It Ain't Over (8 page)

“It’s a Disneyland for deejays,” Heather says. They were even on the beaches. At dusk, “they would literally play a soundtrack to the sunset, timing it so the final piece had this big crescendo as the sun made its last little dip into the water. It was an art form. People applauded when it was over.”

When Heather left Ibiza, she needed a separate suitcase for all the music she bought.

“I thought,
If I can bring just a tiny bit of this back home, I’ll be offering something special.
”

Heather knew good music. But the mechanics of a deejay’s work? That she had to learn. For example, deejays create special effects to rev up a crowd, repeating a cool section of a song over and over or pulling out the bass for an uplifting beat. Most challenging is transitioning from one song to the next, matching the bass beats for a seamless sound. “When you do that wrong, deejays call it ‘boots in the dryer’ because it goes
ba-bump, ba-bump,
” Heather says. “If you’ve got a dance floor going and you mess up a mix, everything stops. Managing a dance floor is high pressure.”

Next, Heather bought a sound-mixer with two CD players for $200, but they sat in the box for six months. “I was totally intimidated.”

Finally, her friend said, “I’m having a fortieth birthday party and you’re deejaying it!”

With only two weeks’ notice, Heather started figuring out how her mixer worked. She deejayed the party, and though her skills were basic, her set was a hit. “And I was hooked,” she says.

Heather finally got a break at a hip Georgetown sushi lounge. The owner put on one of her mixes and a woman in the crowd, who happened to be a young, hip deejay, loved it. “That was huge for me,” Heather says. “She was telling me
I’ve
got good taste.”

Over the next year, Heather learned how to use professional equipment
and met deejays, who would invite her to come to shows and sit in their booths. While she did have some screwups (“I had my share of ‘boots in the dryer’ ”), her new career steadily flourished. By day, she was a full-time mom. But at night or on weekends, with the help of babysitters, her husband, and her mom, who took turns watching the kids, she was usually booked several times a week—a coup in an industry dominated by guys in their twenties. She has spun music in Times Square windows, at parties at the Smithsonian, and at trendy dance clubs all over Washington.

Every gig is different. “One year I did a party at the Jefferson Building here in D.C. They wanted the music to reflect the nature of the classical architecture, so I chose house music with beautiful strings and piano woven in with dance beats. And for a dinner party at an art gallery, the client wanted music that simulated a heartbeat. I did all this research and used American Indian and aboriginal drumbeats. It was challenging, but it was fun to stay on theme.”

Not bad for a woman who is inching her way toward 50.

“When I get my mind set on something I’m just not going to give up,” Heather says, even if that means that along with her fabulous outfit she has to wear reading glasses to see her song list under a club’s dim lights.

“It took a lot of guts to do this at my age, but it comes from an authentic place. I love the music I play.”

Kristi Cunningham Whitfield, 43

Washington, D.C.

F
ive months after Kristi Cunningham and her boyfriend, Sam Whitfield, started dating, he proposed—a business idea, that is.

“We were cooking dinner and having one of those ‘How was your day?’ conversations,” Kristi recalls, “when suddenly he turned to me and asked, ‘What would you think about opening a cupcake truck?’ ” Kristi recalls.

“A cupcake truck? You’re a lawyer, and I’m in transportation logistics. What do we know about cupcakes? Or trucks?”

Sam told Kristi that he and his fellow attorneys had been craving cupcakes that day but no one felt like trekking to a bakery across town to get any. “What if we started a business to bring cupcakes to customers’ neighborhoods?” he asked.

“I actually thought it was a pretty great idea,” Kristi says. “And my mind started whirring: How would it work, exactly? What kind of truck would we get? What flavors of cupcakes would we sell? We just started creating the business in our imaginations.”

The more they brainstormed, the better the idea seemed: There was just one other food truck in all of D.C., and cupcakes seemed like a perfect “truck stop” food: easily portable impulse buys that wouldn’t need a full kitchen setup onboard.

“We had taken a trip up to New York, where cupcakes seemed to be
everywhere
. I figured the cupcake trend would trickle down to D.C. and take off here, too.”

Kristi wasn’t exactly looking for a new career; she was doing well in her corporate job. But after a few months of fantasizing, Kristi and Sam couldn’t let the idea go.

“I remember the distinct moment when Sam looked at me and said, ‘Are we really gonna do this?’ I think we both understood that we weren’t just talking about the business; we were also talking about our relationship. We were in love. If we did this together, how could it not be awesome? So we said, let’s go for it.”

Their first step was to recruit friends and coworkers for a little market research. “We weren’t really worried about whether people would like cupcakes. The real questions were: Would you be willing to eat them off a truck? How much would you pay for a cupcake? And how far would you walk to get it?” The friends were skeptical—but intrigued.

But if they were going to do it, Kristi wanted to do it fast. “I was so nervous that someone else was going to beat us to it, and I was laser-focused on being the
first
cupcake truck—not the second, not the third.”

Since food trucks weren’t common in D.C., there was no well-established playbook for how to get this off the ground. So they cobbled one together. “I was navigating the Department of Health, filling out a million forms, waiting for licenses. And the people who worked at the Department of Consumer and Regulatory Affairs practically thought I
lived
there.”

After learning that the city required the truck to be a certain length and width, Kristi came across the perfect vehicle for sale in Florida. The couple bought a one-way plane ticket, drove the truck around the block twice, bought it, and then drove it home.

“That trip made the business real. It’s one thing to fill out the paperwork to incorporate a business, it was another to fly to Florida and buy a truck!”

After that, says Kristi, “it was like filling in a Mad Libs business plan:
What color should the truck be?
Pink!
What should the logo look like?
A cupcake on wheels!
Should we bake the cupcakes ourselves?
No, let’s hire a professional.”

As the business started to take shape, some friends and family began expressing their doubts. “There were a lot of ‘Are you out of your minds? How are you going to support yourselves?’ ” says Kristi. “We were launching at the beginning of a recession, and people assumed we’d lost our jobs. They couldn’t fathom that we were quitting our careers to start this whole new endeavor.”

Kristi says, “I knew it was crazy, but we just did it anyway.” Still, she admits there were wobbles along the way. “We were learning about each other and each other’s work styles at the same time. Sam’s more methodical and likes to plan things out; I’m more flexible and fly by the seat of my pants. But we’ve figured it out and adapted, both personally and professionally.”

Six months after Sam first brought up the food truck idea, the pair were ready to debut their cupcakes with a stand at the city’s popular H Street Festival. Though they made some rookie mistakes (“We charged $2.75 each, which meant we needed gobs and gobs of change—after that we raised the price to $3”), they sold out of the 600 cupcakes that they had brought. Three months later, once the truck was outfitted with a vending window and had passed inspection, Curbside Cupcakes set out on its first route.

And a few weeks after that—one year to the day after they started dating—Sam proposed again. This time, he meant marriage.

“In the beginning, it was just the two of us, plus the professional baker we hired,” says Kristi. “Every morning, Sam would drive to the commercial kitchen, pick up the cupcakes, and head out in the truck, while I managed planning and marketing.”

Within a couple of months, it was clear the truck was a hit. “We were a novelty, so people would see this bright pink truck and follow it just to see what it was,” she says. Sam would make four scheduled stops a day, plus a “wild card” location based on the number of requests they received via Facebook and Twitter.

As Curbside Cupcakes began taking off, selling out hundreds of cupcakes each day, Kristi and Sam realized it didn’t make sense to continue outsourcing the baking—it was eating up too much of their costs, and the baker wasn’t always available. So, you guessed it: Kristi took over cupcake-making duties, too.

“I was nervous. I know what tastes good, but I’m not a culinary school graduate—this was a business idea. So I started in my home kitchen with one recipe—for chocolate cake. And after thousands and thousands of batches, which Sam and I taste-tested, we hit on a winning recipe.” Then they tackled Curbside’s other bestselling flavors, like carrot cake and red velvet.

Today, Curbside Cupcakes operates three trucks, a kiosk in D.C.’s Union Market, and has a new commercial kitchen with a small café. The business sells hundreds of $3 cupcakes a day in 37 flavors—from key lime to peanut butter cup to dulce de leche—and caters special events, like the time Ford Motor Company bought 1,400 cupcakes in one day.

And two years after they married, Kristi and Sam welcomed another addition to the Curbside Cupcakes family: a baby boy. “The first three months after Drake was born, I would wrap him up in a carrier and bake with him sitting on my chest,” she says. “I’m deeply grateful to be my own boss, to be able to be with my kid and never have to explain my choices to anybody.”

But with all their success, becoming a part of their customers’ lives is their greatest reward.

“We make cupcakes. And that means we get to be involved in people’s celebrations—their birthday parties, their bar mitzvahs, their weddings, their special moments,” including a marriage proposal one guy planned around a special Curbside Cupcakes delivery.

“Back in the early days, when Sam and I would spend hours fantasizing about how exciting it would be to open our own business, we dreamed big. But this is bigger than anything we ever imagined.”

And that’s the icing on the cupcake.

Gaylee McCracken, 61

Cleveland Heights, Ohio

W
hen Gaylee McCracken was just seven years old, her mother was diagnosed with breast cancer. Even at that tender age, she felt drawn to caring for her mother. She also felt scared. Helpless. But she remembers feeling something else: curiosity.

Other children might have reacted to surgery scars and hair loss with an emphatic “Yeccch!,” but Gaylee was fascinated by how the body worked. Soon she was envisioning herself wearing a stethoscope and white coat like the doctors who cared for her mother, and she began to fantasize that she, too, might one day go to medical school.

But when she shared this with her father, an Italian gentleman of the old school, his response was discouraging. “Don’t be a doctor,” he told her. “Marry one.”

Dad wasn’t expressing a chauvinistic attitude, Gaylee believes, but rather the simpler, harder view that life was tough and seldom very kind to
dreamers. “He came from a poor immigrant family and had to drop out of school himself,” she says. “In his mind, dreams were for rich people. People like us had to be practical.”

So practical she became. Gaylee devoted her energies to her studies, winning a scholarship to Bowling Green University, where she majored in English and art. After graduation, she applied for a job as an in-house graphic designer at Case Western Reserve University, where her husband was beginning law school. “I was one of five finalists for the position,” Gaylee recalls. “Our test was to design a brochure. I wanted to distinguish myself, to set myself apart. So I rewrote it.” Gaylee’s display of chutzpah was rewarded: She got the job.