What started with a single photo booth has expanded into a double-digit fleet of units for UWindsor alumna Teisha Gentles. (PHOTO COURTESY OF TEISHA GENTLES / University of Windsor)
By John-Paul Bonadonna
When Teisha Gentles (BA '02) looks back on her journey from University of Windsor student to entrepreneur, one theme stands out: the courage to start over.
Over the last three decades, Gentles has reinvented herself more than once.
She left Toronto for Windsor in search of independence, moved to Florida after graduation, returned to Canada as a single mother to rebuild her career, spent 25 years in the insurance industry and eventually launched a business in a field where she had no formal training.
Today, the University of Windsor alumna is the founder of Hidden Smirk Photobooth, an experiential event company that has grown from a pandemic side venture into a full-time business serving sports organizations, corporations, non-profits and community groups across Ontario.
For Gentles, however, the story begins at UWindsor.
“University is a breeding ground for figuring out who you are as an individual, who you are as an adult, what you’re capable of and what you can achieve,” says Gentles.
“The University of Windsor really shaped who I am today.”
The experience exceeded her expectations. She formed friendships that have lasted nearly 30 years, discovered the confidence to advocate for herself and learned lessons that continue to influence her career.
After graduating, Gentles moved to Florida, where she spent a decade building a life, purchasing a home and eventually welcoming her son. As her priorities shifted, she decided to return to Canada so he could grow up closer to family.
“I moved back and restarted my whole career,” she says.
She became a sought-after professional in commercial insurance, working for several major companies and rising to the role of senior field underwriter specializing in engineering insurance. The work involved assessing complex industrial operations, evaluating risks and helping businesses protect themselves from costly disruptions.
While she enjoyed the challenge, Gentles increasingly recognized that her greatest professional asset went beyond her technical expertise.
“My personality is really what I was being paid for,” she says.
“I was good at building relationships, presenting ideas and connecting with people.”
That realization planted the seeds for her next chapter.
While working remotely during the COVID-19 pandemic, Gentles found herself exploring new opportunities. After attending events that featured photo booths, she became intrigued by the business model and purchased a turnkey setup from an owner looking to exit the industry.
What began as a side project quickly evolved into something much bigger.
Despite having no photography background, Gentles immersed herself in learning the technology, developing client relationships and refining the guest experience. She sought advice from photographers, learned through trial and error and drew heavily on the professional skills she had developed throughout her corporate career.
“I realized my corporate foundation helped elevate me faster than other entrepreneurs,” she says.
“The pitch, client communication and follow-up — those skills came from years of experience in the corporate world.”
The company’s name reflects both its origins and its mission.
Hidden Smirk was born during a time when masks had become part of everyday life. Today, Gentles says the business is about helping people remove another kind of mask.
“Now that we don’t wear masks anymore, I help people remove their emotional masks,” she explains.
“We create a safe space where people can feel their best and create memories.”
The approach has resonated with clients.
What started with a single photo booth has expanded into a double-digit fleet of units, including roaming photo experiences designed to bring the camera directly to guests rather than making guests wait in line. Hidden Smirk now employs nine staff members and serves events ranging from weddings and community celebrations to large-scale corporate activations.
Among the company’s biggest opportunities was a partnership with the Toronto Raptors organization.
Gentles credits a fellow University of Windsor alumnus working within the organization for helping open the door.
“That was one of my lucky breaks,” she says.
“Another UWindsor alum saw what I was doing and brought me in.”
The relationship led to additional opportunities with sports organizations and helped establish Hidden Smirk as a trusted partner for major events.
Her entrepreneurial journey has not been without challenges.
Leaving the security of a corporate career, particularly as a single mother, required a significant leap of faith. Being laid off from her insurance position ultimately became the catalyst that pushed her to fully commit to her business.
Looking back, she sees that experience differently now.
“I knew deep down that I had something unique,” she says.
Today, Gentles remains closely connected to the University of Windsor community through alumni networks and friendships forged during her student years. She continues to view her UWindsor experience as a foundation for everything that followed.
“It’s still the degree that works,” she says with a smile.
For Gentles, success has never been defined by a straight career path. Instead, it has come from embracing change, seeking opportunities and trusting herself enough to begin again.
“There’s no shame in restarting,” she says.
“There is shame in not moving forward.”
This profile is part of a special series celebrating Alumni Week. Discover events and more at uwindsor.ca/alumni.
