8 Questions for a Young Entrepreneur

8 Questions for a Young Entrepreneur

young entrepreneurThis post originally appeared on the Jane Dough.

Kearsley Lloyd knew she always wanted to be an artist but her parents weren’t quite ready for her to fully go for the starving artist life (it makes things so difficult…like eating on a daily basis.)

They encouraged her to study all different aspects of the art industry with experts until she eventually got into a little school called RISD. You’ve probably heard of it.


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Though she was considered a “capitalist sell-out” by her very eclectic classmates for studying marketing and the business side of art with graphic design, her degree has helped her build a thriving business by the ripe old age of 25.

Lloyd is the founder of Tipsy Skipper, an online shoe, accessories and bag company (though she does do pop-up shops) inspired by her love of the sea, sailing and beach towns and all the merriment that comes along with it  (Lloyd is an actual descendent of Captain Morgan.)

She chatted with The Jane Dough about building a business in your early 20′s, the power of social media and the late, great Lilly Pulitzer.

What did you want your career to be as a child?

I’ve been drawing, painting and designing since I could hold a crayon, and althoughI told my parents I wanted to be a firefighter, they wisely steered me to opportunities for study with a number of gifted professional sculptors, painters, ceramicists and photographers throughout my childhood and adolescence – just in case the firefighting thing didn’t work out.

How did Tipsy Skipper come about?

New England – and its extraordinary beauty – has had a tremendous impact upon my artistic identity. I hail from a long line of sailors and, when I’m not in-studio, I am out on the water racing sailboats, soaking up the beauty of the Rhode Island shoreline, and drawing inspiration from the sights and colors that are so vivid there. RISD was the only art school I considered, and I entertained no expectation of being accepted – I was ready to enroll in one of my liberal-arts choices when the RISD offer arrived. While it certainly provided the ideal place to study design, RISD was a huge cultural adjustment that pushed me well outside of my comfort zone initially. It wasn’t easy being the ‘preppy kid’ amidst the stereotypical eclectic artsy types with multiple piercings, fluorescent hair and extensive body art (I vexed a number of my professors and classmates, and have many entertaining stories to tell about being the ‘black sheep/individualist’ of the RISD family!).

In fact, many faculty deplored students they considered ‘capitalist sell-outs’ because they combined marketing/profit-making with an artistic vision. Starving in swelteringEuropean garrets, they contended, was a nobler calling for RISD alums, tuition loansbe damned! I’ve never been good at starving or sweltering (*sigh*), and college wasan expensive four years, so I chose another path. In any case, by senior year, I had made many friends, established my own style and individuality, and found a number ofprofessors open-minded enough to actually appreciate my quirky vision and encourageme to pursue it.

When I enrolled at RISD, I was unsure where my talents would lead specifically, butI was attracted to idea of combining traditional artistic methods with technology, so graphic design was an excellent fit. My designs begin as paintings, usually watercolors,which I manipulate with sophisticated software that enables me to have a high degree ofcontrol over the final creation.

I have always appreciated fashion and textile design and enjoyed wonderful designinternships at Vineyard Vines and Lilly Pulitzer. The inspiration from those interests and experiences made me eager to undertake the year-long RISD senior-year project required of all graphic design majors. I decided to generate a unique line of accessories to featuremy original fabric designs – thus, the birth of what was soon to become Tipsy Skipper! I presented my work to a panel of professional graphic designers and RISD professors, andto my delight, they embraced it, thought it would have tremendous market appeal, andurged me to make the dream a reality.

What is it like to run your own business? Do you work all the time? Have therebeen moments where you thought this was just all too hard?

Running your own business is rewarding, and sometimes terrifying at the same time!I certainly do not keep the traditional hours of 9-5. I work all hours, late at night, early in the morning, and definitely weekends. A customer was recently surprised that I wasavailable to help with a custom order request on Easter. My iPhone allows me to always keep up with social media and emails, and I want to be there when my customers call! Actually, the reason I don’t burn out is pretty simple: I love doing this. If you’re lucky enough to build a career around the thing you love to do, for goodness sake, do it!

By far, the hardest part of starting my business has been the ‘business’ part! As a designer, I would love to spend as much time as possible on the creative side of things,but the reality is that most of my time is devoted to manufacturers and customers,marketing the brand, and handling financial matters. Quite simply, I am the customer service department, advertising agency, accounting office, IT specialist and shipping clerk! I often say that the past two years have amounted to the “Kearsley Lloyd MBA program” because I have had to become proficient in spreadsheets, budgeting, and dozensof other unexpected responsibilities. I’ve been fortunate to have family and friends whoshare their skills, advice and expertise, and a crackerjack professional to help with my website.

What is it like when you see someone wearing your shoes or carrying a bag?

Aha, you’ve struck the best question ever! It’s always amazing to see designs come to life, but to see customers excited is just the most rewarding feeling. I’m always sporting Tipsy Skipper accessories, of course, but it’s awesome to see strangers wearing the products and know that their earrings or clutches are my designs. Also, it’s pretty coolto be on the highway and see a Tipsy Skipper sticker on someone’s rear window or have someone say, “Oh my gosh, I know you! I’ve been on your website and I love yourstuff!” There’s just nothing like that feeling!

What is your advice for other young women looking to launch clothing businesses or just female entrepreneurs?

Go for it! If you’re truly passionate about something, you’ll succeed. It’s so importantto network, learn from others and ask other entrepreneurs for advice, but sometimes there are times to go with your ‘gut’; it’s your business, and you know it best. If you make mistakes (and I have made my share), at least they are your mistakes, and youlearn important lessons from them. One important thing to keep in mind is that havingyour own business means you need to be a good problem-solver. You’ll face many unexpected twists and turns, but don’t panic! There are usually solutions if you apply some creativity. My advice is to sleep on the big decisions – the answers often seemmore obvious in the morning!

Where would you like to see Tipsy Skipper in five years? 10 years?

Ten years makes me 35, and I can’t imagine turning 30 right now, but I can handle the five-year question! I have lots of plans, but smart, steady growth is the main one. Keeping quality high and an eye to manufacturing in the U.S.A. are important factors inmy future vision. As soon as finances allow, my plan is to expand the product line and hire staff, allowing me to focus more fully upon design work.

As a designer, customprojects are particularly enjoyable for me, and since brides have embraced Tipsy Skipperflip-flops, clutches, and bridesmaids’ gifts, I’ve had many chances to make each oneunique and memorable. I’d love to expand this part of the business and hope customprojects will become more numerous. Another lively market has been the college-age customer, and in particular, sororities. The ‘university set’ represents a significantsegment of my clientele, so making Tipsy Skipper more accessible on campuses aroundthe country is certainly on my mind!

Preppy designer icon Lilly Pulitzer died just last week. I know you interned at Lilly in the Print Department. Was she an influence on your brand?

She’s an incredible influence to so many people, and she really paved the way for so many designers – myself included. I’ve always been inspired by her designs, and I actually have many of my mother’s and grandmother’s Lilly pieces – originals! She also had an influence in recent years as the LP designers would consult her and show her the season lineups. The print designers at Lilly always start their designs by hand, and this is something that has always stuck with me with my own print designs. Every print is a painting or illustration first – it really makes a huge difference from designs that start out on the computer. Lilly’s use of color and her lack of fear for expressing color at any season was really unique. It’s ‘Happy Clothing’ as she always said. Looking at her designs is like smelling flowers – it evokes all sorts of happy emotions! I’ve certainly been influenced by her palette – my designs for Tipsy Skipper are colorful, and I’ve always been known for wearing brights no matter what time of year. Bright colors and bold prints just make people smile.

Who are your influencers or role models (besides Lilly Pulitzer)?

I’ve been influenced by many entrepreneurs who have created brands around theirlifestyles; Jonathan Adler, Kate Spade, and Elizabeth McKay, to name a few. However, I think I’m most inspired by the growing community of bloggers and social networkerswho are using their skills to reach new audiences and call attention to brands like mine.They may not be recognized yet as ‘household names’, but I have great admiration for what they are doing and think they are becoming more important by the day. The rate of growth of Tipsy Skipper would never have been possible without this viral communication – it’s quite literally the backbone of small start-ups today. How well entrepreneurs utilize social networking opportunities can make a tremendous differencein how quickly they grow. It has been absolutely critical for me.

You can follow Kearsley @Tipsy_Skipper or Facebook.

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