How To Master Direct Bookings with Phil Kenard & FutureStay

Bill Faeth Unfiltered

Apr 15, 2025•41 min

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Episode description

http://www.futurestay.com/bill

In this episode of Bill Faeth Unfiltered, Bill welcomes special guest Phil Kennard, a seasoned professional from the vacation rental industry. Phil is the founder of Futurestay, a platform that simplifies direct bookings for short-term rental owners. Bill introduces Phil's impressive background, which includes creating video games for Take Two Interactive, and developing a PropTech company for property managers. Phil shares how Futurestay evolved from his own need to manage bookings for his New York apartment. He highlights a surprising industry insight - that most vacation rentals are owned by small-scale operators, not large companies. FutureStay aims to level the playing field for these smaller operators by providing an easy-to-use platform for managing direct bookings, complete with features like dynamic pricing and Google Vacation Rentals integration. Bill emphasizes Futurestay's ability to transform any Airbnb listing into a highly converting direct booking site within minutes. Phil discusses the importance of optimizing Airbnb listings and the benefits of a direct booking loop. The episode offers listeners valuable tips on managing their short-term rental listings effectively, including leveraging OTAs and ensuring their listings are optimized. Bill and Phil also touch on the importance of customer retention and the various ways property owners can increase direct bookings. As a special offer, listeners can get a discount on Futurestay's services by visiting futurestay.com/bill.

00:00 Introduction

01:23 The Hair-Off Challenge

03:19 Phil Kennard's Journey into Entrepreneurship

05:36 From Video Games to Real Estate Tech

11:49 Entering the Short-Term Rental Market

15:17 The Birth of Futurestay

16:14 Future Stay's Unique Value Proposition

19:42 The Journey to Building the Easy Button

20:44 Challenges with Traditional Website Solutions

22:14 The Direct Booking Advantage

23:42 Understanding the Direct Booking Loop

25:02 Incremental Steps to Increase Direct Bookings

28:25 Future Stay's Unique Offerings

30:48 Optimizing Your Airbnb Listing

35:41 Leveraging OTAs for Direct Bookings

38:58 Final Thoughts and Exclusive Offer

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On Bill Faeth Unfiltered, Bill Faeth breaks down the ins and outs of short-term rental hosting, giving listeners actionable advice that they can use to take their businesses to the next level.