The journey to become one of Canada’s most successful business executives and entrepreneurs wasn’t an easy one for Drew Green considering his roots in Toronto.
But the current CEO of Indochino always had his passion for sports he could turn to as an escape from the challenges of growing up and later on the lessons he learned from sports helped him navigate the complex business world in achieving success.
“I came from a pretty underprivileged background. My mom and dad divorced. My mom was a teacher but underpaid because she didn’t have her university degree. So we moved 18 times in 18 years,” said Green. “I think I had a good childhood because my mom was amazing but sports for me was an opportunity to be really good at something.
“And what I learned, that’s really applied to my life, was the importance of teamwork, the importance of leadership, the importance of learning how to win. And what I mean by that is practice is important. Not only doing practice but doing extra practice. And also how to deal with losing.
“We took basketball pretty seriously at the high school I was at. We won provincial titles and all kinds of different stuff. It taught you how to win and how to lose. How to set goals at the beginning of a season and then go after it.
“I played every sport. Volleyball I loved. Football. Basketball was my passion. The ability to work hard. That’s something I’ve passed on to my sons . . . I learned how to work hard from different things but sports teaches you you need to work hard to be good.”
Green was born and raised in Scarborough, Ontario, and went to York University. After playing basketball at university as a point and shooting guard, he went overseas to Australia and Singapore.
At university, he took kinesiology courses.
“I thought I wanted to be a chiropractor. Or a doctor of some sort. I took the kinesiology route but my first business kind of mushroomed. It just exploded and I ended up running that for three of my four years at university and then selling it,” said Green.
“It was a personal training company. It was at a time in the mid-90s when personal training was just kind of taking off. I had so many clients. I hired trainers. I built a gym and then I ended up selling it to go overseas to play ball.
“Playing in Australia took me all over Asia. I think 23, 24 countries, which was an amazing journey.”
Years later, he came back to Canada and began his business career.
“For me, I’ve always been a creator. I’ve created businesses from my teenage years through to now in my late 40s. Indochino specifically is kind of an interesting story. I retired at 39 and was thinking of taking a couple of years off. I have two boys. I just built a business and then Amazon came at me and said hey why don’t you come here and run one of our divisions. So they offered me a CEO role there,” said Green.
“And I actually signed it. I signed the agreement. And Tom Stemberg who was chairman of Indochino (at the time) . . . was convincing and said let’s buy the company, structure it in a way that it’s yours and you come in and you build it. Indochino at the time was a regional business . . . It was a big decision. I’ve always really admired Amazon and was really excited about that opportunity but I’m an entrepreneur and a creator. That’s the story.”
He began with Indochino in 2014-2015.
What is it about being an entrepreneur that attracted Green?
“I think the real answer is the independence. The ability to be my own boss in a way. Yes always you’re reporting to boards and shareholders. But in a way you’re responsible to yourself and your team,” he said. “But I really like the idea of like just creating and kind of being my own boss and having unlimited upside, and creating that upside.
“Through my career, I’ve founded over 15 companies and all of which are still around in one form or another. Some are publicly-traded companies now. I kind of consider Indochino not as a startup but as a re-start. We basically changed everything in the company and we launched into retail in 2015-2016 and the rest is history.”
Green is an award-winning Chief Executive Officer, entrepreneur, and expert in starting and managing high-growth companies. A visionary leader, Green has created one of the world’s fastest growing apparel brands. Between 2015-2023, he established over $100 million in strategic capital commitments for Indochino from Madrona Venture Partners, Highland Consumer, Dayang Group, Mitsui & Co. and Postmedia Network and has secured partnerships with hundreds of celebrities and professional athletes, along with MLB, NHL, NBA and NFL teams. Indochino created, launched, and then expanded to +100 showrooms, employing over 1,000 people across North America, with another 3,500 people in China working daily to produce the one-of-a-kind garments each Indochino customer creates.
Previously nominated as top 40 under 40, as well as CEO of the year, Green has been recognized for his accomplishments throughout his career. In 2017 Green was awarded the Lifetime Innovation in Retail award. In 2018 he was awarded Retailer of the Year by Chain Store Age, and in 2018 Green was selected as The Entrepreneur of the Year, by Ernst and Young.
In 2019 Canadian Business announced that between 2015-2019, Indochino was #1 fastest growing Canadian retailer, with sales globally, and 3rd fastest growing retailer in Canada, amongst retailers with revenues over $100 million. Over the past 25 years Drew has sold billions of dollars’ worth of product globally, online and in store, and is recognized as a direct-to-consumer expert.
Prior to Indochino, Green founded and was Chief Executive Officer of Canada’s first multi-merchant marketplace, which is now owned by EMERGE COMMERCE, which he leads as Chairman and major shareholder. Throughout his career, he has held leadership roles at companies that have created billions in shareholder value through leadership roles at FloNetwork (acquired by DoubleClick). DoubleClick (acquired by Google), and SHOP.COM, (acquired by Market America) amongst others.
Over the past 25 years Green has started or invested in over 50 private companies, venture funds and real-estate assets across Canada, all of which (+50) are still held and being built via DREWGREEN.CA INC. Over his career, he has founded and become chairman of over 15 Canadian companies, including five that are currently public on the TSX and or NYSE, raising over a billion dollars as a Founder, CEO and or Chairman. He also serves as a board member at York University, his alma mater, and awards yearly scholarships for York and UBC students.
Green no longer plays basketball but he’s closely associated still to the sport through his boys who play at a high level with Prolific Prep in Napa. One’s a senior and one’s a freshman.
“I kind of have this approach to work life balance which is I’m always working, I’m always on vacation,” he said. “I know that sounds a little weird but it’s worked for 20 years. My days start super early and sometimes finish super early and then work really late. I usually get up around 4:30. My meetings start sometimes as early as 5 a.m.
“I just try to balance everything to make sure I’m the best possible father. I spend a lot of time with my sons. I’m there for them through their journey, through their goals, through their dreams. And then work is busy.
“My hobby is being a father. At this point that’s kind of my number one hobby. I don’t golf. I don’t do anything of that. I work out quite a bit but not basketball related.”
Indochino has 83 showrooms across North America.
“We have a 50 store rollout in 2024 that we’re working on now and we’ll have more details (in the future) and some other opportunities. We think we’re going to launch between five and 17 new showrooms in 2024,” said Green, adding the new showrooms will all be in the U.S. There are currently 13 locations in Canada.
“I’ve got a 50-store test with a major partner that hopefully will launch sometime in the summer. I can’t give it away too much, but it’s a department store that we’re looking at launching an Indochino concept in.”
