We’re excited to introduce you to the always interesting and insightful Brook Ray. We hope you’ll enjoy our conversation with Brook below.

Brook, looking forward to hearing all of your stories today. Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.

When I was ready to start my travel business, I knew I wanted to offer a few special hosted trips each year, especially in Italy and Croatia. Though I had taken care of all the legalities—forming an LLC, setting up a DBA, opening bank accounts, and so on—I didn’t have any clients lined up for these trips yet. Despite this, I took a bold step and rented an entire villa in Italy for six weeks the following year, hoping to fill it with guests or use it to create marketing content.

I didn’t end up filling the entire six weeks with customers, but I decided to keep the villa anyway, even though it was a huge expense. This allowed me to immerse myself in the daily life of the Italian region I was staying in, and it also provided a perfect backdrop for creating social media content. During my stay, the villa owner asked if some of her good clients could use the apartments I wasn’t occupying. These new guests and I hit it off, leading to many lovely conversations and brainstorming sessions about how to market these trips.

Not only did they spread the word about my business to their friends and colleagues, but the ideas we discussed helped generate significant momentum once I returned to the States. By the time I welcomed the next group of guests to Italy that fall, I was more than ready to wow them, and the trips were fully booked. The following year, I even had a waiting list. To show my gratitude, I invited those wonderful people and the villa owner on the next chartered yacht cruise I organized in Croatia.

You’ll never have a better marketing team than those with whom you truly connect!

Brook, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Hi there! I’m Brook, the founder of Travel with Direction, based in the DFW area of Texas. My journey into the travel industry is rooted in my global upbringing and a lifelong passion for exploration. Growing up in Africa and spending significant time living and working in Europe, I’ve always been surrounded by diverse cultures and breathtaking landscapes. These experiences ignited a desire to share the world’s wonders with others.

My professional background as a sommelier, with 25 years of experience, adds a unique flavor to my travel business. Hosting wine tastings, classes, and elegant dinners has taught me the art of creating memorable experiences. This expertise seamlessly translates into the bespoke travel itineraries I design, ensuring each journey is as enriching as it is enjoyable.

Travel with Direction specializes in creating personalized trips to Europe and Africa. From luxurious villa stays to immersive cultural experiences, my services cater to discerning travelers looking for unforgettable adventures. I handle everything from detailed itinerary planning to on-the-ground arrangements, making sure every trip is tailored to my clients’ preferences.

What sets Travel with Direction apart is my commitment to authenticity and personalization. I don’t just plan trips; I craft experiences that resonate with your soul. Whether it’s a private wine tour in Croatia, a serene retreat in the African savannah, volunteering with sea turtles in Greece, or a culinary journey through local markets, I ensure each moment is special.

I’m incredibly proud of the relationships I’ve built with my clients and partners. Good travel is responsible and sustainable.

For potential clients and followers, I want you to know that Travel with Direction is more than just a travel service—it’s a gateway to discovering the world in a deeply personal and enriching way. My brand is built on a foundation of passion, expertise, and a genuine love for travel and connecting people. I’m here to make your dream vacations a reality, blending my knowledge of wine, culture, and adventure into every journey.

Thank you for taking the time to learn about me and my work. I look forward to creating unforgettable memories with you!

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

Listening and connecting with my clients has been the most effective strategy for growing my clientele. When clients feel truly heard, they naturally want to share their positive experiences with others.

I learned this lesson in a humbling way when I owned a wine bar. Fresh off earning a high-level wine certification, I thought my expertise alone would attract customers. I meticulously curated the wine list, confident in my choices, but business was still slow.

One evening, a friend was at the bar when a lady walked in and asked, “Do you have any white zin?” Feeling superior, I scoffed and replied, “No, they have that on the bottom shelf at the grocery store.” She looked embarrassed and left quickly.

My friend turned to me and said, “You need to be f#^%ing nicer to your customers. You didn’t even listen to what that lady really wanted.” Initially, I was angry, but as the slow hours ticked by, his words sank in. It struck me that no matter how educated or certified I was, I was never too good to listen and connect with people.

From that point on, I focused on truly listening to my clients. This genuine connection created loyalty, and loyal clients are your best advocates. They bring in more business by sharing their positive experiences with others.

Can you tell us about a time you’ve had to pivot?

One significant pivot in my life was when I decided to sell my successful wine bar after 13 years. While I loved the customers and cherished sharing my wine knowledge with them, I realized that my true passion was travel, and the bar was holding me back from fully embracing it.

Running the bar meant I couldn’t travel without constantly worrying about its operation. Moreover, the bar’s earning potential was limited by its capacity, and it would never provide a decent income unless I was there to manage it personally. This setup restricted my freedom to explore travel as a business.

Ultimately, I made the tough decision to sell the wine bar. It was a bittersweet moment, but it allowed me to pursue my dream of creating bespoke travel experiences without being tied down. This pivot opened up a world of possibilities and led to the creation of Travel with Direction, where I now help others discover the joys of travel and adventure, and maybe a little wine!

Contact Info:

• Website: https://TravelwithDirection.com
• Instagram: https://instagram.com/travelwithdirection
• Facebook: https://facebook.com/travelwithdirection.com
• Linkedin: Brook Ray