Hello! Who are you and what business did you start?

I’m Darin Hager and I have been a footwear designer for over two decades with roles as a corporate designer, design consultant, brand owner and entrepreneur. I’ve worked for and with brands large and small including Puma, Sperry Top-Sider, Hi-Tec Sports, Reebok, Etonic, Sebago, CAT, US Army Brand, Blackhawk Tactical Group, Original SWAT, OTB Tactical, Clarks, Dunham, Category 5 Boat Shoes and since 2007, CEO of Heyday Footwear.

My designs (and myself) have been featured, profiled and interviewed hundreds of times in print and digital media including the Shopify Masters podcast, The Business of E-Commerce podcast, The Unofficial Shopify Podcast with Kurt Elster, Maxim Magazine, Playboy and on celebrities including Flo-Rida, Jay Sean, Katy Perry, Trey Songz, NFL Indianapolis Colts Wide Receiver Rob Turbin, UFC legend Tito Ortiz, WWE Hall of Fame Wrestler Billy Gunn, MMA Fighter and actor Martyn Ford, Ms. Olympia Helle Trevino, ID Magazine, The Source, MTV and VH1, Footwear News, Marvel’s Ant-Man, HBO’s True Blood, Fox’s So You Think You Can Dance, Fox’s America’s Got Talent, Hypebeast.com, Freshnessmag.com, The Boston Globe, and HighSnobiety.com. Phew!

What's your backstory and how did you come up with the idea?

As a footwear designer, I couldn’t find the sneaker style I craved at retail and my designs were being hindered by the corporate footwear brands I’d been designing for a day in and day out for over 10 years. In 2007, I set out on my own to do what few other footwear designers had achieved; create my own sneaker brand, on my terms and by myself.

Today, Heyday Footwear designs produce and sell directly to consumer, design-driven performance high top gym sneakers for the freshest in fitness. Our customers are at the pinnacle of bodybuilding and fitness in all its forms or aspire to be. We combine flat soles needed by athletes and outstanding comfort that will enhance your gains with innovative designs and premium materials. We boost our customer's confidence by knowing they have the freshest kicks in the gym.

Heyday is only available online via our website. We cut out the middle man (the stores), so we (the brand) can bring our amazing, premium fitness sneakers directly to you (the customer) at an amazing (not premium) price. People want what nobody else has, and with production limited to just a few hundred pairs per style, you're guaranteed to be part of an exclusive family. As owner and Chief Everything Officer, I guarantee that our customers receive the most outstanding customer service they've ever experienced.

Take us through the process of designing, prototyping, and manufacturing your first product.

I design sneakers by hand and then in Photoshop and Illustrator, creating tech packs explaining all manufacturing details to the factory. My business partner Ian (based in China) collaborates with me on the designs themselves, plus materials, leathers, graphics and everything else. Several weeks and multiple samples are needed to get the design and/or materials just right. Production is usually about 6-8 weeks and shipping from Asia to Boston is another 4-5 weeks where they’re delivered to our office and picked and packed to our customers.

Take everything you see on Instagram and Youtube and throw it out the window as far as the glamorous “entrepreneurial life” is concerned. It’s all fake.

One of the most important items to check off your list when starting a brand is to choose the right name and then having it trademarked in all countries you plan on doing business in. In our case, we started with a US trademark ($4,500) and then added Europe with a specialized trademark called the Madrid Protocol that allows for your trademark to be registered in all EU countries. Later, as we added international distributors, we added more trademarks. We’ve had to take legal action against other brands who tried to use our ™ on apparel and accessories including gyms, ad agencies, coffee companies, and even the mighty Target.

I self-funded the business after a successful career as a corporate footwear designer.

Describe the process of launching the business.

Heyday was launched in 2008 in just a few retail locations in Boston, LA, and Tokyo. The product was really different at that time as well. At that time, the sneakerhead trend was really getting started but almost all brands used Nike AF1’s as a base including, BAPE, Greedy Genius, etc. I wanted Heyday to stand out so I looked to the classic Red Wing wedge work boot for inspiration and then after 2 seasons switched factories and silhouettes to a more athletic look but with many of the same unique details from our first few seasons.

After two years of selling wholesale to retailers (with many issues detailed above), we switched to a direct to consumer model and quickly phased out of our retailers which included Bloomingdales, Finish Line, Sheik, Revolve, ASOS and more.

The important thing to remember about wholesale versus direct to consumer is that your volume will be higher selling to stores who are buying in bulk (that may be as little as 20 pairs up to thousands of pairs per order). Direct to consumer is selling individual pairs to the end-user (though frequently 2-3 pairs per order). One of the main reasons we moved away from wholesale is you’re putting all of your eggs in one basket so to speak.

By that I mean, the store buyers are the ones placing the orders and they are frequently wrong in their forecast of what will sell and what won’t. When you deal with important “key” accounts like Bloomingdale’s, ASOS or Finish Line, the inclination is to produce whatever the buyer’s want. If the shoes don’t sell, the buyer will drop your brand and move on the following season. Essentially, you’re leaving the fate of your brand in the hands of a small group of buyers who are only interested in their own jobs... They could care less about your brand; if it doesn’t sell, they’ll drop you in a flash and pick up whatever new brand they discover the following season or even worse, they won’t even take a chance on a new brand and prefer to keep buying from bigger brands who are likely to sell OR who will take the product back usually at a loss.

As the DTC business improved, so did our product placement in the press. We went from free weekly magazines in a few cities to have celebs like Flo Rida, Trey Songz, Jay Sean, and actors on True Blood, Ant-Man, So You Think You Can Dance, and America’s Got Talent to wear the shoes with many of them requesting custom pairs. We managed to achieve this level of product placement PR without any outside help. PR firms charge anywhere from $1200-$5000 or more per month to do this and while it will speed up the process, it’s costly.

The shoes were being noticed by stylists first in free weekly magazines and blogs and eventually by bigger and bigger stylists. We found that many of the stylists work together or have worked together and tend to “share” new brands. We were lucky enough to fall into the hands of several stylists from FOX so we started getting multiple placements on TV with SYTYCD, VH1, BET, America’s Got Talent, True Blood to name a few.

You should know everything about your business, from how your product is made (and even better, go to the factory), how the website or other selling channel works, exactly who your customers and competitors are.

Cyrus of SYTYCD

In 2015, a chance encounter seeing bodybuilders training in Heyday Footwear led us to completely refocus the business on the exploding fitness market. The shoes were basically the same as we always made, they just happen to provide the features needed in the gym (flat, zero-drop soles, high top ankle support) with the very original style that stands out in AND out of the gym making Heyday much more versatile than our competitors.

This came about because I randomly found bodybuilders on Instagram wearing Heyday in the gym to train. In 2014, the whole fitness/organic food/healthy lifestyle started getting very big with Whole Foods, Yoga pants, and athleisure clothing, wearables like Fitbit and Apple Watch brought a healthier lifestyle to the masses. The world of bodybuilding lives and dies on Instagram so that’s where we focussed on brand awareness. We also got more exposure by having booths at fitness expos like Fit Expo and Bodypower with upwards of 100,000 attendees per show.

6’8” 325 lb action movie star and MMA fighter Martyn Ford

Through starting the business, have you learned anything particularly helpful or advantageous?

We’ve probably encountered every obstacle imaginable in our 10 years. Shady retailers who don’t pay their bills, factories who cheat, steal, lie and even attempt to extort us, customs exams, typhoons at sea, no sales, no money, no inventory, too much inventory...we’ve persevered and overcome it all. Make sure you know every aspect of your business inside and out (or at least to be conversant enough to speak with someone in an agency or a freelancer in a knowledgeable way).

IG fitness star 2M followers @Anita_Herbert

We started on Shopify in 2016 and it was one of the best moves we made! It’s so easy to use Shopify, I was able to set up my initial store in just 2 hours after having been on another platform that needed a developer in order to do anything. The Gurus are also the best in the business!

Soooo many apps! Some favorites are Shippo, Klaviyo, Judge.me, Zipify, Recart, Wheelio, Message Mate, Bold Upsell, SaveMySale, Socialphotos, and Shoelace.

What have been the most influential books, podcasts, or other resources?

The Unofficial Shopify Podcast with Kurt Elster was actually the podcast that convinced me to switch to Shopify after hearing how a competitor was using the platform. Several years later, I was a guest on the podcast (and at least 10 others). The book that had the most influence on me and the business has to be The New Rules of Retail by Robyn Lewis.

The author goes into detail explaining the progression of retail from the 1800’s era general store, to the Sears Roebuck catalog to department stores, specialty stores, malls and finally to direct to consumer which we switched to after being in the wholesale model for our first few years.

That book showed me that my thoughts about going direct to consumer in 2010 were right on the money as that was still a somewhat novel model 10 years ago.

Advice for other entrepreneurs who want to get started or are just starting out?

I highly recommend the following to aspiring entrepreneurs:

You should know everything about your business, from how your product is made (and even better, go to the factory), how the website or other selling channel works, exactly who your customers and competitors are and to “network, network, network” you never know when someone you meet could be important in the future (and maybe you could help someone else to pay it forward).

Study the true definition of Entrepreneur: An entrepreneur is an individual who creates a new business, bearing most of the risks and enjoying most of the rewards. The entrepreneur is commonly seen as an innovator, a source of new ideas, goods, services, and business/or procedures.

and enjoying most of the rewards. The entrepreneur is commonly seen as an innovator, a source of new ideas, goods, services, and business/or procedures. Take everything you see on Instagram and Youtube and throw it out the window as far as the glamorous “entrepreneurial life” is concerned. It’s all fake...Forget the Lambo’s and private jets (many of the posts you see are just using rented cars and planes etc). The risk part is what people don’t really understand until its throat punches you. Repeatedly.

Are you looking to hire for certain positions right now?

Believe it or not, I had to close Heyday in 2019 (after 12 years) because we weren’t able to raise the $2MM we needed to continue and to scale. Even with all of the success I’ve had, without the necessary cash flow and cash in hand, we couldn’t continue. It sucks but one needs to move on and start fresh again. So...if there’s anyone out there with a truly awesome role that I could fill in footwear or e-commerce, reach out to me! [email protected]

Where can we go to learn more?

If you have any questions or comments, drop a comment below!

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