Big Bro’s Barbershop: Cultivating Community and Confidence Through Haircuts

Help support Big Bro’s Barbershop as they relocate and renovate on their GoFundMe.

Driven by a vision to create a safe space for transgender and queer people to gain peer support, access essential resources, and truly feel like they belong, Jessie Anderson opened Big Bro’s Barbershop. Founded in 2015, the shop was initially located in a windowless, secluded art studio in Vancouver. Thanks to community support, Jessie’s business continues to thrive as he prepares to relocate to a new, larger space.

Small Business BC connected with Jessie, the owner of Big Bro’s Barbershop, to learn about his entrepreneurial journey and how his business has grown since his Best Emerging Entrepreneur win at the 2016 Small Business BC Awards.

Inspiration Behind Big Bro’s Barbershop

Jessie Anderson, owner of Big Bro's Barbershop smiling with his arms crossed posed outdoors on a bright day.Jessie has a long history of cutting his hair, “It’s a very powerful thing to take control of your own presentation,” he said. “As a queer person with clippers, I naturally got into sloppy kitchen haircuts on friends and roommates.” From there, his vision for Big Bro’s Barbershop grew clearer.

“Trans people generally feel, at best, tolerated in public spaces, rather than welcomed or fundamentally included,” Jessie said. He wanted to create a permanent space that the trans community could call their home—a resource that, unfortunately, remains uncommon.

“The core vision for Big Bro’s Barbershop was that it would be a place where I, a trans person, could be consistently found during business hours, for other trans people to gain peer support and resources from,” he explained.

While developing his business model, Jessie realized a few key things. First, the sales process of cutting hair naturally facilitates conversation, which would help create the safe, affirming space he sought. Second, haircuts are a service unlikely to be replaced by online alternatives, making a brick-and-mortar space ideal.

Jessie’s Hopes For Clients’ Experiences

Big Bro’s Barbershop goes a step further in their service. “Obviously it’s my hope that my trans clients – and everyone else, for that matter – feel safe within our shop,” Jessie emphasized. But, his top priority is making sure his clients feel heard in terms of their concerns and expression for their hair. “My lived experience as a queer and trans person means that my clients have faith in me to listen to exactly how they choose to express themselves,” Jessie said. 

“Many of our clients have lost friends and family due to coming out, and it is very lonely celebrating the start of one’s transition without having one’s loved ones present,” he said. Big Bro’s Barbershop has fostered a tight-knit community, where staff is always ready to celebrate clients’ milestones and empathize with their hardships. “I’m always happy to play the role of the “Big Bro” through peer support, mentorship, and shared celebration,” Jessie said.

Challenges and Successes

In having to juggle so many roles as a small business owner, Jessie explained that he’s had to accept that he won’t excel, or even succeed, at everything. “Sometimes it’s heartbreaking when an idea flops, or a piece of equipment breaks, or an interpersonal issue comes up in the workplace,” Jessie said. Reflecting on nearly a decade of experience, he added, “I’ve learned to breathe, sit with that heartbroken feeling for a while, and then get right back into planning a new solution.”

Despite these challenges, Jessie’s dedication and resilience have paved the way for hugely rewarding moments. Since Big Bro’s Barbershop is one of a kind, it’s no wonder that people travel to experience it firsthand. People from all over BC, as well as Bellingham, Indiana, Arizona, and even the UK, have sought out his business

Additionally, their MLA, Niki Sharma, visited the shop and sang their praises at the BC Legislature. “It’s always very cool to receive affirmation that my business is serving the community in distinct, tangible ways,” Jessie said.

Winning Best Emerging Entrepreneur at the 2016 SBBC Awards

“My shop didn’t even have a proper storefront in early 2016,” Jessie explained. Winning Best Emerging Entrepreneur at the Small Business BC Awards in 2016 is what allowed Jessie’s Barbershop to grow beyond his small, secluded art studio and into the 850-square-foot space he’s been in since. 

After all these years, it’s time for Big Bro’s to expand again. “This fall, we’ll be moving into a 1250-square-foot space at 2375 East Broadway, where we’re finally investing in a renovation and really designing the space for ourselves,” Jessie said. Instead of placing furniture anywhere possible and making it work the best they could, Big Bro’s has the chance to create the perfect space for them.

Role of Community Support

He explained that his community is the whole reason his business is still standing. “The trans community is fantastic at sharing information, and folks have spread the word about my shop far and wide, without me having to invest much into advertising at all,” he said. When the shop is in times of need, clients are also eager to donate their time and expertise in any way they can.

Advice for Queer Entrepreneurs Getting Started

Before starting Big Bro’s, Jessie worked on queer-targeted media and event production. This allowed him to familiarize himself with his community and target audience, as well as introducing him to the risks and rewards present in business.

“I think that a lot of common queer traits lend themselves nicely to entrepreneurship: tenacity, ingenuity, frugality, and true care and empathy for others are all hugely beneficial to running a small business,” Jessie said. He recommends starting with smaller projects and connecting or collaborating with folks who can offer mentorship and guidance. “Throw an event! Sell your art! Try drag!” he said.

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