At CEO (Boardroom Media) we track over 1,000,000 startups and over 5,000,000 people who hold key positions in these companies. We use this directory of startups to highlight top employees, founders and board members we think deserve more appreciation than they are currently getting.
This list showcases the top Chicago based CEO’ operating in the Leisure space. If you think a CEO’ is missing from this list, feel free to contact our editor on [email protected]
The individuals on this list have been included because of exceptional performance in one of the following categories:
- Innovation – Operating as a key part in an extremely innovative business or startup.
- Growth – Operating as a key figure in the growth and upscale of a market leading business or startup.
- Management – Showing exceptional management skills.
- Societal impact – Putting their business on the map for their positive societal or environmental impact.
Our Data – We source our data from OSINT (open source intelligence) and public directories such as Crunchbase, SemRush and many more. The data from these sources should be treated with a degree of caution and verified yourself.

Greg Caplan
Founder and CEO of Remote Year
Greg Caplan started as a Founder-in-Residence with Lightbank in January, 2011. In August 2011 he co-founded oBaz.com, a e-commerce site focused on rethinking the way people shop online. oBaz uses personalization and social features to create a brand new shopping experience. Greg has a BBA from the Stephen M. Ross School of Business at the University of Michigan.
Follow Greg Caplan:
About Fit Club, Groupon, Remote Year, Spot: Remote Year provides a foundation for professionals to travel and work remotely with interesting people.
Brian Dewey
Co-Founder & CEO of Koloni
Follow Brian Dewey:
About Koloni: Koloni is a sharing platform that enables users to own and deploy their own smart lockers, bike share, scooters and so much more.
Andrew J. Lansing
President and Chief Executive Officer of Levy Restaurants
Andy Lansing is President and Chief Executive Officer of Levy. Under his leadership, Levy has topped over 200 locations in North America and around the world, with more than 35,000 team members delivering Levy’s signature hospitality to guests. Andy began his career with Levy in 1988 as Vice President and General Counsel, overseeing and directing legal affairs for the Company. He was promoted to Executive Vice President for Levy in 1991, and President and Chief Operating Officer in 1995. In his tenure, Andy has directed, managed and actively recruited the industry’s top specialists to become part of Levy’s team and foster the Company’s strategic growth. In 2004, Andy was promoted to President and Chief Executive Officer.
Follow Andrew J. Lansing:
About Levy Restaurants: Levy Restaurants is a hospitality company that runs restaurants and vending machines in entertainment and sporting venues.

Daniel Valenti
Founder / CEO of TripWeave
Follow Daniel Valenti:
About TripWeave: Explore some of the world’s coolest places with your peers on a self-led journey.