Oct 16, 2023 · 1h 3m · how-i-built-this
Herschel Supply Co.: Jamie and Lyndon Cormack
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of How I Built This, Canadian brothers Jamie and Lyndon Cormack share how they combined action sports sales experience with nostalgic heritage branding to transform Herschel Supply Co. into a globally recognized backpack and lifestyle brand.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 38.9% of the talking time here. How this is scored →
Guy as informed peer 1.9 Guest teaching 2.1 Guest disagreement 0.3 Guy pushing back 0.3
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:26 Lyndon rejects Jamie's claim that magazine failed
Lyndon openly interrupts and contradicts Jamie's assessment that Sequence magazine had no traction, insisting it was an admired and meaningful creative achievement.
Hardest push from Guy ▶ 48:55 Guy presses on simulated heritage positioningGuy compares Herschel to Mickey Drexler's resurrection of Madewell, pressing whether the founders intentionally positioned a new company to look like a vintage century-old entity.
Biggest teaching moment ▶ 25:48 Lyndon explains sneaker segmentation strategyLyndon explains to Guy how the legacy backpack sector was stuck in boring stationery store aisles, whereas Herschel adopted footwear-style tiered drops and cultural hype.
Guy holds their own ▶ 48:55 Guy cites Mickey Drexler's Madewell playbookGuy displays deep retail apparel knowledge by referencing his interview with Mickey Drexler and the strategy of reviving defunct trademarks to establish instant brand authority.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Prairie Roots and Childhood Hockey Dreams in Calgary | 1 | 0 | 0 | 0 | Guy Raz sets an easygoing tone exploring the brothers' childhood in Calgary and early hockey aspirations. The Cormack brothers respond collaboratively with nostalgic anecdotes. | |
| Early Post-School Ventures and Sequence Magazine | 2 | 1 | 2 | 0 | Guy asks whether Jamie's early skate and snowboard publication Sequence gained traction. Lyndon playfully counters Jamie's self-deprecating claim that it had zero traction. | |
| Action Sports Sales and Brainstorming the Backpack Concept | 2 | 3 | 0 | 0 | Guy inquires about the genesis of the backpack concept while both brothers worked in sales. Jamie articulates the market gap for minimalist, purposeful everyday bags. | |
| Defining the Product Niche and Maintaining Day Jobs | 2 | 2 | 0 | 0 | Guy probes how the brothers balanced their full-time corporate jobs at Vans and K2 while ideating the company. Lyndon explains treating their day jobs as risk insurance. | |
| Crafting the Herschel Brand Identity and Nostalgic Narrative | 3 | 3 | 0 | 1 | Guy asks whether they intentionally crafted a heritage narrative before the physical product. Jamie and Lyndon describe constructing the brand ethos around nostalgic utility. | |
| Mid-Roll Teaser: Developing the Perfect Backpack | 0 | 0 | 0 | 0 | Mid-roll break containing episode teasing and sponsor advertisements with no host-guest interaction. | |
| Sneaker Industry Strategies and Bag Deconstruction | 3 | 4 | 1 | 1 | Lyndon rejects the notion of the backpack as a passing trend and details how they borrowed tiered releases and hype mechanics from sneaker culture. | |
| Cold Contacting Overseas Factories and Meeting a Manufacturer | 1 | 3 | 0 | 0 | Guy tracks how the brothers cold-emailed overseas manufacturers with a crude PDF. Lyndon describes landing an initial meeting in Vancouver with a Chinese factory owner. | |
| Bootstrapping and Family Investment from JP Morgan Brother | 2 | 3 | 0 | 1 | Guy drills into their startup financing and how their commodities trader brother stepped in with initial capital, leading up to Jamie's hands-on prototyping trip to China. | |
| Agenda Trade Show Debut and GQ Feature Breakthrough | 2 | 2 | 0 | 0 | The brothers recount improvising their booth out of discarded wooden pallets at the Agenda trade show and securing an unexpected feature in GQ's gift guide. | |
| Pitching Nordstrom with a Shiner and the 7,000-Unit Gamble | 2 | 2 | 0 | 0 | Lyndon humorously narrates pitching Nordstrom with a hockey black eye, followed by Jamie discussing the anxiety of placing a 7,000-unit opening production order. | |
| Mid-Roll Teaser: Major Endorsements and Scaling Up | 0 | 0 | 0 | 0 | Mid-roll commercial segment and podcast promotional material. | |
| Urban Outfitters Success and Building the First Team | 2 | 2 | 0 | 0 | Guy questions their reliance on retailers rather than active advertising. Lyndon details their rapid 26% weekly sell-through rate at Urban Outfitters. | |
| Year-Round Seasonality, Quitting Day Jobs, and Global Expansion | 4 | 2 | 1 | 2 | Guy cites Mickey Drexler and Madewell to press whether Herschel deliberately marketed itself as an old brand. Lyndon clarifies they intended familiarity without deceptive claims. | |
| Rapid Scale, Continuous Profitability, and the Oprah Mishap | 2 | 3 | 0 | 0 | Lyndon emphasizes that Herschel remained profitable since 2011 despite extreme growth, and Jamie shares a missed e-commerce opportunity after being picked for Oprah's Favorite Things. | |
| Navigating the COVID-19 Crisis and the Sustainability Pivot | 2 | 3 | 1 | 0 | Guy asks if the pandemic benefited their brand. Lyndon quickly clarifies COVID was disastrous for travel and school products, while Jamie outlines their pivot to 95% sustainable materials. | |
| Post-Pandemic Rebound and Reflections on Timing and Momentum | 2 | 2 | 0 | 0 | Guy closes with his standard luck versus hard work question. Jamie and Lyndon explain how hard work converts fortuitous timing into lasting business momentum. |
Statements from this episode (17)
Pre-Herschel bags were too busy and lacked a generational brand
“So, for us, when we looked at bags in general, I think it was the one category that probably our generation didn't have. One that we could call our own. It seemed like there was the right denim, the right footwear, the right eyewear, the right watches. Bags ju…”
Vans sales contacts became Herschel's initial retail accounts
“Conveniently enough especially with how a brand like Vans bridged itself from action sports to fashion, we were already going to places and selling to stores that would ultimately end up being some of our first accounts.”
The pre-2009 bag market was a race to the bottom
“There wasn't a bag company that had a heartbeat. It was more of a race to the bottom than a race to a story”
Backpacks accrue higher sentimental value than footwear or apparel
“The value at point of purchase is so much less
Then the sentimental value they have once they own it.
And it's different than so many other industries that I've looked at more than footwear or denim or, you know, any other purchase.
Once they own a backpack, b…”
Herschel operated like a sneaker brand rather than a bag company
“In the early days, we act like, more like a sneaker company than we did a bag company, because that's more what we were into. And we weren't into how bag companies, especially in our price category, were acting. And I think that was an important distinction.”
Herschel's founders launched the brand with no manufacturing knowledge
“The biggest weakness here, guys, is that we didn't know how to manufacture. We could see it. We could see it on the wall. We could see the lookbooks. We could see how we wanted to story. We could see and feel and hear what this brand even, like, we knew exactl…”
Founders cold-emailed hundreds of bag factories found via Google
“We literally turned to Google and started to Google things like how to make backpacks, how to start a backpack factory, where to make backpacks, and we took our little PDF on the same email, and we sent it to, like, hundreds of email addresses we found in comp…”
Initial factory samples had quality stitching but failed the aesthetic vision
“Shapes were off guy, measurements were wrong, details weren't there. The bags were stitched properly, the quality was there, but the shape, the feeling, the drape, the total aesthetic we were going for wasn't even close so.”
Herschel was featured on the cover of the GQ gift guide
“GQ the next day requested one of our bags to be shot in their studio, and we ended up on their, the front cover of the GQ gift guide for that year”
Herschel took risk ordering 7,000 units against just 4,000 wholesale orders
“I mean, we had collected orders of about 4000 pieces, and I think the minimum order after talking to our facility in Asia was 7000 is what they wanted us to order to be able to produce every single SKU, and those are some big conversations for us.”
Multi-brand retailers validate new brands to consumers
“Their job as retailers and as merchants is to curate offerings. So if you're sitting next to other awesome brands, they're telling the end consumer that this brand is cool too.”
Herschel sold 7,000 to 8,000 bags in its first year
“It was between the seven and 8000 units that we sold”
Herschel expanded to five countries globally by its second year
“Year two and three, we were in five countries around the globe, not just in North America.”
Herschel Supply Co. has been consistently profitable since 2011
“Year one didn't turn a profit, albeit it was a very small year, but since 2011 and on, we, we've always been profitable.”
COVID-19 lockdowns severely harmed Herschel's commute-dependent business
“COVID was not good for Herschel at all. The majority of the products we make are people going to school, people going to work, people going to the gym, people going to festivals, people going on trips and, you know, it really set us back. To be honest, it was …”
Herschel pivoted to 95 percent sustainable materials during the COVID pandemic
“We switched over a 95% of our fabrics and materials to be from a sustainable fabric. That's a big, big decision as a brand that is selling millions and millions of pieces a year to go and do that, and to have the team that has to touch every single department …”
Hybrid work environments directly benefit Herschel's bag business
“The hybrid work environment now that most people are in, it's pretty good for Herschel too, because you're taking your laptop with you from your work to your home, from your home back to work, so you need a bag or something to carry your stuff.”