Pineapple Escapes, LLC
My career path has been so strange. I seriously couldn’t make this stuff up if I tried… From high school teacher to college professor, to selling travel as a side-gig, to owning my own agency. It’s been a wild ride!
In 2014, I started my Ph.D., was working full-time online as an assistant professor, was working a side job doing website management, my kiddos were in Kindergarten and First Grade, and when one of my friends reached out and said, “I think you’d be a great travel agent” I said “sure.” I mean it wasn’t like I had anything else going on or anything…???
Honestly, I just thought it would be fun and I might be able to earn a few discounts. I had NO IDEA that I was truly starting my own business that would eventually outearn my Assistant Professor salary and become my primary job. I’ve been lucky to grow my own agency and we now have 15 agents (and I’m hiring!) and despite COVID-19 and the mess that is 2020, our agency is blossoming!
One of the questions I receive fairly often is why our agency is named Pineapple Escapes. Well, the short story is that I just like pineapples!
The longer story is that I have a history with pineapples, starting from when Mike and I traveled to Maui for our honeymoon in 2004 and I bought the most adorable pair of white shorts with pineapples on them from J.Crew especially for our honeymoon trip. I absolutely loved those shorts and they have been my “goal shorts” for years. ???
On my very first trip to Walt Disney World, I fell in love with Dole Whip. It was hot and the Dole Whip was so refreshing. It was the perfect treat and my love affair with Dole Whip, Disney, and pineapples grew exponentially!
Originally, I started my agency with the name Jamie Weitl Travel. I quickly realized that was waayyy too confusing when it was being used by other agents and I didn’t need my name associated with everything. My logo already had a pineapple due to my love of pineapples, so I worked with my agents to brainstorm possible agency names — keeping with the pineapple theme and thinking about web addresses that were available. On a drive with Mike (probably coming home from a swim meet), he and I brainstormed ideas as well. I posted the ideas in our agent group and everyone was on board with the name “Pineapple Escapes” and the website was available — so our agency was born.
What I love about our name is that it is simple but encompasses all that I want our agency to represent. We want to be our clients’ go-to experts for helping them to create lasting family memories. We want to help our clients’ escape the real world to relax, unwind, and rejuvenate. The pineapple represents welcoming and hospitality and this is how we want everyone who reaches out to our agency to feel – welcome and cared for!
The pineapple also represents sunshine and tropical climates – some of my favorite vacations! Our agency sells everything from a one-night hotel stay in Milwaukee to a luxury tour in Europe, but I’ll admit to loving Disney, Universal, Hawaii, All-Inclusives, and cruises – with that relaxing pineapple vibe, the most!
I am still working part-time in website management, but my primary career is travel. I do miss parts of teaching, mostly the connections with students, but I’m lucky to have connections with my clients. With my education and training background, I’ve found a career where I can thrive and that makes me feel passionate! I love helping my agents grow their business. I love the opportunities to travel with my family. I love the opportunities to travel on my own. I love how the agency tailors well with my “next big idea” that will hopefully be debuting in 2020… I love it all! And I’m so excited for the future of our agency and how we continue to bloom in the post-COVID world!
