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Timothy Boyle
Chairman, Chief Executive Officer & President, COLUMBIA SPORTSWEAR CO

How Columbia Sportswear Stands Out in a Crowded Market | Problem Solvers

📅 Jun 22, 2026 Entrepreneur Podcasts 23 MIN 23 VIEWS 54 SEGMENTS · 2 SPEAKERS
A viral ad from Columbia Sportswear caught Jason's eye. After he wrote about it on LinkedIn, the company reached out. So Jason sat down with Tim Boyle, CEO and third-generation owner of Columbia Sportswear, to find out where the idea came from and what it reveals about how to reposition a legacy brand. The outdoor apparel industry had gotten serious and self-important. Columbia decided it was time to bring back fun. Hosted by Jason Feifer Subscribe to Entrepreneur Daily https://info.entrepreneur.com/daily-n... Subscribe to E+ https://info.entrepreneur.com/subscri... Talk to Jason at his In...

What Timothy Boyle said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Timothy Boyle, CEO of Columbia Sportswear, discussed the company's shift toward humor-driven marketing to stand out in a crowded market. He explained that over 40% of sales are outside the US and that in China alone, they face about 700 competitors, so differentiation is key. Boyle traced the brand's humorous roots to the 1970s campaigns featuring his mother testing products on him, and noted that after her passing, the company moved away from that tone. He credited his son's global agency search, which led to A&E in London, for reviving the approach, including the viral Flat Earth challenge. Boyle emphasized the importance of asking retailers and consumers for feedback, using prototype testing and direct questions. He also discussed other stunts like 'Nature Calls' bear scat beer, and said the business has improved, though he couldn't directly link it to the campaigns.

Key takeaways

  1. Over 40% of Columbia's sales are outside the US, with about 700 competitors in China alone.
  2. The Flat Earth challenge was part of a broader strategy to reposition the brand around joy and fun, reviving 1970s humor.
  3. Boyle approved the Flat Earth idea immediately, and it still receives daily entries, showing ongoing engagement.
  4. The campaign was shortlisted for a major award at Cannes, indicating industry recognition.
  5. Boyle advises that being different is essential, and self-examination over self-defense helps in accepting criticism.

Numbers and commitments

FigureWhat it refers toTypeAt
40% Share of Columbia's sales outside the US metric 3:27
700 Number of competitors in China metric 3:27
1938 Year Columbia was founded timeline 3:27

Chapters

  1. 0:00Flat Earth challenge origin
  2. 3:27Differentiation in crowded market
  3. 5:02Reviving brand humor
  4. 10:56Learning from retail partners
  5. 16:24Evaluating risky ideas
  6. 17:52Measuring campaign success
  7. 19:43Top-of-funnel marketing value
  8. 22:24Advice on brand voice

Questions asked in this interview

12
  1. 0:30As it turns out, this company was looking for a repositioning in the marketplace addressing a question of sales and how do we get sales up?
  2. 4:45And how old were you at the time?
  3. 6:29And so how do you think about how you exist in that crowded ecosystem?
  4. 10:37And then number two, what kind of things were you hearing that made you think we've got to start thinking differently?
  5. 14:00So, did you hear this idea and say, 'Oh, yeah, that's great.' or did you hear this idea and say, 'Absolutely not.' and somebody had to convince you?
  6. 16:13How what's your method of evaluating whether or not a risky idea is worth doing?
  7. 17:05Did you hear from a lot of people?
  8. 17:49How do you measure success for an idea like this?
  9. 18:18Like yeah that's a funny idea but did it sell product?
  10. 19:29I mean, if you put out that flat-earth thing and it got everybody talking and there was absolutely no way of knowing whether or not it moved a single unit. Is that still a success?
  11. 20:10And so, it sounds like you're thinking about that in the same way. Is that right?
  12. 21:32And what do you advise others to think about?
Timothy Boyle 0:00 ↗
I'm Tim Boyle, I'm the CEO here at Columbia Sportswear. And this message is for flat-earthers. You guys claim there's an end to the earth? Well, just go snap a picture. Send it to us and you get the assets of the company. We had to think about a different way to talk about the company and we sort of allowed ourselves to be lulled into the hey, everybody talks about the outdoor products like this. Beautiful nature, things are wonderful, never yeah. So, how do we differentiate ourselves?
Jason Feifer 0:30 ↗
Running a business means solving problems. I tell you how the smartest entrepreneurs do it. Hi, I'm Jason Feifer, editor-in-chief of Entrepreneur Magazine and this is Problem Solvers. I was just flipping around on YouTube or whatever as you do and I came across this video that stopped me cold cuz it was just so fun and unusual. It was the CEO of a company that you've probably worn the clothing of or at least certainly seen others wear the clothing of. Columbia Sportswear company. CEO Tim Boyle is standing there at his desk and he says essentially, 'Hey, flat-earthers. If you can prove that the earth is flat, like if you can actually get to the end of it and send us a video of a cascading nothingness off of the edge of the earth, then I'll give you the whole company. I'll give you everything.' And then he basically just goes walking around the company showing all the things that he would give. And this thing had gone viral and it was so fun and seemed to just capture the joy of the outdoors that I got to wondering, where did this come from? Why did they do this? And so I just started googling around and I found some answers. As it turns out, this company was looking for a repositioning in the marketplace addressing a question of sales and how do we get sales up? And had recognized that the outdoors industry, the outdoors sports wear industry had just become really self-serious. Not something I had thought much about, but as soon as I read it, I thought, well, yeah, that's true. It is all about the beauty of nature or the serenity of this or whatever, but there wasn't a lot of joy and fun and Columbia had recognized that there was an opportunity to position in joy and fun. To capture that thing that of course is also the reason that people go out into nature. And this was the flat-earthers thing just part of a longer and larger campaign to do just that. So anyway, I wrote about this on LinkedIn cuz I loved it so much. And then I heard from someone at Columbia who said, 'Hey, do you want to talk to Tim Boyle about this?' And I said, 'Yes, of course I do.' And so today, I am delighted that I've got CEO and Chairman Tim Boyle of Columbia Sportswear Company to talk to me about where this came from and how to think about repositioning an old brand in a new era. Tim Boyle, welcome to Problem Solvers.
Timothy Boyle 3:06 ↗
Thank you very much. It's thrilling to be here with you, Jason. Appreciate it.
Jason Feifer 3:09 ↗
It's a thrill to have you here. So, okay, Tim, you heard my setup here.
Timothy Boyle 3:13 ↗
Yep.
Jason Feifer 3:13 ↗
Take me into the thinking and maybe let's start by acknowledging that humor is not new to this brand, but humor was not a part of the brand more recently.
Timothy Boyle 3:27 ↗
That's true. So, the overriding premise is, and we talk about this all the time in the company because we're a global company. Over 40% of our sales are outside the US, so we know how to make stuff and we distribute it all over the world, but nobody needs another brand of apparel and footwear. There are zillions. In fact, our business in China, our management there tells us we have about 700 competitors in China. So, no again, there's plenty of places. So, it's all about being different and differentiating yourself. So, if we go back to the real founding of the company, which was, you know, we were founded in 1938 by my mother's parents. But, in any event, we ended up really starting a large business in the '70s. And that was based on an advertising campaign which the basic premise was my mom, who was the president of the company, putting me through all sorts of tests. And those tests included her being relatively mean to me to make me go do all sorts of stuff outside to prove that the garments worked well.
Jason Feifer 4:45 ↗
And how old were you at the time?
Timothy Boyle 4:47 ↗
Oh, I'm in my late '70s now, so when I was in my late '30s, early '40s then.
Jason Feifer 4:55 ↗
Okay. So, you've got mom ordering you around basically as a way of stress testing the clothing that you're wearing.
Timothy Boyle 5:01 ↗
Yes.
Jason Feifer 5:01 ↗
Yeah.
Timothy Boyle 5:02 ↗
And humorous. I was on top of a car that went through a car wash. She drove over me with a Zamboni. Threw me off a cliff. Left me on the top of a mountain. I mean, there's just anyway, it was a lot of fun. But, you know, when my mom passed, we had to think about a different way to talk about the company and we sort of allowed ourselves to be lulled into the hey, everybody talks about the outdoor products like this. Beautiful nature, things are wonderful, never yeah. So how do we differentiate ourselves? And that's when my son did a global search for a new advertising agency and he found these people in London called A&E. And they really understood, 'Hey, we know what the nature of the company was initially. Let's go back to those kind of roots doing tests of all different kinds. And by the way, it's not about marketing with television commercials anymore. It's really about getting noticed online.' So, that was the premise. And actually their offices in London are very close to the Flat Earth Society's headquarters.
Jason Feifer 6:20 ↗
I didn't know there was a Flat Earth Society.
Timothy Boyle 6:22 ↗
Yeah, there is. So, one of the guys thought, 'Hey, let's do a challenge.' So, there you are. That's how it happened.
Jason Feifer 6:29 ↗
That's how it began. I love that. Okay, there are two things that I really want to pick up on of what you just said. Number one was about positioning in a crowded marketplace. And I want to share something that was said to me a while ago that's always stuck with me and get your reaction to it. And the number two is let's talk about how to recognize white space in the world of ideas, right? It's to recognize that everyone has zigged and so it's time to zag. So, to start, you had said in China alone you've got 700 or so competitors. And what that reminded me of was a conversation that I had had a while ago with someone also in the sportswear industry, so to speak, which was the president of Reebok. And he had told me that he always tells his team that you can't compete on quality anymore. Because at this point, manufacturing is so good that it's very easy to produce quality. Everybody's quality in some way or another. And so, if you are, and this was his example, he said, 'Let's say that you create a new scissors company. You cannot market yourself as having the sharpest pair of scissors because everybody has the sharpest pair of scissors. And so, it's got to be about something else. It's got to be about the story that you tell and the way that you identify with people.' And I'd love for you to react to that and maybe think about that thinking in the world of your own business. You make quality products, but you must be aware that you are not the only ones in the world making quality products. And so how do you think about how you exist in that crowded ecosystem?
Timothy Boyle 8:02 ↗
We think we have a very high quality system to produce garments and deliver them on time to retailers and consumers. And we do that, but that's not enough. You have to have an emotional connection, and you have to hopefully, you know, at the end of the day, the outdoors is about having fun and not necessarily about death-defying activities at all times. This is about a fun environment and let's have some fun with it. And so that was the origin of the process and marketing. And so we're just continuing that and we've done other stunts, some of which have not gotten the kind of uptake that the flat earth challenge did, but yeah, we're doing more of those things.
Jason Feifer 8:50 ↗
Yeah. And then let's think about that white space of ideas and maybe your advice to other founders or CEOs on how to recognize it. And this is not of course just the outdoor apparel industry. This is every industry. Every industry does this. And that can be frustrating until you realize of course that it creates a massive opportunity where once everybody has gone to one side of the room, you can go to the other side of the room. I would love to hear you talk about how to recognize that and maybe how you've done that throughout your career.
Timothy Boyle 9:26 ↗
Yeah, you know, for the outdoor industry typically the origins were, you know, this person wore this garment to Everest. And if he can climb Everest, I can wear this when I go pick up my newspaper in front of my front door, which by the way never happens anymore, right? So, we spend a lot of time talking to retail customers. When I say retail, I'm talking about people who own retail stores. What is it about our products which are different? And so, we try in the product development process and design process to provide garments that are high performance, but different. And we oftentimes are different by color, fabric, pricing sometimes. Just all different. But at the end of the day, when you talk about branding, that's when you can call into question the kinds of activities that we've been doing with the Flat Earth challenge and others. So, you really end up learning this by asking people their opinions and being open to criticism and advice.
Jason Feifer 10:37 ↗
If you could break that down for me, that would actually be really interesting. So, number one is what kind of questions are you asking? Like what's a good strategy for drawing out useful information from your retail partners? And then number two, what kind of things were you hearing that made you think we've got to start thinking differently?
Timothy Boyle 10:56 ↗
Well, it is about asking. So, we would and still do frequently take prototype garments in advance of a season and show them to retail buyers, and they're more than happy to tell you whether or not you're on the right track or you're off track or whatever. And they'll tell you, you know, what price you need to be at with your products and what people think about your brand. So, all that stuff is knowable if you're willing to go just ask people, and they're more than happy to give you advice. And so, you can't rely on one or two people, but we found that over time individuals who maybe run a small retail store, somebody who's doing the buying themselves, and they're observing what's happening on the floor, they can tell you, 'Hey, I just saw five people walk up to that garment because of its color, and three of them bought it, but two didn't like it, you know, whatever. You can find out a lot about that kind of activity.'
Jason Feifer 12:00 ↗
Yeah. If you just listen and accept criticism.
Timothy Boyle 12:03 ↗
Mhm. Mhm. I, you know, it's funny I often give people this advice when talking about consumer research, which is it's so valuable to ask someone either a customer of yours who maybe isn't buying more or isn't recommending you to others, or someone who isn't buying at all, you know, some version of, 'Hey, if you didn't buy this, what would be the reason? If you didn't recommend us to other people, what would be the reason?' You know, you could go over to somebody who's wearing Columbia Sportswear and say, 'Hey, if you didn't tell your friends to buy Columbia, what would be the reason for that?' And the reason I like that question, I'm just curious for your thoughts or if you've done something similar, is because it's hard to ask people, 'Hey, what don't you like about something?' It's almost too broad, they don't know what to say, but if you put it in the framing of, 'Why are you not making a specific decision?' they suddenly might think, 'Well, why wouldn't I recommend it? Because of the price.' Or, 'I wouldn't recommend it because I had this experience once and it didn't quite do what I want.' Or whatever it is. I wonder what you've learned over the course of running Columbia about how to really get inside the mind of the person you're selling to, whether that's the retailer or the consumer.
Yeah, I mean, we do a lot of it and actually there's nothing like going and physically doing it. I mean we're doing a podcast now and we're talking digitally which is great, but there's nothing like being in the same room and touching the products. This is the tactile stuff that we talk about all the time. We don't sell digital stuff. We sell real stuff that people put on and have to like the way it makes them look and how it feels. It's a tactile business.
Jason Feifer 14:00 ↗
Okay, so Tim, this advertising agency, I presume, brings you the idea of the flat Earth thing. It's a bold idea. It is bold in a number of different ways. Number one, it is a change in tone from how the company had been talking more recently. Number two, you're at the center of it. And number three is it's touching a cultural issue and even though I think the vast majority of people on this round Earth understand that it's round, there are still plenty of very vocal and can be angry people who think otherwise. So, did you hear this idea and say, 'Oh, yeah, that's great.' or did you hear this idea and say, 'Absolutely not.' and somebody had to convince you?
Timothy Boyle 14:43 ↗
No, no, I said absolutely yes.
Jason Feifer 14:46 ↗
Huh.

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APA

Boyle, T. (2026, June 22). How Columbia Sportswear Stands Out in a Crowded Market | Problem Solvers [Interview transcript]. Entrepreneur Podcasts. CEOInterviews.AI. https://ceointerviews.ai/interview/1037522/

MLA

Timothy Boyle. "How Columbia Sportswear Stands Out in a Crowded Market | Problem Solvers." Entrepreneur Podcasts, 22 Jun. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/1037522/.

BibTeX
@misc{boyle2026_1037522,
  author       = {Timothy Boyle},
  title        = {How Columbia Sportswear Stands Out in a Crowded Market | Problem Solvers},
  howpublished = {Interview transcript, Entrepreneur Podcasts. CEOInterviews.AI},
  year         = {2026},
  month        = {jun},
  url          = {https://ceointerviews.ai/interview/1037522/},
  note         = {Speaker-attributed transcript with timestamps}
}