Carmen Rossi is a successful serial entrepreneur who has launched over 70 businesses across various industries-hospitality, restaurants, real estate, cannabis, clothing, law, travel, and more. He also owns and operates some of the biggest nightclubs and restaurants in Chicago, along with iconic campus spots like KAMS and Red Lion.
His secret? The ability to truly listen. Carmen has an unmatched talent for tuning into what people want and turning those desires into unforgettable experiences. That’s his superpower, and it’s fueled his extraordinary success.
Carmen’s entrepreneurial journey began early-in college, where he started a dormitory loft-building company, a painting company that hired fellow students, and a travel agency that sold over 1,000 spring break trips. Unlike the stereotypical innovator creating entirely new ideas, Carmen admits his strength lies in refining existing concepts and mastering their execution. It’s this pragmatic approach that has guided him through trial and error, with an open embrace of failure.
“Failure is welcomed here,” he says, seeing college as the perfect arena for experimentation and growth.
Carmen’s story offers not only inspiration but also valuable insight for anyone aspiring to make an impact in their communities. He emphasizes the importance of identifying unmet needs in neighborhoods before launching ventures, creating everything from vibrant sports bars to upscale dining experiences. His hospitality empire includes over 40 businesses, such as Hubbard Inn, Cardozo’s Pub, The Joy District, The Dime, and HVAC Pub in Chicago.
During this episode, Carmen shares his love for pop culture, his admiration for films like Risky Business and Yes Man, and his belief in amplifying social connections through business. He explores his philosophy of saying “yes” to new opportunities and creating ventures that bring people together in memorable ways.
Carmen offers practical advice to young people, promoting the “rule of large numbers.” He encourages taking large-scale action and learning from setbacks. As he puts it, “I’m not going to ask two people out on dates, I’m going to ask 20. And if I get 20 rejections, I know I need to change the pitch.”
Right after our conversation with Carmen, we were so inspired by his ideas that one of our own projects took off, going viral within a week. That’s the power of Carmen has-he sparks immediate action and creativity in others.
This episode is a masterclass in entrepreneurship for anyone looking to understand how to build and run multiple successful businesses.
We were incredibly lucky to spend an evening with Carmen Rossi, and we hope you enjoy this conversation as much as we did.
*EPISODE LINKS:*
- Carmen Rossi's Company: 8hospitality.com/
- Follow Carmen's latest venture, DIVAN: divanchicago
- KAMS: kams_illini
- Red Lion: redlionchampaign
*OUTLINE:*
0:00 - Introduction
1:12 - Childhood
6:03 - Adult Conversations
11:16 - Aaryaman's American College Experience
16:53 - Carmen's First Visit to UIUC
20:07 - Carmen's First Business
28:41 - Carmen's Guide to Starting Successful Local Businesses
31:30 - How to Assemble a Team
37:50 - How to Discover Yourself in College
43:29 - Ideas for Dates at UIUC
44:33 - Carmen's Regret
48:28 - How to Start a Business in College
1:02:50 - How to Ask Someone Out
1:10:45 - Failure
1:15:19 - Listening
1:20:40 - Carmen's Playbook for Experience-Driven Businesses
1:29:15 - Building for Yourself or Others?
1:36:00 - Delegation
1:45:25 - What's next for Juan David & Aaryaman?
2:09:16 - Compete With Yourself, Not Your Peers
2:17:33 - Say Yes
2:22:58 - Carmen's Reflections on The UIUC Talkshow Experience
2:23:00 - Advice to young people
🚥 Overrated or Underrated Section 🚥
2:27:56 - ⚙️ Restaurant Mechanical Systems (HVAC, equipment, etc)
2:29:38 - 🍕 Chicago Deep Dish Pizza
2:34:18 - 🍝 Eataly
2:41:27 - 🥚 Incubators & Accelerators
2:46:38 - 🍺 Bars: KAMS & Red Lion
2:52:56 - 🍟 The Founder Movie
2:56:42 - Closing Words
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