EP 245: The Hospitality Industry Is About to Split in Two (And Most Hosts Aren't Ready) with Gil Chan

I genuinely think the hospitality industry is entering one of the biggest shifts we've seen in years — and the hosts who survive over the next 3–5 years are going to think very differently than the ones who thrived during the Airbnb gold rush. In this episode, I sat down with Gil Chan, founder of Crafted Stays, to talk about where hospitality is headed, how AI is changing the way guests search for stays, and why branding and direct bookings matter more than ever moving forward. We talked about why relying completely on Airbnb is becoming increasingly risky, how AI tools like ChatGPT are already changing trip planning behavior, what makes a direct booking website actually convert, why amenities alone are no longer enough to stand out, and the difference between "having an Airbnb" and building a real hospitality brand. One of my favorite parts of this conversation was talking about the "middle tier" of hospitality slowly disappearing — and why the brands that deeply understand their guests and intentionally create experiences are going to be the ones that win long-term. If you want to connect with Gil and learn more about Crafted Stays, you can visit craftedstays.co, follow along on Instagram @craftedstays, and listen to his podcast, Booked Solid. If you loved this episode, I'd love to connect with you too. You can find me on Instagram @theweberco or learn more about working with me and my team at theweberco.com. If you're ready to build a stronger hospitality brand, improve your marketing, increase direct bookings, and create a business that doesn't rely entirely on OTAs, you can apply to work with us directly through the website.