Introducing New Team Member Don Littlefield

Hello to my fellow Tour Professionals!

I am very excited to be joining the amazing team at TripSchool!

Since the time I first met Mitch and Alan, I have been amazed at the knowledge that they possess, and how willing they are to share it in so many formats with all of us!

My role within the TripSchool group is to help to educate and train our start-up and existing tour business owners and operators. I will lead efforts specifically under entrepreneurship and business development, including the very successful Start a Tour Business Workshop currently being offered.

But first, let me introduce myself to those that I have not already met. I am born and raised in Portland, Maine, a real tourism destination for travelers all over the world. I have lived in this city my entire life.

Before I found my calling as a tour guide and manager, I worked in many different industries. My background includes operations management and sales positions in small companies, hospitality chains, major corporations, and non-profits.

About ten years ago, I started showing people around the breweries in my hometown as the first employee for a start-up craft alcohol tour company. Once Portland started to gain prominence as an eating and drinking destination, I honed my skills as an adult tour guide, leading thousands of half-day tours around Maine and parts of New England allowing my thirsty guests to learn more about the craft alcohol industry.

My varied background in retail and restaurant management, data collection and reporting, technology sales, real estate, and non-profit leadership helped me assist in this new company’s growth. We moved it forward by opening other locations in New England. Eventually, we acquired a national-level company called Brews Cruise, Inc., which has long offered the same types of craft alcohol experiences.

My role in Brews Cruise is to help each of our individual owners and operators around the country grow and expand their businesses. I work to connect more thirsty guests directly to these local craft alcohol experiences. I personally work with each owner to design and execute their business development plans, assist them with developing creative tour ideas, and help them craft social media content and marketing strategies for the Brand and the individual operators.

I am also a multi-day tour manager for students and adults. I am a licensed tour guide in both New York City and Washington, D.C., and have led several tours in those cities over the past few months. I have realized that I enjoy this style of leading tours for one group over multiple days. It allows me to develop a real connection with the travelers and to find ways to amaze and delight them with the overall experience.

By joining the faculty at TripSchool, I will be following the model that has been successful for Mitch and Alan. I will share as much knowledge from my experiences as I can.

I am one of you and am eager to help as many tour company entrepreneurs as possible with their business struggles.

Let’s Grow!
-Don
Head of Entrepreneur Development