Alright – so today we’ve got the honor of introducing you to Jesse Alexandre. We think you’ll enjoy our conversation, we’ve shared it below.

Jesse, appreciate you joining us today. Being a business owner can be really hard sometimes. It’s rewarding, but most business owners we’ve spoken sometimes think about what it would have been like to have had a regular job instead. Have you ever wondered that yourself? Maybe you can talk to us about a time when you felt this way?

The short answer to that question is yes, I am happier as a business owner. As I dig deeper into that answer, I will admit that it has it’s challenges. As a Travel Advisor, you are always “on” as you constantly have clients traveling either for business or leisure. In an ironic twist, this means that my vacations are not truly vacations. At any moment a client may need a last minute trip, in destination assistance, have a canceled flight or really anything that could happen while or before traveling. Those are the rare times that I think about having a regular job as I would be a cog in the machine instead of the machine itself.

Despite this, I wouldn’t change anything at all. I still get to do something I love. I also still get to travel, I just have had to adjust my expectations of “time off”.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My name is Jesse Alexandre and I am the Owner of Play Harder Travel LLC. My role is to help make my clients travel dreams come true. From conception to execution, I can provide the tools and suppliers to procure your dream vacation, destination wedding, honeymoon, bachelor/bachelorette party, generational get together, couples getaway, best friends trip or any other type of travel. I assist with flights, transfers, accommodations and excursions. My main focus are all-inclusive vacations and cruises. I focus on the Caribbean, Central America and South America. I occasional will handle Disney Vacations and portions of Europe though they are not my focus from a business standpoint. My company is part of the Independent by Liberty umbrella. What that means is not only do you have that “mom and pop” feel and level of service but you still receive the big company resources and backing that allows me to “push my weight around” if needed.

The take away that I want my clients or potential clients to know is that Play Harder Travel LLC is not a large company where your trip is just a number in their book. Every trip that we procure for our client is handled as though we are going on the trip ourselves. When you call Play Harder Travel LLC, you are calling me as the Owner. I want to make sure I fully understand what you are looking for and what will make your trip one to remember. Once your vacation has been booked, we make sure you receive all of the information needed to be as prepared as possible for your vacation so that you have that peace of mind needed to truly enjoy yourself.

Can you talk to us about how your side-hustle turned into something more.

My path to creating Play Harder Travel LLC, turns out to be a full circle type of story. I used to work for a prominent travel company. I worked for them for over 5 years. I loved what I did helping clients with their travel needs. I was offered a job not in the optical industry with a prominent sunglasses and reading glass provider. The job offered paid more than my current job and at that time in my life my financial considerations were more important than my professional satisfaction. Approximately 8 years into my 12 year career in my new job, I saw an ad posted by Independent by Liberty. In short, it provided an opportunity to start up your own travel business. The business could be a side hustle or be your main source of income, that was determined entirely by you as a business owner. My love for travel never left me and I saw this as an opportunity to get back into travel with minimal risk and still keep the job that “paid the bills”. Eventually my side hustle became large enough to where a choice needed to be made. In anything I do I need to perform at a high level and the amount of work at both jobs required a decision in order to maintain my expected level of execution. In the end I chose to quit my job of 12+ years and go all in on the travel business. I have not looked back.

Interestingly enough, I found a job that provided both financial stability and professional satisfaction.

What’s been the most effective strategy for growing your clientele?

This may sound cliché but the best way to grow your clientele is to provide good service and be educated in your field. As a business owner that is just starting out, finding clients can be very difficult. Luckily, Independent by Liberty does provide a pool of clients as one of their business membership options. This of course requires investment, which is needed in any business that is starting out. What I have found is that the initial client is great and provides a “jumping off point” but their experience is truly what makes me as a business owner successful.

When I execute for my clients, they in turn tell their friends and family. Most of my clients have come from referrals. I don’t advertise much and my social media game needs some fine tuning, so I rely on my clients having a good time and being happy with what I have provided them. This also requires me as a business owner to be knowledgeable about what I am offering. I have had to educate myself on different destinations, brands, suppliers and systems. All of this requires either a financial or time investment. These investments are what allows me to provide a memorable trip for my clients which in turn allows me to grow my business with referrals.

Customer service has turned into somewhat of a lost art. I make sure that my clients realize right away that their experience with Play Harder Travel LLC. is different and something they want to share.

Contact Info:

• Website: playhardertravel.com
• Instagram: @playhardertravel
• Facebook: https://www.facebook.com/playhardertravel

Image Credits
All images taken by Jesse Alexandre