We caught up with the brilliant and insightful Skylar Bennett a few weeks ago and have shared our conversation below.

Skylar, thanks for taking the time to share your stories with us today So, let’s imagine that you were advising someone who wanted to start something similar to you and they asked you what you would do differently in the startup-process knowing what you know now. How would you respond?

If I were starting over today I would seek out more guidance from those that have succeeded in my same space before me. This could be from books, online courses, real life relationships or anything else. Being a successful entrepreneur is a balance between having the confidence to take steps forward even when you may not know everything you feel you should, and knowing when you don’t know enough and need more knowledge or guidance before taking steps. I’ve always sought out knowledge through different business books but I was always frustrated with the lack of specific direction with the specific problems I was facing as a business owner. In 2020 and into 2021 I began searching for information regarding the specific problems I was facing and the results were incredible. After facing serious financial issues and struggling to maintain profitability we found Profit First by Michael Michalowicz which completely changed our business. Later we began taking online marketing courses from Harmon Brothers, one of the leading firms in the industry, which helped us achieve consistent profitability in our marketing efforts. Then we implemented the Entrepreneurs Operating System (EOS) after searching for a way to more effectively operate our company and found the book Traction by Gino Wickman. These are just a few examples of the incredible positive impact seeking out solution based knowledge can provide. Someone has likely done what you are trying to done right now, or something similar, and they can help you get where you want to be much faster than if you try to do it on your own.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m just a normal guy who has practiced relentlessly to become more than that. I’m a Husband to an incredible Woman who has supported me through the difficult process of starting and growing a business. I’m a Father to 4 rambunctious boys who constantly keep me laughing, crying and provide countless opportunities for me to be patient and loving. At heart I’m a small town country boy who feels most at home on a dirtbike in the woods. I’m the son of an entrepreneur who has always had the desire to start my own business, but never knew quite what it would be. After getting a degree in Accounting from ASU I knew I didn’t want to be a CPA. A friend suggested Commercial Real Estate and after realizing it had all of the components of a career I thought I’d enjoy, I sought out a local AZ firm and solidified a job out of undergrad. After helping other business owners lease or buy real estate I gained the confidence to start my own business. Kevin Shoemaker, my current business partner, also worked at the same Real Estate Firm. After having the idea for a machine washable necktie we began working on “The Tough Tie” as a side project. That side project quickly snowballed into an actual product that we were ready to sell. After feeling inspired to commit fulltime to The Tough Tie I quit real estate and committed all of my time and energy to building the business. Kevin joined in full time a few months later and for the past 5 years we’ve grown The Tough Tie into Tough Apparel, a fully fledged apparel company that now offers multiple products, has a solid online presence, appeared on ABC’s Shark Tank, survived Covid and is continuing to grow and evolve every year. Our goal at Tough Apparel is to provide men everywhere with durable professional apparel that gives them the confidence to go out be the best version of themselves possible.

The biggest thing we want our supporters to know is that we support them whole heartedly and we’ll continue to do everything we can to make their lives better. Our goal is to be a positive influence in the lives of everyone we come in contact with, whether that be through our products, content or personal relationships.

Okay – so how did you figure out the manufacturing part? Did you have prior experience?

This has been one of the biggest challenges and learning opportunities over the past 5 years of starting and growing Tough Apparel. Tough Apparel started life as The Tough Tie, and our only product was just that, The Tough Tie. The Tough Tie is a refresh of the age old necktie. We realized there needed to be a stronger, more durable necktie on the market that didn’t fall apart and could be easily washed in the washing machine. Oddly enough this didn’t exist in 2016, and still doesn’t today outside of The Tough Tie. Initially we worked with a local seamstress/designer to come up with the design of the tie. The materials and sewing were something that had never been done before for a necktie. This made manufacturing of the product extremely difficult since a normal necktie manufacturer was unable to produce the product for us. After sampling with several contract manufacturers in the US we finally found one that was able to make the product for us. We worked with this manufacturer for almost 3 years until Covid hit and they stopped manufacturing everything that wasn’t medical. This happened simultaneous to us airing on Shark Tank. So 2 weeks prior to airing on Shark Tank we had super low inventory and no way to make more of our product. We reached out to several other manufacturers but they also had stopped work on all non-medical products. With no other options we purchased our own sewing machines and taught ourselves how to sew the neckties. That was back in April of 2020. Here we are in February of 2022 and we are still manufacturing our own neckties. Our small team of sewers has sewn thousands and thousands of neckties. Manufacturing our product has been a huge blessing and challenge to our growing company. While it’s not something we see doing ourselves indefinitely it has allowed us to survive covid and increase the quality substantially of our staple product, The Tough Tie.

Let’s talk about resilience next – do you have a story you can share with us?

Roughly 3 months after starting the business we had some inventory and online sales were slow. Someone suggested participating in an elementary school carnival where other local businesses would be setting up booths to sell products to parents. We hesitantly agreed. After hours of preparation and building a booth we sold exactly 1 tie at that event. $36 of revenue for hours and hours of work. We were discouraged but not defeated. Later we signed up for another event, this time at a mall instead of an elementary school so buyer intent was much higher. We sold exactly 8 ties at that event. Seeing the potential of these events but knowing we hadn’t found the right ones we continued signing up for more and more. 4 months after the elementary school carnival we did an event where we sold 100 ties and made over $3000. Now more than 4 years later we still participate in several popup shopping events throughout the year, the biggest of which generated over $50,000 in revenue in just 2 days last fall. We easily could have given up after that first event but we knew if we could just get in front of our customers they would love our products. And we were right. Resilience is the only thing that’s kept Tough Apparel alive through the years and even though things are better now we know that it’s going to take a massive amount of additional resilience to get where we want to be.

Contact Info:

• Website: toughapparel.com
• Instagram: https://www.instagram.com/tough.apparel
• Facebook: https://www.facebook.com/tough.apparel