Diaspora: Where Southern, West African and Caribbean traditions come alive in Chicago
Diane Sooyeon Kang is a food and travel photographer and writer with a passion for storytelling. She has traveled the world extensively, working with esteemed publications and brands. You can find more of her work at dianeskang.com.
For Rob Carter, founder of Diaspora, food is a bridge to history, identity and community. Inspired by the rich flavors of Southern, West African and Caribbean cuisines, Diaspora brings Rob’s heritage to life through dishes that tell a story. What started as a pop-up in Chicago has become a platform to share his roots, tackle the challenges of entrepreneurship and prove that food has the power to unite people across cultures and generations.
Growing up in a family where food was central to daily life, Rob’s path into the culinary world began at an early age. “My grandmother was my first mentor, even though she didn’t know it,” he recalls fondly. As a child, he often helped her prepare meals that fed large groups; this instilled in him a deep appreciation for hospitality and the ability of food to bring people together. His grandmother lived with 21 siblings and cousins, making her well-suited to cooking for small crowds. Her Southern cooking became the foundation of Rob’s culinary identity.
While Rob’s early experiences shaped his love for food, becoming an entrepreneur was not without its challenges. Despite years of working in upscale restaurants, including Michelin-starred Vie Restaurant and stages at Band of Bohemia and Blackbird in Chicago, the leap to running his own business was daunting. “You don’t learn business by working the line,” he says. “You learn by doing, making mistakes, and figuring out what works.”
One of the toughest lessons has been the art of timing. Organizing pop-up events — where crowds are unpredictable and profit margins are tight — has proved to be a learning curve. “I once did a pop-up during Lollapalooza weekend, and it was a disaster,” he recalls. “The city was buzzing with festival-goers, and my event was completely overlooked.” These setbacks, however, have helped him refine his approach, teaching him to be more strategic and adapt when necessary.
In addition to timing, Rob’s journey has highlighted the importance of collaboration. Managing partnerships and navigating last-minute cancellations has been a source of stress. “It’s tough when you rely on other people’s schedules, and then they cancel,” he says, referring to a series of collaborations that fell through in June. Yet, these challenges have only fueled his determination to push forward and remain flexible
Technology has provided a new set of opportunities and challenges. Going digital, especially for a small business with limited resources, can be daunting. But for Rob, the shift is not just about convenience — it’s a way to craft a brand and tell a story. “You have to build a community before you even open your doors,” he shares, describing how Diaspora is leveraging social media to connect with people and create buzz before opening a physical space. The goal is to have a loyal following already in place by the time the doors open, so the business doesn’t have to build momentum from scratch. “People want to know when the space is opening, not when we’re trying to convince them to come. That’s the difference,” he says.
As he continues to grow Diaspora, the chef remains focused on creating meaningful experiences for his guests. Whether through pop-up dinners or catered events, he aims to foster connections and create spaces where people feel part of something special. “It’s about building trust,” he explains. “If people feel like they’re part of something meaningful, they’ll keep coming back.”
Looking to the future, the chef envisions expanding his culinary offerings while also keeping the spirit of collaboration alive. While the idea of a brick-and-mortar restaurant is tempting, the rising costs of rent and food have made him cautious. Instead, he’s focused on continuing to build a strong presence through pop-ups and collaborations before taking the plunge into opening a physical space.
For Rob, this journey is about more than just food; it’s about culture and the connections that can be formed around the table. “I want to create something bigger than just a restaurant,” he says. “It’s about purpose, community and connection.”
Chicago’s small business owners are shaping their communities with purpose. In this series, we highlight the entrepreneurs behind local gems – each of them building something bigger than just a business. Through Solo, Mozilla’s free AI-powered website creator, they’re exploring new corners of their community online. Check out Diaspora’s Solo website here.