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The Corporate Dropout  

The Corporate Dropout

Author: Rachael Seda

Hey go-getter, welcome to "The Corporate Dropout" I'm Rachael, your go-to gal for all things hustle and grind (while still living it up in life). From building a 7-figure empire to gathering a dream team for my marketing agency, I've got the tea, and I'm spilling it all. Get ready for bomb marketing hacks, unfiltered business tales, and iconic chats with boss entrepreneurs who've been through the highs, the lows, and everything in between. We're diving deep, keeping it 100, and serving up the inspo every entrepreneur needs. Swipe out of that 9-5 mindset and slide into the world of "The Corporate Dropout".
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Language: en

Genres: Business, Business News, Careers, News

Contact email: Get it

Feed URL: Get it

iTunes ID: Get it

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115: Leading with Hospitality: How Jon Dempster Grew Four Restaurants in Cape Charles
Episode 115
Thursday, 20 November, 2025

What does it take to build a thriving restaurant group in a small coastal town? In this episode, Rachael sits down with Jon Dempster, the restaurateur behind E&O Pub, The Shanty, Deadrise Italian Kitchen, and Brown Dog Ice Cream in Cape Charles, Virginia. Jon shares how he turned one dockside dream into four community-favorite restaurants, each grounded in hospitality, teamwork, and heart. You'll hear how Jon navigated the ups and downs of entrepreneurship, built a loyal team in a high-turnover industry, and learned to balance business growth with family life. He also opens up about the importance of pivoting, staying people-first, and finding calm in the chaos of restaurant ownership. To learn more, visit the show notes. Connect with Rachael on Instagram!  

 

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