The Success Circle

Meet Drew Lewis of Pride Travel

By November 1, 2018 December 6th, 2018 No Comments

Meet entrepreneur Drew Martin Lewis, the founder of Travel in Pride, a concierge travel agency catering to the LGBTQ community and their friends. Lewis started his travel agency a few years back when he saw a gap in the billion dollar travel industry and wanted to create a brand that spoke to members of his demographic as an openly gay and proud African American male. His focus was simple, he wanted his brand to celebrate, promote and visit gay prides around the world! Since inception he’s lead travel groups and tours to some of the biggest world pride events, and festivals in countries including Brazil, Thailand, Curacao, Los Angeles, DC, and more! We had the chance to speak with Lewis and learn about his tenets for success, and how he formed a habit of winning as an entrepreneur.

The 21 Day Brand: What made you want to be an entrepreneur?

Drew Lewis: I originally started out trying to supplement my own travel addiction; both with the extra income as well as the access to better control my own destinations and bookings. As time progressed I began to realize that through my intense and excessive research, and real-life experiences garnered from each trip, it put me in an elevated knowledge bracket from other travel planners. This lead me to a desire to work with others who may not have the time or ability to know the questions they should be asking or to seek out those answers. And as I learned things that have escaped the masses (such as 5 Days in Havana or How to make the most of Carnival in Rio), I have begun to share this information to ensure they can have experiences like no other.

The 21 Day Brand: With the world already being a noisy place, why did you choose your industry and what did you do to stand apart from your competition?

Drew Lewis: I chose my industry because it was already something that I had interest in. While I had learned some things years prior about travel; I would be in a different position and place if I hadn’t followed through on my dream. The obligation to share this information propelled me and my business to new places. The reason I stand out from many of my competitors is based on the fact that I remain consistent in engaging with my followers. I ensure that I share a different part of myself. I don’t have the components of a¨thirst trap” travel blog, or the access to have a luxury blog one can aspire to. I do have the ability to plan and execute trips well; weaving a narrative and mosaic that people can live vicariously through.

The 21 Day Brand: What drives you? Fear or Motivation?

Drew Lewis: My continued need and desire to travel is a big motivation! It makes the business work as well as satisfies my wanderlust personality. By continuing to travel and research each trip for myself and others, my knowledge expands. I’ve learned new methodologies to book travel and earn passive income. I’ve learned to work with new customers and obtain new business. From being a standalone travel agent, to a travel blogger and now working on group travel; I am continually evolving by collaborating with experts to ensure that my small share in the travel industry grows larger, inspiring the millions of members of the LGBTQ community that both regularly travel or yet haven’t had the opportunity to travel.


The 21 Day Brand: What one habit do you feel has been essential for your success?

Drew Lewis: I would absolutely look at my research habits. Even when it came time to start my business; I had to do research to figure out how it was possible. I had to discover what was the best route to go through. This has continued as I have recalibrated business goals. I began to seek out ways to diversify and expand the brand that is Travel in Pride. And as Travel in Pride moves forward, (if the past was any indication) we will continue to build upon the habits that made the business successful in the first place.

The 21 Day Brand: Looking back, What advice would you give to yourself, prior to starting this business.

Drew Lewis: Review your business plan frequently and don´t be afraid to make changes and adjustments when needed. Flexibility is needed for any small business. Success, even moderate success, is not always going to come with Plan A. If you make the small adjustments needed to your plan, small successes can continue to grow. Remaining consistent in your work, consistent in your follow up with other businesses, clients and customers will go a long way to creating lead generation and building a base of loyal brand evangelists.

To learn more about Drew Lewis’ business, please visit:

Alaina Pinkney

Alaina Pinkney

Founder of The 21 Day Brand. The 21 Day Brand is an educational initiative for entrepreneurs that offers Articles, E-books, Masterclasses, Workbooks and more, on the art of brand building. The goal of the 21 Day Brand is to give burgeoning entrepreneurs and start-ups, step-by-step resources to building a brand from scratch with an endgame of creating a profitable business.

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