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“5 Things I Wish Someone Told Me Before I Started”, with Stephanie Carter of the Wallaroo Hat Company

Know that things will always be harder than they look at first blush — but remember that anything worth doing takes hard work. (If it was easy everyone would be doing it.)

I had the pleasure of interviewing Stephanie Carter. Stephanie is an award-winning entrepreneur, philanthropist, activist and visionary. In 1999, Carter became one of the early pioneers of the sun protection apparel movement when she launched Boulder, Colorado based Wallaroo Hat Company. A vanguard in the headwear industry, Carter combined fashion and function by introducing UPF 50+ sun protective hats for women, men, and children. Her passion and innovations in the headwear industry did not go unnoticed. In 2015, Carter was elected the first female president of The Headwear Association (THA) in its 105-year history. Since Wallaroo Hat Company’s debut over two decades ago, Carter has grown the company into a leading global brand and certified B Corporation. Wallaroo is now represented in over 10 countries including, Canada and the United Kingdom. Certified B Corporations are a new type of business that balance purpose and profit and are required to consider the impact of their decisions on their workers, customers, suppliers, community, and the environment. Carter is committed to this global movement of using business as a force for good.

Thank you for joining us, Stephanie! Can you tell us a story about what brought you to this specific career path?

During a trip to Australia in 1999, I noticed my mother-in-law gardening in a colorful, wide brimmed fabric hat. I had never seen anything like it before and I purchased several and brought them back to the US. I contacted the designer of the hats and asked if he would be willing to design hats and collaborate with me if I founded a company in the United States. I founded Wallaroo Hat Company in April of 1999 and we became partners and pioneers of the sun protective clothing and accessories industry. Wallaroo focuses on manufacturing UPF 50+ hats that provide a 97.5% UV block and our collection includes styles for women, men and children.

Can you share the most interesting story that happened to you since you began leading your company?

Over the course of the last few years we have had a lot of contact with customers who discovered Wallaroo hats after being diagnosed with melanoma. One of those customers is Tracy Callahan of the Polka Dot Mamma Foundation. Tracy has had multiple surgeries for melanoma including on her face. She is a strong advocate for Wallaroo hats and created an organization that promotes skin cancer screenings and awareness about the dangers of the sun. Tracy is a Wallaroo Ambassador and a huge advocate for our brand. She recently held the largest skin cancer screening on record in South Carolina and beat the Guinness Book of World Records previous record.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

At the very first trade show I ever attended we had a lot of customers referring to “keystone” pricing. (The only Keystone we were familiar with at that time was the Ski resort in Colorado.) People would make a reference to that expression and we would stare blankly back at them not really knowing how to respond. We quickly learned that keystone pricing is an industry term referring to doubling a wholesale price for retail purposes. Since I had never worked in the retail industry previously there were a lot of “firsts,” but that was one that has always stuck with me.

What do you think makes your company stand out? Can you share a story?

Being a 100% female owned and operated company definitely makes us stand out. In an industry that is dominated by companies owned by men, Wallaroo has a competitive edge and a unique way of doing business. In 2015, I was elected as the first female President of the Headwear Association in its 105-year history. We are definitely making an impact in the headwear space and breaking through the glass ceiling that previously existed.

Wallaroo is also a Certified B Corp, which is a new kind of business that balances purpose and profit. Wallaroo works with other likeminded companies to consider the impact of our decisions on the environment, customers, suppliers and our community. It is a group of businesses using business as a force for good.

Are you working on any exciting new projects now? How do you think that will help people?

In January 2020, we are launching a new hat brand called Carkella Headwear. This line features new customizable hats that are designed for the resort, golf and travel industries. The Carkella line will transform the way corporate customers brand their resorts and provide a different and unique way of promoting their organizations. The majority of hats in the Carkella line are made from a revolutionary new material that can be packed for travel, golf, hiking or other activities and still maintain its original shape when unpacked. Stay tuned for more details…

What advice would you give to other female leaders to help their team to thrive?

Never take yourself too seriously and always be open to feedback. Running a company requires a lot of patience and open mindedness. I have found that some of the most creative ideas and opportunities have come from my internal staff and being open to new ideas has helped Wallaroo grow and thrive over the last 20 years.

What advice would you give to other female leaders about the best way to manage a large team?

Delegating responsibility is an important part of being the leader of large team. Understanding that everyone who works at an organization brings different strengths to the business is critical. Figure out what skills different team members have and make sure they work on projects where they will find the most success. A happy and successful employee is a productive employee.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am extremely grateful to my Australian designer, Peter, who has worked with me since the inception of Wallaroo in 1999. He has provided countless hours of business advice, recommendations and support over the last 20 years. He has been instrumental in helping to pioneer new lines and innovations for our company. I appreciate his sense of humor, guidance and true friendship. Wallaroo would not be the company that it is today without his involvement.

How have you used your success to bring goodness to the world?

As Wallaroo has grown and become more self-sustaining, I have had the opportunity to move into some philanthropic projects that I am passionate about. I believe that we should all find ways to serve those who are less fortunate than ourselves if we are afforded those opportunities. I am currently helping found a 501C3 organization called, PridePads Africa ( We are manufacturing biodegradable, compostable sanitary pads and distributing them to girls in rural parts of Cameroon, Africa. There are huge stigmas around menstruation and large gaps in menstrual hygiene education and our goal is to help keep girls in school. Girls typically miss between 4–6 days of school a month once they begin their periods and eventually end up dropping out of school due to too many missed days. Our goal is to change the paradigm with education and access to sanitary pads so that these girls will understand that education is a right and not a privilege. They deserve to be educated and achieve great success in their lives like other girls around the world. This is something I am very passionate about and I want to make an impact and make a difference in this way.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Take chances and trust that it will work out.

2. Know that things will always be harder than they look at first blush — but remember that anything worth doing takes hard work. (If it was easy everyone would be doing it.)

3. Being an entrepreneur is one of the most rewarding things you will ever do and also one of the hardest.

4. You will work harder for yourself than you would ever work for someone else’s company. Even though you work for yourself — you are never really “on vacation.”

5. Make sure to take time to do the things you love regarding your own down time.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would love to live in a world where everyone is given equal opportunity to education. Communities thrive when people are given access to education. I have seen first-hand the difference an education can make in the poorest corners of the world. The fears and biases that persist in our world are largely based on ignorance. When we are given the chance to see the world through educated eyes, we have a greater ability to understand and have compassion for our fellow humanity. It starts with one person at a time, but the ripple effect is real, and it can spread and create change.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“It’s none of my business what other people think about me.”

I love this quote because I believe it demonstrates that if we are sure of our purpose and we know we are living our lives in the right way — other people’s opinions of us should not matter. I believe and have taught my children that we cannot change other people or control their actions, but we can control ourselves and our actions. We must always strive to live our lives to our highest purpose and make the most of the time we have on this planet. Too many people get caught up worrying about what other people think about them and make decisions based on those opinions. If we were free to make decisions based on what was best for the planet, fellow humanity and ourselves the world would be markedly different.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them :-)

I would love to meet Melinda Gates and Michelle Obama. They are both strong and powerful women who use their influence to effect great change in the world. I have been impressed by how they withstand the barrage of criticism often leveled against them and how they always take the high road. They both work tirelessly to make a difference in the world and to help people who are less fortunate than themselves. I have great admiration for women who hold positions of authority in the United States and never allow themselves to be defeated or beaten down. Leadership requires courage and strength and they are exemplary in that way.

Thank you for all of these great insights!



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