Leadership: Shoulder to shoulder, Lyndon and Jamie Cormack lead global phenomenon Herschel Supply

The two brothers guide the business together while giving their team freedom to excel

So, this is where my kids’ backpacks got their start. At Herschel Supply Co. headquarters in East Vancouver’s rough-hewn Railtown neighbourhood, the atmosphere on a sunny August morning is brisk. About 130 of the company’s 170 employees work here, alongside founders Lyndon and Jamie Cormack, who are chatting with staff. The ground floor of the 28,500-square-foot digs is open space, natural light and dark wood, offset by a many-headed chandelier whose tendrils could represent Herschel’s rapid worldwide expansion. The company the Cormacks established in 2009, named after the Saskatchewan town that is their ancestral family home, now sells its retro-inspired, fashion-forward bags, apparel and accessories in 72 countries.

In a few days, Lyndon is heading to Shanghai, where Herschel has one of its four satellite offices. For the business, which manufactures in China, being a hit with style- and budget-conscious young consumers from Tokyo to Paris to New York also means battling a rising tide of Asian-made knockoffs. “We spend out of our ears to protect our brand not only here at home but globally, and the tap’s never going to get turned off,” Lyndon, who would win most staring contests, says from the edge of his seat in the staff lounge. “It’s a constant fight, but we take it extremely seriously.”

He shares that intensity with Jamie, the senior Herschel co-founder by two years, whom I meet in his sparsely decorated office. The Cormack brothers are friendly people who show a genuine interest in others, but they didn’t get where they are by being timid. If Lyndon comes off as a firebrand who can rally the troops, Jamie is a smouldering presence with an edge of his own. On the windowsill behind his desk sits a sculpture of a hand with its middle finger raised. Right now, Jamie is most excited about Herschel’s new travel and rainwear jacket lines. “It’s good and bad,” he says of leading a business with his brother. “It’s good that I know we’re both fighting for the same goal, and that’s for this brand.”

Before Calgary-raised Lyndon and Jamie launched Herschel, they were sales reps for U.S. apparel icon Vans and Seattle-based sporting goods retailer K2 Corp., respectively. Lyndon admits that early on, their parents worried that the siblings would have a falling-out. But they’ve made it work, he says, pointing out that their older brother, Jason, is also involved in the company. “I run the benefit of Jamie being my best friend well before we started the business together, and we’re equal partners, so there’s no hierarchy,” Lyndon notes. “We make decisions together. We’re each other’s best sounding boards. We have disagreements, but they’re short-lived. There’s the beauty that there’s no candy-coating in our conversations, so things can move really quickly.”

Jamie recalls how thrilled they were to start the company. “We saw that there was a hole in the bag market and the accessory market,” he remembers. “But globally, I don’t think we had a clue how big that open market share was.” Back then they were probably closer colleagues, Jamie observes; today, with the business growing so quickly, they try not to step on each other’s toes. He handles design and production, while Lyndon takes care of sales, marketing and other tasks. “Although we talk a lot about it and really get aligned on it, we work less closely,” Jamie says.

Jamie Cormack

How do you spot and encourage talent?
I stopped hiring, other than major hires, I would say three years ago. I let my managers and leaders hire their own teams; I think that’s important. I help, and I will obviously give my opinion, but I want them to hire their own team so that team can feel right to them and it’s going to be their style.

What was your biggest leadership mistake?
In the beginning, it’s hard to let go. I probably didn’t let go early enough. I probably stayed in the trenches a little bit too long, probably became a little bit of a workaholic because of leadership. I think it took me a little while to realize that, “Hey, this is a really talented team that we have out here, and I can let go, and I know they’re going to get the job done.”

JAMIE: What three things would you tell a young person who aspires to become a CEO?

1. Show up properly on the front end of your business and the back end. The front end [is what] people can see; the back end is just as important—the financial side, the operations side, your systems, your policies. If the back end of the business is there, it’s going to help you show up properly on the front end. 

2. Be easy to do business with. If you’re easy to do business with, people want to come back. It seems so simple, but it’s one of the hardest things to do. 

3. Continue to push yourself. I think I learn something new every day I’m here, from everybody, too. If you’re constantly pushing yourself, it keeps that passion going. I think that’s everything, because I love to fight for the brand.

Lyndon, who reckons the Herschel crew would be friends even if they didn’t work together, regards his employees as family, too. With that in mind, the company gathers its local and international staff, along with its distributors, in Vancouver a couple of times a year for product launches. “We’re very transparent, especially within these walls, about how business is going and how we can get better,” he says.

As a leader, Jamie adapts to the situation. For example, he says, he talks differently to a designer than to a product manager. His overall style? “I’m hands-on. I spend probably 10 per cent of my day in my office in front of my computer, and 90 per cent is walking from section to section.” But having made his expectations clear, he lets people own their roles: “I think they have more ownership of the brand because they have that freedom to run their section.”

To that end, Herschel began hiring department leads early on, Lyndon explains. “Rather than allowing people to graduate into a position, we went to the top first and also allowed those people to hire their own teams.” Herschel is a brand that listens—and keeps an open mind about how it can improve, he adds. “We’ve had ridiculous success,” Lyndon says. “And it certainly has not been from a couple guys’ idea. It’s been from a whole bunch of people buying into that we can do this differently and better and smarter.”

Lyndon calls his leadership style inclusive. “We surround ourselves with people who are exceptionally good at their jobs,” he says. “I would describe myself as a proud generalist, somebody who likes to have a light touch on everything but allows the people around me to get the job done and celebrate their own wins.”

He also strives to matter as a leader. His test: if you put the team behind a one-way glass and asked them, would they care if he showed up at work tomorrow? “My goal personally is to make sure I matter to the business,” Lyndon says. “Because if I don’t, then I think should probably just go.”

Jamie, who says his parents gave him a lot of confidence, always knew what his goals were when he launched his first business—a sales agency in 2003—and worked in previous roles. At Herschel, he aims to steer managers in the same direction: “You want to lead with confidence, but more than anything, you want to know what you’re trying to achieve before you get into anything.”

Although Lyndon says he always had a knack for clearly defining that outcome, he used to be more stubborn about how to get there. He now knows there can be many paths to the same result. Something Lyndon isn’t very good at: being comfortable in the face of success. “I find comfort is, as a brand, a sign of weakness, and potentially an opportunity for people to come and smash you over,” he explains. “I like getting on my toes a lot more than I like digging in my heels, and so I think that attitude is probably a little contagious.”

How do you lead a company in an industry where tastes can change overnight? For Jamie, it means striking a balance between the commercial—products that customers keep coming back to—and the progressive. “We’re big on core items here, but [we] also have enough where we’re pushing the market in an exciting way.” To make that happen, Jamie pushes his designers and creatives. “I’m going to call a spade a spade,” he warns. “I’m going to tell you if I think something is terrible, and I’m also going to tell you if something is great.”

If there’s one thing that gets Lyndon excited about the future, it’s Herschel’s continued growth. That expansion doesn’t just equal more revenue to invest in new systems; it also lets him and Jamie hire more collaborators so they can strengthen the brand. “It’s an overused quote around here,” Lyndon says, “but the windshield for us is a hell of a lot bigger than the rear-view mirror.”

Lyndon Cormack

Are you a born leader, or did you learn to lead?
If there’s a whiteboard in front of me, I like to have the pen in my hand, and if there’s a microphone around, I don’t mind it near me. Throughout my life I’ve had a natural gift of the gab, [and] I don’t have a lot of nerves when speaking to people. Whether it’s an individual or a large group, those nerves got shot long ago. And so I think maybe there’s a bit of a natural ability to crowd people together and speak and articulate in a way that others can’t.

What’s a common myth or misconception about leadership?
There’s things about culture and creating culture. I think culture creates itself. If you allow people to be themselves, they’re going to naturally perform better.

LYNDON: What three things would you tell a young person who aspires to become a CEO?

1. Get that title out of your head. Don’t be a title chaser. Earned authority is the most important thing, not title authority or a nameplate.

2. Be inclusive and collaborative, and know that the team is going to help elevate you more than they’re going to help suffocate you. The team’s going to lift you up, not put you down.

3. Make sure you matter. Make sure people care that you’re there.