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How I built my business: Ailsa von Dobeneck

Our journey began with a “cheers” in 2021. Tomeka Bryant and I previously had worked together in the rail industry, ran into each other at a conference in St. Louis and got chatting. A juice bar in a caboose car always had been top of mind (and center of heart), and when we saw a 1947 rusty, old red caboose for sale online, we said, “Well, if the bones are good, let’s go for it.” We traveled to Missouri to pick her up, moved her to Mississippi and began the hard work.

I moved across the country, and Tomeka made her house headquarters. We invested almost every night and weekend, had contractors help (an equal mix of wonderful and awful experiences), had industry friends get on board and built a brand based on sunshine and positivity. We were determined to bring something new and fresh to the Coast. A year and a half later, we opened The Juicy Caboosy in Long Beach. It what we hoped it would be: a vibrant and fun outdoor restaurant that focuses on fresh-squeezed juice, cocktails and caboosy- made food.

Tomeka Bryant (l) and Ailsa von Dobeneck (r), co-owners of The Juicy Caboosy in Long Beach.

Now that the caboosy is up and running, it is a great time to reflect. It all starts with an idea, simple idea. After the idea comes a laundry list of considerations: financing, time commitment, partnership and brand vision, to name a few. The biggest piece of advice I can offer from our experience is to take some time (as long as it takes) to get a full understanding of what lies ahead and how best to get to a place of success. Surprises will happen and, as they say “the best laid plans….” However, if you have as much of the organization as possible done on the front end, it is easier to navigate rough waters. Plan. Plan. Plan.

If you have a business partnership, make sure you spend time nurturing that connection, listening to the other person’s ideas and respecting the other’s investment in the journey. This is essential. Everyone brings different strengths to the table, so make sure you are using them to their fullest potential. The journey is a hard one, and it is better when shared. If you are sitting on the idea of a lifetime, the only choice is to go for it; jump in the deep end. Know it will be hard, but worth it, and you will rise to the top. Cheers to you, and always remember to be sweet and stay juicy.

Ailsa von Dobeneck is co-owner of The Juicy Caboosy and specializes in the menu side of the house and brand management. She can be reached at or (757) 749-0851. The Juicy Caboosy is located at 407 Mason Ave., Long Beach, and can be reached at (228) 265-7964.

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