From City Hall to CEO: Why Urban Planning Needs More Entrepreneurs
August 26, 2025
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Discover why entrepreneurial thinking is vital in modern urban planning, and how EO Accelerator Chelsey Jersak was inspired to build a business that bridges vision with execution to solve challenges one project at a time.

My entrepreneurial journey began at ancient ruins outside Mexico City. I was studying archaeology, standing in the heat at Teotihuacan, when heat exhaustion hit—and with it, sudden clarity. As I recovered and looked toward Mexico City in the distance, I realized I was far more fascinated by that vibrant, living metropolis than the ancient stones around me. That moment led me to abandon archaeology for urban planning—and eventually, to leave the security of city government to build my own business.
Today, I run a specialized consulting firm that helps real estate entrepreneurs navigate the complex world of property redevelopment, otherwise known as infill. But the path from city planner to entrepreneur wasn't obvious or easy. It required recognizing that the entrepreneurial mindset I'd developed wasn't just compatible with urban planning—it was desperately needed.
The Problem Only Entrepreneurs Could See
During my formative years on the City of Edmonton's zoning bylaw team in the early 2010s, I witnessed what I call "the dawn of infill." Edmonton had countless large lots with small houses that could be subdivided to create more housing. The demographics were shifting—mature neighborhoods had lost 25% of their population while maintaining the same number of houses. We needed solutions.
Working on those zoning bylaw changes, I saw a massive gap: The rules were strict and the process was complex, yet there was no guide to help people navigate the opaque system. The development community included many small businesses—entrepreneurial builders who needed support but couldn't find it.
That's when I realized: As a small business, I could help other small businesses build better cities while building their companies.
Why Traditional Planning Wasn’t Enough
The urban planning profession attracts dreamers. Many are drawn to the theoretical—creating 25-year master plans, envisioning utopias. But there's often a disconnect between these plans and the reality of regulations, market forces, and financial constraints. Few planners are trained to navigate the messy middle: permits, policies, community politics, pro formas.
Working in city government revealed something important: Entrepreneurial thinkers exist everywhere, even within large bureaucratic institutions. Some thrive there, creating change from within. But for those with a certain mindset—the compulsion to see problems and immediately connect them to solutions—the pace of institutional change can feel glacial.
When you see a problem that needs solving today—not in five years after committee reviews—entrepreneurship becomes less of a choice and more of an inevitability.
Bringing Human Needs into Focus: An Entrepreneurial Lens
Entrepreneurs don't just chase market gaps—they see human needs that aren't being met. One of the biggest issues facing cities today is housing affordability and fit. That's why I co-founded Wello, a company exploring new models of shared housing.
Most city plans focus on built form and unit counts: density per hectare, units per lot. But that lens obscures the diversity of real human needs. We assume people live in nuclear families—not that they live in relationships, communities, or shifting life stages. What about people who've gone through divorce and want to co-own with a friend? Newcomers who would rather live with others than rent alone? Professionals who would rather travel than pay 100% of rent solo?
They're not fringe cases. According to Statistics Canada, roommate households grew by 54% between 2001 and 2021, making them the fastest-growing household type in the country. But good luck finding housing options that account for them.
Entrepreneurs are often the first to recognize when systems don't match reality. Sometimes that means pushing back on outdated regulations. Other times, it means prototyping new models, not just new buildings. That’s what my company is trying to do.
The Turning Point: From Solopreneur to CEO
The most challenging leap wasn't starting the business—it was scaling it. When I began, I had no entrepreneurial role models. I didn't know any successful entrepreneurs until someone introduced me to Entrepreneurs' Organization and the EO Accelerator program. Suddenly, I wasn't alone.
Finding that entrepreneurial community was transformative, but the real game-changer came when I received advice that terrified me: "Hire the most expensive person you can possibly afford."
It felt risky, even reckless. But bringing in highly qualified technical staff—professionals who could perform independently—transformed everything. It allowed me to step out of technical operations and focus on growing the business.
This is the evolution every serious entrepreneur must navigate: Performing all the roles yourself, then systematically giving them away. For those of us who see our businesses as our creative output, the letting go is profoundly difficult. But it's essential.
Why Urban Planning Needs Entrepreneurs Now
The most successful urban transformations happen at the intersection of vision and execution—exactly where entrepreneurs excel. We see problems and immediately think about solutions. We get instant feedback from the market. When something works, we know it. When it doesn't, the numbers tell us quickly.
This agility is exactly what modern city-building needs. While others spend years planning theoretical futures, entrepreneurs are making real changes now—building actual housing, creating real density, solving immediate problems.
My clients are real estate entrepreneurs: agile problem-solvers using housing as a tool to achieve greater financial, environmental, and social sustainability. They're not waiting for perfect plans or ideal conditions. They're building the future one project at a time.
The Entrepreneur’s Edge
What I love most about being an entrepreneur in urban planning is the ability to see a problem and solve it—immediately. There's something electric about facing a challenge and having the freedom to tackle it head-on. No bureaucratic approval processes. No committees. Just action.
For urban planners considering entrepreneurship, my advice is simple: Stop waiting for clarity. Stop searching for your perfect "why." Clarity emerges from doing. You learn by trying, adjusting, and trying again. The bias toward action matters more than finding your passion.
Because ultimately, cities aren't built by plans—they're built by people willing to take risks, solve problems, and create value where others see only obstacles. That's what entrepreneurs do. And that's exactly what our cities need more of.
First-time EO Blog contributor Chelsey Jersak is an EO Accelerator in Mexico City and the founder of Situate Inc., a specialized consulting firm focused on infill development and urban redevelopment strategy in Edmonton, Alberta, Canada.