How a Talented Baker Took a Whisk and Turned Her Passion Into a Sweet Gig

By day, Jennifer Jacobs is an associate producer for the Home Shopping Network. But when 5 o’clock rolls around, she disappears into her kitchen, taps play on her favorite podcast, Radio Cherry Bombe (aptly about creative and powerful women in the food industry) and starts filling orders.

As the 30-year-old owner, baker, cake designer, taste tester, dishwasher, bill payer and grocery shopper of Wandering Whisk Bakeshop, Jacobs estimates she spends at least five hours in her kitchen each night.

Never did Jacobs think her hobby would turn into a full-fledged business — providing a comfortable side income that helped her buy her first home.

Let’s Whisk Back to Jacobs’ Baking Beginnings

A detail of a whisk
Jacobs works at HSN during the day and spends her evenings filling orders for her baking business, Wandering Whisk Bakeshop. Chris Zuppa/The Penny Hoarder

Some of Jacobs’ most vivid childhood memories place her alongside her mom as the duo churned out a variety of Christmas cookies, many harking back to their Romanian descent. None of them were particularly fancy — just good, comforting sweets.

When Jacobs entered high school, her friends became “obsessed” with the desserts.

She recalls they’d make up excuses around the holidays to stop by her parents’ house. “Oh, we want to come see your Christmas tree,” they’d say. The night would end with them indulging.

To this day, her friends expect an invite to “see the Christmas tree.”

After high school, Jacobs attended the University of Central Florida, where she studied event management. She didn’t spend any time in the kitchen until after graduation, when she took a high-stress job in New York City. Baking became her go-to method for unwinding at the end of her jam-packed workdays.

New York City exposed her to a vast array of new desserts. She was constantly sniffing out new neighborhood bakeries. Pinterest also boomed at this time, and Jacobs would spend hours pinning new treats to her virtual inspiration board.

There was only one complication…

“I had this miniature oven that didn’t even fit a full-size cookie sheet,” Jacobs says. “I would bake on these tiny cookie sheets, but I would just do whatever I could.”

Still, baking remained a hobby. “I’d never at that point thought, ‘Oh, I could start a business from it,’” she says.

But things changed when she discovered red velvet cookie sandwiches — that’s when baking shifted from a hobby to a side gig.

How Red Velvet Cookie Sandwiches Sparked a Side Gig

Cake and cookies are pictured
A tasty assortment of Jacobs’s treats are on display. Chris Zuppa/The Penny Hoarder

After two years in New York, Jacobs began to burn out.

She moved back to the Tampa Bay area, where she took a job with HSN.

Her new work schedule — 5 p.m. to 2 a.m. — paired with a larger kitchen, allowed her plenty of time and space to bake during the day.

She began experimenting more and more. Around Valentine’s Day in 2014, she whipped up some red velvet cookies sandwiches and took them into work.

That day, two coworkers asked Jacobs if they could order more.

“I’m like, ‘Uh, sure, you can give me 20 bucks to make you cookies,’” Jacobs says. “And I remember going home being like, ‘Mom, someone wants to pay me for my cookies!’”

She took to her kitchen that night, baked two dozen cookie sandwiches and hand-delivered them the next morning. When she checked in to see how their families received the treats, her coworkers, only slightly ashamed, admitted they ate them before their families even had a chance.

The co-workers offered up another $20 to order more. (A dozen cookie sandwiches now go for $42.)

Jacobs laughs at the memory and says these cookie sandwiches now have a “cult following” at HSN.

“I like to think these were the start of my business,” Jacobs says of the cookie sandwiches.

At this time, she passed around handmade business cards that read, “Jen’s Cakes, Cupcakes & Sweets.” She catered to her family, friends and coworkers.

Invest In Yo’Self: Jacobs Finesses Her Homegrown Hobby

Jennifer Jacobs celebrates winning a cooking competition.
Jacobs celebrates winning a baking competition in 2016. Photo courtesy Jennifer Jacobs

Jacobs knew how to bake, but at that point in her career, her decorating skills were “real minimal.”

She started taking classes at her local JoAnn Fabric and Crafts. In 2015, she attended a one-week, intensive course at the San Francisco Baking Institute, a culinary school where she learned the science behind baking.

“I wanted to be able to develop recipes and not just be like, ‘Oh, I can follow a recipe,’” Jacobs says. “I wanted to learn why you need cream, butter and sugar. Why is it important to add salt to the recipe?”

Although the week-long trip cost her $3,000, Jacobs considers it one of the greatest things she’s ever done. Plus, she purchased her first white chef’s coat, which made her feel more confident. She also splurged and got a pink one, which she wears now.

Back home in Florida, Jacobs also frequented her local public library, checking out any and every baking resource it offered. She favored the Le Cordon Bleu textbooks. Her weekly book hauls became a joke at the library — that she’d run out of books to check out.

And she did. So she started scavenging other local libraries.

In August 2015, Jacobs decided to debut her skills to the public and, with some encouragement from a friend, entered the Great St. Pete Cupcake Contest.

There were  something like 75 entrants that year — half novice (that was Jacobs) and half professional. She took home third place in the novice category and first place in people’s choice for her Banana Nutella Cupcake, a banana cake layered with chocolate ganache and topped with Nutella buttercream icing.

In 2016, Jacobs entered the contest again, taking home people’s choice once more. But this time, the judges created an extra award specifically for her: best buttercream icing. Since then, the not-too-sweet topping has become one of her signature creations.

How Jacobs Set Herself Apart From Every Other Homebaker

Jacobs wears the signature apron that reflects her brand. Chris Zuppa/The Penny Hoarder

Jacobs hasn’t paid a penny for marketing or advertising. Her success has been a result of organically building a strong brand and a loyal following.

It started with the name: Wandering Whisk.

The wandering part, Jacobs says, represents her love for travel. Anywhere she goes, she researches bakeries. “I land, and I’m like there’s five bakeries of my list the first day,” she says. She hops from bakery to bakery, pocketing bits of inspiration along the way.

She’ll even glean creativity from cocktails, dinners and regional staples.

Take, for example, the time she traveled to Belgium. That’s where she fell in love with its cookie butter. She brought home containers of the sweet spread, which inspired her to create cookie butter cookie sandwiches, a chocolate-chip sea-salt cookie with crunchy cookie butter cream filling.

Then there was that time in Napa, when she picked lavender. The fragrant flower sparked an idea for a lavender macarons as well as a lemon lavender cake — lemon cake with a lavender glaze and layers of lavender buttercream.

“I’ll think, ‘Wow, that flavor’s really nice; I could translate that into a cake,’” she says. “I’m just baking little pieces from everywhere together.”

Once Jacobs nailed down a name and logo, her brother, Tyler, created her website. It was June 2016, and her venture was starting to feel concrete.

“I wanted to put it out that I’m a full-fledged business; I’m not just a girl in my kitchen,” she says. “It felt much more official.”

To lock down the business side, Jacobs established herself under the Florida Cottage Food Law, which means she doesn’t need a license or permit to operate, nor is her operation ever inspected. Basically, it means she’s allowed to work out of her home without having to go through tons of food licensing procedures.

Jacobs also has food liability insurance. Additionally, she’s crafted, with the help of a lawyer, a contract, which she sends out with each order. This contract protects her from any liabilities.

“It’s important to make sure you’re covering yourself,” she says.

Once all the logistical ends were tied, Jacobs began utilizing Instagram, a photo-centric social media platform that beautifully showcased her artful masterpieces. She has set up a makeshift studio and takes all her own photos with a refurbished camera she invested in.

Her Instagram strategy has been to focus locally. She says it’s great she gets followers from around the world, from as far away as Australia, but her goal is to turn her followers into a profit.

“It’s great when you have 20,000 followers, but if no one’s engaging with you, and no one’s ordering your product, it means nothing,” she says.

In order to capitalize on her Tampa Bay-area audience, she works with wedding planners to create stylized shoots that get shared on Instagram. She also takes part in local events, like St. Petersburg’s annual Localtopia festival, which posts to the platform.

“People that don’t take advantage of [Instagram]… I think it’s almost crazy, because it’s free publicity,” she says.

One of the best parts of gaining a following has been her uptick in order requests that fit her brand. A year ago, customers would ask for a cake like something they saw on Pinterest. Now, more and more requests feature Jacobs’ own work — a screenshot of one of her own Instagram posts.

Looking Toward Her Sweet Future

Jennifer Jacos holds up a cake.
Jacobs shows off a cake she decorated at The Penny Hoarder’s headquarters. Chris Zuppa/The Penny Hoarder

One question simmers: “What’s next?”

In 2017, Jacobs proved she could manage a full-time career while striking up a successful side business.

This year, she has hopes to hire her first Wandering Whisk employee. She’d also love to be featured on the “Today” show — or any national morning show, for that matter.

“I’ve also heard Harry and Meghan need a wedding cake,” she jokes. When rumors swirled that Prince Harry loves all things banana-flavored, Jacobs’ friends and family pegged her as the perfect fit. “Banana cake is my No. 1 cake…,” she says.

Whether or not she gets a call from the royal couple, Jacobs plans to keep on whisking.

If you want to learn more about how Jacobs turned her passion into a thriving side business, take a gander at her exclusive tips.

Carson Kohler (@CarsonKohler) is a staff writer at The Penny Hoarder. She could really go for one of those banana Nutella cupcakes right about… now.