From the earliest days of his childhood, Greg McDonough grew up believing in the power of a positive attitude. His older brother, born handicapped and partially blind, faced considerable adversity in life, but nothing could shake his kindness and optimism. “Paul is always in a positive mood,” Greg says today. “He goes out of his way to connect with strangers and is always looking on the bright side. Watching him, I learned that life really is great if you have the right attitude.”
“I believe positive things happen to positive people, so I’m positive about most everything in life. My optimism allows me to persevere where others give up, so I’m able to help where others can’t.
As a kid, Greg remembers being in bed at night and hearing Paul have seizures in his room next door. In those moments, his fear would paralyze him into inaction. He got in the early habit of grinning and bearing a bad situation, waiting for it to pass. But with time, Greg came to understand the importance of taking control and using his unyieldingly optimistic attitude to turn things around. “Now, I like taking on the toughest challenges, whether it’s completing an Ironman triathlon or stepping up to help a business that’s really struggling,” he says. “I believe positive things happen to positive people, so I’m positive about most everything in life. My optimism allows me to persevere where others give up, so I’m able to help where others can’t. I’m here on earth to do things that other people don’t want to do, creating positive outcomes that align with the positive attitude that fuels me.”
In truth, Greg feels fortunate to be here on earth at all. He can still remember a summer day when he was four years old, and he was so hot that he went walking from window to window on the second floor of their home in Fairfax, Virginia, searching for a breeze that would cool him off. The next thing he knew, he was waking up in a hospital bed with a cracked skull and a broken neck. When his mother had come out to see his broken body suspended in a bush after the fall, she screamed so loudly that his father heard it over the roar of the chainsaw he was using to cut wood out back. “That bush broke my fall, stopping my head about four inches from a concrete slab below,” he says. “I consider myself very lucky to be alive.”
Born in Annandale, Greg spent his formative years in the house his family moved into when he was three years old. The area was far more rural than it is today, and he remembers the thrill of playing intense games of bounty hunter—tag, essentially—that would last hours or even days. Summertime was dedicated to swim team, and Greg would play football on the weekends with the other kids in the neighborhood. He ran track and swam competitively, but soccer was his favorite sport.
Greg’s father grew up in a poor family in Liverpool, while his mother grew up just outside of London. An adept construction engineer, he took a job building hotels in Vegas, where he frequented jazz clubs and hung out with Miles Davis after his performances. They moved to Tahoe, where Paul was born, and then to Virginia, where Greg’s father took a construction management job building Metro Center. He was laid off just as the family had settled in, and when he was offered a job in Chicago, Greg’s mother was staunchly opposed to the idea of moving. Instead, he decided to stay put and joined forces with a friend to take on consulting work.
One project led to another, so they decided to formally launch their own company, Alpha Corporation. Through his childhood, Greg watched his father grow the company into an international presence of 300 employees and $40 million in revenue—until drama in the leadership ranks prompted Greg’s father to strike out on his own with two of the five partners. They started from scratch as McDonough Bolyard Peck, again growing the venture to an international force of 300 employees. “My father is an entrepreneur who’s excellent at what he does,” Greg affirms. “Not only can he grasp complex problems or projects, but he can also sit in front of a jury and explain those complexities in ways that others understand. I mirror that skill today when I walk my clients through the histories and trends of complicated financials and P&Ls.”
Despite his obvious professional prowess, Greg’s father rarely discussed business with the family. “He was the kind of guy who got the job done during the day and tried not to bring his work home with him,” Greg remembers and even recognizes that he struggles to do the same. “It’s very different from the relationship I have with my daughter, Sasha, who’s been very engaged in my entrepreneurial work since she was only seven years old. She’s very interested in what’s going on, and we love having conversations about how we’re going to start a business together.”
Greg’s mother, a caring and skillful stay-at-home mom, was the leader in the family, and the one who always made magic happen. Because Paul required 24-hour care and considerable medical attention, their parents would come up with creative ways to spend time together. For instance, they always made a point to spend quiet time together before bed—a practice that would figure prominently into Greg’s success later in life. “We’d go through a kind of meditation ritual together that involved counting, deep breathing, and memory exercises,” Greg recalls. “It taught me how to methodically control my emotions, which has been an invaluable life skill in managing the stress and grit of being an entrepreneur. If I wake up in the middle of the night feeling panicked or anxious, I know how to calm those voices and return to a state of rest.”
Each year was highlighted by a month long visit from Grandma Eve, Greg’s pioneering grandmother who lived in Pinner, England. She embraced vegetarianism, followed kabbalah, and used homeopathic medicines—ideas that were generations ahead of her time. Greg enjoyed talking business with her through his high school years, and when he turned eighteen, he spent the summer with her in England. “I’ll never forget when we hopped the Concord to Paris for my birthday that July,” he recalls. “She must have been saving money for ten years to pay for that trip. Grandma always put others first.”
“He always taught me that getting the deal done is more important than the deal itself because walking away with something is better than walking away with nothing,”
Greg was an average student through elementary and high school, excelling in math but struggled in English, and always longed to be active outside instead of stuck in a classroom. He made his first buck mowing lawns, and he started helping out at his dad’s office at the age of ten. As he got older, his dreams of becoming a professional soccer player or a fighter pilot in the Air Force evolved into an interest in following in his father’s footsteps as a successful engineer. “He always taught me that getting the deal done is more important than the deal itself because walking away with something is better than walking away with nothing,” Greg says. “He also stressed the importance of putting the good of the company and its culture above the good of himself. That was impactful.”
Upon graduating from high school, Greg attended George Mason University, where he joined a fraternity. It was at Mason that Greg started his leadership journey, spending two years as the President of the school’s largest fraternity. Greg recalls using his positive attitude and determination to motive the chapter during a time when moral was particularly low. “I told them, we were focusing on the wrong thing, and that we needed to move on,” he recounts. “We couldn’t go back to the ref and ask him to change the score because the game was already over. I told them the past is the past, and there’s nothing you can do about it, so focus on the future and on being positive. I told them to double down on tomorrow and come prepared with the right mindset.”
Greg’s confidence, leadership, and vision in that moment was raw and innate, without training our counseling. And in its pure form, it touched the team. One fraternity brother approached him afterward to let him know how inspirational the words had been. “He said, ‘Greg, this is who you are, and this is what you do best,’” Greg remembers. “It was a defining moment that planted a seed—one that’s just now truly coming to fruition. And the next day, with our new mindset, we won.”
While he began to find his footing as a leader at the fraternity, Greg continued to struggle academically. The Dean advised that he spend a year at the local community college and then return to Mason to get his degree, but Greg’s father stood up for him, insisting Greg would figure it out. “I recently sent him a thank-you letter for that because it was a pivotal moment that kept me in education,” he says today. “He was right, and once I figured out what I love, I took off.”
Greg decided to switch his major from Engineering to Economics because it seemed like the path of least resistance out of school. In his last semester, he had to take an elective and chose Finance—the class that finally proved the perfect fit for Greg, and the catalyst that redefined the course of his future. “From my first report on Bank of America stock prices, I loved the process of drawing understanding and insight from information and data,” he says. “I vividly remember sitting in class just two weeks into the course and realizing it was exactly what I was supposed to be doing.”
Greg aced that class, and though he had planned to leave academia for good once he graduated, he found himself instead eagerly re-enrolling at George Mason to complete a second degree in Finance. He aced that degree as well and then immediately started a master’s program at George Washington while working at Fannie Mae, focusing his studies on accounting and finance, venture investing, mortgage trading, and foreign exchange.
Greg spent five years in Fannie Mae’s investor relations department before his Senior VP, Jayne Shontell, had the opportunity to start a small corporate venture capital group focused on investing in Series A and Series B venture deals. Greg agreed to go with her, jumping at the opportunity to put real dollars to use in real companies. “Through that experience, I saw that I could apply my finance knowledge to small business, solve problems, and actually see results,” Greg affirms. “That’s where my entrepreneurial journey really started.” Greg was then invited to be an executive in residence at Dexma, one of the companies in their portfolio.
When the economy shifted and Greg’s job description grew considerably more conservative, Greg decided to venture out on his own to launch a company helping startups. Grandma Eve wrote him a check to help him get started, and he named the business Pinner Financial Management, after her hometown. He picked up six clients, including a startup called Pay Rent Build Credit, a credit authority designed to capture rental payment data so low-income families could build credit while paying rent. Greg helped them raise $2.5 million in venture capital and then sell.
After two years of solo practice, Greg decided to roll his practice into Longstreet Partners, an investment bank in Tysons Corner, Virginia. Two years later, in 2006, he married Monique, a driven and talented marketing, journalism, and sales executive. The two had met in college through a group of mutual friends, weaving in and out of each others’ lives for many years until sparks suddenly flew when they crossed paths at a wedding. They dated, married, and are now the proud parents of two daughters, Sasha and Simone.
Despite their busy world of work and parenting, Greg and Monique have fallen in love with undertaking Ironman Triathlons together— ultimate tests of strength, endurance, and willpower that add new depths to their relationship. “There’s something really special about having a goal with your partner,” he says. “We wake up early together to train. Sometimes I watch the kids so she can get her run in, or she’ll watch them so I can do my swim. We became clearer communicators with each other, and there’s nothing like being there on race day and knowing she’s doing it with me.” Greg and Monique make family vacations out of their Ironman competitions, selecting exciting destinations like Lake Placid, New York and Zurich, Switzerland. They’ve also launched a website, triathlonparents.com, and authored a book with advice for other parents interested in embracing the challenging—yet rewarding—family tradition.
Also in 2006, Greg took a position as the CFO for EEI Communications, a company specializing in editorial, proofreading, and formatting services for government agencies and associations. The company experienced considerable success until 2009, when it was hit hard by the recession. For the next several years, Greg took extreme cash flow management measures and did all he could to keep the company afloat, but by 2012, it was time to decide between shutting the doors or embarking down the Chapter 11 bankruptcy process.
Greg knew he was being paid less than market rate, and he considered jumping ship for better prospects, but one board meeting changed his mind. “I remember sitting there with the rest of the management team, and the attorney pointed out that someone who experiences the bankruptcy process from the inside picks up invaluable experience that not many people have,” Greg recalls. “So I decided to do the exact opposite of what most people would do in that situation. Instead of pulling out, I doubled down and recommitted to making the journey successful. I decided I was going to make a real serious play at turning the business around.”
Greg spent the next several months soaking up all he could, supplementing his real world experience with coursework that earned him a certification as a Solvency and Restructuring Analyst. As the only business owner in those seminars, he was able to see opportunities with small- and middle-market companies that most people overlook in their efforts to serve bigger companies. And thanks to his hard work, EEI improved. “I wish I had known in 2009 what I know now,” he reflects. “I see now that when you’re going through dire straits, it’s best to get in, stop the bleeding, and get reorganized so you can emerge stronger. If you’re spending today’s profits on yesterday’s problems, you can’t prepare for a better future. It’s a hard process, but with the right advisors, you can make it out on the other side. I also would have taken bigger risks and made bigger changes at the time. We had a great core business with clients that loved us, and we just needed to get back to the fundamentals. That guidance is one of the value-adds I bring to clients today.”
“It’s incredibly helpful to begin with a clear understanding of your business’s core, and with an ultimate exit strategy in mind,” he says.
As a leader, Greg brings passion, positivity, and energizing solutions to difficult situations. Looking toward his next tough challenge, he has set his sights on helping entrepreneurs get the most out of their efforts. With a focus on business leaders living month-to-month and payroll-to-payroll, his rich and nuanced bank of firsthand experience will provide the tools, mindset, and methodology entrepreneurs need to skip the turbulence on the road to success. “It’s incredibly helpful to begin with a clear understanding of your business’s core, and with an ultimate exit strategy in mind,” he says. “Once your business is whittled down to its fundamentals, you can model out according to your vision, strategically aligning every decision with where you want to go. This approach makes a big difference in cutting out incremental missteps that compound to a big impact down the road.”
In advising young people entering the working world today, Greg echoes the lessons learned from his parents, who taught him to genuinely appreciate what he has. “Gratitude is truly a freeing, empowering thing,” he affirms. “Of course there are times in life when I want what I want, and I want it now. But you have to put that kind of thinking out of your mind. Accept that you might not get exactly what you want now, or ever. Stop complaining, put your head down, and get the job done. Focus on being the best you can be at what you do, and have faith in the process. If you can open yourself to gratitude, you’ll have a better experience along the way.”
It’s this simple, unassuming gratitude that fuels Greg in his mission to take on the toughest. After a full day of confronting complex business challenges or triathlon competing, he finds rejuvenation and contentment in the small miracles that define his life. He and Monique support Innisfree Village, where his brother Paul lives, and the Challenge Athletes Foundation, which buys prosthetic limbs for paraplegic individuals who want to compete in Ironman events too. “I believe in helping people achieve their goals, whatever they may be,” Greg affirms. “And in my own life, I’m just grateful that I can get in my car and visit friends, or go hit golf balls, or go for a run. Gratitude for small things helps create opportunity for great things, fueling the stamina it takes to succeed.”
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