Betsy Berman (left) and Andrea Strahl (right). (Source: Betsy Berman, Andrea Strahl)
Travel Advisor Success Stories focus on savvy advisors and how they achieved success. Here’s a look at Betsy Berman and Andrea Strahl, co-owners of Black Sheep Travels, an affiliate of Travel Experts.
How did you get your start as travel advisors?
Travel has always been part of who we are. We’ve each spent years traveling – curious by nature, always planning the next trip and noticing the small details that make a journey feel effortless and meaningful.
We also believe time is the ultimate luxury: You can make more money, but you can’t make more time.
Early on, friends and family started coming to us because they knew we’d make it seamless and thoughtful, and we realized there was something special in that: the ability to take what feels overwhelming and turn it into something exciting and personal.
That’s what hooked us. Travel advising is part creativity, part problem-solving and part taking care of people, and we genuinely love all of it.
How did you build your business over the years?
We built Black Sheep Travels the way we build trust: one trip, one relationship, one ‘they really get us’ client at a time. We started with a standard that we weren’t willing to compromise on and built from there.
Our earliest clients became our biggest advocates because they felt supported in a rare way: responsive communication, honest guidance and an experience that was elevated but never fussy. Over time, that word-of-mouth momentum became the heart of our growth.
As demand expanded, we became intentional about building a company, not just planning travel. We invested in the behind-the-scenes foundation: clear processes, strong training and the right people to complement and strengthen what we do.
Building a truly collaborative team culture, one that stays deeply high-touch while delivering consistent, thoughtful itineraries and advice across many trips at once, has become our hallmark. And it helps that we genuinely adore our team as both colleagues and humans.
What characteristics make you successful advisors?
We both arrived at travel planning with a ‘suitcase’ full of valuable, diverse experiences: a passion for travel, strategic planning and organization honed over years spent in both human resource consulting and marketing.
We are different in the best way, and that’s part of why we work so well together. One of us is naturally big-picture and instinct-driven; the other is a detail hawk who can spot the missing piece from a mile away.
The common thread is that we both care deeply. We listen carefully, ask a lot of questions and take our clients’ time seriously. We’re proactive, so our clients don’t have to worry about the ‘what ifs’ – we’ve already thought them through.
And we genuinely value relationships: with our clients, hoteliers and on-the-ground partners. Those relationships aren’t transactional for us; they’re how we consistently create trips that feel personal and beautifully executed. We’re as careful with our clients’ limited time as we are with their financial investment.
What have been your greatest challenges?
The biggest challenge has also been part of the gift: growth. When you’re known for white-glove service, scaling without losing the feeling of having someone in your corner is very important.
We’ve had to be thoughtful about systems, hiring and boundaries, because our promise to clients is that we will show up, and we mean it.
Travel planning also has a way of keeping you humble. Flights change, weather shifts and the unexpected happens. That’s when we’re most valuable: staying calm, moving quickly and solving problems discreetly and swiftly so clients can stay present and enjoy the trip.
What have your greatest accomplishments been?
We’re proud of the trust we have garnered. There’s nothing we take more seriously than being handed the trips that matter most; honeymoons, anniversaries and the ‘we’ve waited our whole lives to do this’ journeys.
We’re also proud of the culture we’ve built as partners. Black Sheep Travels feels personal, not corporate; imaginative, not cookie-cutter. Creating an environment where a high level of thoughtfulness is the norm – for our clients, for our team and for our industry partners – has been one of the most meaningful accomplishments of our careers.
What tips can you provide advisors new to the industry?
Ask better questions. Don’t start with a destination; start with why they’re traveling and what they want the trip to feel like.
Be obsessive about small stuff. The magic lives in the details: access, pacing, thoughtfully selected hotels, villas, yachts, personalized activities and expert guides make every moment feel effortless and intentional.
Let your care show. Clients remember how you make them feel, especially when something changes and you handle it seamlessly.
Build genuine relationships. In the end, this is a relationship business that continues to compound over time.
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