Measuring Up

Drew Green (BA ’97), founder and CEO of Canada’s Indochino menswear brand, has built his company into a global success. Yet, his most meaningful work is empowering student athletes through philanthropic initiatives that ease financial burdens and fuel basketball aspirations.

Green’s passion for supporting York University stems from his own experience as a cash-strapped student. As the only child of a single mother in Scarborough, Ont., Green understood early on that he would need to finance his own education. The varsity athlete and fitness enthusiast leveraged his passion and skills, establishing himself as a personal trainer. He systematically grew this business while balancing his academic commitments and his position as guard on York’s basketball team.

“It kind of mushroomed,” Green says, sitting in his souvenir-cluttered Vancouver office, still a bit jet-lagged from a long flight back from Hong Kong. “As my clientele grew, I started hiring trainers at a facility downtown and eventually sold the business.”

As with many entrepreneurs, Green learned the ropes not in a classroom, but through hands-on experience with his self-made venture. “The experience provided me with the opportunity to learn how to start a business, to build a business and see how to create value. That experience helped form the rest of my business life.”

Over the past three decades, Green has built an impressive career as an award-winning entrepreneur and investor. He has founded, developed and sold multiple companies in both the U.S. and Canada. His expertise extends to raising hundreds of millions in equity investments for various firms. Green also serves as a director for tech startups and has held a position on the York University Alumni Board since 2022. Most recently, he became an owner (and Chair) of the Canadian Elite Basketball League.

But he is perhaps best known for transforming Indochino from a small online bespoke tailor into a global brand that now creates custom clothing for customers in more than 50 countries, supported by a network of 145 retail locations across major North American urban centres. Under his leadership, the brand has also forged partnerships with the NBA and NFL, outfitting rising stars such as RJ Barrett, now a shooting guard for the Toronto Raptors. His passion for basketball extends to helping the next generation succeed on and off the court.

Green’s commitment to supporting student athletes is rooted in his own experience. He was offered a basketball scholarship from the University of British Columbia after high school, but chose York University instead, finding the idea of moving across the country at 18 too daunting. At the time, York didn’t offer sports scholarships, making it necessary for Green to fund his education through his personal training business.

In recognition of these challenges, Green established the Drew Green Lions Award at York University. This annually endowed scholarship supports high-achieving male and female basketball players, with a particular focus on students from Scarborough, his home community.

The Drew Green Lions Award not only alleviates financial pressures, but also recognizes recipients’ exceptional accomplishments both on the court and in the classroom. By empowering the next generation of talented Lions, the scholarship aims to strengthen York’s basketball programs and boost their competitiveness among Ontario’s top-tier university athletic programs.

While Green entrusts the University’s staff with selecting candidates from among the applicants, he underscores the importance of supporting high-achieving student athletes who might otherwise struggle to balance academic and athletic commitments due to financial constraints.

“What I try to do with the awards is hopefully look for athletes from Scarborough – my hometown and a place I’m very proud of – and help them realize their dreams of being a student athlete or varsity athlete at university.”

Green has established a similar scholarship at the University of British Columbia. Over the past 10 years, this initiative has provided awards to a dozen students, further demonstrating Green’s commitment to supporting student athletes across Canada.

At York, Green makes a point of taking the scholarship recipients out for lunch and getting to know them personally. This hands-on approach reflects his broader philosophy of giving back. “It’s a great thing, right? I think any time you can be grateful for your journey and give back with gratitude, then we need to do that. It’s something we’ve tried to do as a family for decades, regardless of our status or ability.”

Green emphasizes that the point isn’t just about providing young people with opportunities to play basketball. As a father of two sons who compete at top U.S. schools, he firmly believes in the character-shaping power of sports, particularly team sports.

As he puts it, “You learn how to fall in love with something and gain a passion. You learn how to work, and work really hard to improve at something. You learn the value of teamwork. You learn how to win. You learn how to lose. You learn how to be a leader. You learn how to serve others, and to pick up your teammates and make them better.”

Although Green no longer plays basketball, the experience of nurturing young athletes continues to shape his life and philanthropic efforts. Through his scholarship, he’s not just funding education – he’s passing on the valuable lessons that shaped his own success, ensuring that the next generation of student athletes has the support they need to excel in all aspects of their lives.  ■