Status: OPEN
Grumpy’s Diner in Madison, Florida is a Restaurant Impossible story about a mother teaching her son to lead. After Robert Irvine’s intervention, Justin gained the confidence to carry on the family business – and customers are loving the results.
From Real Estate to Restaurant
Jessica Webb was a real estate agent who saw an opportunity in 2018. She opened Grumpy’s Diner in Madison, Florida with no restaurant experience, learning on the go. By the time Restaurant Impossible arrived, she had accumulated almost $200,000 in debt.
Jessica wanted to pass the business to her son Justin, but there was a problem: he lacked the self-confidence and vision to lead the diner into the future.
The Episode (Season 21, Episode 6)
Title: “Mistrust and Malaise in Madison”
Air Date: June 3, 2022
Filming: Late January 2022
Robert Irvine traveled to Madison with a dual mission: fix the restaurant’s operations and get Justin to believe in himself. Sometimes Restaurant Impossible has to build up a person before it can build up a business.
The Transformation
Beyond the physical renovation, Robert focused on building Justin’s confidence. Leadership isn’t just about knowing what to do – it’s about believing you can do it. By the end of filming, Justin was ready to step up.
Reviews Since the Makeover
Customers have responded enthusiastically. Recent reviews highlight:
- The Mile High Club sandwich with raspberry jalapeño jam
- Sweet potato fries
- Homemade pies (they’re now “Grumpy’s Diner & Pie Shop”)
- Fresh, flavorful food
- Friendly, attentive service
A November 2025 reviewer called it “a perfect stop when passing through or spending time in Madison.”
Visit Information
Address: 244 SW Range Ave, Madison, FL
Hours: Mon-Sat 7am-3pm (Fri until 8pm), Sun Brunch 11am-2pm
Known For: Mile High Club Sandwich, Homemade Pies
View Grumpy’s Diner on Google Maps →
Grumpy’s Diner proves that passing a business to the next generation requires more than training – it requires building confidence.
Last verified: January 2026
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