Meet the Team

Jon wears all the hats at Tipsy Pickle - general manager, handyman, teacher, vibe manager - but what he’s most passionate about is creating moments of magic for guests and helping his team grow. He pushes staff to master their skills and become the best version of themselves while they’re with us, leaving the world a little better than they found it.

His go-to order is a Nitro Cold Brew and a Big A** Breakfast Burrito with steak. If Jon were a pickle, it’d be spicy and crunchy, as they all should be. His super useful and impressive skill is that he has an oddly heroic ability to open jars when no one else can. Off the clock, you’ll find Jon running (yep, by choice), camping with his dogs Rye and Goose, or wrangling his squad of nieces and nephews back home in Georgia. 

Walk-up song: Right Above It by Lil Wayne. Life motto: “You only live twice — the second time is when you realize you only live once.” Stop and say hello at your next Tipsy Pickle visit!

Jesse is the Director of Hospitality at Tipsy Pickle, turning drinks, dinks, and bites into full-blown experiences. He thrives on crafting menus, watching them come to life behind the bar, and seeing that first sip spark a guest’s smile. For him, it’s never just a cocktail - it’s connection and creativity.

His go-to order is Queso Fries, paired with whatever fun concoction he dreams up that day. If Jesse were a pickle, he’d be a spicy dill with a twist of sweet heat because he’s bold, sharp, and always keeping things interesting. His not-so-useful but impressive skill is he can name any Taylor Swift song in under 10 notes.

Off the clock, Jesse is serving on the board of Twirl to the World and sweating it out at the gym. At home, he’s probably in the kitchen, cooking for friends and family (and making it look way too easy). 

Walk-up song: Doses and Mimosas by Cherub. Catchphrase: “Chaotic, but make it charming.” Stop by and meet Jesse at Tipsy Pickle! He’ll keep your glass full and the good times rolling.

Wynn is the Director of Pickleball, and Pickleball Pro, at Tipsy Pickle. He makes every court experience seamless, hospitable, and fun. Above all, Wynn loves teaching - from youth to pros - he enjoys hanging out, laughing on court, hitting balls, and helping everyone up their game. 

His go-to order is a plain Double Smash Burger with bacon and water… he has the pickiness level of an 8-year-old. If Wynn were a pickle, he’d quit being a pickle and become bacon instead. His not-so-useful but impressive skill is that he can supposedly do magic tricks… this is yet to be seen.

Off the clock, Wynn is living his best life with his pup Bella, a black Bernedoodle, and his fiancé Megan - he mostly tags along to eat all the good food she cooks.

Walk-up song: All I Do Is Win by DJ Khaled. Catchphrase: “GAMETIME.” Stop by and meet Wynn next time you’re at Tipsy Pickle!

Rebecca is the person behind Tipsy Pickle’s social media and events, capturing the magic, memories, and good vibes every day. She loves showing off the fun, cheeky, and not-too-serious spirit of Tipsy Pickle. 

Her go-to order changes daily, but she loves a Not at the Table, Carlos. If Rebecca were a pickle, she’d be bread and butter because nothing beats sitting on the beach with a bologna sandwich in one hand and a bread and butter pickle in the other. Her not-so-useful but sometimes useful skill? Breaking into a house with a card (only her own, don’t worry… we’re a little worried).

Off the clock, Rebecca is outside with the farm animals (currently housing a donkey named Moscow), reading, or hanging with her friends, family, and two senior pups, Harley and Nina.

Walk-up song: The Largest by BigXthaPlug (as she gets ready to miss five balls in a row). Life motto: “Too early to worry, too late to cry.” Stop by and say hello next time you’re at Tipsy Pickle!