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Al Check, co-founder of Odyssey Multiday Software, joins Peter Syme to dissect what actually goes wrong behind the scenes: the 50-page PDFs nobody reads on their phone, the rooming list confirmations that get missed (and cost you money), and the staff member who quits and takes all the spreadsheet knowledge with them. This session covers the operational realities of coordinating guests, guides, suppliers, vehicles, and itineraries across overlapping trips. Al shares how operators can move from reactive firefighting to systems that actually scale—without necessarily buying new software. Peter challenges the conversation with a dose of reality: technology isn't your problem if you're under $500k in revenue. Sales is. The discussion includes practical frameworks for evaluating when your business actually needs better systems, why "bespoke" is often an expensive illusion, and how to structure communications so your team stops asking "what am I doing today?" To learn more about the Odyssey Multiday Software smart transition program at https://www.myodyssey.app/odyssey-tra... --- Key Takeaways *1. Growth doesn't create chaos—it reveals it.* If your systems work fine with one trip per week but fall apart at three, the problem was always there. Adding staff is the expensive band-aid; fixing the underlying structure is the actual solution. *2. One source of truth changes everything.* When your customer data, supplier bookings, itineraries, and operations all pull from the same place, downstream communication becomes automatic. When they don't, your team is copy-pasting between systems and hoping nothing breaks. *3. The 50-page PDF roadbook needs to die.* Everyone—including older travelers—is on their phone. Sending an A4 document that's unreadable on mobile means all your hard work disappears the moment guests need it most. Digitize or lose the value. *4. Most "bespoke" tours aren't actually bespoke.* Operators think every trip needs custom building. In reality, 80% of what you sell can come from master templates with minor adjustments. True bespoke is expensive—reserve it for when it's actually needed. *5. Systemize anything you repeat.* If a task happens more than once, document it or automate it. This isn't about software—it's about not being the only person who knows how things work. *6. The 30-day rooming confirmation will cost you money if you forget it.* Supplier deadlines don't care about your chaos. Automated reminders and structured communication flows prevent the charges that eat into your margins. *7. Your guides need information, not surprises.* Clear run manifests, customer dietary requirements, bike heights, special needs—all in one document, sent automatically. Guides who show up prepared deliver better experiences. *8. Airline-style luggage labels are a small detail that signals professionalism.* A branded, durable label with all the right information tells customers their bag is handled. A rubber-banded note with a name scribbled on it tells them it might end up in the wrong hotel. *9. Staff management is one of the biggest operational headaches.* Matching drivers, guides, mechanics, and briefing staff to a shifting schedule of overlapping trips is genuinely hard. Rostering tools that integrate with your tour data save managers hours of coordination. *10. Technology investment should match your revenue and chaos level.* If you're a small operator doing under $500k, your problem is probably sales and marketing—not systems. Get customers first, experience the chaos, then solve the real problems you actually have.