Cash Flow Positive Part 2: Should You Take Direct Bookings with Gil Chan
What does it take to turn a direct booking website into a real revenue driver?
In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell is joined by Gil Chan, tech founder, short-term rental host, and the creator of CraftedStays—a platform that helps STR hosts easily build customizable direct booking sites without breaking the bank.
Drawing on his background in e-commerce, Gil walks through the parallels between retail and hospitality, explains how to structure a site that actually converts, and shares his strategies for guest vetting, trust-building, and long-term nurture campaigns. He breaks down what most hosts get wrong about direct bookings, and what to focus on instead—starting with knowing your ideal guest avatar and optimizing every piece of the guest journey around them.
From lead magnets and email flows to the psychology of brand visibility, this episode is packed with insights on how to grow your direct bookings sustainably—without trying to master every marketing channel at once.
If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!
In This Episode You'll Learn:
- Why e-commerce and STRs are more similar than you think
- What your direct booking site must include to build trust and convert visitors
- How to structure your site around your “guest avatar”
- What most STR owners misunderstand about branding and professionalism
- How to handle guest vetting on direct booking platforms
- Why starting small (with the right tools) beats outsourcing everything
- Gil’s favorite ways to collect and nurture guest emails automatically
- What a good year-one direct booking rate looks like—and how to scale it
- And much more...
Guest Bio:
Gil Chan is a short-term rental host, tech entrepreneur, and founder of CraftedStays—a platform that makes it easy for hosts to build fully integrated, conversion-focused direct booking websites. With a background as a product director in e-commerce, Gil saw the gap between STR operators and the tech tools they needed to take control of their businesses. After building the first version of CraftedStays for his own properties, he left his six-figure job in tech to grow the company full-time. Today, Gil helps hosts across the U.S. build their brands, attract the right guests, and increase revenue—one click at a time.
Resources:
Connect with Kenny on LinkedIn
The Ultimate Guide to Direct Bookings