. In the meantime, his two younger brothers—one biological and one adopted—came along. With three little boys, Guy’s parents decided they needed more room than they could find in a city apartment complex. The kids loved Columbia, a suburb with a small town feel where everybody knew everybody else. “We lived on Eaglebeak Row in the Village of Long Reach and I can still drive through there now and tell you the name of the people who lived in every single house,” smiles Guy. “All us kids would go out with our backpacks and our bikes, go play in the creek, or go on adventures. Before Harrison Ford ever made Indiana Jones, there we were in the creek. We’d take our bikes and ride all over without even hitting a street. Nobody worried about stuff back then and we would be gone all day. My life as a kid was amazing. My parents absolutely succeeded in giving us the life they wanted us to have.” The family made meals together, went to church consistently, and on occasion made a trip to King’s Dominion or Disneyworld. Guy compares his childhood to the “black Cleavers,” referencing the idyllic homelife depicted on Leave it to Beaver.

During the week, Guy would walk to school, which was only a few blocks away. In the summer he’d go swimming, and as he got older, he picked up a paper route. Then he began cutting grass in the summer and shoveling snow in the winter. “I got known in the neighborhood as a hustler,” he winks. His parents wanted to instill a work ethic in the kids, and though they had a small allowance, a part-time job was expected to cover extra expenses.

Guy thrived in athletics, but academics were another story. He had undiagnosed ADD, and while he did all right, he certainly wasn’t very committed to his studies. He was a voracious reader, loved all kinds of music, and had a great social life. But he was more focused on having fun and making money at his job than on school.

Both of his parents had gone to college. His mother was from a more well-to-do family and had been expected to go, but his father paid his own way. They were appalled when Guy began rebelling and declaring his intention to skip college altogether. ‘It was like blasphemy,” he recalls.

After graduation, Guy did end up attending Howard Community College for a little over a year before setting out to focus on his professional life. He left college and took a job as a shoe salesman at a department store. He fell in with a bad crowd, and for a few years, was more focused on partying than his future. Then, while working in a liquor store, he met an older woman with whom he began a relationship and moved to Maine. Despite being in his early 20s, Guy became a foster parent to a 13-year old teenage boy while he was in Maine. “The kid never had a shot from the start,” Guy says. “He’d had no success with other foster parents so they paired him up with me. And over the course of those years we made tremendous progress. He trusted me. The last I heard he was still making good progress, aged out of the program, got a job, lived on his own, and was doing well. I basically became his big brother and am glad I was able to have an impact on his life.”

Eventually, Guy’s relationship with the woman ended, and he moved back home. His mother helped him land a warehouse job in Columbia where, fatefully, he was introduced to the world of government contracting. “I had no pride and was willing to do whatever it takes to make money,” remembers Guy. “I didn’t know who I was working for during the first year or so. Everyone in the building had a security clearance except me. I’d say, ‘Who’s the guy in the black suit?’ ‘He’s from Langley.’ ‘What’s Langley?’ It was surreal to me, I was even directly involved in Desert Shield and Desert Storm. I was supporting the manufacturing line and learning all sorts of trade. I could source part numbers and build entire material lists from equipment. If the equipment that we created did not work, somebody would die. I still remember the first time somebody said that to me, and I thought they were joking. It was both interesting and disconcerting. The quality of our work potentially could mean the difference between life or death.”

“If I were to hit the lottery tomorrow and win $20 gazillion, I’d wake up tomorrow and do the exact same thing.”

Around 1990 after two years into his work, Guy began to get noticed. The company had just been sold to another business called North Atlantic Industries (NAI), and the President of NAI took a liking to Guy. He offered Guy a new opportunity—a position in marketing. Guy quickly took to sales like a fish to water. He met several career mentors, including Maryke Guild, who taught him contracts, and two coworkers who taught him about purchasing.

Guy remembers the environment there as being “like a family” where he even knew the janitor, Harry, personally. To the amazement of the owner at one point, he earned the business half a million dollars just by calling in rebates for computer components. But in 1994, the markets turned down, and Guy’s whole division was laid off. “I didn’t know what I wanted to do next and didn’t think I had any marketable skills,” remarks Guy. “I had just spent six years working in support of the intelligence community. I wasn’t sure how I could convince someone to hire me since we couldn’t openly talk about what we were doing, even if I knew what it was.”

Fortunately, Guy landed a sales gig at MCI, where he once again thrived, would often hit 130%, 150% or 180% of his quota, and received trophy after trophy for his success. After a year and a half there, Guy returned to government work as an inside salesperson with Pulsar Data Systems, an 8(a) company, where he was able to quickly earn them a million-dollar contract with the Navy. After stints at a couple of other small businesses, Guy headed back to MCI, now WorldCom. While there, he was also bartending on the side, a job he loved because of the personal interactions. One day while having lunch with a friend at the bar where he worked, he met a group of women; one of them was Margaret, his future wife. Nothing might have come of it, but the following day he learned that she worked next door to MCI. The rest is history.

As Margaret’s and Guy’s dating relationship intensified, his career also ramped up a notch. At WorldCom, Guy was now an outside salesman and was selling more and earning more. When a national sales competition between all 7,000 salespeople was announced, Guy was on a mission. He was a competitor, and he wanted the top prize. Through the weeks, he continued to place first or second company-wide and finally walked away with the top spot and all the benefits that entailed.

He’d found great success at WorldCom, but once again government contracting called to him. He joined A&T Systems in Silver Spring in a business development role. It was a $60 million company, and he wound up bringing in a $70 million contract during his time there. In a classic case of David and Goliath, he helped them beat out the former EDS by bringing on a $600 million firm as a subcontractor. From there, Guy jumped over to help his wife’s business take off and never looked back.

“She’s my partner,” Guy says of Margaret. “She is absolutely in my corner. It’s not that I can do no wrong because I almost always can. But she is the pinnacle of people who believe in me. She is my biggest fan and my biggest critic all rolled into one. She started the company and will never let me forget that it was her company and that I stole it. I’ll never live that down. When I had the hole in my leg, Margaret had the home nurses train her so she could take care of me. And she took care of our daughter and our business during that time. If it wasn’t for her, everything would’ve fallen apart.”

Throughout his career, Guy has received a multitude of nicknames, speaking to his many close relationships, mentors and mentees. He’s referred to variously as “Go-To Guy,” “Professor,” and “Edutainer” for his classic blend of informative and fun presentations. Go-To-Guy is the one that stuck and is how he’s known in business today. “I picked this tag up from my Navy and Air Force customers in the 90’s for being so reliable.” As a leader, Guy considers himself to be “engaged.” “It’s interesting, but it’s only recently that I’ve started considering myself a leader,” he muses. “I would say I lead from the front. I like being in the mix, but I don’t ever think I’m better than anyone.”

To kids entering the working world today, he advises the path he didn’t take, i.e., college. “I’ve done well for myself, but I’m probably one of the last that could manage to not go to college,” he reflects. “I don’t think the environment is conducive to that anymore. So invest in your education. Invest in knowledge. However you need to get it, get it. If I could talk to myself at 22, I’d probably say, ‘Shut up and listen more. Learn what your gift is and use it.’”

Although he may have had a bumpy start to his career, Guy has done that and more. Today, he has no regrets. “If I were to hit the lottery tomorrow and win $20 gazillion, I’d wake up tomorrow and do the exact same thing,” he smiles. “Like a lot of other people, I was chasing the dream of being able to find the thing that I love to do and call it a job. I found it, and it’s not really a job. I love every single thing about it. It’s fun, it helps the government, it helps industry, and it helps people achieve their goals. We work to make things better for them.”

Guy Timberlake

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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