Alumni Spotlight: Anthony Askew
By: Serena Maria Daniels
Anthony Askew has both Highland Park and Detroit in his blood. His great-grandmother moved to Highland Park in the 1950s, making him a fourth-generation resident of the small city surrounded by Detroit, where he still lives today.
Born at Henry Ford Hospital, he attended Detroit Public Schools and graduated from Martin Luther King Jr. Senior High School’s magnet program. As he puts it, “I’m still very much a Detroiter, but certainly have a very special place in my heart for the city of Highland Park.”
That dual identity shapes his work as founder and CEO of City on the Rise Development.
Before becoming a developer, Askew built a career in finance and community development. After studying business and economics and earning a law degree, he returned to Detroit in 2015 and joined the Detroit Economic Growth Corporation, where he helped launch and manage the Motor City Match program.
Through that work, Askew got an early look at how development projects come together. But it also revealed a deeper imbalance.
Many of the entrepreneurs receiving grants were Black business owners — often Black women — committed to serving their communities. Yet when Askew looked at the property owners connected to those same projects, the demographics told a different story.
“I'd say almost 80% at one point of the businesses we supported with grants were Black-owned businesses,” Askew says. “But I’d say when it came to property ownership, the numbers were the opposite.”
The disparity stuck with him. Askew saw entrepreneurs doing everything right still lose control of their spaces or find themselves vulnerable to landlords with little connection to the neighborhood.
“I just saw so many examples of entrepreneurs that did everything the right way and that were true assets to their community that got penalized to put it nicely, or they were railroaded, just kind of kicked to the side by somebody who cared nothing about what that business meant to the cultural fabric of the city,” Askew says.
For Askew, the lesson was clear: if neighborhoods were going to shape their own futures, more local talent needed to move into development.
After leaving the DEGC, he began consulting before launching his first project — a single-family rehabilitation in Highland Park, about six blocks from where he grew up.
The process was far from easy. It took nearly two years to secure his first construction loan, and the timeline collided with the onset of the COVID-19 pandemic. At the time, many lenders doubted whether homes in Highland Park could support higher values.
“They didn't think that the house would be worth more than, you know, [$70,000] or $80,000 and when I finished, it appraised for 200,” he says.
Around that time, he enrolled in the Building Community Value development training program in 2018 as he transitioned fully into development.
For Askew, the program wasn’t simply about technical knowledge. It was about building confidence in a field where Black developers have historically been underrepresented.
“It’s important to build what I would call developer confidence,” he says. “You can sort of feel like a fraud because this is a system, this is a practice, this is an opportunity that we've been left out of,” Askew says. “I think for folks who have a community focus, it’s important to be able to say, I am a developer and not look over your shoulder like somebody is going to discover that you’re telling a lie.”
BCV helped him sharpen the financial tools needed to move projects forward and understand how many moving pieces — from financing to partnerships — must align to make development work.
Since then, Askew’s work has expanded from single-family rehabs into multifamily, mixed-use, and adaptive reuse projects across Detroit and Highland Park.
City on the Rise Development is currently working on several projects, including a 25,000-square-foot mixed-use development in North Corktown with 21 apartments and 3,000 square feet of commercial space. Another focuses on converting a long-vacant mansion in Detroit's Brush Park neighborhood into luxury condominiums.
At the same time, Askew remains committed to community-centered development. He has partnered with Shamayim "Mama Shu" Harris, founder of Avalon Village, a community development project that she founded to lead the development strategy for Highland Park’s first community land trust, which aims to stabilize housing and preserve long-term community ownership.
Still, the path hasn’t been easy. Financing projects in Detroit often means navigating a limited pool of lenders and complex capital stacks. In Highland Park, the challenge can be even greater — convincing investors that the city’s potential is real.
For Askew, that skepticism feels familiar.
“Folks are saying today about Highland Park what they were saying about Detroit 10 years ago,” Askew says. “It’s almost like I’ve seen this movie before. I felt the same way about Detroit, because I've lived in Atlanta, Washington, DC, Harlem, and certainly traveled to many places, here and abroad, and I've seen this story before, like, ‘oh, no one cares about this place, there's nothing here of value.’”
Asked what advice Askew has for the next generation growing up in Highland Park and thinking about its future, development requires resources and relationships, but that those are within reach.
“Anything you imagine for this place is possible, and you are equipped to be the person that drives the change that you want to see.”
For a fourth-generation Highland Parker helping reshape the built environment, that belief isn’t just aspirational. It’s the work taking shape block by block.
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