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From Pro Athlete to CCO: How Matthew Kyle Took His Game from the Court to the Boardroom

“You’re going home.”

Matthew froze. He could hear his heart pounding loudly in his chest as Coach started walking up the line of basketball professionals, getting closer and closer.

“This is it,” Matthew thought, his palms sweating.

But before Coach got to Matthew, he stopped. Right in front of Jimmy. Jimmy had flown with Matthew to Portugal to play on the Galitos F.C. professional basketball team just two days earlier, yet he was already getting cut?  “Pack up your things Jimmy.  We will pick you up in the morning to take you to the airport,” Coach said.

For Matthew, that was the moment when life became real. He had been a standout on the Yale basketball team before turning professional. But the harsh reality of what it meant to be a pro athlete was a turning point that has shaped who he is today.

See, in college basketball, you’re conditioned to think like a “team player” where everything from your performance to your attitude is about supporting your teammates to victory. Passing the ball is the nice thing to do. But in professional basketball, staying on the team is all about making points and grabbing rebounds. And winning is a matter of life or death.

If you want to succeed in pro basketball, you often cannot afford to pass the ball to your teammates, because your individual stats determine how much you’ll get paid and that teammate of yours may not be able to finish the play if you give the ball to them. And the guy guarding you on the other team? It doesn’t feel like he’s trying to stop you from scoring points; it feels like he’s trying to send you home. Because if he stops you from being effective and you cannot prove yourself by scoring as many points as possible, you could be on the next plane. No matter how good your attitude or teamplay is. 

Being a pro athlete gave Matthew clarity. He learned quickly about what he had to do to be well-prepared to win. And the expression “Take one for the team” had new meaning: it’s not about sacrificing yourself for the team but about performing your best, making the right decisions and putting teammates in positions to be successful so you are accountable to the team. 

Matthew’s basketball career took him around the world to play against some of the best foreign teams, and one of his biggest highlights was when he had the chance to spend 10 days on the team during the NBA’s New York Knicks’ pre-season camp.  It was short lived but it catapulted him to a chance to play in Japan.  Matthew played 1 season for the Toyama Grouses, taking the team to their deepest playoff run in history, but he knew that basketball would not be forever.  His final full season as a pro was disrupted by the Tohoku earthquake and tsunami disaster which made Matthew think of what could come next.

Matthew was ready for an out. Basketball was great, but examples of pro players who transitioned to making it in the corporate world were hard to come by, and he was ready to pave the way. 

After the season in 2011, Matthew spent a summer interning for Ernst & Young in Tokyo to start gaining some experience to help make that transition.  He had intended to play another professional basketball season before completely switching from basketball to the corporate world, but as the summer of 2011 grew to an end, he realized that he didn’t want to leave Tokyo.  

By the time he realized he wanted to stay in Tokyo, there was little time left to find a job to actually stay in Tokyo. If he wanted to make the jump from basketball to business, he’d need to find a job in 5 days or else he would risk losing two basketball contracts pending his agreement. But he knew this kind of challenge all too well and was ready to make it happen because his life truly depended on it. 

After 4 days of ferocious networking, he landed an interview with a professional services firm.

“I see you don’t have any experience in this line of work. What can you bring to the table?” the hiring manager asked during the interview. 

“My game”, Matthew thought. 

Within 5 days, he had the job. What kind of job? Well, Matthew wasn’t exactly sure, but boy oh boy, was he about to find out! He was new to the world of professional services and excited that he had a solid future in Japan as an Engagement Manager. And who was Matthew’s team leader at the time? None other than weConnect’s cofounder, Scott Smoler.  

In the early days of corporate life, Matthew gained a holistic understanding of Immigration, HR and the Tax sides of business. He learned by being deep in the trenches between clients and technical specialists, and explaining the in’s and out’s of doing business in Japan to executives in America, Europe, Israel, Australia, New Zealand and the Middle East. 

After learning the ropes, he started taking on projects where he could deepen his understanding and help clients understand the different business culture and customs in Japan. It was through these client meetings that he discovered what he enjoyed the most: Sales.

And many years later when he and Scott started building weConnect, that drive from Matthew’s days in basketball kicked in full force. Getting out there and winning new business is how he’s translated his passion from the court to the boardroom. 

“I genuinely love meeting people who are excited about something, and most people starting, expanding and growing a business are very passionate. It’s great to have inspiring conversations while still being able to talk about how weConnect can help them make their vision a reality. 

“Plus, I think the fact that I was not a technical expert in the beginning helped me learn the rules of the trade from an outsider’s perspective. That’s helped in having real, high-quality conversations with business owners who are learning about how things work in Japan and Asia for the first time,” Matthew reflected.

One of Matthew’s proprietary techniques for finding new business? “If I see someone I want to talk to at an event, I stand next to them. 8 times out of 10, they ask me how tall I am. Since they are the ones to start the conversation, it’s easy to get personal, fast, and I can quickly figure out if they’re a fit for our services.  

“It’s easy to structure my follow-ups after an event because I have that much more information to work off of. My height is a great conversation starter and has helped me vacuum up business cards for years!” Matthew laughed. 

His height of 6’11” was essential in helping him start a career in basketball, and it’s still helping him to this day in business. He definitely gives the expression, “having a 30,000 foot, holistic, business discussion,” new meaning.

Want someone accountable to you? You’ll want Matt and weConnect on your team. Contact us here.

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