Jennifer Shea – Founder of Trophy Cupcakes

Entrepreneur, baker, author, and cupcake lover are just some of the words used to describe Trophy Cupcakes founder Jennifer Shea. Jennifer had always loved cooking and baking, but it wasn’t until she saw a cupcake shop in New York City that she realized what she wanted to do. When she went on tour with a rock band doing marketing and promotions, she used that time to also test out different candy shops and bakeries around the U.S. and Europe.

Now, Trophy Cupcakes has four locations in Washington state. Jennifer has also written a cupcake cookbook and appeared on Martha Stewart – amazing! Even with all her success, Jennifer continues to be hardworking, kind, and generous with her time. It was incredible to discuss with Jennifer how she got to where she is today, challenges she faced along the way, and what it means to be a leader.

Name: Jennifer Shea
Education: BS in Nutrition and Dietetics from Bastyr University
Follow: @trophycupcakes / Instagram / Facebook / Trophy Cupcakes

Carpe Juvenis: How do you define ‘Seizing Your Youth’?

Jennifer Shea: It’s about identifying your dreams, your bliss, and really focusing on what you’re passionate about. It’s also about taking steps to make your dreams happen. The people who realize their dreams are the ones who put one foot in front of the other and just do it. Even if your dreams or goals seem out of reach, just start talking to people about how to accomplish them. You’ll be amazed how the pieces will start to come together.

CJ: You majored in Nutrition and Dietetics at Bastyr University. How did you determine what to study?

JS: I’ve always loved food (who doesn’t), especially cooking and baking. But I honestly had no idea what I wanted to do right out of high school. I was already interested in nutrition because I was a vegetarian at the time. But, because I couldn’t put my finger on what my passion was or what my career was going to be, I landed on nutrition by accident at a job fair. I came across Bastyr University’s booth and saw that they had a whole foods nutrition program, which sounded fascinating. I decided to just go for it.

CJ: You spent some time touring with a rock band doing marketing and promotions after college. What was that experience like and what did you learn from it?

JS: It was a really exciting time, but super hard, too, because it’s rough to live out of a suitcase day in and day out. I was glad I’d majored in nutrition, but I wasn’t seeing myself in that profession in a typical capacity. I happened to meet and date a guy soon after passing my boards and he asked me if I wanted to go on tour and sell T-shirts. To the horror of my mother, I said yes.

I’d worked really hard in school and had a full time job, so I needed a break and touring sounded like a dream come true. I also didn’t want to be the girlfriend stuck at home while her boyfriend was on tour doing who knows what. So, I basically created a position for myself in the band. I eventually called myself their Merchandise Manager and I figured out how to help make sure the band got all of the profits. I really got into figuring out what made their fans tick and what kind of merchandise they would love.

I introduced a whole line of pillowcases with song lyrics going across the cases and badges that were exclusive to each tour so as you went to more shows you could collect the different patches. I had a lot of fun with it, and it taught me a lot about merchandising and presentation. It was a good first experience with having my own little business.

CJ: You opened Trophy Cupcakes in Seattle in 2007. What inspired you to open a cupcake shop, and what does your role as founder entail?

JS: I first saw a cupcake shop while visiting NYC and I instantly knew it was what I wanted to do. My life flashed before my eyes. I realized that I’d been complaining that I didn’t know what my passion was, yet I baked all the time. I didn’t know that I could turn my hobby into a career. Touring was a great way to do research because I visited so many candy shops and patisseries in the U.S. and Europe. I took mental notes about architecture, design and perfect little details I saw.

My role as founder has changed a lot over the years and it’s always morphing. In the beginning, I did everything—from baking the cupcakes, to opening the register, to training and managing employees, to doing payroll, to coming up with new flavors and marketing. When you’re a small business, you have to do it all yourself. I should’ve just slept in my shop, really. I would get there at 4am and leave at 9pm. As we started to grow, I was able to bring in more experts.

Right now I focus on marketing, social media and innovation. I’m also our brand ambassador, making sure that we are living up to our brand promise and that my team understands what that is. I also act as the face of the company. I do several speaking gigs each year about how I got started. I also teach classes in my shops and online through Craftsy.com. I also wrote a book, which took a lot of my time, but was totally worth it.

CJ: In your role as founder, leadership is important. How have you learned to lead and what does it meant to be a leader?

JS: That has probably been the most challenging part of having a company. I haven’t always been a good leader and work really hard at it now. I think being a good leader means understanding how differently people work. It’s not a one-size-fits-all situation. Everyone has a different way of getting motivated and inspired. You have to really listen…really see people. If you can take the time to see what makes people tick, you will have a much easier time inspiring them and leading them to represent your company the way that you want.

On another level, I try to inspire others to do something amazing with their lives beyond Trophy. I like telling people my story because I didn’t come from a background where I had parents who pushed me toward business. I didn’t have money or experience that would have made you guess I could do this. I really just followed my dreams and figured it out along the way. The more I believed I could do it, the more the doors to success just kept opening right in front of me.

CJ: What have been the greatest challenges in running your company, and what do you wish you had known before opening your shop?

JS: Entrepreneurs have to be naive because if they knew how hard it was before they started, they wouldn’t do it. I always say that entrepreneurs succeed because they don’t know any better.  I didn’t know anything when I started. I had taken some business courses as part of my registered dietician training, but I didn’t have any experience with the business of baking.

I wish I’d known there are so many people out there willing to help you and you don’t have to do it all by yourself. I have that type of personality where I think I have to do everything myself, but I learned that it’s okay to ask for help and that there are all kinds of women/young entrepreneur groups in just about every area that can be super helpful. I also wish I had asked someone to be my mentor earlier on, so that he or she could give me pep talks. I recommend finding a support system—a group or person—that can help you with business-specific problems along the way.

The thing I wasn’t expecting was for me to stop baking. I thought I was always going to be the one baking the cupcakes, but the more I learned about business, the more I realized that when you run a business there’s a point where you have to be steering the ship and looking at the big picture. If I was in the kitchen for 8-10 hours per day, I wouldn’t be able to determine our next move.

CJ: Almost a year ago you published your first book, Trophy Cupcakes and Parties. We love that your book not only provides recipes, but also party how-to’s. What was your book writing process like?

JS: The publisher came to me and asked if I wanted to write a cookbook. That sounded exciting right off the bat but I knew the cupcake cookbook world was already saturated. (I have so many of them myself!) I said I loved the idea of writing a book, but in order for it to be marketable it needed to have more than just recipes. I wanted to help people learn how to plan parties. I also wanted to appeal to more than just bakers.

Little did I know this book would be 10 times as much work as a cookbook. Every single cupcake recipe includes party ideas and a craft, plus suggestions for décor, drinks, and food. Writing all of that content and then photographing it was challenging. But I love the way it turned out. I tried not to do anything that would be dated; I wanted everything to be classic so the book would always be relevant.

Touring with the book through Williams Sonoma stores was super fun and I love that I now have fans across the country and beyond!

CJ: What should a teenager or young adult who wants to have their own bakery and run their own business do now to set themselves up for success?

JS: Believe you can accomplish your dreams, then know that believing is half the battle, doing is the rest. Also, embrace your fear! Everyone is scared. The key is to know that fear is a part of the process and not be paralyzed by it. This mentality is not necessarily easy if you weren’t raised that way. I started reading books about manifesting and having an abundant state of mind, and that really changed my life. I also started doing guided meditations focused on love, success and manifesting…amazing! I would also recommend traveling and going out of your way to meet people who are inspirational to you. You can meet almost anyone if you come from an authentic place, and you’re not pushy. Most people are happy to help you or answer questions. Sometimes even brief encounters can really end up paving a road for you.

I believe in synchronicity and that if you’re following your dreams, the universe will end up putting things in your path that will help you down the road. Be adventurous and put yourself out there even if you don’t know where you’re going. I didn’t necessarily know where I was going. If I hadn’t gone on tour (and horrified my mother), Trophy may not exist today.

CJ: What does a day in your life look like? How do you balance your career roles and goals? How do you stay organized and efficient?

JS: Every day is a little different, depending on what projects I’m working on. And as an owner, you have to wear lots of hats. But usually, I wake up early and meditate (this sets the tone for my day), then I get my son ready for school. My workday starts with checking in with the bakery, which is the heart of our business. I really like knowing first thing in the morning that the bake has gone well and that everything in our stores is “Trophy-quality.” I try to visit each shop and I check in with our general manager, work on social media, and talk to employees working on different projects. I may do a talk for a local Girl Scouts or entrepreneurs group. Or, I may have back-to-back meetings about a million different things. My goal is to get to a point where I make sure to do something for myself each day beyond meditating.

Balance…it’s super tricky. If you are super passionate about what you’re doing, it’s very easy to lose site of family, friends and even yourself. I have learned that it’s very important to take time out of your business path for self-care. If you are not well rested, taking the time to recharge (through exercise, spending time with family or reading a good book), you will eventually crash and burn. You cannot be a good boss, entrepreneur, friend, (fill in the blank) if you don’t make time for yourself to recharge each day.

I stay organized through using tools like Basecamp — it keeps all of my to-do lists in one place. I also use my calendar religiously so that I don’t overbook or forget meetings. I also try to never schedule meetings for Mondays. That gives me an entire day to plan my week and tie up any loose ends from the previous week.

CJ: You have had many amazing career moments in such a short period of time, such as being featured in Vanity Fair magazine, appearing on The Martha Stewart show, and releasing your first book. What other goals do you have for Trophy?

JS: My goal is to continue figuring out how to make Trophy a relevant and inspiring business to the community and to myself. What we do is about so much more than cupcakes. We sell little pieces of happiness and people feel emotionally invested in it. I’ve seen people eating Trophy cupcakes on their first date. I’ve also seen people serve Trophy cupcakes at their wedding, and then again at their baby shower.

The best businesses stay fluid and I think there always has to be a fresh idea and a new outlook for what Trophy is giving to everyone. That’s what I stay focused on. I also really want to open something that’s exciting with more offerings and where people can have more celebrations.

CJ: What is your favorite book?

JS: Daring Greatly by Brené Brown.

CJ: If you could enjoy an afternoon eating cupcakes with anyone in the world, dead or alive, who would it be and what kind of cupcake would you bake?

JS: My dad. He passed away when I was a baby, so getting to spend an afternoon with him would be a dream come true. I would create an angel food cupcake with chocolate whipped cream filling for him. It was his favorite type of cake that my grandma used to make him.

CJ: What advice would you give your 20-year-old self?

JS: I would tell my 20-year-old-self to believe in me, and the power of the universe. It took a lot of years before I believed that I really could do anything. I spent a lot of years flailing and not really seeing that I had a passion. Who knew that your hobby, what you love to do most, could be your career?! I’d tell me, “Just get out there make your dreams happen!”

Jennifer Shea Qs

Images by Carpe Juvenis