Oakleaf Cakes Bake Shop —a hidden gem of a bake shop in the heart of Back Bay, Boston —is the study and hangout spot for the thousands of college students in the area, including myself. On any given day, fresh baked goods are rotated daily and sit on a long, white display counter, surrounded by espresso machines, juicers, and tea kettles. This week alone, Oakleaf featured vegan sticky buns, chocolate chunk cookies, homemade marshmallows, red velvet cupcakes, and muffins. This small, neighborhood shop has been on quite the journey since founder Amanda Oakleaf and her partner first opened it in 2008 as students.

Oakleaf Cakes Bake Shop was founded by Amanda Oakleaf in the midst of the 2008 recession in her Boston basement studio apartment. At the time, Amanda was a MassArt student studying oil painting. It was the summer before her senior year, and she desperately needed a job. Itching to combine her creative passions for food service and art, Amanda was inspired to create a shop that produced made-from-scratch, fresh cakes, and baked goods, with the highest quality ingredients possible. She also wanted to treat her employees with extreme care and respect, having had both positive and negative experiences working in food service prior to 2008.

“I had experience working with a few different types of people, some were great, and some that were not great,” Amanda said in a recent interview with Spoon University. “What inspired the opening of the bake shop was mostly because I needed a job. It was the fall of 2008, and which was when I was entering my senior year at MassArt, and things were not looking too hot. I never had the cute dream of ‘I am going to own a bakery one day.’ It was more like, ‘I have these things combined — food service experience, an art degree — and here is what I can do with it.’”

There have been many versions of the bake shop since 2008. At the time, Amanda and her partner Tyler created a website and a cake business out of their basement apartment in Brigham Circle, trying to make ends meet as soon-to-be college graduates. In 2010, as inquiries increased, they made the decision to open up their first storefront in Winthrop, MA. The sole focus of Oakleaf was on custom cakes, and inquiries were pretty steady.

“Winthrop is a nice town, but it is a small town,” Amanda said. “The businesses are not as diverse, the customers are different, and the vibe didn’t feel right.”

In 2013, the team decided to bring the shop back home to Boston, to a beautiful little storefront on Westland Ave, down the street from Boston Symphony Hall. The goal of the move was to add the café element to the brand, and share the Oakleaf love with a larger audience in the city.

“Having the café gives people a reason to come in and see the cakes, and be in the space longer, rather than just grab-and-go,” Amanda said. “It allows people to taste our food without having to buy a big, giant custom cake, and acts as a good taste test for those who want to order something larger later.”

Amanda and Tyler, who is now her husband, hope that the shop is a comfortable, inspiring place that students can spend time in to do homework, catch up with friends, or get their daily cup of coffee. College students also make a large part of the workforce, cementing a connection to the larger Boston community.

“My husband and I started the business together, but now we are a team of people,” Amanda said. “We have the local college kids who are the baristas, the back-of-house, full-time bakers, pastry chefs and artists, and cake consultants. There is a whole staff now and it is not just me, so I owe a lot of our success to them.”

Today, you can find coffee chains in almost every neighborhood of Boston. What separates Oakleaf from the rest is that they are a resilient bake shop that stays true to the student population and its community.

“We want to show customers that we are real people,” Amanda said.

Amanda shared that she wants customers to feel welcomed and accepted when they are in the bake shop. She also wants every single customer to leave with the best experience possible. This especially means welcoming feedback and recommendations of items that they would like to see on the menu.

Like many other restaurants and coffee shops, Oakleaf was forced to close its cafe doors during the beginning of the pandemic. It was fortunate to keep up private cake orders for families in need of small celebratory treats while in lockdown, but it still wasn’t the same. Amanda and her team were lucky to have had emergency funds saved, as well as the government-funded PPP loan to stay afloat.

“We shifted most things online so people could pre-order to pick them up,” Amanda said. “Most of our business is custom cake orders, like wedding cakes and large corporate orders. The café was doing pretty well before COVID, but then we lost all of the Symphony Hall guests because events were no longer taking place there regularly.”

Fast forward two years later, Oakleaf is back on its feet, focusing on custom cake orders and catering private events. Amanda and Tyler hope to re-launch their cake decorating classes post-pandemic, because they believe that it truly shows customers a deeper appreciation for the art of baking.

Running a shop today is very different from how it was when Amanda started 14 years ago. Amanda shared that no day looks the same. Her advice for upcoming entrepreneurs is when things get tough, it is important to tap into your “why.” Amanda believes that knowing “your why behind the what” and leaning on your team members are the keys to success.

“Don’t let your lack of expertise scare you away,” Amanda said. “Some on-the-job-training will happen. You’re capable of more than you realize right now, and don’t be afraid to put in the hustle.”