When I first found out Jennifer Shea, the brains and beauty behind Trophy Cupcakes, was coming to Chicago on her book tour I’ll admit, I wasn’t super intrigued.  Baking has never been my thing, we’ve all been to our fair share of cupcake shops, and I’d take a pepperoni pizza over a sweet treat every time.  However, when I found out Jennifer’s book signing was happening at one of my favorite Chicago shops, Magnificent Milestones, I figured I’d google Jennifer and find out what this cupcake craziness is all about… and I’m so glad I did!

First of all, Jennifer’s story isn’t exactly as “vanilla” as owning a cupcake shop (or 5) may sound.  She turned down her first real job offer to go on tour with a major rock band (I’ll tell you who later) and sell t-shirts… yeah, keep reading!  She eloped to Hawaii just her and her husband, would ideally dine with David Bowie and Mother Teresa… oh, and that little cupcake shop?  Turns out she’s not just your town baker.  This girl is a business woman, and she’s sitting a top a cupcake empire!

Needless to say, I was impressed!  So impressed, that this Thursday I’ll be hosting Jennifer’s book signing at Magnificent Milestones.  Check out my interview with Jennifer and then come see us Thursday night!

In a world of cakepops, macaroons, brownies, cookies, and even croughnuts… Why cupcakes? Cake is a part of our history. Ever since the invention of flour, cake has been a part of human celebrations. In the past, you had to wait for a very special occasion to enjoy a slice of cake, but cupcake shops have made it possible to celebrate with this delectable treat any day you like. Yes, cupcakes were a fad and the media has moved onto macaroons and croughnuts, but cupcakes are here to stay! They’re simply the perfect celebratory treat. They are cute, individual, customizable, portable and delicious (when done right!).

Cupcake shops and bakeries seem to be in every neighborhood these days, what about your first shop in Seattle has garnered national attention from the likes of Vanity Fair, Martha Stewart, etc.?  In other words, what’s the secret ingredient in your success?

Other than really good butter, I’d say the secret ingredient to my success is passion. I searched for that “perfect fit” for years, then one day in New York City, I walked into a cupcake bakery and it hit me! I had been baking my entire life and in that moment, knew immediately what I wanted to do. I started cultivating the idea for Trophy Cupcakes in 1996 and opened early in the game, so we received a lot of attention right away as one of the “next big things.”

However, I didn’t open the shop because I knew cupcakes were going to be a fad. I opened it because I have a genuine passion for baking amazing cakes and wanted to bring love, happiness, celebration and a little piece of perfection into people’s lives. My cupcakes and that idea struck a cord immediately. Soon after we opened, I was invited to be on the Martha Stewart show and Trophy was featured in countless magazines and on a number of TV shows. I believe when you find your true passion and move toward it, success follows – as long as you believe in your dream and allow yourself have it.

We think rock and roll makes the world go round!  Will you tell our readers the roll that rock played in sparking the idea for your business and getting it off the ground?

Well, I received my degree in Nutrition. I worked my way through school and was quite tired when I finished. As fate would have it, I met a boy right as I was being offered a “real job.” He asked me if I wanted to go on tour and sell t-shirts for his band. Hmmm…real job or go on tour with a rock and roll band? To the horror of my mom, I chose to go on tour and the most amazing thing happened. I became friends with another one of the band members (who was also in this band called The Foo Fighters), and ended up sharing my cupcake dream with him. To my surprise, he offered to be my investor! I then used touring around the world as an opportunity to visit every bakery, patisserie, candy shop and confectionery I could find, which helped me create the Trophy brand. So, going on tour was the best “bad” decision I ever made!

These days you’ve settled down with your husband and son, how do you balance work with your personal life?

Finding balance is my biggest challenge. It’s so easy to get caught up in and overwhelmed by a career, especially one you are so passionate about. I often feel totally frazzled. Having a child has really helped me though; he has helped me learn to slow down and laugh more. I now try to focus on taking care of myself first, then family, and then focus on work. If I feel balanced personally, I’m a much better mom, wife, friend and business owner.

I can only imagine how many weddings Trophy Cupcakes have been apart of, what was your own wedding like?  

It’s funny because I am one of those girls who planned her wedding in her head her whole life. But I ended up eloping! I had always wanted a big wedding, but Trophy was in full swing and I got pregnant after our engagement. So, we just hopped on a plane to Hawaii and had a lovely wedding (just the two of us) on the big island, followed by a two-week honeymoon. Someday, we will have a reception!

What’s the best party you’ve thrown in the past year?

A Rock and Roll Fifth Birthday Party for my son. We hosted it at a local rock club, complete with a kiddie rock band, tattoo parlor and merchandise booth. Everyone had so much fun, including the adults. Many of the parents said it was the best time they’d had in years, and they couldn’t remember the last time they’d been to a rock club!

You and your husband are having a dinner party and you can invite 6 people (living or dead) go!

This is a hard question! I’m going to go with: Martha Stewart, Buddha, Albert Einstein, Wes Anderson, David Bowie and Mother Theresa

While your business is clearly expanding is it ever difficult to think about something as specific as cupcakes everyday?  How do you keep the creativity flowing and the ideas fresh? 

It can be difficult, but also really nice because we can focus on doing one thing really well. I have found the best way for me to keep creativity and fresh ideas flowing is to take care of myself. If I don’t step back and take time for myself, everything suffers. It’s a hard commitment to make because it’s so easy to say “I’m too busy to eat right” or “I’m too busy to take a vacation.” But, I can guarantee making yourself a priority makes your whole life better, both personally and professionally.

What’s one of the strangest order requests you’ve had at the bakery?  

I can’t think of anything super strange, but we do get custom orders for just about anything you can think of, which are actually really fun to do. Black Sabbath cupcakes, periodic chart cupcakes, cupcakes with pictures of people’s dogs on them, boobie cupcakes (for a breast cancer fund raiser). We’ve done it all!

What’s your favorite thing featured in the book? 

That would be the Lavender Crème Brulee Cupcake featured in The Paris Party. I created that recipe through a lot of trial and tribulation, and am so happy I finally got it to work. It’s not the easiest recipe in the world – but it’s so good!

Where do you see TC in 5 years? 10?

That’s a hard one! I can think of five scenarios that would all make me very happy. I have learned to keep a wide-open mind about what could happen with the business because so far it has exceeded my wildest dreams. What I do know is that I need to dream really big and just see what happens next!

[Photos by Rina Jordan]


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4 Responses to Getting to Know Jennifer Shea of Trophy Cupcakes

  1. giedre says:

    How fun! And now I’m totally craving a cupcake. ;)

  2. What a wonderful interview! Loved hearing Jennifer’s story + inspiration. xo, Laura

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