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Female Disruptors: Stacey Keller of Ponyback On The Three Things You Need To Shake Up Your Industry

An Interview With Candice Georgiadis

“Be Patient”. I am a big fan of Gary Vee and one of his key messages is to be patient. For me this is a message I need to tell myself everyday. We are all in a hurry, but instead of trying to get to the ‘goal’, instead focus on enjoying the journey. I think when you have a small business, you often get so caught up on survival that you forget to take a moment to stop and look at the big picture. This message helps me to stop, take a moment to be grateful for my current situation and think about all of my 15,000+ customers who now have a hat they love and adore.

As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Stacey Keller, Founder and CEO of Ponyback Inc.

Stacey conceptualized Ponyback with the hopes of helping others like herself find comfortable, stylish, and flexible headwear that can accommodate long hair in any style. Watching her sons enjoy a wide variety of hat

options without constraint, Stacey knew it was time to revamp the hat industry. She successfully crafted a prototype for her viral, patent-pending design after dismantling a brand-name hat in her home.

Graduating from Wilfrid Laurier University with a Bachelor in Business Administration, Stacey worked in accounting before pivoting into education. Teaching high school business for ten years, Stacey decided to combine her knowledge in business with her passion for starting a small business and officially launched Ponyback in June 2020.

Today, Ponyback embodies so much more than just an accessory. Through insightful messaging, content, and deep connection with her audience, Stacey is innovating Ponyback into a community that invites everyone to love themselves, embrace their style and support one another. This unique narrative and brand character is what sets Ponybck apart and is the key to driving meaningful innovation in the fashion accessory industry.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Absolutely! Like many entrepreneurs, I was faced with a problem. I wanted a cute baseball hat. I was obsessed with the hats I’d buy for my sons, fitted, fullback — they were just so nice. I really wanted one too, but in the summer I’m usually rockin’ a high pony or messy bun — which do not work with a fullback. Your other option is an adjustable hat with the hole just above the adjustable strap — my ponytail was never naturally at this height, and I didn’t like the look.Then, I found out about ponytail hats, but most products on the market had a permanent opening for a high pony above that adjustable hole. I didn’t like the look of this, what if one day I wanted to wear my hair down? That was when I realized what I wanted was a fullback hat with a closeable opening. I had the crazy audacity to think I could make this myself. I don’t have experience in the hat industry, but I got out my sewing machine and one thing led to another. By using my kids magnetic toys, I created a magnetic back seam in the hat that when closed didn’t look like an opening was there! At that moment, my heart lit on fire and I was obsessed with making it a reality.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Women and people with ponytails have long been frustrated by the traditional baseball cap. Not much attention has been given to this category in the hat industry. Lots of women complain, “hats don’t look good on me.” Well not only may your hat not work for your hairstyle, it may also sit on your head too low, pushing your ears out, or needing to tuck them into your hat. Lots of Ponyback customers remark, “I wasn’t a hat person before Ponyback”. This tells me that traditional baseball hats were missing the mark and not meeting the needs of an entire category of people.

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?

In my first meeting with my manufacturer they asked me if I had a tech pack. I said that I didn’t but that I’d get them one. The entire time I was actually thinking, “WHAT IS A TECH PACK?!” I had no idea what it was, what needed to be in it or how to create one. I learned from this that you don’t need to necessarily have all the industry knowledge and know-how when you start. Obviously, arm yourself as best you can with research, but what will get the job done is just messy action. Say yes, jump in, and swim. You’ll figure out a way to find the answers. Luckily, I had randomly made a connection with an industry expert on Linkedin a few weeks prior and was able to lean on my new connection for help and support in this area.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

One of my mentors is Marnie Conksy, the CEO and Founder of Thigh Society. I randomly met Marnie in a Shopify Slack group. She was on a podcast with some ecommerce pros speaking about diversity and the importance of diversity for her brand. I loved her insights, and so I simply reached out on Slack to compliment her on her great podcast episode. I didn’t have anyone in my network that I knew personally running a successful bootstrapped ecommerce business at the time, so I asked if I could pick her brain. Since that meeting, we chat regularly, support each other on social media and have become friends. Marnie has given me a great belief in myself; a sort of ,”I can do it, too” mentality.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Disrupting something means you are making significant changes to something that needs a bit of change. Disruption oftens comes as a shock to people because they’ve become accustomed to having something done a certain way, and disruption is a shock to the system that says “oh, we can do things differently. I didn’t know this was possible!” Disruption can be big like Uber coming in and completely overhauling the way we see transportation, or as small as when socks went from basic sports socks to cool, colorful trendy accessories, and even landing in sock subscription boxes. That is innovation mixed with a bit of disruption.

As humans, it’s in our nature to resist change. As the saying goes, old habits die hard. Disrupting an industry won’t happen overnight when you offer a new solution, something that hasn’t been done before, people will be hesitant to change. Of course you’ll find like-minded people in the early days, those early adopters, but mass market appeal may take time.

I don’t think I’d distinguish any disruption as good or bad. I think they are all part of an innovation and an idea that gets us thinking. Some work and some don’t, but it’s all part of the human need to create and build something. Ultimately, a disruption is when you’re creating a benefit to people’s lives

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

#1. “Take messy action”. From the start, I consistently took action, made the next move and then another and another. Your business won’t get off the ground if you’re not moving forward. Your actions don’t need to be perfect. It is a continuous process of constant iteration. Test and learn, over and over. I did not have any industry experience prior to starting Ponyback. Admittedly, looking back, an industry expert would have known and likely prevented some headaches like quality defects in the manufacturing process. But all of your ‘mistakes’, or ‘unknowns’ will likely lead to a problem, and all problems have solutions. So, I just tackle each problem with the messy action principle again to move forward and solve it, with the best information I know at the time.

#2. “Be Patient”. I am a big fan of Gary Vee and one of his key messages is to be patient. For me this is a message I need to tell myself everyday. We are all in a hurry, but instead of trying to get to the ‘goal’, instead focus on enjoying the journey. I think when you have a small business, you often get so caught up on survival that you forget to take a moment to stop and look at the big picture. This message helps me to stop, take a moment to be grateful for my current situation and think about all of my 15,000+ customers who now have a hat they love and adore.

#3. “Networking is key.” As I mentioned before, I had no experience in the hat industry; but what I did have was an unabashed “I’m going to put myself out there” type of mentality. I’ve joined all the entrepreneurial groups I could, I said ‘yes’ to all the “hey, I know someone you should talk to!” invitations; and I put myself out there on LinkedIn and was able to connect with an industry expert consultant who had worked for one of the major hat brands. I’ve been able to find help and support from either Google or someone that I’ve been able to connect with through my many networking opportunities.

We are sure you aren’t done. How are you going to shake things up next?

I really want to continue to help more women access great quality baseball hats that meet their needs. I’d love to develop satin-lined products for those with curly hair. I also want to continue to customize the hat design to fit heads of all shapes and sizes, to be a brand extremely inclusive and welcoming.

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

I truly believe that the biggest challenge facing women disruptors is the mindset battle. Being a successful entrepreneur requires a high level of mental resilience to taking risks, and making messy actions as I mentioned previously. Tony Robbins states that being a successful entrepreneur is 80% psychology, and 20% skill. We could likely have a lengthy nature vs. nurture debate here, but I believe that there are a couple of factors that add to the difficulty of women overcoming some of these mindset challenges.

#1. Not having as many role models available to show us what it is like to overcome the obstacles. Times are changing and I do feel very lucky to be a female entrepreneur in 2022. In addition to Marnie who I mentioned earlier, there is Sarah Blakely of Spanx, and Joanna Griffiths of Knix. I think the importance of seeing that other females can and are leading disruptions in their respective industries, and making change is a powerful mindset builder for women like me.

#2. In many cases, we may not have the same exposure to risk taking and failure. Obviously this statement depends on the type of upbringing you may have had. In my case, as a young child, I avoided at all costs anything that was dangerous. I never had a broken arm or a severe injury of any kind. The reason was because I never took any risks that may have caused me harm. When I compare and contrast my childhood to my husbands. He was constantly taking risks, attempting new slightly dangerous things, and was encouraged to do so. I think your risk tolerance is a practiced behaviour. I think this ‘practice’ with risk, does contribute to a type of mental resilience. One that if more practice with risk was had in early childhood, would likely help you to overcome risk in entrepreneurship mental mindset battle. Obviously, this would happen on an individual family level, and may not correlate with gender, but it was my particular experience. I have felt at times the strain and pressure of the ‘risk’ of what I am tackling and enduring on a daily basis. It is something that I am constantly working on, but for me, it does make me uneasy and unsure some days. When I have a low-confidence day, I try to remind myself of some truths. If all of this were to implode tomorrow, I would be fine. I would be loved, safe and healthy. For me, I am still practicing my mental resilience, but I am aware of it — and I think that is likely the first step in making meaningful change.

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

Gary Vee and the way he enjoys learning, educating and working is very enjoyable to me!

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. :-)

The movement I’d like to inspire is one of love and self-acceptance. For much of my life, I pushed against ‘who I was.’ I was trying to be something that others wanted. When I finally learned to accept myself as I was, for who I was, and stopped caring about what others thought, there was a sense of relief. I had been wasting so much time consumed by leading a life of pleasing others instead of leading a life that loves and accepts myself. One of Ponyback’s values is to create a sense of community, a welcoming feeling where you can show up just as you are, with your unique interests and personality. There is no one size fits all; we are an inclusive, welcoming community. Before my ecommerce store opened, I had an Instagram account where I would share updates about starting my business. My designer had asked me for a tagline to put on our labels and stickers. I didn’t have one, so I put a call out on my Instagram to help craft a tagline for Ponyback. I had a great response and many in my IG community responded with suggestions. I was able to take two that I liked and combined them to make, “Your style fits here.” To this day, I’m so amazed by how this tagline perfectly illustrates that your hairstyle fits into our hats, but that on a deeper level it also represents the sense of belonging.

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

I love the Michael Jordan quote, “You miss 100% of the shots you don’t take.” On hard days, when I feel overwhelmed — I will remind myself of this. I think of my future self in 30 years and wonder if she is looking back at me — would she regret it if I gave up and didn’t try. And the answer is always YES! I take a deep breath and resume my messy action, because armed with great patience — I’m going to live a life that is unknown, unpredictable, and scary — but I’m taking all of my shots and enjoying every moment of it in deep gratitude.

How can our readers follow you online?

Follow us @ponybackstyle and on TikTok @ponybackstyle

This was very inspiring. Thank you so much for joining us!



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