Gwendolyn Rogers’s Bittersweet Path To The Cake Bake Shop

If Gwendolyn Rogers were a cake, she’d be Red Velvet, pink roses on the outside with a bittersweet, dark filling. She was born in New Orleans in 1965. Her parents divorced when she was 6. Her brother lived with her father. She lived with her mother, who remarried and moved the family to Seattle and then Idaho.

“She started baking cakes when she was too little to even reach the counter, so she would stand on a chair,” her mother, Diane Cooper, recalls. “She would make funny cakes for Halloween, birthday parties.”

For Rogers, baking was a pleasant distraction from an otherwise difficult childhood. She insists she was an ugly duckling—a bit chunky, with glasses and braces. (Her nickname was Donut.) Her mother’s second marriage dissolved. Her older brother died in a motorcycle accident when he was 21. In an act of spite, her father delayed the funeral so it landed on Mother’s Day.

“I basically raised myself. No offense to my mom. She would admit she was going through difficult times,” says Rogers, who now talks to her mom every day. “I look back, and I wouldn’t have it any different. If it hadn’t been like that, I wouldn’t be as independent as I am.”

After high school, Rogers enrolled in the San Francisco Art Institute to study photography, but had to drop out because she couldn’t handle the tuition. She landed a booking job at L.A. Gear, where she worked with star athletes like Joe Montana. Broke, she slept in her car a few nights before her friend Ed Flory, one of the models she hired, lent her his couch.

Flory remembers Rogers as a good agent, one who made sure he was taken care of. Even in those early years, her entrepreneurial spirit was apparent. “She was aggressive,” he says. “She always wanted to be seen as a business person, always looking for better opportunities.”

In 1987, Rogers moved to L.A. to work for a modeling agency. Through a series of connections, she met J.B. Rogers, who had grown up in Indy and graduated from Park Tudor School. J.B. hired Gwendolyn as production assistant on a movie that eventually lost its funding. She didn’t see him again until they met at a party a year later. J.B. stood out from most of the guys in L.A. because he was a gentleman, Rogers says. And unlike the models she knew, he wasn’t poor.

After dating for five years, they married in 1995 and moved to Sun Valley, Idaho, where they had three kids. Using that as a base, J.B. worked as assistant director on hits such as There’s Something About Mary (1998) and American Pie (1999). They bought land and built a dream house. Rogers skied four hours a day and picked up her boys after school.

She planned to live out her days in that fresh mountain air. Everything was perfect until the stock market crashed in 2000. The good news was that Rogers had yanked her husband’s life savings out of the market and poured it into the house before the downturn. The bad news was they still couldn’t pay the mortgage when Hollywood production dried up. The only way to save the house was to rent it, move to Indiana, and live with her mother-in-law here. Rogers posted the home on upscale rental sites for big money—sometimes $30,000 a month. Renting the house became her part-time job.

During this period, Rogers also began to dream about opening a sit-down bakery. Indy needed such a place. She used to buy doughnutholes from Taylor’s Bakery, eat them in her car, and think, God, I wish there was a place I could sit and have a nice cup of coffee and eat my doughnut and not feel like a closet eater.

A friend gave her some tough advice: Work out of your home for five years and see if you garner a following. Rogers was skeptical. She was pushing 50. She didn’t have five years. But for about three, she baked desserts and gave them to friends to sample. When one offered her $60 for a cake, she was thrilled to cover the cost of her ingredients. Word got around. She catered.

“Another incentive was that I am tired of being the girl cooking,” Rogers says. “I want to be the girl having the party. That was a goal: To get to that next level where someone else would cook for me. What would that feel like? I am still working on that part.”

In 2013, she entered a cake contest in London and made the initial cut from a pool of 3,000. The next step: send a photo of the cake and write an essay explaining why she wanted to be in the contest and what made her cake so great.

“I booked a ticket and I wasn’t even in the contest yet,” she says. (If she had waited until the last minute, she couldn’t have used her airline miles.) “This is how I do things. I just do it and hope it’s going to be. Instead of waiting for it to become, I just make it happen—as it’s happening.”

Her mother-in-law thought she was insane.

A week before the contest, Rogers learned she had made it into the final 30 and “Could she and her cake be in London by Wednesday?” She could. She already had a ticket.

Rogers packed two huge suitcases of cake materials. She couldn’t afford a hotel, so she stayed with a British couple, friends of a friend. She brought her 9-year-old son, Weston, on a companion ticket. Her British host family had a tiny oven that held a single cake pan. It ran on Celsius. They didn’t have a mixer. Rogers made two cakes in case one flopped. It was “eight hours of stories, music, and me baking. I made two cakes. They both turned out perfect. Of course, I gave one to them because they were so kind.” She and her son slept in the attic and listened to the rain. “It was magical,” she says.

The British couple drove her and her cake to the convention center the next morning. When the judge, celebrity chef Peter Sidwell, host of the weekly TV show Britain’s Best Bakery, walked in, women screamed, snapped selfies, pressed for autographs.

“My legs were literally shaking, I was so nervous,” Rogers says. “Oh my God, what have I gotten myself into? There were all these other cakes lined up on the table. I was the only chocolate.” Her cake was so, well, American: no nuts, no fruit. Sidwell winnowed the competition down to three, sampled each again, and pointed to Rogers.

“It was the most amazing day of my life,” Rogers says. “I was like, If someone else liked it who judges cakes all day long, then maybe I can actually do this.”

But that was just the beginning. She had her eye on a Broad Ripple cottage she thought would make a good bakery, but she had to secure a bank loan and renovate it. She built fake cherry trees and hunted down twinkling lights from the Netherlands. She shopped all over for uniforms, then had the idea to embroider her logo over the back pockets of the khakis so staffers couldn’t carry their cell phones. She schlepped decorations from unsavory storage units without lights. For four years, she has washed staff uniforms at home to save money. “People think I have money like crazy but I don’t,” she says. “I am still struggling.”

Sitting in the Broad Ripple Cake Bake, she opens her laptop and pulls up a photograph of her old house in Idaho (now sold) on a rental website. She points to a photo of her former kitchen, then to the Cake Bake bar. Same faucets. Same sink. Same pillows. Then it clicks: Cake Bake was a way to rebuild what she’d lost. Only instead of a house, she built a restaurant. A pretty space filled with pretty things. A place that made her happy.

Rogers with her dedicated staff

Is any cake worth $15 a slice? Rogers gives me a piece of chocolate cake to sample. I’m no foodie, but it was the best chocolate cake I can remember. Moist, almost earthy, not too sweet but not bitter either. The double layers of ganache and malty fluff were creamy and pungent. The frosting was serious, a commitment. In all, four chocolate melodies forming a symphony of yum. The slice was enormous. It took me four sittings to finish it. My pretty pink box sat in the fridge while I scorned inferior sweets on the counter and eventually threw them away. Why settle for less? It was the best $15 I didn’t spend.

Of course, not everyone loves Cake Bake. When people complain about the place, they mostly roll their eyes at the prices. Rogers makes no apologies. Madagascan vanilla beans, Valrhona chocolate, fleur de sel harvested from the Isle of Rhe in Southern France—such fixings don’t come cheap. The ingredients of her signature chocolate cake cost $52.86, she says, not including labor. (The cake takes four hours to make.) Her Inside Out German Chocolate Cake is topped with Belgian chocolate fudge, toasted coconut, pecans, and almonds. The carrot cake is decorated with mini silk roses. On the bakery website, each dessert is photographed in soft lighting on her Pillivuyt French Porcelain Cake Stand ($210).

“It’s not enough for it to taste good,” she says. “It has to look good, too.”

With three layers of Valrhona chocolate, the Caramel Popcorn Cake (which costs as much as $185) typifies Roger’s luxe approach to baking. “It’s not enough for it to taste good,” she says. “It has to look good, too.”

This promise holds even when a cake is delivered to say, Oprah, who put Cake Bake’s mint chocolate chip cake on her “O” List in April 2018. Shipping is a 30-step process. After baking, the cake is immediately frozen and wrapped in an acetate collar, bubble wrap, dry ice, a Cake Bake box with a silver-foil-pink-satin ribbon, stickers, a card, care instructions, an insulated box, and finally a Cake Bake designer shipping box. Rogers figured all this out through trial and error, by ordering cakes from other companies and studying their technique. Packing supplies alone cost $32. She says she loses money shipping cakes, but it’s worth it. She’s building a brand. She spent $5,000 sending cakes to Williams-Sonoma before she landed a deal with them. She spent another $1,800 getting the cakes photographed.

Rogers knows when to spend money and when to bargain. “I guess it’s my Idaho upbringing—growing up a country bumpkin,” she says. “I don’t like paying full price for anything. Ever. I always feel like there has to be a better way.”

Other keys to her success: A masterful marketer, she puts her logos and patterns on everything, from rubber spatulas to pens to take-out napkin rings. It also helps to have a husband with Hollywood connections. And her timing was good. She rode the heels of the cupcake explosion ignited by Magnolia Bakery in New York City and Candace Nelson, who opened her first Sprinkles shop in Beverly Hills in 2005. But don’t call Cake Bake a cupcake shop.

“It’s not what I’m about,” Rogers says. “A cupcake shop is not about the experience. It’s just, ‘I want a sweet thing and I’m going to go, put it in a box, and I’m going to leave.’ Here you sit down and hear the music, the clanging of china, the laughter, and it becomes part of your day. A cupcake shop is not part of your day. It’s a drive-through.”

There’s another essential ingredient to Rogers’s success, one that plays out in real time as the owner greets a woman at one of Cake Bake’s little round tables. She returns to the bar brimming with excitement. “Her husband just happens to be Darius Rucker’s agent,” Rogers says. “I am going to see Darius Rucker tonight and I love him, and she’s like, ‘I’m going to get you in there.’ So I was like, ‘I want to bring him a cake,’ and she was like, ‘Let me call my husband right now.’”

This is Rogers’s signature move. She slips a pretty foot in the back door. Brings celebrities a free cake. Someone snaps a picture. Rogers posts it on social media. Orders flood in. If you can’t be Matt Damon, you can at least eat the same cake.

Of course, it doesn’t always work. John Mellencamp never responded, though six months later one of his people bought a bunch of cakes to take back to Bloomington. The Darius Rucker gambit may not pan out.

“We’ll see what happens,” Rogers says. “We’ll have to follow up with this story. I’ll let you know if I made it.”

As Rogers and I leave the Broad Ripple shop to drive to Carmel, a thin, blonde woman apologetically stops her and asks if she will pose for a photo. Erin Wirthwein, who is dealing with skin cancer, came out to enjoy an iced tea and chocolate silk pie on the patio. She calls Cake Bake a hidden gem, her happy place.

“I was feeling bad and I thought, You know what would make me happy? To come to Cake Bake,” Wirthwein says. “I called a girlfriend, but no one could come, and I said, ‘I don’t even care. I am going to enjoy this moment, sitting outside in the beautiful weather and surroundings.’ It has made me feel good today.”

She lathers Rogers with praise. “You’re just a doll. People walk in and they light up. I’m sitting by the door so I can see. They’re just in awe.”

Post photo, Rogers ducks back into Cake Bake, waves her magic wand, and the woman’s tab disappears. We climb into her car with the license plate TCBS. “It’s so sweet,” Rogers says. “See? I’m making a difference. If I make just one person happy, it makes everything I’m doing worthwhile.”

As we leave, Rogers receives a call from longtime employee Alison Sidwell on her cell phone. “I wanted to give you a call about your good deed,” she says. “She cried when she saw the bill, then she tipped Jess in cash for the exact amount.”

“Yeah, Jess!” Rogers says. “The good deed went all the way around full circle.”

Sidwell is used to her boss’s spontaneous generosity. When she quit a better-paying baking job to work minimum wage before Cake Bake even opened, Rogers promised they would go to Disney World some day. The bakery opened in November. Rogers took her to Disney the next month. Working at Cake Bake is seldom easy—bakers and servers pirouette around a cramped 308-square-foot kitchen—but Sidwell has no regrets.

“I took a huge risk and it continues to pay off,” she says. “I quickly learned that Gwen makes a lot of promises that are big, and she keeps them all.”

Since then, she has worked as a kitchen manager, personal assistant, retail manager, office administrator, and front house manager, although her official title, the one on her business card, is Fairytale Cake Designer. (Many staffers have Disneyesque titles. Dishwashers are called Porcelain Cleansing Specialists.) Sidwell credits Rogers with teaching her the importance of confidence.

“A lot of my job has been chasing after this person with all these huge ideas,” Sidwell says. “You pick up your feet and go as fast as you can.”

As Rogers enters Carmel, she oohs and ahs. Look at the woman watering flowers! Look at the fountain! We park. The location of the second Cake Bake is ideal, a corner retail space in Carmel City Center, steps away from the new $40 million boutique Hotel Carmichael set to open in Spring 2020.

Inside, the restaurant is under construction, a skeletal maze of steel posts. Men in hard hats balance on ladders and make noise. Unlike the Broad Ripple location, this one will serve a broader menu of savory entrées. She points out the future dining room, the two private rooms, the terrace, then downstairs to the bakery, a $47,000 oven that can cook 120 layers every half-hour, an 80-gallon mixer, the kitchen and laundry, then upstairs to the second floor, to the offices, the corner window, the view.

We stand on the balcony. Rogers imagines how it will all be. People leaving the Palladium will drop by for steak au poivre or a champagne nightcap, sitting outside in cafe chairs identical to those in the Tuileries Garden in Paris. She imported a chocolate-making machine from Italy. She ordered a unicorn for the front window. Rogers shipped the mythical beast to a mechanical wizard who will animate the creature’s head. A plain unicorn wasn’t good enough. Rogers wanted one that moved.

“I’ll have to decorate for Christmas,” she says as she gestures over the railing. “I have to put wreaths on every dormer. I have to put lights in every gutter.”

J.B. is excited for Carmel, even if the investment is a little scary. “Anyone is nervous when you’re on the line for big numbers,” he says. But he’s struck by how much the banks have changed their tune. When Gwendolyn proposed the first shop, “most banks wouldn’t even talk to her. She couldn’t get in the door,” he says. “They said, ‘No, no, no, no.’ The second time, the banks are calling her.”

Of course, Cake Bake isn’t the first bakery in Carmel. Kate Drury, founder of The Flying Cupcake, whose Carmel location sits across Rangeline Road from Rogers’s future location, says she isn’t worried about new competition. She supports female entrepreneurs. Any business that brightens the area is a good thing. “It’s exciting,” says Drury, who also has a restaurant in Zionsville. “The city center needs something like that.”

The Cake Bake Shop in Broad Ripple

With a laugh, Drury also warns that opening a second location means exponentially more work. She compares it to being a parent: One child is hard, but the second child is three times harder than one. Keep going and, at some point, you wonder: What did I do?

Stress, Rogers admits, is the worst part of her job. Some nights, she dreams she’s drowning. (She has separated the financials of her two restaurants in case one goes under.) She doesn’t want to disappoint anyone. Not a single customer. Someday, she hopes Cake Bake is bought out by a certain corporation she can’t name but isn’t hard to guess. Until then, life is work. She doesn’t have much time for friends. She twice canceled surgery to fix the painful veins in her leg. How does she relax? “I cook,” she says. “It’s my yoga, tennis, and therapy.”

Rogers’s old friend from Sun Valley, Colleen Weaver, understands why it’s so hard to get together. She also understands why Cake Bake succeeded in Indy. Rogers had the vision, the drive, the product, and the marketing savvy. She imagines Carmel will lead to bigger projects. “She’s a girl who dreamt a dream,” Weaver says. “She not only could see it, she believed it, and she could execute everything. That’s what makes her a superstar.”

Rogers and I ride back to Broad Ripple, where Cake Bake is still buzzing with lunching ladies. A young mother hugs a baby on her hip. They wear matching zebra shirts and shimmery gold tutus. Another customer rolls in an older woman in a wheelchair. She appears to have only one leg. Rogers is right. People aren’t just here for a sugar fix. They are hungry for happiness, a haven, an experience—some magical mix of Disney, Willy Wonka, and Tiffany wrapped up with a silver-foil-pink-satin ribbon. They want a to-go box. They want Pixie Glitter. They crave the fantasy that Gwendolyn Rogers delivers.

The next morning on the Cake Bake Facebook page, there’s a photo of Rogers, her husband, and Darius Rucker. Rogers arrived to the Ruoff Home Mortgage Music Center hours early and was escorted to a private area where Rucker’s trailer was parked. She held out her signature chocolate cake. And, yes, he let her in.