In this exclusive interview, Carmen Rossi, founder of 8 Hospitality and a leading figure in Chicago’s business world, opens up about his entrepreneurial journey. From his early ventures in college to building a multi-industry empire, Rossi shares his unique perspective on risk, failure, community engagement, and the importance of giving back. This conversation offers a rare glimpse into the mind of a man who has shaped Chicago’s hospitality scene and continues to redefine what it means to be an entrepreneur and civic leader.
Taking Risks with Purpose
For Carmen Rossi, risk isn’t just an element of entrepreneurship—it’s the cornerstone of success. “Risk is absolutely at the core of success—without it, you miss the chance to push boundaries, challenge yourself, and fully capitalize on new opportunities,” Rossi explains. However, his approach to risk is anything but reckless. He underscores the importance of balancing optimism with realism and surrounding oneself with a trusted circle of advisors and mentors.
“Strong mentorship and a trusted circle are crucial for grounding your vision in reality,” he adds. This strategy ensures that his ventures—spanning hospitality, law, and real estate—are built on informed decisions and a clear vision. Rossi’s ability to weigh risks while staying flexible has enabled him to push boundaries in fiercely competitive industries.
Creating Distinctive Ventures
Rossi’s portfolio is a testament to his ability to juggle multiple industries while maintaining a consistent vision. From the fast-paced world of hospitality to the structured domain of law, he ensures that each business retains its individuality while contributing to a unified goal.
“One thing I love about having a wide array of ventures is that every day is different from the last,” Rossi says. “Across the board, we’re successful as long as we focus on the central theme that we win as a team.” His emphasis on building and developing strong teams has been instrumental in maintaining consistency across his businesses. By engaging in active discussions with his staff, Rossi fosters a sense of shared purpose and understanding that keeps his ventures aligned.
Innovating Through Collaboration
Staying ahead of trends in industries as dynamic as hospitality and real estate requires more than just intuition—it demands collaboration and constant learning. Rossi attributes much of his innovation to the insights he gains from his mentors, colleagues, and personal experiences. “I rely heavily on my relationships with mentors and colleagues to brainstorm and glean valuable feedback,” he shares.
This willingness to learn and adapt has helped Rossi create experiences that resonate with customers while standing out in competitive markets. By combining external feedback with his own instincts, Rossi continually redefines what it means to deliver exceptional service.
Learning from Failure
Failure is an inevitable part of any entrepreneurial journey, but Rossi views it as an opportunity rather than a setback. “I celebrate failure as a learning exercise—but ideally not a business model,” he quips. His perspective on failure is rooted in its potential to provide valuable insights.
“Assuming you survive, the idea of failing can be a positive if you truly understand what went wrong and how to improve the process next time,” he explains. For Rossi, each failure is a stepping stone toward greater success, providing lessons that inform his approach to future challenges.
Leading with Confidence
Rossi’s confidence as a leader stems from his belief in the transformative power of risk and failure. “If you want your project to have an impact and a wide reach, you have to be all-in,” he says. This philosophy extends to his team, where he fosters a culture that embraces learning from mistakes.
“I try to bring that mindset to my team—that failure happens, and it’s okay because it’s just another opportunity to learn,” Rossi explains. By encouraging his team to view challenges as opportunities, he creates an environment where innovation and resilience thrive.
The Role of Chicago
Chicago is more than just a backdrop for Rossi’s success—it’s a central character in his story. “I truly believe that Chicago is the greatest city on the planet,” he declares. Rossi credits the city’s diversity, cultural richness, and entrepreneurial spirit for creating an environment where his businesses could flourish.
“Chicago is one of the few cities where anyone with an entrepreneurial dream has the opportunity to bring it to life,” he adds. Despite arriving in the city without significant connections or resources, Rossi’s drive and the city’s supportive ecosystem allowed him to turn his ambitions into reality.
His deep connection to Chicago extends beyond business. Rossi’s ventures are rooted in the communities they serve, and he takes the time to understand the unique needs of each neighborhood before opening a new business. “Identifying the specific needs of the community before opening the business is crucial,” he emphasizes.
Giving Back
Philanthropy is a cornerstone of Rossi’s business philosophy. Through initiatives like Chicago Knight Life, he integrates community service into his ventures. “Since the very outset, giving back has been one of my top priorities, and something my partners and staff enthusiastically support,” he says.
This commitment to giving back stems from a deep gratitude for the opportunities Chicago has provided him. By aligning his businesses with local charities and community organizations, Rossi ensures that his ventures contribute positively to the city he calls home.
Looking Ahead
As Rossi reflects on his journey, his focus is on creating unique, experience-driven hospitality concepts that cater to evolving customer preferences. One example is DIVAN, a venue that combines the elegance of a steakhouse with the vibrancy of a jazz club and cocktail lounge.
“I’ve been inspired by the shift in customer mindsets during the pandemic,” Rossi explains. “People want locations that offer a full night of entertainment.” By curating immersive experiences, Rossi is shaping the future of hospitality while staying true to his entrepreneurial roots.
Advice for the Next Generation
For aspiring entrepreneurs, Rossi’s advice is clear: pursue your passion and seek mentorship. “The hospitality community is more than just competitors—we’re also allies, eager to see each other succeed,” he says. Networking and collaboration are key to building a successful business, and Rossi encourages young entrepreneurs to embrace the support of their peers.
As he continues to expand his ventures, Rossi remains grounded in his values of community, innovation, and purpose. His legacy is one of resilience, creativity, and a profound commitment to giving back—a legacy that will inspire future generations of entrepreneurs.
In the ever-evolving world of hospitality, Carmen Rossi is a name synonymous with bold ideas, heartfelt leadership, and a deep love for the city that made it all possible.
Creative Credits
- Written by
- Sarah Miller
- Senior Editor
- Laura Notorangelo
- Photography
- Meagan Shuptar
- Retouching
- Brianna Kish
- Hair & Makeup
- Mo Drennon of The LAB Artist Agency
- Features editor
- Christina Rosas Anastasiou
- Clothing provided by
- Nicholas Joseph Custom Suits & Bespoke Clothing
