Robert Mills turned a high-school spark from Eddie Murphy’s Boomerang into Bespoke Insurance, a fully independent Black-owned brokerage. His mission centres on representation, financial education, and training the next generation of Black insurance professionals.
When Robert Mills walked into a movie theatre in the early 1990s to see Boomerang, he wasn’t only watching Eddie Murphy on screen. He was catching a glimpse of ownership. The film’s confident portrayal of a Black-owned marketing firm planted a seed. Decades later, that seed grew into Bespoke Insurance, an Ontario brokerage that recently celebrated one year as fully independent, Black-owned—and, as reflected on its site and team roster, largely Black-operated.
Mills’ path to ownership wasn’t a straight line. He entered the industry in the late 1990s, absorbed everything he could, then made a life-altering decision in 2010: leave a stable salaried role to build his own book of business from zero. He launched Bespoke in November 2019, just months before the pandemic. The timing was tough, but the mandate was clear—create a brokerage where Black professionals could thrive, and where Black communities, too often overlooked by traditional insurance, could find straight answers and tailored coverage.
“I wanted to create a space where our people feel comfortable being themselves,” he says, noting how representation across leadership and day-to-day staff matters.
“If you’re serious about the business and want your own shop one day, come work with me. I’ll show you the path.”
Why Black ownership has been rare in the industry
Mills is candid about the structural and cultural hurdles that have kept Black ownership scarce in insurance. He points to a historical absence of visible owners to model the path, a lack of awareness in the community that insurance can be a lucrative, multi-track career, and the kinds of roadblocks that make entrepreneurship in regulated financial services feel inaccessible. The result, for years, was a talent pipeline that rarely led to the top.
That’s exactly what he is changing through hiring, mentorship, and an internal culture that centres professional development. The majority-Black team visible across Bespoke’s channels isn’t symbolic optics—it is the operating reality that guides clients through complex choices with cultural fluency and trust.
Closing the protection gap, one conversation at a time
Ask Mills what “closing the protection gap” looks like and he doesn’t reach for jargon. He reaches for everyday scenarios, the ones that can make or break a family’s finances.
He talks about the hidden cost of a single non-payment cancellation on auto coverage. He recalls a contractor facing a six-figure claim whose affordable liability policy kept a business alive. He shares the story of a young father who died weeks after a conversation about life insurance, a reminder that a modest monthly premium can rewrite a family’s future.
The work starts before someone becomes a client.
Bespoke shows up at community events, partners with groups like sickle cell associations, and serves as an informal help line for realtors and mortgage brokers fielding insurance questions from Black households and entrepreneurs. Word of mouth travels quickly when answers are clear and relatable.
How Bespoke translates education into impact
Bespoke’s approach is grounded in practical, culturally aware guidance that treats education as a service, not a sales tactic.
- Speak plainly about consequences. From auto policy cancellations to eligibility issues, staff explain how short-term choices affect multi-year costs.
- Protect small businesses. Tradespeople and side-hustlers get realistic packages, such as general liability, that match risk to budget.
- Normalize life insurance. Term policies are framed as a foundational tool for intergenerational stability, not a luxury.
- Meet people where they are. Partnerships with community groups and professionals extend reach beyond the brokerage’s walls.
Training tomorrow’s Black brokers and founders
Mills refuses the “crab-in-a-bucket” mindset. His vision is to build a place where entry-level hires, including young Black women and men early in their careers, can see a path to senior titles—and, if they choose, to ownership. He’s transparent with recruits who say they want their own brokerage one day: come learn here, then go build. The goal is a multiplying effect—five new brokerages seeded by alumni, then five more after that.
He is taking that message to high schools and planning more outreach, making the case that insurance isn’t a back-office mystery. It’s a dynamic field with multiple tracks—brokerage, carrier, underwriting, product, claims—where Black talent can lead at every level.
Services with breadth, advice with context
Bespoke’s offering spans personal lines and commercial coverage: business, home, auto, and life insurance. The common thread is context. A client who sends remittances, juggles gig work, or runs a family business deserves advice that accounts for those realities. Representation inside the firm makes those conversations faster, clearer, and more empathetic.
What clients most often ask Bespoke to solve
Before listing policies, Mills’ team focuses on the real problems people bring in the door.
- Household stability: Getting the right auto and home coverage while avoiding avoidable premium penalties.
- Small-business resilience: Matching liability limits to contract requirements to protect income and reputation.
- Family security: Choosing straightforward term life coverage that safeguards children and builds a financial cushion.
Technology, AI, and an independent future
Mills is realistic about technology’s impact. Insurance evolves slowly, but AI is reshaping workflows. He welcomes tools that automate routine tasks so staff can spend more time advising clients, recruiting new talent, and expanding community education. The bigger industry trend he’s watching is consolidation, with large players rolling up smaller brokerages. His strategy is the opposite: remain independent, grow on his terms, and eventually acquire firms to scale a Black-led platform.
“I want to leave a footprint,” he says. “When I’m done, I want five people to say they started their brokerage after coming through Bespoke. Then they create five more.”
The stakes and the promise of representation
Bespoke’s milestone as a fully independent Black-owned, largely Black-operated brokerage is significant for optics, but the deeper value is functional. Clients often exhale when they walk in, recognizing a team that understands cultural nuances and financial pressures without a long preamble. That comfort accelerates good decisions. It also keeps talent in the industry. A 22-year-old who starts at Bespoke doesn’t have to decode workplace politics to advance. They can build skills, earn responsibility, and step into leadership.
For Mills, that’s personal. He remembers waiting for a turn that didn’t always come in corporate spaces. Ownership gives him the latitude to open doors for others right now.
Where ownership becomes legacy
Robert Mills’ story reads like a blueprint for community-minded enterprise. Inspired by a 1990s movie that modelled Black excellence in business, he chose a regulated, under-explored sector, took a risk, and built an operation that centres representation and rigour. Bespoke’s independence matters. So does the makeup of its team. In a field where trust is everything, a largely Black-operated firm serving overlooked communities is both symbol and solution.
The next chapter is already in motion: deeper outreach, a growing sales force, and a training pipeline that treats ownership as an achievable goal. If Mills succeeds on his own terms, Ontario will gain more Black-led brokerages, more culturally fluent advisors, and fewer gaps in coverage for families and businesses that need it most. That’s what legacy looks like when ownership, education, and opportunity move together.
