Today we’d like to introduce you to Jon Piotrowski and Lindsay Matheson of The Lucky Pony.
San Diego natives, Jon + Lindsay, were dreaming of a way to perfectly marry their decades worth of expertise between bartending and user experience strategy. The idea was simple, create something that felt equal parts craft and connection. That vision eventually became The Lucky Pony, a mobile bar company built to bring thoughtful & modern beverage experiences to every event.
Jon grew up in Poway and brings over a decade of bartending and bar management experience to the business. He’s worked with some of San Diego’s top hospitality groups: Modern Times, The Waterfront Group, and Consortium Holdings and is passionate about delivering the kind of hospitality that makes guests feel genuinely cared for. You’ll find him at every event, ensuring everything runs smoothly and exceeds expectations.
Lindsay, born and raised in Point Loma, spent two decades shaping digital and brand experiences for companies like Hyundai, Microsoft, Qualcomm and Intuit. She leads all creative direction for The Lucky Pony from web and print design to marketing and client experience and loves crafting details that feel intentional and memorable.
What really sets The Lucky Pony apart is their seasonal craft cocktail and mocktail program. They take a garden-to-glass approach, sourcing locally whenever possible and creating handcrafted syrups, garnishes, and mixers in-house. Every menu is unique to the season, creative, fresh, and delicious.
After months of searching, they found the perfect vintage horse trailer bar, one they’d admired for months and when its owner decided to sell, they took it as luck from the universe. That moment was the start of The Lucky Pony.
Today, they lead a talented team of accredited bartenders and mixologists who share a love for craft, creativity, and inclusion. Whether it’s a wedding, corporate event, or private celebration, their goal is always the same: to create an experience guests will remember long after the last sip.
We all face challenges, but looking back would you describe it as a relatively smooth road?
Starting a business from the ground up is never a straight line. It takes a lot of determination, resilience, and a deep belief in what you’re building, especially when your business is rooted in craft. Because our model revolves around locally sourced, seasonal cocktails and mocktails, there’s a tremendous amount of behind-the-scenes work that goes into every event.
People often see the final four-hour service, but what they don’t see are the two full days beforehand spent sourcing fresh ingredients, crafting syrups, batching mixers, and testing recipes until everything is just right. We care deeply about quality and experience, and that level of care takes time.
There have been plenty of learning moments along the way, refining our processes, finding the right client base, and learning how to balance the creative with the operational. But every challenge has made us better. More than anything, it’s taught us that showing up with consistency, creativity, and heart is what keeps a business like ours growing.
As you know, we’re big fans of The Lucky Pony. For our readers who might not be as familiar, what can you tell them about the brand?
You’re not just hiring a bartender, you’re hiring a luxury craft cocktail experience
The Lucky Pony isn’t just a bar, it’s an experience. We bring beautifully styled mobile bars, curated seasonal cocktails & mocktails, and over 15 years of bartending expertise to weddings, private parties, and brand activations across San Diego.
“The aesthetics and bar set looked so posh and professional. The presentation of the drinks were the best, just like in a high end speakeasy! I cannot recommend them enough.”
– Lanna; wedding attendee
“I had The Lucky Pony Mobile Bar at The Prehistoric Prom at the San Diego Natural History Museum! I have been thinking about this drink since then. The creaminess of the drink, the color, the taste, so delicious! The bartenders were fantastic and friendly!”
– Aureilia, The Nat event attendee
Contact Info:
- Website: www.theluckypony.com
- Instagram: @theluckyponymobilebar
Image Credits
Tommy McAdams @tommymcadams
