Masters in Travel

In this episode of Masters in Travel, Brianna sits down with Olivia Tambosso, a luxury travel advisor whose career began on the inside of one of the world’s most respected luxury hotel brands: Aman. After years in guest-facing operational roles in Morocco, Thailand, and Japan, Olivia brings a rare perspective to the travel advisor side of the industry. Together, Brianna and Olivia explore what true luxury looks like behind the scenes, from anticipating client needs to understanding the operational realities that shape a hotel stay. Olivia shares how her time at Aman taught her to communicate more clearly, advocate more thoughtfully, and view hotels as collaborative partners rather than simple suppliers. This conversation is a reminder that luxury travel is not just about beautiful rooms or impressive amenities. It is about care, nuance, relationships, and the small details that make clients feel deeply seen.

What if the reason you feel stuck isn't because you're not working hard enough, but because you're too busy executing to decide what actually matters? In this solo episode, Brianna unpacks why so many travel advisors find themselves in a cycle of nonstop busyness that somehow still feels stagnant. She breaks down five specific ways advisors get stuck: building for everyone instead of someone, being great at what they do but unable to explain why, growing a business they don't actually want, treating everything as urgent, and delegating tasks without delegating ownership. This isn't a productivity pep talk. It's an invitation to pause, get intentional, and start leading your business like the CEO you already are. If you've ever felt like you're working harder than ever but not moving forward, this episode will help you see where the real shift needs to happen.

In this month's Shop Talk, Brianna and Whitney get real about navigating a chaotic start to the year while balancing the mental load of running a travel business. From January wave season overwhelm to learning when to walk away from inquiries that don't fit, they explore what it means to lead with honesty in client conversations. Whitney shares her journey toward being more transparent about pricing, profitability, and what it actually takes to create the level of experience clients are asking for. Together they unpack the importance of time studies, working backwards from budget or priorities, and refusing to people-please their way into unprofitable bookings. It's a candid conversation about setting boundaries, educating clients through honesty, and building trust by ripping back the curtain on what truly makes a travel business sustainable.

What if staying with a host agency as an experienced travel advisor isn’t about settling, but about scaling smarter? In this episode, Whitney is joined by Margaret Haas Wolf of Brownell to explore what true mutual investment can look like between a host agency and an established travel business. They discuss why support should evolve as advisors grow, not disappear, and how strategic partnership can impact margins, confidence, and quality of life. Margaret shares how engaged host agencies can help experienced travel advisors make more intentional decisions, from refining fees to simplifying operations. This conversation offers a thoughtful reframe on what success can look like beyond commission splits and why the right support at the right stage can change everything.

What if familiarization stays didn’t require waiting for an invitation or hoping the timing worked out? In this episode, Whitney sits down with Lotte Gossage, founder of Hotel FAM Club, to challenge the way travel advisors think about FAMs and hotel partnerships, offering practical insight into positioning yourself as a professional partner rather than a passive participant. Lotte shares how her background in hospitality and sales shaped a more proactive, business-first approach to creating familiarization opportunities. They unpack why travel advisors should stop being grouped with influencers, how hotels actually evaluate ROI, and what decision-makers on properties really care about. If you’re ready to take control of your FAM strategy, this episode delivers a fresh and empowering perspective.