In this episode of The Corporate Dropout, Rachael sits down with Jon Dempster, the restaurateur behind E&O Pub, The Shanty, Deadrise Italian Kitchen, and Brown Dog Ice Cream. What began as a small idea in Cape Charles has become a collection of community favorites known for genuine hospitality and a people-first approach to business.
Jon shares how he’s built lasting success in an unpredictable industry through adaptability, mentorship, and heart. He and Rachael talk about leading with calm in high-pressure environments, creating a workplace that values connection, and balancing growth with family life while keeping community at the center of it all.
In today’s episode you’ll learn:
- How Jon turned one idea into four thriving Cape Charles restaurants
- Why pivoting can be a business owner’s greatest advantage
- The role mentorship and teamwork play in long-term success
- How to build a hospitality culture that keeps people coming back
- Ways to balance growth, leadership, and family life as an entrepreneur
- Where to eat next time you’re in Cape Charles
& SO MUCH MORE!
About Jon Dempster
Jon Dempster is a Cape Charles restaurateur and all-around idea guy who believes the best way to lead is by never getting too comfortable. He opened his first spot, The Shanty, back in 2012 and has been on a roll ever since—launching Deadrise Italian Kitchen, joining the Brown Dog Ice Cream crew, and most recently bringing the beloved old Kelly’s Gingernut Pub space back to life as the new E&O Pub. Jon shows up every day aiming to get just 1 percent better—whether that’s perfecting a recipe, mentoring his team, or dreaming up the next big event—and he keeps himself as accountable as anyone on his crew, proving that growth can be serious business without ever losing the fun.
Resources
Visit each restaurants’ website:
https://eandopub.com/
https://shantyseafood.com/
https://deadrisecapecharles.com/
https://browndogicecream.com/
- Follow E&O Pub on Instagram @eandopub
- Follow The Shanty on Instagram @shantyseafood
- Follow Deadrise Italian Kitchen on Instagram @deadrisecapecharles
- Follow Brown Dog Ice Cream on Instagram @browndogicecream
Calling All Corporate Dropouts!
Have you or someone you admire ditched your 9 to 5? We want to hear from you! Send us an email [email protected] to be considered as a guest.
The post 115: Leading with Hospitality: How Jon Dempster Grew Four Restaurants in Cape Charles appeared first on MIX+SHINE | Marketing & Social PR.