Hats weren’t exactly my starting point. In 2011, I started a blog for my family, assuming the role of writer and influencer. Over the years, I became largely known for my blog. The more I shared, the more people began recognizing how much I loved hats, as I wasn’t often seen without one in photos.

My husband Jon picked up on that before anyone else did. He said, “If you keep wearing hats, you’re going to be known as the crazy hat lady.”

People asked where I’d bought my hats, and I often told them I bought them from the men’s section. Historically, men’s hats have been around longer than women’s hat brands have. There just wasn’t a place for women to shop for this accessory—at least, not yet.

I eventually started selling the brands I approved of through my blog. In 2015, my husband and I started selling our own creations: very structured brimmed hats for women. As an owner of several businesses, Jon has been an entrepreneur for years. I had my own ideas of how marketing could work as a result of my blogging experience and took note of what other brands were doing to grow their audiences.

Change was on its way. Our family was known for the photos we posted online, usually with our kids standing against brightly colored walls. Jon recognized that as the kids grew, we most likely weren’t always going to get to do what we were doing.

Creating Gigi Pip and making hats became my exit strategy and what I’d focus on next.

In the beginning

We started by selling hats online, storing them and fulfilling orders in our one spare bedroom. When we launched on Black Friday, it ruined Thanksgiving that year. We were so nervous about hitting that green light at midnight that it was more important than eating turkey. Since then, Gigi Pip has grown continually.

Some challenges have surfaced. Our first professional disagreement was when we couldn’t agree on the font for our logo. Jon had funky letters pieced together, and I wanted something classic. Hiring a graphic designer was our solution; the logo she created has never changed.

Our tagline, “For the woman who wears many hats,” gave us a sense of purpose and helped our vision fall into place. When our days really got crazy, I went back to that. In our business, we are wearing all the hats, literally and figuratively. Gigi Pip is still small, and we find joy in celebrating women in the many hats they wear.

Confidence is our north star and makes everything come to life. Instilling confidence in women means we remind them of their power every time they put on their hats. It’s a thrill to see a woman go from being a little timid at first to absolutely owning the space she takes up as she overcomes doubt and steps into her own.

And created a hat brand specifically for women and the many “hats” they wear.
And created a hat brand specifically for women and the many “hats” they wear. | roslyn smithers

Blogger-turned-businesswoman

Last year, Gigi Pip’s success allowed me to change “hats.” I chose to step away from blogging and assume my role as a business owner. Blogging all those years took a mental toll on me, and our employees, friends and family saw that firsthand.

You carry a heavy load as a business owner. You fear imposter syndrome and constantly try to balance work and life. It’s overwhelming. If you’re not careful, it can take over everything else.

Entrepreneurs know this already, but there’s no clocking out at the end of your day. Some aspects of what you’ve created are always on your mind. This is where I credit Jon—he stepped in and carried both of our loads so I could relocate my footing. Because of this, I was able to show up at my best. Ironically, it was during my downtime that I felt I had to rebuild my own confidence. I trusted my team to take us to the next level of success.

Most of our revenue comes from online sales, as people aren’t going into stores as often to shop for hats. Still, I like the human connection connected to retail and the experience of people coming in and trying things on. To that end, we converted a shipping container into a traveling retail store that allows us to visit events, pop-ups and music festivals so customers can have their own hands-on experiences.

When we outgrew our spare bedroom and took a chance at opening a flagship store in downtown Salt Lake City, it felt like a real turning point for us. We invested in one amazing employee and made it work with retail in the front, studio and fulfillment in the back, and customer service built right in. Talk about wearing all the hats! From that point on, it felt more real to me. Initially, Gigi Pip felt like more of a hobby, but now it was clear we were really doing this.

We also opened half a dozen locations throughout Texas. While it wasn’t a total flop, it didn’t work out. Still, it forced us to learn how to manage a retail store successfully from another state. It meant losing money to figure that out, but we had to experience the disappointment of that initial quick fix to learn what we wanted to do, using all we learned to open stores elsewhere.

An eye toward the future

We’ve had some cool opportunities, including hosting events for the Country Music Association Awards in Nashville and hosting a Grammy Awards party. We have found new ways to familiarize customers with what we offer.

Beyond other festivals and corporate parties, we’re looking to open new stores in the coming years. I’d love to open one in Nashville, Tennessee and some of the bigger, more hat-oriented locales. No matter how many stores we open, though, Utah will always be home. We opened our new warehouse here recently, which was a big step for us. Instilling confidence internally under the same roof has really taken our company to the next level.

Gigi Pip represents an idea for a women’s line of hats that I never fully expected to catch hold like it did. We wanted to see if we could build what I really loved to do into a self-fulfilling business. Seeing it succeed means the world, and it is fueling additional dreams for us.

For example, we just went to an event called Cowboy Christmas, which is tied to the National Finals Rodeo (NFR) in Las Vegas, and it was as thrilling as it was intimidating. Other, more established hat brands were there (like Stetson)—brands that have seemingly been around since the beginning of time. After all, cowboy hats have been worn forever. Still, we find confidence in doing our own thing. We create our own spin on Western fashion, offering a more modernized look.

Our goal is to not be afraid to play in that same arena. When I feel intimidated, I return to my purpose of creating a hat brand for women, and that gives me more confidence in what we offer. I do want people to take us seriously, and going to male-focused events like NFR is rewarding.

And created a hat brand specifically for women and the many “hats” they wear.
And created a hat brand specifically for women and the many “hats” they wear. | roslyn smithers

More starts than stops

When we had our grand opening last fall, I’d stopped promoting Gigi Pip on my personal Instagram account, but I couldn’t stop worrying about doing so. Did my business have enough of a backbone to stand on its own without me? Maybe it did, and maybe it didn’t. The goal was to have Gigi Pip succeed on its own without requiring me to be the product as well.

The day before we opened, I was on the verge of a full-blown panic attack. That morning, my phone dinged with a camera notification that someone was at our building at 5 a.m. My mind raced to who it could have possibly been when, in actuality, people had started lining up, waiting for our doors to open five hours later.

And I had an “aha” moment when that happened. It gave me the strength I needed to believe in myself, my team and all we had built. We have a really good thing going, and it’s getting better as we learn our way forward.

It’s my hope that when you put on one of our hats, you’ll remember that you, too, are confident and capable of anything you set your mind to. Nothing would make me happier.

Earned advice

  • Write down your strengths. There will be days you can’t see them through the dark.
  • Trust your gut. There was a point when I tried to design hats for everybody. That wasn’t sustainable, and it got us off track for a while. Always remember why you started, dig deep, and never stop believing or trusting your gut.
  • Make time for hobbies outside of work, even if it’s reading a book. Find ways to disconnect from your business so that when you’re actually there, you’re really there.
  • Be present. If you have kids and try to run a business at the same time, you know how hard it is to do both. Try to stay exactly where you are and focus on what you’re doing at that moment. Be with who you’re with. Look people in the eyes and really listen. It’s tricky not to let your brain go to where you are not, but if you can master this, you will feel the difference. Whatever you have to do to stay present, do it, be it meditation, journaling or therapy. Clear your mind so your heart can be present.

In the beginning, it was hard for me to run a business while being the mom of three boys. I initially worked in the office only two days a week initially. Now that our kids are in school all day, I have shifted to coming into the office daily, and I love it. Work is closer to home than it has ever been.

While we were getting settled into our new space, the kids watched us head to the warehouse at 6 a.m. and not come home until 4 a.m. the following day. That went on for weeks. It took a huge toll on us, but along the way, my children have had the opportunity to cut the red ribbon, see new places and watch mom and dad work really hard. They’ve even helped set up booths, check out customers, take out the trash, ship orders, build shelves and break down boxes. This is the life and example I want my boys to see so they can learn what it means to work really hard, find and nurture their own confidence, and develop passion and purpose along the way.

And created a hat brand specifically for women and the many “hats” they wear.
And created a hat brand specifically for women and the many “hats” they wear.