Darin Hager | Heyday Footwear

Darin Hager is the founder and Chief Everything Officer at Heyday Footwear, a unique and stylish footwear brand that’s been the darling of hip hop artists and bodybuilders alike.

Initially a wholesaler, Heyday Footwear shifted gears entirely and is now a direct-to-consumer brand on Shopify, with tens of thousands of raving fans all around the world. Heyday Footwear products have appeared on shows such as MTV Unplugged, So You Think You Can Dance, True Blood, and America’s Got Talent. The shoes have also graced the feet of mega-celebrities like Flo Rida, Trey Songz, Jay Sean and many more.

The story of Heyday Footwear is filled with valuable insights on audience targeting, wholesale versus retail, and the value of having an incredible passion for your products.

For the Love of Shoes

Darin graduated from Boston's Wentworth Institute of Technology in 1995 with a degree in industrial design. That’s when he started gaining real-world experience through their co-op program, initially as a product model maker. But after nearly cutting his thumb off on a table saw, he wanted a change.

After a brief stint in toy design at a division of Marvel Comics, which Darin more or less hated, he made his way into footwear design, which is apparently a very common transition.

"Toy design, footwear design, and car design," says Darin, "are three disciplines that, once you get into them, it's really hard to leave and go in a more general direction. Because you've got people, who can let's say draw vehicles. Drawing and conceptually coming up with shoes? There's a similarity there."

Darin started working as a corporate footwear designer with brands including Hi-Tec Sports, Puma, and Sperry Top-Sider, all the while honing his eye for design and building a name for himself. But after ten years in corporate design, Darin was tired of the grind. He decided to go out on his own.

Darin began consulting with prominent brands instead of working directly for them, including work with Daymond John from Shark Tank. But he didn't limit himself to top sneaker brands. Darin also designed tactical boots for the US military and law enforcement.

Finally, in 2007, with a little push from a friend, Darin decided to start his own footwear brand, and Heyday Footwear was born.

What's clear from Darin's journey is that he comes into the entrepreneurial world with a metric ton of experience and passion for what he does, and has thrived in large part because of them. That's a lesson I think we can all get behind.

Good God, Wholesale Sucks!

As I mentioned at the outset, Heyday Footwear didn’t start with an e-commerce business model. For years, the brand operated solely as a wholesaler. While small at first, Heyday Footwear worked its way up through the wholesaler ranks, eventually selling through major retail chains like Bloomingdales, Finishline, Asos, and Revolve.

Business was good, but Darin wasn’t in control.

“I was really leaving my future in the hands of five or ten people; the buyers,” Darin told me. “The buyer from Bloomingdale's would say something like, ‘I just looked at the whole line you presented, but I really want you to take a bit of this, a bit of that, and put them together, and then change this. Oh, and here's an order for a thousand pairs.’”

And what do you do when somebody from Bloomingdale’s offers to buy 1,000 pairs of shoes from you? “I was like, ‘okay, fine,’” says Darin. “Damn, I'm Bloomingdale’s now. Give me the money.’”

Those are some sweet looking kicks. Why would you want to change perfection?

This put Darin in a difficult position. The buyers thought they knew better than him when it came to trends and style, but they didn’t. More often than not, the buyers were wrong. And when the buyer was wrong, Darin was the one that they blamed.

“So then something doesn't sell,” Darin lamented. “And I'm like, wow, they really made the wrong choice. They should have picked this product instead of making their own, you know, and frankensteining it from a little bit of this one, a little bit of that one. And when they made the wrong choice they never blame themselves for making the wrong choice. They blame the brand.”

What's worse, this was all happening during the down economy after the 2008 financial crisis. And if you thought the problems with large retail brands were terrible, the issues with smaller retailers were a close second.

"All the little independent shoe stores had no credit," Darin told me. "They'd order SKUs at the trade shows, and three months later I'd reach out and say, ‘Okay, your shoes are in. I've got to run the credit card that you gave me, but it's coming back as declined."

“They’d say, ‘Ah, that was my partner's card. He didn't have the authorization to make any buys.’ It didn’t matter what the excuse was. There was always an excuse. They didn’t give a shit. They didn’t care about the brand.’”

Because these were all made-to-order products, Darin was stuck with the inventory and would need to figure out a way to get it off the shelves, one way or another.

But because of the down economy, he couldn't push the product. And even though Darin had a small sales team, the sales people weren't making any money. Eventually, they quit.

Darin continued, “I was like, ‘oh shit, what the hell am I going to do? I have no sales team. I’ve got product. I’ve got wholesalers that are screwing me, but I knew I had customers that loved the shoes. So, I decided to go direct to consumer and whatever wholesale accounts I had, I dropped. I actually walked away from it completely.”

The Challenges of Switching Business Models

But the switch from wholesale to selling direct-to-consumer wasn't without its challenges.

“In wholesale, you can get much bigger volume,” Darin said, “because you have a store or a chain of stores buying, you know, buying a lot of product versus in ecom you're generally selling one pair, two pairs, three pairs, but not fifty pairs. Not a hundred pairs. Not a thousand pairs.”

The shift into direct-to-consumer resulted in an immediate drop in revenue for Heyday Footwear, but the sacrifice was temporary and would ultimately give Darin a bigger slice of the pie.

“There was also an increase in margin,” Darin said, “because when you're selling wholesale, generally the pricing is called keystone, which is doubling it. So I'm buying it for maybe double what it costs the factory. I'm selling it to a wholesaler who's buying it for double what I pay and then they're selling it for double what they pay. So who's making the most money in that equation? The retailer.”

And now Darin is the brand and the retailer, which means he has control, but he also makes the most money in the equation.

Online Retail Before Shopify

When Darin was in the process of phasing out his wholesale clients, Heyday Footwear only had an informational website, which obviously needed to change.

Luckily, the web designer who'd made several versions of Heyday Footwear's site already had since moved out to San Diego to start his own agency. And they'd recently developed an online shopping cart product. Darin became their first customer.

“I was the first store on it,” Darin told me, “so I had lots of attention from them as they were figuring everything out. And then a year or two went by and, you know, they were adding more and more stores and my special status as the guinea pig store started to disappear.”

Darin admits that he was a bit of a demanding customer. After all, this shopping cart platform was a far cry from the ease of Shopify.

“If I wanted to change a photo or text, add a product, or do anything at all, I had to email them and ask them to do it,” said Darin. “And I'm sure they probably got tired of doing it.”

But as fate would have it, in August of 2016, Darin heard about something new. “I think it was actually on Kurt's podcast, The Unofficial Shopify Podcast. One of my competitors of sorts was talking about how they were on Shopify. I went and checked out the site, and I built out my store in two hours. That day I called up the agency, and I was like, ‘Hey, I'm done. I'm leaving.' I'm sure they had a celebration."

Darin has never regretted that day. “I've been on Shopify since August 1st of 2016, and every year business has gone up. We were up 23% top line from 2017 to 2018. And, uh, you know, things are going well.”

Heyday Footwear’s Rise to Prominence

“Initially we were a streetwear brand,” Darin told me, “Which is, I don't even know how you would really describe streetwear. Streetwear could be anything at this point. If Hypebeast says it's cool, it's cool. Even if it's a Supreme branded toilet paper roll holder.”

That made me laugh because I know exactly what he's talking about. A brand gets hot and gets a bunch of press to the point where it can sell almost anything, and people will buy it. Think about Elon Musk's Boring Company hat or the later-developed "flamethrower." Both are overhyped, overpriced, and the only reason people bought them was that Elon Musk was selling them. And yet the "flamethrower" sold out in less four days.

“It’s very flash in the pan,” says Darin. “And those Hypebeast kids, maybe they have loyalty to certain brands, but I think they’re really just loyal to what Hypebeast and those other streetwear-influenced sites say is cool.”

Regardless, following on from the hype, Heyday Footwear wound up going from something that the cool kids were wearing to getting in big with prominent stylists and celebrities.

Heyday Footwear's Red Mission Trainers – August 2018

"Other stylists started picking up the shoes," Darin told me. "And I started moving up the ladder as far as what stylists I was working with. I got shoes on an R&B singer named Trey Songz who had a show on MTV about his tour, and he was wearing the shoes all throughout that season. Then I got shoes on So You Think You Can Dance and I worked with them for five seasons. I got shoes on True Blood, on America's Got Talent. I met with Justin Bieber's costume designer outside of the Boston Garden at his tour bus because they wanted to see the shoes. And Katy Perry for a world tour. I had shoes on Flo Rida for an album cover and a couple of the videos. And it just sort of steamrolled. More and more celebrities were wearing the shoes.”

The crazy part about Darin’s roster of celebrities and hit TV shows is that he struggles to name them all. In short, the who’s who love Heyday Footwear gear.

Selling to the Wrong Audience

However, things weren’t perfect. While Darin was, and still is, a bona fide hustler who has put in more than his fair share of effort to make Heyday Footwear into what it is today, sometimes that hard work can be misdirected. For example, it took years for Darin to realize that he was focusing on the wrong audience.

As Heyday Footwear became ever more popular, one of the most significant followings was in the hip hop & dance community. Dancers from shows like So You Think You Can Dance loved the product, so the shoes were displayed in front of millions of viewers during the show’s season. And when the show wasn’t running, these dancers taught choreography classes all around the country, mostly to teen girls who loved the show.

Darin, sensing an opportunity, did what any entrepreneur would do. “I'd set up a booth at these classes and, you know, I’d kill it. There was the choreographer from the show who wore my shoes on the show, and then he's wearing the shoes leading a thousand kids in a hotel ballroom.”

So, mostly by accident, teen girls became one of Darin's biggest audiences. But there's a problem with that, of course, which is that teen girls don't have any money. They were reliant on their parents to buy Darin's shoes.

"I had the moms and dads at the classes who would buy the shoes," says Darin, "but the rest of the year when I wasn't doing those tours, there wasn't as much business. It was sort of a seasonal business almost. You know, when So You Think You Can Dance was on, and the dancers were using my shoes, there was business. When I was out for a couple of months, you know, doing different cities and doing these tours, there was business. But otherwise, it would slow down. And it just sort of dawned on me that there's just not enough teenage girls with money that can buy the shoes themselves."

But one day, while perusing Instagram, Darin noticed a popular bodybuilder wearing the shoes. “I reached out to him,” Darin said, “gave him some shoes, and he would wear them and do videos. And then I started finding more people in fitness wearing them.”

At that point, Darin had a breakthrough.

The Perfect Fit

"I thought, you know, fitness is really getting to be a big market," Darin told me. "You had Fitbit, you had Apple watch, you had organic food and Whole Foods, and there was just a whole athleisure clothing thing going on. Yoga pants, Lululemon. There was just this whole perfect storm of fitness and healthy living stuff that was happening around 2014–2015. I just got into it at the right time."

Almost overnight, Darin refocused all his efforts toward targeting bodybuilders and people in the fitness market. But the product? It stayed the same.

“I didn’t change the shoes at all,” says Darin. “They were exactly what bodybuilders needed. Flat soles, high tops, interesting designs, interchangeable components, lightweight, sturdy, versatile and they didn't look like gym shoes because they weren't gym shoes. They were streetwear shoes and hip hop shoes, and they just happened to be perfect. I inadvertently had a performance shoe that if you wore them out of the gym, it didn't look like you just came from the gym. You could throw on some selvage denim and a shirt and pair my anaconda high tops. Go out to dinner, go to the club. Nobody would know you just left the gym and everybody would be staring at your kicks because they were so unique looking.”

@jay_dog_5percenter looking #gainful in @heydayfootwear Desert Sand Tactical Trainers

And that’s the best part of this story. He changed the audience, not the product.

While Darin is undoubtedly on the lookout for trends in design, he remains committed to making products he loves and wants to use himself, not in chasing the next hot fad. It's this dedication to the craft that created the #MyHeyday Black Tactical Trainer 2.0  and the Monster Anaconda Super Shift High Top Sneakers and made Heyday Footwear gear some of the most eye-catching and fashionable shoes on the market for hip hop artists, fitness junkies and bodybuilders alike.

Putting Your Money Where Your Mouth Is

But Darin’s commitment doesn’t stop there. Last year, in an effort to connect more deeply with his customers, Darin undertook his own fitness journey.

“I would do fitness expos,” Darin told me, “and I’d have a big booth. And my customers are all there, all these huge bodybuilders who are totally shredded. And here I was selling performance product for them, except I just looked like a regular person. Not fit at all. And at one point I was actually embarrassed. Like, ‘I don't look like my customers.’ One day, I decided that I needed to look like my customers.”

Darin started on the keto diet, a high-fat, moderate-protein, low-carbohydrate diet. Within a couple of months, Darin noticed a considerable difference. He also began working with a bodybuilding coach who was familiar with the ketogenic diet. And now, the results speak for themselves.

"I always had friends and other models modeling for the brand because I couldn't," Darin said. "No one wanted to see a picture of me. Well, now I'm all over the website. That was a personal goal of mine. I'm 47 years old, and I have a six-pack. I've never looked like this in my whole life. And you know what? Most of my customers are going through a fitness journey or transformation themselves, so I can take part in their journey with them."

Not only is that an incredible personal achievement on Darin's part, but it's also a fantastic way for him to show customers his commitment to their lifestyle. It's an undertaking that's only fueled the intense loyalty that Darin's customers have for Heyday Footwear.


And that's only the half of it. My interview with Darin was filled with so many interesting stories and unique insights that there was just too much to contain in a single article.

In the second half, we’ll share all of Darin’s tactical advice for online entrepreneurs, including Darin’s philosophy on reselling, why special customer service touches matter, and the one thing he would do differently if he had a time machine.

Ryan Chatterton

Judge.me Editor, Content Strategist, Digital Nomad, Coworking Influencer, Lover of Wine & Tacos