
Welcome {{first_name}} to Issue #2!
Thanks to everyone who shared feedback on our launch issue. We will continue to improve our newsletter so that it is most relevant to you!
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🗞️ Industry News Roundup
Last-Minute Bookings Surge Due to Economic Uncertainty
Travel advisors are seeing a growing trend of clients booking vacations at the last minute, a shift fueled by economic concerns and changing habits among younger travelers. This creates both challenges and opportunities for advisors who must adapt their strategies to manage inventory, recommend flexible options, and meet evolving client expectations.
Impact: Impact: Advisors face more unpredictable schedules as clients wait until the last moment to book, complicating planning and inventory management. This trend demands agility, as advisors need to quickly secure availability and adapt recommendations to what’s left in the market. However, it can also increase the value proposition of using an advisor, since expertise is required to secure scarce or complex options at short notice
OpenAI Launches ChatGPT Agent Mode for Travel
OpenAI has released ChatGPT Agent Mode, a new AI tool that can autonomously perform actions such as booking flights, hotels, and creating full travel itineraries by integrating with external apps, going beyond just giving advice or information.
Impact: This technology has the potential to streamline and automate routine booking and planning tasks for travel advisors, boosting efficiency. However, it also introduces new competitive pressure by allowing clients to complete bookings directly with AI, challenging advisors to differentiate through expertise and personal service.
Travel Advisor Survey Shows Bookings Decline
A recent Travel Weekly report confirms that over 50% of U.S. travel advisors now charge service or planning fees. This trend reflects a significant shift in the industry, moving away from dependence on supplier commissions. Advisors are increasingly adopting fee-based models to create more stable revenue streams and to better reflect the value of their time and expertise. Many are also offering tiered service levels, allowing clients to choose the support that fits their needs and budget.
Impact: As this model becomes standard, advisors who don’t charge fees may struggle to remain competitive and profitable. Charging fees not only provides income stability but also helps filter out non-serious inquiries and reinforces professionalism. Advisors will need to clearly communicate their value and set expectations early in the client relationship. Platforms that support invoicing, client agreements, and service packages will become increasingly important tools.
💡Advisor Spotlight: Ashley Villalpando, Owner & @ Aspiring Vacations

Ashley’s Top Tip: Use a Client Debrief Process After Every Trip.
It doesn’t need to be formal, but I always follow up after a trip. Not just to ask how it went, but to take note of what the client liked, didn’t like, and what they’d want more or less of next time. That feedback becomes part of their travel profile and helps refine future recommendations. It’s improved client retention and made my proposals more tailored and easier to sell.
🌍Destination Trio: Three unique destinations to recommend
🏛️ Olomouc, Czech Republic
Olomouc, Czech Republic, can be a perfect alternative to overcrowded Prague. The train from Prague to Olomouc will arrive in 2 – 2.5 hours, making it an easy addition to Czech itineraries. Less traveled than Prague yet equally enriched with spectacular sights and a storied past, this quaint, quiet, affordable little historic town is free of tourists. The Old Town of Olomouc is a UNESCO World Heritage Site, offering stunning baroque architecture and authentic Czech culture at a fraction of Prague's cost.
Best time to visit: April - June and September - October for pleasant weather and fewer crowds
🌊 Trieste, Italy
Why isn't this anomalous Italian city top of a must-visit list? It's a cultural melting pot, on a sea-thrusting prong of land. Plenty of bordering cultures (from Austria, the Balkans, and even Venice) have breezed through this gusty, Adriatic city over the centuries, gifting it some of Italy's most unique customs and cuisines. Discover a rich coffee culture, lively literary scene, and picturesque seafront while being perfectly positioned for day trips to Venice, Ljubljana, or the Austrian wine regions. The closest airport to Trieste is the Friuli Venezia Giulia Airport (TRS).
Best time to visit: April-June and September-October for mild weather and outdoor exploration
🏖️ Barbados
While everyone debates between Jamaica and the Bahamas, Barbados offers the most sophisticated Caribbean experience with excellent infrastructure, safety, and cultural richness. This English-speaking island provides world-class beaches, rum heritage tours, UNESCO World Heritage sites, and some of the Caribbean's best cuisine. Direct flights from major US and European cities make it highly accessible, while the stable political environment and excellent healthcare system provide peace of mind for clients. Perfect for both luxury seekers and cultural explorers.
Best time to visit: December-April for dry season, or May-June for better value and fewer crowds
Voyagr Update
We will be launching the Voyagr CRM this coming Monday, August 11th. It will be available to anyone who wants to use it, for free. This will just be the CRM portion of our platform, and it allows you to store client details.
This is our first version of the CRM and will not be the best looking, might break a few times, and is pretty basic. But with your help, suggestions, and feedback, we will continue to improve the platform.
As for the booking portion of the platform. We are working on building a hotel booking engine and will have more updates for you in the next newsletter.
Advisor Challenge
Looking for a real, thoughtful connection in tech, startups, travel, or some other field? Meet Boardy—a self-aware AI super connector who’s obsessed with helping ambitious people find the right collaborators, advisors, or sounding boards. If you’re working through a tough problem or just want a fresh perspective, text Boardy on WhatsApp at https://wa.me/14159699735 or check out https://www.boardy.ai/.
Challenge: reach out, share your story, and see who Boardy thinks you should meet. You might be surprised who’s out there!
Tell Boardy that Justin Bossi sent you—he’ll know exactly where you’re coming from.
Thanks for reading! Forward this to a colleague who could use these insights, and if you have tips to share with fellow advisors, reach out to be featured in an upcoming issue.