When Glen Hellman’s three-year-old son looked up at him and declared he wanted to be a hockey player, Glen was surprised. Glen had never been to a game before in his life, let alone played the sport himself, and had decided to bring the boy on a whim. But when his son’s mind was set on hockey, then so was his.

At the time, Glen lived in Maryland but commuted to work in Denver, where he was the CEO of a struggling company. Still, he knew his son’s dream was worth making time for. “When everyone else was getting ready to go skiing for the weekend, I’d take the evening flight back east and get home around 1:00 AM,” he remembers today. “A couple hours later, I’d wake up to take him to the skating rink. But since I’d never played hockey myself, I couldn’t actively participate the way I wanted to. So, at 42, I learned how to play, taking lessons and joining a beginners men’s team. I became a coach, and I coached my son’s team.”

Through the many practices and games, Glen soon saw that the joy he got from coaching was about more than helping his own son, who grew up to lead his high school team to the Maryland state finals as captain. It came from an innate, fundamental affinity for the work of guiding others to success, and he grew deeply invested in the well-being and growth of each child on the team. One day, he ran into the mother of a kid he had spent extra time with because his father wasn’t around much. “I never got the chance to thank you,” she said. “In school, my son was asked to write a paper about the most important person in his life, and he wrote about you.” “That moment stands out in my memory as one of my proudest,” Glen says. “Right alongside the time I saw my son pause in front of a wide open goal. Instead of making the goal himself, he passed the puck to a teammate who had never scored a goal in his life.”

For almost thirty years of his professional career, Glen was involved in the lifecycle of companies. It wasn’t until 2007 that he realized the passion he had for coaching his son’s hockey team was more than a pastime. In fact, it was a calling. Now the owner and CEO of Driven Forward, a flexible coaching program for busy executives, Glen applies his decades of experience to helping small business leaders overcome the challenges of isolated leadership and expand the success of their life’s work.

A fixer of things that break and a breaker of chains that hold others back from achieving their full potential, Glen is hardwired to lead teams, act swiftly, and embrace and overcome uncertainty. He launched Driven Forward as an alternative to more rigid, structured coaching programs, and as a way to protect clients from the common mistakes that bring down even the best. “When I look back at the failures I’ve seen in the business world, few of them were driven by bonehead management or malicious actors,” Glen points out. “They were mainly due to a series of very small, bad decisions that led them over a cliff and into a death spiral. I realized from personal experience that those decisions are made from the “loneliness at the top” which is exactly what we fight to overcome at Driven Forward.”

Today, Driven Forward works with owners of businesses with annual revenue that typically ranges between $1 million and $40 million, with a focus on small companies. The program consists of half-day sessions and a la carte one-on-one meetings, which can be conducted in-person or remotely. This allows Glen to serve clients as far away as Romania, though most of his clients are spread across the United States. He also does executive team coaching for companies, providing complete confidentiality in each one-on-one meeting to work out challenging dynamics. “My job is to coach and to help each person perform better,” he says. “When that’s applied to a team dynamic, the goal is to make everyone more cohesive and work better together.”

Recognizing that fit is paramount in establishing a coach-client relationship, Glen has an in-depth intake process comprised of a personality assessment, a coaching meeting, and more. This is particularly important to prepare clients for his blunt, no-nonsense approach, which has earned him the nickname “Mr. Cranky.” Thanks in part to Driven Forward’s philosophy of directness, a recent client sold his business for $20 million. Another client was able to double his $800,000 business and increase his personal wealth five-fold. “I visited this client’s office recently, and on his wall is a list of five things I taught him, entitled ‘Mr. Cranky Says,’” Glen laughs. “That meant something to me.”

Glen also serves as an Executive in Residence at the University of Maryland’s Office of Technology Transfer, where he coaches cutting edge inventors on how to build successful companies around their discoveries. “One of my favorites was when I matched a serial entrepreneur and commercial pilot with a sharp University of Maryland aeronautics professor,” Glen says. “The professor had developed an innovative Unmanned Aerial Vehicle (UAV), or drone, and today, they’re running a great company.”

Taken together, Glen’s work is a steady stream of puzzles to figure out—exactly the kind of life he’s wired for. “My coaching philosophy is rooted in constantly asking ‘why’,” he says. “I need to know why things tick, so I’m not afraid to ask the tough questions.” It’s a defining character trait that hearkens to his New York City roots with street-smart parents who raised him in Brooklyn until the age of four. Glen’s father, a tough but kindhearted man who lived through the Depression and served as a navigator on a bomber during World War II, was a salesman and account manager at JP Stevens, a large textile company. At age 36, he married Glen’s mother, who gave birth to both Glen and his older sister in the same year. Four years later, they had another son and moved to New Jersey, where his mother later became a real estate agent. “She was demanding, outgoing, and successful,” Glen recounts.

Growing up in a solid middle class neighborhood, Glen enjoyed playing touch football with friends. He started playing guitar when he was in third grade, and played in bands through his sophomore year of high school. Sunday night was family night, often spent watching Ed Sullivan or a Disney movie together. Summers were spent at the swim club, where they had camps, swim team, and movie nights.

Through those years, Glen’s father modeled a strong work ethic and sense of discipline. He would leave the house at 7:00 AM and walk two miles to a bus stop, which was double the commute time but half the cost. When Glen was twelve, his father decided to start his own business selling toys—quite a jump for the rule-abiding, risk-averse man who loved routine. On weekends, he would visit toy stores throughout Long Island, Manhattan, Brooklyn, and New Jersey, and Glen would often join him for the long drives. “I remember spending hours in the car just talking,” Glen recounts. “He led by example and was always consistent, so you knew what you were going to get and what was expected of you. He never complained and was a wonderful father who worked incredibly hard to provide for us.”

When Glen was fourteen, he told his father he wanted to be a comedian, to which he replied, “There’s a guy who works in the mailroom who’s a comedian. He makes no money.” The comment stuck with him, and later helped propel him toward sales instead. His life path was also shaped by his experience on the track team, where he performed well in junior high but truly excelled in high school, when his mile relay team won second in the state across all divisions. “The time we ran in 1974 is still the school record in both the mile relay and the 1,600 meter race, and I’m still close with my relay team and coach,” Glen says. “I think of myself as an individualist, but the times when I ran on my own were significantly slower than the times I ran with three other guys who were counting on me. I realized I’m driven to not let people down.”

Academically, Glen would get high grades on his written content, while failing at spelling and handwriting, and struggling in math. Only later in life did he realize his poor performance was due to Attention Deficit Disorder, which gives him the ability to hyper-focus on things he truly enjoys, but delays his capacity to grasp unengaging concepts. “I thought I was just stupid,” he says. “I did really badly in school and couldn’t get into college when I graduated. I thought I should become a plumber, but my parents forced me to go to community college for which I am thankful.”

With that, Glen enrolled at Montgomery County College in New Jersey and then went to Montclair State for a year, where he ran track and used an early digital equipment mini-computer to write a computer game program. He improved his GPA enough to get into the University of Maryland, where he took business classes and was a founding member of the Fiji fraternity chapter. Upon graduating, he struggled to find a job but set his sights on the cutting-edge field of technology. And because he only had a 2.2 GPA, he figured sales was his only option.

Glen began investigating, only to discover that IBM required a 3.5 GPA and Xerox required a 3.0. Fortunately, his girlfriend at the time worked in an office at Maryland and had access to one of the first word processors with a screen. He used it to generate his resume, fell in love with the technology, and hunted down its maker, a startup called Lexitron. “They told me they didn’t have a training program and only hired people from IBM and Xerox,” he says. “But I wouldn’t leave. I told them they didn’t have to pay me. I’d carry the bags for the sales team. I just wanted the chance to learn.”

With that persistence, in 1978, Glen landed a job in their federal branch. He made his numbers that first year and earned $24,000, making his first sale to the U.S. Department of Veterans Affairs and then working with clients like the White House Communications Agency and President Carter’s speechwriters. Glen then approached the Master Chief of Naval Operations, who explained that he needed a program to track incoming inquiries. Glen built an application tailored to that need, which prompted the Navy to place an order for $300,000 worth of word processors from him. Using the same technique of writing software to sell hardware, Glen landed another client and then put together a training program for the software he was writing.

By his third year on the job, Glen was making $103,000 and had married his college sweetheart. Out of the company’s 200 sales reps, he was third in the country. The following year, after the company was bought by Raytheon, he was promoted to manager, shifting from government to commercial work and managing people over a decade older than him. By age 26, he had a $20 million quota. “I realized for the first time that, if I loved what I was doing, I could do it well,” he remarks. “I saw that I loved puzzles, and that I actually wasn’t dumb. I also realized that, once the puzzle was solved, I became a poor performer. If I wasn’t learning, I wasn’t interested.”

By that point, Raytheon no longer felt like a puzzle, so he left and soon found his way to a $2 million company called Progress Software. As its eighteenth employee, he met his million-dollar first-year quota and soon became manager of everything east of the Mississippi, with offices in Chicago, Dallas, Atlanta, Boston, Jacksonville, Raleigh, and New York. “During that time, the company went public, and I did well on the stock as I read everything on stocks, mutual funds, and modern portfolio management,” he says. “I’d come in at 10:00 AM, manage the stocks, do a forecast, answer questions, and go home at 3:00 PM. Now with a $20 million quota, I was the top performer of the three regions almost every year, and I was bored stiff. After we went public, we stopped doing things because they were the right things, and started making decisions based on how it would affect the stock price for that quarter. I didn’t like the focus on short term goals, and I wasn’t learning anymore, so I left half a million dollars’ worth of options on the table and walked away.”

Ready for a new challenge, Glen joined forces with several former clients to launch an early salesforce automation company called SaleSoft. “In the days before the internet, we designed a great system that synchronized work across multiple locations,” he explains. “We won a huge deal with Digital Equipment, beating our main competitor, but then we failed.” At forty years old, and as the third largest non-institutional investor with $100,000 of his own cash invested in the company, Glen was the first to be fired—an act to appease the investors.

On his own, Glen came across a consulting company hoping to ride the dotcom wave. He joined them and rebranded the business into a product company called Call Technologies Inc. (CTI). “We sold software to streamline the back offices of telecom companies,” he says. “I did the marketing, packaging, investor relations, and hiring, building the company and then running its most profitable product line. We raised $9 million to start the company, and four years later, in 2001, we sold it to 3Com for $100 million.”

In that sale, Glen was contracted to stay on a year, where he ran the telecom software division for 3Com as a general manager overseeing about 80 employees. He then had the choice of taking cash, which would have amounted to $4 million, or stock. Glen chose stock, and that year, he was the best-performing account at Alex Brown at a whopping $6 million in value. Everything changed, however, when the dotcom bubble burst in June. “In a week, I probably lost around $3 million,” he says. “What I learned was, it didn’t kill me. I lost a little sleep over it, but not much. I realized that the money came out of nowhere, and I can always get it again, and it doesn’t mean that much.”

After leaving 3Com, Glen was called by a headhunter to interview for the CEO job of a company in Denver. After five years of operation, they had around 380 employees, including a masseuse, but less than $1 million in revenue. “The first thing I did was let the masseuse go,” Glen laughs. “Then I told everyone there would only be about 70 of us left in ninety days. Otherwise we had no runway.” Through that time, Glen focused on building the business, just as he had with Call Technologies. In the end, he recommended to the board they close the company down, and as a result returned $6 million to its venture capitalist investors. He was then tapped to join the board of a company in Herndon, where they fired the company’s CEO two months later and put Glen at the helm. “I had never been a board-member-turned-executive, and it really highlighted the stark difference between the two roles,” Glen says. “As a CEO, you have to figure things out yourself, and it can be very isolating. You share the sausage with the board but not the sausage making.”

Twelve months later, Glen saw that while the company was treading water, it didn’t have the money to grow. He recommended winding it down and then took a job with a consumer products software company looking to do business in Asia. He traveled around in Japan, Korea, and Hong Kong, eventually selling that company to take a job with a parking meter company and a proxy advisory firm. “I loved the chaos of dealing with a new crisis every day and always facing something new,” Glen recalls. “But by that point, I was in the business of putting companies out of their misery and harvesting organs. I would lay off a lot of people and close up shop, getting as much value for the investors as possible. I acted like I was this tough guy and it didn’t bother me, but boy, it really began eating at me. After I put down the last company, I couldn’t do it again.”

Glen’s personal life, as well, was extremely challenging through that period. In 2004, after 24 years of a contentious marriage, he tore himself away from one particularly intense argument with his wife only to find one of his sons balled up on the floor in a puddle of tears. “I knew we couldn’t keep doing that to the kids,” he remembers. “I decided it was time for me to leave.”

The decision to divorce his wife launched one of the hardest periods of his life, and on top of losing most of his assets, he almost lost his kids. “Each weekend I had them was like Sisyphus rolling the rock up the slope,” he says. “When I picked them up on Friday, they almost refused to get in the car with me. I’d work all weekend to remind them of what we were, and by Sunday, we finally had a good relationship again. But then I’d drop them back off and have to go through the whole cycle over again the next time. That was really tough, but we worked through it, and now I have an unbelievably good relationship with them. Through making money in corporate M&A, losing millions and almost losing the people who are most important to me, my life’s lesson was that money and things don’t matter. Your friends and family are far more important.”

Through that difficult time, in 2006, Glen met Nancy, the woman who would become a true partner and an incredibly positive, stabilizing force in his life. The following year, he came across Vistage International, the executive coaching program that allowed him to get out of corporation hospice care and into corporation wellness care. Nancy stuck by Glen from the time he closed his last company, to the time he started earning money as a business coach fourteen months later. They married in 2013, and in 2014, Glen finally achieved his lifelong dream of being a comedian by putting together a five-minute standup act. “It went fantastic, and as soon as I proved to myself I could do it, I never had the urge to do it again,” he laughs.

Now, when Glen isn’t coaching, he’s writing, authoring several blog posts a week with a book on the way. In advising young people entering the workforce today, like his oldest son who graduated magna cum laude from Harvard and is now top of his law school class there, he highlights the importance of remaining open to learning. “If you believe you know it all and can do it all, you’re in trouble,” he says. “I failed starting a company at 39 after being in business for 18 years. I have learned lessons from every job, boss, and experience I’ve had. Young people today should take jobs knowing that the point is to learn. Observe your boss, your peers, and how things work, and be patient.”

Beyond that, Glen coaches us to stay connected to what matters. For Glen, personally, that means Nancy and their kids—the only things that are truly irreplaceable in his life. And professionally, that means reaching beyond management to be a transformative leader. “Management is how you take care of kids when they’re two years old, putting gates on the stairs and plugs in the electrical sockets,” he says. “But if you’ve only managed your kids by the time they’re seventeen, you’ve failed. For me, leadership is caring about your team, setting a model of behavior, and being consistent with what you say and what you do. It’s coaxing your people to be self-managed. It’s asking the tough questions and working through the answers. And above all else, its having the courage to take action, coaching each client through chaos to the stable success they deserve.”