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

Follow Kenny on Instagram

Connect with Gil on LinkedIn

CraftedStays.co

The Ultimate Guide to Direct Bookings

Booked Solid Podcast

Should you take direct bookings—and what does it take to make them work?

In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell unpacks the real considerations behind building a direct booking strategy. While many hosts focus on software and site setup, Kenny zeroes in on the biggest challenge: attracting the right traffic. He explains how to create repeat business, leverage your property’s location, and build trust with potential guests—without relying on OTAs.

You’ll learn how to think in terms of guest journeys, content marketing, and simple tactics like email and signage to grow your brand over time. Whether you’re just starting to consider direct bookings or trying to make an existing strategy more effective, this episode offers clear, actionable guidance on how to do it right.

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:

• The top three concerns people have with direct booking sites
• How to identify and market to your “warm” and “cold” traffic segments
• Why repeat business is more powerful (and cheaper) than new traffic
• Simple ways to promote your brand inside your property
• How to use email and social to stay top-of-mind year-round
• Why promoting your market, not your property, builds trust
• How lead magnets and content marketing drive real results
• And much more...

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Are you pricing your short-term rental based on facts—or just following what everyone else is doing?

In today’s episode of the Cash Flow Positive podcast, Kenny Bedwell sits down with Jake Cohen, founder of Step By Step BNB and a seasoned revenue manager overseeing 300+ listings. Together, they unpack the real strategies behind sustainable revenue, debunking myths and simplifying key concepts like RevPAR, booking windows, and market dynamics.

Jake breaks down the difference between pricing for high and low seasons, why most hosts underestimate the power of good photography, and what it really means to “be booked first” when it matters most. He also explains how to calculate and interpret RevPAR, set minimum night stays with intention, and use tools like PriceLabs to monitor real-time market behavior.

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 RevPAR is Jake’s #1 metric for STR health
• How to adjust your pricing based on seasonality and demand
• Why minimum night stays should change based on booking windows
• What most hosts get wrong about high vs. low season pricing
• How to calculate your property’s RevPAR (and why it matters)
• Why listing optimization is just as important as price strategy
• How to simplify your pricing—and book more with less effort
• And much more...

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Step By Step BNB

Price Your STR Facebook Group