Tourpreneur Tour Business Podcast

Ryan Connolly went from finance analyst to glacier guide to co-founder of Hidden Iceland. In this episode, he shares the numbers behind their most pivotal business decision: cutting small group tours that represented 50% of their departures but only 10% of revenue.That shift to exclusively premium and luxury private tours helped the company grow by 5% while improving quality and profitability. Ryan explains how relationship marketing drives 70% of their bookings directly without OTAs, why they lead with education when working with travel advisors, and why PR outperforms paid advertising when selling luxury experiences.Plus, the story of how a three-year journey across 40 countries led him to Iceland, where he met his wife on a glacier tour and built a business with two partners.Top 10 Takeaways for Tour Operators1. Cut unprofitable segments ruthlesslySmall group tours accounted for 50% of Hidden Iceland's departures but only 10% of revenue. After eliminating that segment, they grew 5% by focusing resources on premium and luxury private tours where margins are higher.2. Partner with competitors instead of viewing them as threatsWhen customers can't afford Hidden Iceland's luxury pricing, Ryan personally introduces them to partner companies that serve the budget segment. This maintains relationships and positions them as helpful experts rather than pushy salespeople.3. PR drives better ROI than paid ads for high ticket salesOver 450 articles in publications like Condé Nast, Forbes, and CNN have driven 70% direct bookings. For luxury trips ($20,000+), earned media builds trust better than Facebook or Google ads.4. Lead with personal story in first customer contactRyan's initial email starts: "Hello, my name is Ryan. I'm originally Scottish. I've lived in Iceland since 2016. I originally trained as a glacier guide..." This builds immediate trust and differentiates from transactional competitors.5. Educate travel advisors. Don't just sell to themHidden Iceland runs webinars teaching agents about Iceland's seasons, distances, and what each time of year offers. Not sales pitches. The education first approach builds meaningful advisor relationships that generate 30% of bookings.6. Vet activity partners on safety and environmental standardsBefore partnering with snowmobile companies, helicopter tours, or other providers, Hidden Iceland shares their own safety and environmental policies first, then asks partners to reciprocate. This creates collaboration, not just transactions.7. Train guides to be themselves, not follow scriptsInstead of teaching guides what to say at each stop, Hidden Iceland tells them: "Be yourself in the most authentic way possible and create genuine connections." This leads to reviews that praise the guide more than the destination.8. Choose conferences strategically. Avoid the herdRyan skips luxury travel conferences if more than 2 or 3 other Iceland companies will attend. Less competition means easier differentiation and more meaningful conversations with travel advisors.9. Keep the sales process low tech and high touchDespite having a CRM (LEMACS), Hidden Iceland puts key itinerary details in the body of emails and offers phone calls early. For luxury clients, human connection trumps slick automation.10. Build the business with partners you trust implicitlyRyan emphasizes: "Don't set up a company with anyone you don't trust inherently and that you believe will communicate effectively during the hardest times." Through pandemics and volcanic eruptions, Hidden Iceland's three owners have never shouted at each other because they chose partnership carefully.

Kevin and Sylvia launched iRide Arusha in July 2024, offering motorcycle tours and rentals in Tanzania. Within 18 months they scaled across four East African cities through a franchise model called iRide Africa, with partners operating in Rwanda, Nairobi, and Mombasa. The franchise structure allows riders to cross borders and book multi-country tours.The episode covers operational realities: importing equipment across borders, navigating tourism regulations, managing multi-country payment processing, and running rentals and guided tours as two distinct businesses with different customer profiles and sales cycles. Kevin and Sylvia share how they find customers through motorcycle clubs, price for premium buyers, and use immediate response times as a competitive advantage.TOP 10 TAKEAWAYS1. Test adjacent niches when your market is saturatedRather than launch another safari company in an oversaturated market, Kevin and Sylvia identified motorcycle touring as an underserved adventure niche in East Africa. Consider what adjacent experiences your destination supports that competitors aren't offering.2. Franchise models can scale faster than going soloWithin 18 months, iRide expanded across four East African cities through franchise partnerships. Partners share mechanics, bikes, marketing resources, and customer referrals. This creates a network effect where riders can start in one country and end in another, adding value no single operator could deliver alone.3. Target communities, not just individualsKevin reaches out directly to motorcycle clubs in major US cities. One Chicago BMW Riders club is bringing eight people in February. Booking one club creates the revenue of eight individual customers with a fraction of the acquisition cost. Find the clubs, associations, or communities that match your experience type.4. Customer service is a competitive advantage in developing marketsTheir immediate response times and willingness to hop on Zoom calls builds trust fast, especially for customers who've never been to Africa.5. Platform diversification requires testing, not guessingiRide is on Get Your Guide, Viator, Klook, WeTravel, and fielding Facebook messages, but hasn't found the magic channel yet. Test widely, track what converts, double down there.6. Price for the experience you're actually delivering, not your self-doubtKevin admits they severely underpriced at launch. Beginner business owners often can't see their own value clearly. If you're offering wow moments and authentic connections, charge accordingly.7. Guided vs. rental requires different marketing and operationsRental customers (experienced, self-sufficient, quick decision makers) need less hand-holding than guided tour customers (more questions, longer planning cycles, higher price points). These are functionally two different businesses with different messaging, pricing, and customer profiles.8. Gross revenue and net income are very differentVehicle maintenance, cross-border parts sourcing, and insurance eat into margins constantly. Build cash reserves and expect hidden costs, especially in asset-heavy businesses.9. Local language fluency unlocks competitive advantagesSylvia's Swahili fluency helped navigate Interpol holds on imported bikes, handle tourism police complaints from competitors, and build long-term supplier relationships. Language access isn't just customer-facing—it's operational power.10. Differentiation isn't just what you do, it's how guests connectGuests consistently cite the vastness of the landscape and local interactions (like lunch with Sylvia's 88-year-old farming grandmother) as their standout memories. Design for connection points your format uniquely enables.

This conversation with Jeff Gayduk, publisher of Premier Travel Media, reveals an industry at a transformative inflection point where specialized group travel is experiencing unprecedented growth despite predictions of its demise. Speaking from his unique vantage point overseeing multiple travel industry verticals, Gayduk identifies 2026 as a watershed year driven by three major events—the World Cup, Route 66's centennial, and America's 250th anniversary—while highlighting the explosive growth in niche markets from pickleball tourism to multi-generational family trips. The discussion underscores a fundamental shift in how travel experiences are designed and marketed, moving away from cookie-cutter itineraries toward highly specialized, passion-driven offerings that leverage everything from sports tournaments to career readiness programs, with successful operators focusing on authentic relationships and deep expertise rather than trying to compete with legacy brands on traditional offerings.10 Key Takeaways1. Group Travel is Experiencing Its Most Exciting EraThe group travel market has undergone a complete transformation since COVID, moving from a defensive position of proving relevance to an offensive surge of innovation and growth. Special interest groups, family bonding experiences, and educational opportunities are creating unique travel products unavailable to individual consumers. The pandemic's forced separation actually accelerated demand for meaningful group experiences rather than diminishing it.2. Three Major Events Will Define 2026 TourismThe World Cup across 16 North American cities will bring 6.5 million visitors with 40% from overseas, creating massive opportunities for tour operators in hub cities. Route 66's anniversary and America's 250th celebration will generate patriotic tourism and historical programming throughout the year. These events create both standalone opportunities and chances for creative tour operators to build complementary experiences around the main attractions.3. Sports Tourism Has Become the Industry's Hidden GiantYouth sports tournaments drive consistent weekend travel with families spending whatever necessary for their children's athletic participation, creating massive but underserved tourism segments. Adult amateur sports, particularly pickleball, are seeing explosive growth with facilities featuring 32-64 courts becoming destinations themselves. The opportunity lies not in the games themselves but in creating experiences for the downtime between matches, serving families who are tourists without tour infrastructure.4. The Student Travel Market Has Evolved Beyond Class TripsCareer readiness programs are emerging as students face AI-driven uncertainty about future employment, with manufacturers and trade schools becoming unexpected tourism partners. Small, specialized STEM groups and performance ensembles are replacing massive band trips, creating opportunities for highly targeted educational experiences. College visit tours have become sophisticated multi-campus experiences as the stakes for education choices continue rising.5. Niche Specialization Beats General Tourism Every Time"The riches are in the niches" has proven true as operators who focus on specific passions outperform those trying to compete on standard itineraries. Technology now enables operators to reach highly specific audiences globally rather than being limited to local marketing through yellow pages and park districts. The tighter the niche, the easier it becomes to market and the more likely customers are to pay premium prices for expertise.6. Multi-Generational Travel Represents Billions in Untapped OpportunityOlder Americans with disposable income are funding entire family trips, from luxury yacht cruises to Disney vacations, often including extended family and friends. These trips require sophisticated customization that big operators can't provide, creating opportunities for bespoke tour designers. The spending on these milestone celebration trips is "mind-boggling" according to industry data, with grandparents willing to invest heavily in family bonding experiences.7. DMOs Are Underutilized Partners for Tour OperatorsDestination Marketing Organizations spend hundreds of thousands on marketing but need tour operators to provide the actual bookable products visitors seek. DMOs possess mountains of data and local insights that operators often don't know to request, creating missed opportunities for partnership. The relationship should be symbiotic: DMOs drive inspiration and awareness while operators deliver the experiences that fulfill that inspiration.8. Legacy Operators Must Balance Old Customers with New AcquisitionLarge traditional operators face the challenge of serving aging loyal customers while attracting younger demographics with different travel styles and expectations. Successful adaptation includes smaller group sizes, slower itineraries with longer stays, and the integration of river cruising as a bridge product. The human relationship element that made these companies successful remains their key differentiator even as they modernize their offerings.9. Travel Advisors Are Specializing to Survive and ThriveThe successful travel advisor model has shifted from selling airline tickets to becoming highly specialized experts in specific destinations, cruise lines, or travel styles. Good advisors serve as client advocates navigating an increasingly complex travel landscape, especially for multi-generational or special interest trips. The question remains whether there's a sufficient pipeline of new advisors entering the field to sustain this specialized, high-touch service model.10. Experience Design Trumps Destination MarketingModern travelers seek transformative experiences rather than destination checkboxes, with operators succeeding by creating unique access and authentic local connections. Events from Taylor Swift concerts to World Cup matches are becoming trip anchors, with some operators building entire experiences around events without even including tickets. The shift represents a fundamental change from "where are we going" to "what will we become through this experience."

Pete Syme talks with Drew Falkman about vibe coding, a way for tour operators to build custom software tools using plain English prompts instead of traditional programming. Drew explains how AI tools like ChatGPT and Claude have been trained on code repositories, allowing them to generate working applications from simple descriptions. The conversation covers why this matters for small operators, what you can build, the learning curve, costs, security considerations, and how this technology could shift the relationship between tour operators and the software they depend on. Pete emphasizes that operators already have the same AI access as hundred million dollar companies and encourages spending at least an hour daily experimenting with these tools.Top 10 TakeawaysYou can build tools without coding knowledge. AI tools trained on code repositories can generate working applications from plain English descriptions, making app building accessible to anyone.Most SaaS tools don't fit your exact workflow. You end up paying for applications where 80% of features you're not using because they're designed for other industries, but the things you do use aren't quite refined enough.Start with internal workflows, not customer-facing apps. Build tools for internal processes first. Don't go public with what you build until you have experience, as you can get 80 to 90% correct quickly, but that last bit is more challenging.Map your processes before building. Write down all your processes on paper, rank what's most important, and list what you really don't like doing. This helps identify where custom tools can have the biggest impact.The learning curve has three main steps. First, learn to plan what you want to build (20 to 30 hours). Second, design the workflow and user interface (a few hours). Third, understand data and databases (a couple days). Total time to get comfortable is roughly a few weeks of focused learning.Tools like Lovable cost around $20 per month. There are small monthly fees for vibe coding platforms, plus hosting costs if your tool is public-facing. Tools like Lovable, Bolt, Replit, Magic Patterns, and N8n each serve different purposes.Keep data storage minimal for security. Don't store sensitive information like credit card numbers or social security numbers. Use third-party authentication (Google, Microsoft, Apple) and payment processors like Stripe to handle sensitive data.You can build custom booking flows and optimize conversions. Create your own booking engine where you control every step, then use analytics tools to see where people drop off and experiment with improvements to increase completion rates.This threatens the traditional SaaS industry. Large companies spending millions monthly on SaaS are already exploring vibe coding to reduce costs. What happens at that level will cascade down through the industry to the tools small operators use today.Just try it to understand the possibilities. Go to lovable.dev, run a prompt, and build something. You won't fully understand what you can do until you experiment. You have nothing to lose with free versions, and no one else will see your experiments.Want to learn vibe coding yourself? Drew teaches courses on building apps without code. Visit drewfalkman.com to explore free resources and paid courses that walk you through the process step by step.

Born from a wine import business and shaped by deep relationships with multi‑generational wineries, Joy of Wine Journeys built a premium, multi‑day model with a ~75% repeat rate. Natalie shares why they skip big cities, how “depth over density” creates value, and how pricing, partnerships, feedback, and tight ops compound into growth.Top 10 takeaways1) Repeat guests keep coming back. About 75% rebook, often bringing friends and family. Nail the first trip and lifetime value follows.2) Win the in between. Don’t try to run Paris or Venice. Guests fly into a gateway, then the tour connects the regions in between where long winery relationships unlock access and stories.3) Fewer stops, deeper moments. Five wineries in ten days. Hosted visits. Family meals. Time to linger. People remember conversations and rituals, not mileage.4) Price for the value you deliver. Raise prices as the experience improves. Let booking behavior and guest comments set the ceiling, not nerves.5) Partners make you resilient. When a bus failed, local partners mobilized vans, cold water, and support within the hour. Good relationships turn problems into loyalty moments.6) Feedback is the roadmap. Debrief during and after each tour, then keep, change, or cut. Trim bloat, smooth pacing, and upgrade hotels, meals, wines, and transport.7) Know who you serve. Average age ~63. Well traveled. Hungry for hosted, exclusive experiences without snobbery. Design pacing, teaching, and access for that person.8) Confirm, confirm, confirm. Book a year out, then reconfirm at six months, three months, one month, and day‑of. Fewer surprises. Smoother days.9) Help in the cities even if you don’t operate there. Refer guests to vetted guides in Venice, Milan, Paris, Nice, and Florence so the whole trip feels looked after.10) Use tech to support margins, not as the magic. TravelJoy for CRM, WeTravel for euro payments, Travelfy for itineraries, QuickBooks for the back office. The differentiator is still access, hosting, and relationships.