Boss Lady Series: Kelly Jensen from Rollick

Being a creative person I have always found to be a blessing and a curse. Most creatives-at-heart really have to get out there, work hard, and take a risk if they want their dreams to materialize. Many jobs that provide security don’t always fill that need which is a huge reason I even started my blog! I decided to highlight friends and people that I have come across through this wonderful endeavor to help share their stories and hopefully inspire others to start their own passion project, whatever it may be. So… welcome to my first post of my new series, Boss Ladies!

Putting your dreams in motion and starting something you love from scratch can be scary and hard but the journey, lessons, and fulfillment are worth it and my friend Kelly knows a thing or two about this! Kelly started her a clothing brand Rollick that is fashionable and funny and totally reflective of her infectious, lovely personality. Enjoy her story!

Name: Kelly Jensen

Age: 29

Location: Seattle (born and raised!)

Education: Washington State University- go Cougs!

Occupation: 9-5 as a merchandiser at Cutter & Buck, 5-9 as owner of Rollick


What was your major and why did you pick it?

I majored in apparel merchandising, and it’s still is a little crazy to me that I’m doing exactly that in my career! I picked that major because I knew I was interested in business and good at the “numbers” part, but I’d always had an interest in the apparel industry and liked that the apparel merchandising major combined the two. 


What was your first job out of college?

I worked as a sales person at Nordstrom for a few months, but sales are just not my jam (I wish I was better at it!). I went from there to work as an assistant planner at Eddie Bauer at their corporate office. 


Where have you worked since and how did those skills help you start your own company?

After a couple years at EB, I came to Cutter & Buck as a merchandiser, hoping to be more involved in working with product design. It’s been a great experience getting to learn the entire production process of a garment, from concept, to sampling, to sales reps, to the consumer. There are SO many steps that go into making a simple polo, and it’s been eye opening to see how it all works. It’s also been incredibly helpful to work for a company that is primarily a wholesale company, as that is who I work with when getting product for Rollick. It helps me to know the lingo and how the whole buying process works. 


What made you start Rollick?

I’m someone that has always needed to have some kind of creative outlet. That’s taken different forms over the years, from sewing, to DIYing, to planning our wedding. But last year I started to think about what I am most passionate about and how I could turn that into something that would excite me and could potentially become a career someday. I’ve always been a bit of computer nerd along with a fashion lover, so an online shop seemed like the perfect fit!

Once I started really digging into what I wanted the Rollick brand to be (before I even had a name), I discovered that there was a much deeper root to my drive to start this little biz. Throughout my time in school and post-college career, I’ve never totally felt like I fit in to the fashion world. There is so much pretension and “I’m too good for you” attitude, and I have often felt intimidated and like an outsider, even though, in my mind, fashion should be for everyone! I decided that I wanted Rollick to be fun, inclusive, and real. No super-serious models. No “it girl” mentality. No overly-cheesy cuteness. Just fun, wearable clothes (and a sassy/punny attitude) that fit perfectly into the lives of the real rad women that wear them. 


What has been the biggest success?

I’m not sure I can point to just one thing that has been the biggest win for me. Since launching in November, I’ve been testing, trying, and tweaking so many processes that it’s basically all been an experiment! Some things that have worked great so far are working with influencers, pop up shops, and email marketing. I totally believe in my product and brand, so now it’s just a matter of getting the word out. Finding ways to reach my dream customer is now my number 1 priority, and these have been great ways to find them!


What do you find most difficult?

As I’m sure any side-hustling business owner will tell you…there aren’t enough hours in the day! When I get home from my 9-5 I try to spend at least a couple hours on Rollick and try to squeeze in as much as I can on the weekends, but it’s just such a busy time of life (I’m lookin’ at you, weddings ;))! Finding the balance between being a business owner and being a good wife/employee/friend/daughter/dog-mom has been really hard and I feel pretty spent a lot of the time. BUT, I absolutely love working on Rollick and it hardly feels like work, so I’ll keep hunting down those pockets of time so that I can keep working toward my goals and dreams. 


What advice would you give to those who want to start their own business?


Hah but no, really. If starting this biz has taught me anything, it’s that once you start pushing past the fear of failure, the fear of judgment, the fear of “what if?”, you can do pretty remarkable things. You don’t want to look back in 5, 10, or 30 years and ponder on what could’ve been if you’d only tried.

There’s no denying that it can be hard as hell – financially, energy-wise, and emotionally. But at the end of the day, you’re the only one you have to count on, and if you believe it yourself, there’s nothing else you need. 

Start small, make lists, and start taking baby steps each day – you’ll be amazed at how far you can come in a short amount of time!


What has been the biggest learning experience so far?

In general, I would say that if you’re not constantly putting yourself in front your customers, they will forget about you. People nowadays are just inundated with advertising everywhere, so the second you’re not putting yourself at the top of their feed or in their inboxes, someone else will take your spot. I had a super successful initial launch of Rollick back in November based on my own network of like-minded ladies, but after the holidays, it was definitely crickets. It’s been a learning process of how to stay top-of-mind to my customers, but also finding new ones.


What are your favorite Rollick pieces?

They’re like my babies! You can’t pick one! Hah but if I had to choose, one of my favs is the Back That Sass Up moto leggings, because they are SO comfortable, make your hiney look fabulous, and I just love the name. I’d also have to include the “Cute But Kinda Weird” graphic tee, because it basically sums up everything I love about the Rollick customer. You can be cute, stylish, and still a total weirdo who’s 100% comfortable in her own skin .. 


What do you hope for Rollick in the future?

I would love to see it continue to grow and grow and eventually have my own line of tees within the shop (because I’ve got puns for DAYS ;)). I’m still on the fence about if I’d like to take it to a brick and mortar location, but you’ll just have to stay tuned to see what happens!


Where do you see yourself in five years?

Rollicking around in small business ownership euphoria!  I would simply love to be running this biz full time, with a small team of fabulous lady bosses to help Rollick to continue to grow. I dream of bringing its inclusivity and authenticity to as many women as possible, and really hope I can continue to do so over the next 5 years. I’m also thinking I may have a baby (or 2!) by that time, so things should get interesting! 


Describe your own taste and style:

I was raised in the USA’s capital of casual/sloppy dressing (flannel and granola all day err day), but despite that, I always feel the need to be put together, even if that’s just in jeans and a tee. I love finding simple styles with an interesting twist or detail in fabulous fabrics, and think that’s especially important for Rollick, as there has to be something unique about a piece for someone to want to try a new brand. I lean toward neutrals (blame it on the permanently-grey skies) and clean lines, but am always looking for new silhouettes and interesting ways to wear a tried-and-true style. I like my style (and Rollick’s) to easily take me from work, to drinks, to Netflix, and to be looking and feeling great all the while. 


Quick fire:

Favorite color: grey. Does that count?  Also loving wine-inspired colors (and drinks) for fall

Favorite movie: Meet the Parents and Step Brothers (awkward humor, all the way) 

Favorite food: Cookies! 

Favorite brunch spot + order: We live next door to a bakery called Grand Central (it’s a problem…), and their breakfast sandwiches are just insanely amazing. You’ll find me there basically every Sunday morning (occasionally a cookie will make it into my order….#oops). 

Favorite book: I rarely read for fun anymore (upsetting, I know) but I simply adored Tina Fey’s Bossypants. 

Dream destination: Renting a car in Ireland and exploring castles and pubs for a week.

Favorite article of clothing you own: A camo jacket that I pilfered from Rollick. I seriously wear it ALL the time and love hat it’s comfy, casual, but special because of its details. And no one can see me in it 😉 (any other introverts out there?)


Last notes:

Whether you’re thinking about starting your own business, are getting into blogging, or just like cute clothes, my hope is that Rollick can inspire you to embrace what’s unique about YOU and to never stray from that! There’s so much comparison and competition out there nowadays, but life’s way too short to change yourself for anyone else. At the end of the day, YOU DO YOU!! 





Be sure to check out Rollick and have fun shopping away! I can genuinely say I love the collection Kelly has curated and my own pieces from Rollick have garnered many compliments and are super cute and comfortable!

It’s always great to support and learn about the boss ladies out there who are following their dreams and making things happen! Thanks Kelly for sharing and telling your story! :o)


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