Meeting Shawn Maile is an experience. He’s energetic, quick-witted and passionate about his brand, but he can also be quiet and pensive, always looking for an opportunity to learn. All of these qualities have translated into how he deals with his Caribbean Entrepreneurship journey: the highs, the lows, the success, and the failures. You can grab a bit of a view of what his entrepreneurial journey has been like in the interview below.

What is the name of your company?

Trek Tours

What products or services does your company provide?

We offer guided hiking tours and excursions to visitors to the island.

If you were headlining a UN event or Ted Talk, how would you love to hear/see your company introduced?

At Trek Tours we believe that scenery needs to be EXPERIENCED, and not seen through a bus window. Join us as we trek to the most scenic and rewarding parts of Antigua. You need not be an athlete to participate, but you need to be interested in experiencing Antigua’s incredible scenery in an active manner!

So grab your camera, pack the kids, and get your soles ready because we’re going hiking!

What inspired the birth of this company?

As part of a social club the partners were involved in planning weekly hikes for over two years. After moving on to other interests there was still a desire to showcase the natural beauty of Antigua so Kerri, Craig and I decided to start our own hike company. We built the company from the ground up hoping to deliver an awesome hiking experience each and every time.

How do you think your company solves any of your village, community, country or region’s problems

We contribute to the tourism product in an environmentally friendly, organic and sustainable way.

Do you have any co-founders and/or notable team members?

Kerri Gore
Craig Williams
Curtis Kelsick – Website

What would you say has been your greatest challenge as a company thus far and how have you overcome it or how are you working to overcome it?

Maintaining customers during the off season. We are working to overcome it by investing more in marketing the company during the off season.

What would you say has been your greatest triumph/achievement as a company thus far?

There have been a few, particularly the linkages we’ve been able to form with various international press houses via the Tourism Authority. Being featured in multiple magazines promoting the island, such as The Antiguan, Treasure Islands Guide, and Caribbean Tourism Magazine, is also another major accomplishment.

Additionally being recognized as the premier brand for hiking in Antigua amongst hoteliers as well as our top 20 ranking on TripAdvisor in outdoor activities. Reading the awesome reviews from our guests on TripAdvisor is always an awwwww inducing moment. We also sponsored a group of young people on a hike to Fort Berkeley. This was in partnership with the HALO Foundation to bring Christmas cheer to a group of less fortunate young people .

What would be your advice to other Caribbean entrepreneurs?

It’s the perfect time to be an entrepreneur. Let’s make it happen!

What is your vision for entrepreneurship in your country or in the Caribbean?

I would like to see a space and a platform for entrepreneurs to connect, share ideas and provide support to each other. An incubator of sorts where persons with an idea can grow it into something tangible with the help of other like minded creatives.

What would you say has been your most valued entrepreneurial lesson during the journey so far?

Some things take time and you must be willing to invest the time to learn the lessons. That, plus the fact that you’ll never know everything there is to know about running a business as things change from season to season and you have to be able to accept the good and the bad. Learn from your mistakes and move on to the next task at hand.

The Man Behind The Company


Shawn Maile

Country of Birth

Antigua and Barbuda

Country of Residence

Antigua and Barbuda

Favorite Music Artist


Favorite Song

Where I come from – Chronixx

What is the book/books that you’ve given most as a gift and why?

How to Work Six Jobs on An Island. Because I wrote it 🙂

What are the three books that have most influenced your life?

1. The Slight Edge by Jeff Olson

2. The Tipping Point by Malcolm Gladwell.

3. Rich Dad Poor Dad by Robert Kiyosaki

What recent purchase of yours has most positively impacted your life?

All natural Neem deodorant and Spirulina

How has a failure of yours set you up for later success?

In January of this year I was teaching two part time classes and working at my day job as well. I was on vacation from my day job from December going into January so it was all good. When I went back to work in February I was running an after school program with my coworker. I think I had it all under control but I soon realized I had gotten myself into a bind. I couldn’t leave my coworker to handle the program on her own and I couldn’t teach both classes and still be at the program 3 afternoons a week. I had to drop a class. By this time I had become attached to both classes. Already learnt the names and personalities and had a good rapport. I had to cut one class and change the times for the other. I felt like I was disappointing them but it had to be done. On top of that I had to source the lecturer to replace me. It took some doing but I found a replacement. The class DID NOT like how things went down and did not like the style of the new lecturer. I had to see them when I went to class and of course they asked why they got dropped and not the other class. It was not a good feeling. This experience has taught me to pace myself and not bite off more than I can chew.

What is a quote that you think of often or live your life by?

Let’s move the world 🌎

What is one of the most worthwhile investments that you have made?

My education.

In the past three years what belief, behavior or habit has most improved your life?

Realizing that my mental health and physical health are two of the most important aspects of my life that need to be curated, nurtured and improved. Coming of age as a Caribbean man has also been an eye opener. Realizing that we’re here on this earth to give more than we take is a humbling experience.

What advice would you give to a school leaver in your country about the braving the uniqueness of the entrepreneurial environment in your country?

I would tell them to have conversations with people who’re doing the thing they want to do. To volunteer at organizations they like and to seek knowledge and experiences over pay cheques and popularity. Ignore anyone who does not see what they see. Ignore the hype. It’s going to be hard work but it’s going to be worth it. What’s unique about the entrepreneurial journey is that you’ll find company along the way. You’ll find people who’re just as passionate as you are to move the world.

When you feel overwhelmed/unfocused what do you do?

I sit with my feelings. I embrace the funk knowing that I will come out better on the other side having been through a tough situation.

Who most inspires you? What about their life, habits or model have inspired you?

Right now I’m vibing off of Shawn Stevenson from The Model Health Show. His podcast is truly amazing and uplifting. Definitely worth a listen.

Find Trek Tours on Social Media

Instagram: @trektours
Twitter: @trektours
Facebook: @trektoursantigua