Direct Booking Success Podcast

Direct Booking Success
  • 5.0 (9)
  • MARKETING
  • UPDATED WEEKLY

The Direct Booking Success Podcast is your go-to show for honest, actionable marketing advice tailored for short-term rental hosts. Hosted by Jenn Boyles — vacation rental marketer, former host, and founder of Direct Booking Success — this podcast is all about helping you break free from OTA dependency and build a business you actually enjoy. Each episode delivers down-to-earth insights, from guest interviews to solo episodes packed with proven strategies that boost visibility, increase guest loyalty, and bring in more direct bookings. No fluff. No burnout. Just clear, kind guidance to help you grow with confidence. Whether you’re brand new to direct bookings or looking to refine your marketing game, this podcast is your place to feel empowered, supported, and inspired to take the next step in your business — without the overwhelm.

  1. Why I’m Done Teaching STR Marketing the Old Way

    04/16/2025

    Why I’m Done Teaching STR Marketing the Old Way

    Hey, it’s Jenn. After hitting serious burnout at the end of 2024, I stepped back and started rethinking everything about how I teach short-term rental marketing. I realized that hosts don’t need more content, they need clarity, support, and a system that actually gets the work done. In this episode, I’m pulling back the curtain on why I’m done teaching marketing the old way and introducing you to what I’m building instead: the STR Content Lab. If you’re tired of doing it all yourself or feeling overwhelmed with information overload, this one’s for you. Key Takeaways✨ Clarity Over Content More templates and checklists aren’t the answer, you need a clear path that fits your business and life. ✨ Support Over Solo Hustle You shouldn’t have to figure this all out alone. Community and real-time help are game changers. ✨ Done Is Better Than Perfect Perfection kills momentum. Imperfect action is what builds confidence and results. If you enjoyed this episode, please take a second to subscribe, leave a review, or share it with a fellow host. It means the world to me! Head to directbookingsuccess.com/strcontentlab

    12 min
  2. 5 Ways to Master Direct Bookings Without Overwhelm or High Costs with Jamey King

    01/27/2025

    5 Ways to Master Direct Bookings Without Overwhelm or High Costs with Jamey King

    Are you feeling overwhelmed by the tech and cost of managing your direct bookings? Without the right system in place, you risk lost revenue, double bookings, and a frustrating guest experience. In this episode, we break down exactly what you need—from secure payments to owning your brand—to make direct bookings effortless and profitable. Jamey King, Senior Marketing Manager for North America at eviivo, joins us to share his expertise in streamlining technology and helping property owners take control of their bookings. With years of experience working with brands like VRMA, Point Central, and Safely, Jamie offers valuable insights into building a strong foundation for direct booking success. In this episode, you’ll learn: The key systems every property manager needs for seamless direct bookingsHow to increase revenue by maximizing control over pricing and promotionsThe power of guest relationships and how personalization enhances the experienceWhy owning your brand is crucial for standing out in a competitive marketHow to access and leverage guest data to drive repeat bookingsThe importance of reducing overbooking risks and keeping operations smooth Jamey emphasizes the significance of having a reliable property management system (PMS) to help automate and optimize direct bookings without excessive costs or complexity. He also highlights how eviivo provides an all-in-one solution designed to keep direct bookings simple, secure, and profitable. “The goal is to capture guest dollars while maintaining control over pricing, guest experience, and your brand. When you own the booking process, you own your success.” – Jamey King Connect with Jamey King LinkedIn: linkedin.com/in/james-king-bb4842b Email: Jamey.King@eviivo.com Resources Mentioned in This Episode Eviivo website: https://eviivo.com/us/ Book a Demo with eviivo: https://eviivo.com/us/book-an-appointment/  Show notes are available at: https://directbookingsuccess.com/podcast/ Work with Jenn to maintain consistency in your marketing and boost your direct bookings without spending so much money on it: https://directbookingsuccess.com/apply/ The ULTIMATE all-in-one marketing platform for short-term rentals – Check it out: https://bookdirectpro.com/ FREE GUIDE – 10 Ways to Drive Guests to Your Website Instead of Airbnb: https://directbookingsuccess.com/10-ways-to-drive-guests-to-your-website-instead-of-airbnb/ Follow Jenn on Instagram: https://www.instagram.com/directbookingsuccess Join Jenn’s free Facebook group – the Marketing Hub: https://www.facebook.com/groups/strmarketinghub

    41 min
  3. Unlock the Power of Your Vacation Rental Website with Jodi Bourne

    01/13/2025

    Unlock the Power of Your Vacation Rental Website with Jodi Bourne

    Are you ready to turn your vacation rental website into a booking powerhouse?  In this episode, we explore the art of creating high-converting websites with website strategist Jodi Bourne. With her extensive experience in the vacation rental industry and as a guest herself, Jodi shares invaluable insights on crafting a digital presence that not only looks great but drives revenue. In this episode, you’ll learn:  Learn how to craft a compelling digital front door that instantly appeals to potential guestsUnderstand the three primary goals of an effective website: creating FOMO, building trust, and converting visitorsGain insights on using professional photography and video to showcase your propertyExplore the importance of storytelling and personal branding in your “About Us” pageUncover common website mistakes that hurt trust-building and conversions Jodi Bourne, with her extensive experience of staying in over 70 vacation rentals, brings a unique perspective as both an industry expert and a seasoned guest. Her approach combines technical know-how with a deep understanding of guest psychology, helping you create a website that resonates with your ideal visitors.  “There’s going to be people that are going to choose your property regardless. You want to be honest and upfront with them in your imagery and videos. So show it at your best light, but also be truthful.” - Jodi Bourne About Jodi Bourne Jodi Bourne is a vacation rental consultant and website designer passionate about helping property owners create standout guest experiences and achieve business success. With over a decade of experience and a portfolio of strategies tailored to vacation rentals, Jodi combines her hospitality expertise with a deep understanding of branding, marketing, and direct bookings. She specializes in building guest-centric websites and implementing start-to-finish strategies that drive bookings and foster repeat guests. Having stayed in 67 vacation rentals herself, Jodi uses her insider knowledge to design spaces and experiences that resonate with travellers. Her innovative approach consistently helps owners increase profitability while elevating the guest experience. Connect with Jodi Bourne Website: jodibourne.com Instagram: instagram.com/heyjodibourne  Resources Mentioned in This Episode Tyann Marcink Hammond’s About Us Page: https://bransonfamilyretreats.com/about/ About Page Blueprint: https://jodibourne.com/trusted-host-about-page-blueprint/ Website Mistakes Checklist: https://jodibourne.com/build-a-vacation-rental-website-checklist/ —------------------------------------------------------------------------------------- Show notes are available at: https://directbookingsuccess.com/podcast/ Work with Jenn to maintain consistency in your marketing and boost your direct bookings without spending so much money on it: https://directbookingsuccess.com/apply/ The ULTIMATE all-in-one marketing platform for short term rental is finally here! Check it out: https://bookdirectpro.com/ FREE GUIDE: 10 Ways to Drive Guests to your Website instead of Airbnb: a...

    32 min
  4. Beyond Airbnb Using Hospitality to Build Direct Booking Loyalty with Chad Harker

    01/06/2025

    Beyond Airbnb Using Hospitality to Build Direct Booking Loyalty with Chad Harker

    Are you ready to take your short-term rental business to new heights?  In this episode, we explore the remarkable journey of Chad Harker, a savvy entrepreneur who has transformed his single-room Airbnb listing into a thriving portfolio of seven properties with an impressive 75% direct booking rate.  In this episode, you’ll learn:  The importance of providing exceptional hospitality as a foundation for successHow to leverage guest data to create personalized experiences and drive repeat bookingsStrategies for building local partnerships to enhance your offeringsTips for implementing upsells that benefit both guests and hosts “If you’re utilizing the right tech, it could go such a long way with being able to buy back some of your time and operate at a higher level.” - Chad Harker About Chad Harker Chad Harker is a real estate investor and short-term rental entrepreneur passionate about transforming properties into exceptional spaces that maximize guest experiences and profitability. With three properties—soon expanding to six units after renovations—he combines real estate investing expertise with short-term rental strategies to create high-performing spaces for himself and the investors he partners with. Chad’s approach focuses on adding value through legal suites, direct booking strategies, and guest-centric branding, achieving a 75% increase in direct bookings and fostering repeat guests. On track to surpass Edmonton’s top-performing rental, Chad’s model exemplifies how thoughtful renovations, strategic operations, and independent marketing can redefine what short-term rentals can achieve. Connect with Chad and Eco Escapes Eco Escapes Website: www.ecoescape.com Instagram: https://www.instagram.com/chad_harker780 Resources Chad mentioned in the podcast Linkbase: https://linkbase.ca/ Chad shares his journey from conventional real estate investing to short-term rental success, offering practical advice for those looking to follow in his footsteps. Whether you’re just starting or looking to scale your existing operation, this episode is packed with actionable tips to help you achieve direct booking success.  —------------------------------------------------------------------------------------- Show notes are available at: https://directbookingsuccess.com/podcast/ Simplify your STR Marketing in 2025! Join the DBS AI Content Sprint Workshop! In this live, hands-on workshop, I will guide you through creating 3 months of content targeted to your ideal guest. Here’s what you’ll learn: ✨ How to use AI to craft engaging, personalized content. ✨ A proven strategy to save time while driving direct bookings. ✨ Step-by-step guidance to simplify your marketing efforts for 2025. 📅 Date: January 9, 2025 You will leave with a full written guide, lifetime access to the training video, and a strategy you can replicate anytime. Save your seat and start 2025 with a clear, actionable plan to grow your bookings and profits with 3 months of booking-driving content.  👉 https://mydbs.live/sprint Use...

    27 min
  5. Simplify Your 2025 Marketing with AI for Direct Booking Success

    12/30/2024

    Simplify Your 2025 Marketing with AI for Direct Booking Success

    As we step into 2025, are you ready to revolutionize your short-term rental business? In this episode, we're exploring how to simplify, streamline, and set yourself up for success using AI in the new year. Discover how to create a strategic marketing plan that goes beyond mere consistency, focusing on purpose-driven content that resonates with your ideal guests. Learn how AI can be your secret weapon in content creation, automation, and optimization, freeing you up to focus on delivering exceptional guest experiences. Here’s what you will be getting: Reflect on key lessons from 2024 and how they shape our approach to resilience in 2025Understand how AI can enhance your marketing efforts without replacing your unique touchGet insights on crafting a three-month content calendar tailored to your ideal guestsLearn about the upcoming DBS AI Content Sprint, a 90-minute workshop to jumpstart your 2025 marketing strategyDiscover how to integrate AI with tools like Book Direct Pro for seamless campaign management Plus, get a special discount code for the DBS AI Content Sprint, where you'll create three months of targeted social media content with proven strategy in driving direct bookings in just 90 minutes! You’ll leave with a full written guide, a lifetime access to the training and a strategy that you can rinse-and-repeat anytime. Don't miss this opportunity to start 2025 with a clear plan and less stress. Your journey to simplified, effective marketing begins here! —------------------------------------------------------------------------------------------------------------------ Show notes are available at: https://directbookingsuccess.com/podcast/ Simplify your STR Marketing in 2025! Join the DBS AI Content Sprint Workshop! In this live, hands-on workshop, I will guide you through creating 3 months of content targeted to your ideal guest. Here’s what you’ll learn: ✨ How to use AI to craft engaging, personalized content. ✨ A proven strategy to save time while driving direct bookings. ✨ Step-by-step guidance to simplify your marketing efforts for 2025. 📅 Date: January 9, 2025 You will leave with a full written guide, lifetime access to the training video, and a strategy you can replicate anytime. Save your seat and start 2025 with a clear, actionable plan to grow your bookings and profits with 3 months of booking-driving content.  👉 https://mydbs.live/sprint Use discount code: DBSPODCAST40 to join the workshop for only $29 —------------------------------------------------------------------------------------------------------------------ Work with Jenn to maintain consistency in your marketing and boost your direct bookings without spending so much money on it: https://directbookingsuccess.com/apply/ The ULTIMATE all-in-one marketing platform for short term rental is finally here! Check it out: https://bookdirectpro.com/ FREE GUIDE: 10 Ways to Drive Guests to your Website instead of Airbnb: https://directbookingsuccess.com/10-ways-to-drive-guests-to-your-website-instead-of-airbnb/ Follow Jenn on Instagram:...

    12 min
  6. How We Mastered Direct Bookings for Short-Term Rentals in 2024

    12/23/2024

    How We Mastered Direct Bookings for Short-Term Rentals in 2024

    As we wrap up an incredible year of growth and learning in the short-term rental industry, it's time to reflect on the valuable insights that have shaped our success. In this special episode of the Direct Booking Success Podcast, I'm sharing my favourite moments from 2024 - a year filled with practical strategies, inspiring stories, and expert advice. From reaching listeners in 38 countries to recording over 23 hours of content, this podcast has become more than just a source of information. It's a thriving community of property managers and hosts passionate about growing direct bookings and building sustainable businesses. In this episode you’ll learn:  Inside-out hospitality: Learn how treating your team will genuine care translates to exceptional guest experiencesFilling calendar gaps: Actionable strategies to boost bookings during slow periods without resorting to discountsThe power of video reviews: How authentic guest testimonials can significantly increase your conversion ratesStrategic consistency: Why blindly following the “just be consistent” mantra might be holding you backOptimizing your direct booking website: Essential tips for creating a seamless, mobile-responsive booking process Highlights from 2024Inside-Out Hospitality with Lauren Madewell"Inside-out hospitality is all about taking care of your own people first, so they care for others naturally."Discover how Lauren's approach to prioritizing employee well-being naturally translates into exceptional guest experiences. Learn about her creative marketing strategies that make her properties stand out in the competitive Smoky Mountains market. Listen to Episode 106 - The Truth About Airbnb Income, Hint… It’s Not What You Think: https://www.youtube.com/watch?v=pEHQ0UTrCYo&t=2s Learn more about Lauren and Auntie Belham’s Cabin Rentals:  Website: https://www.auntiebelhams.com/ Instagram: https://www.instagram.com/auntiebelhamscabinrentals/  Reviving Your Marketing After Peak Season "Your past guests are your biggest fans—remind them why they loved staying with you." Explore effective strategies to fill booking gaps without resorting to discounts or desperate measures. Find out why email marketing remains a powerful tool for reconnecting with past guests and driving repeat bookings. Listen to Episode 115 - Reviving Your Marketing After a Busy STR Season: https://www.youtube.com/watch?v=dTTMNVE2gKY Building Community with Damian Sheridan "A simple phone video from a happy guest can increase your bookings by 25%—it’s that powerful." Gain insights from industry veteran Damian Sheridan on reducing OTA reliance and leveraging video reviews to boost conversions. Learn how authentic guest testimonials can significantly impact your booking rates. Listen to Episode 94 - Why You Should Stop Chasing 5-Star Reviews and Do This Instead: https://www.youtube.com/watch?v=1ngfx2O6DOk&t=7s Learn more about Damian Book Direct Show: https://bookdirect.show  SCALE Rentals: https://scalerentals.show  The Truth About Consistency in Marketing"Being consistent isn’t enough if your efforts miss the mark—align your strategy with your goals." Challenge the common advice of "just be consistent" and discover why strategic consistency is key to driving results. Understand how to focus on quality over quantity in your marketing efforts. Listen to Episode 107 - Why Consistency in your Marketing Isn’t Enough for Direct Bookings: https://www.youtube.com/watch?v=fxFKqYRyUM8 Optimizing Your Direct Booking Website with Bart Sobies"If you’re not testing your booking process on all devices, you’re leaving

    24 min
  7. Using Instagram to Get More Direct Bookings with Katie Bessant

    12/16/2024

    Using Instagram to Get More Direct Bookings with Katie Bessant

    Are you ready to turn your Instagram followers into paying guests? In this episode, we explore how to harness the power of Instagram to drive direct bookings for your vacation rental property. Join me as I chat with Katie Besant, founder of the Holiday Hive and social media expert with years of experience in the tourism industry. Katie shares her insider knowledge on creating content that not only catches the eye but also converts scrollers into bookers. In this episode, you’ll learn how to: Discover the three types of content you need to post for maximum impactLearn why Instagram Stories are your secret weapon for conversionsUncover the truth about hashtags and how to use them effectively in 2025Find out how to optimize your profile to attract your idea guests “Instagram is the new business card nowadays. If I’m out and about, people don’t ask my business card, they ask my Instagram.” - Katie Bessant About Katie Bessant Katie Bessant, owner of The Holiday Hive, is a social media expert dedicated to helping holiday cottage owners and tourism businesses elevate their digital presence and generate more bookings. Growing up in South Devon, Katie has been immersed in the tourism industry her entire life, from working in her family’s B&B to becoming a successful Airbnb superhost. With experience spanning roles like waitressing, cleaning holiday lets, and leading marketing for one of the UK’s largest holiday letting agencies, Katie combines her deep industry knowledge with her passion for social media to empower property owners to stand out online and thrive. Connect with Katie and The Holiday Hive Website: https://theholidayhive.com/ Facebook: https://www.facebook.com/theholidayhiveofficial/ Instagram: https://www.instagram.com/theholidayhive/ Youtube: https://www.youtube.com/@HolidayHive  Tiktok: https://tiktok.com/@theholidayhiveofficial  Linkedin: https://www.linkedin.com/in/katie-bessant/ Stop letting potential guests slip through your fingers. Tune in now and learn how to make Instagram work for your vacation rental business! The key moments on this episode are: 00:00:00 Instagram: A Booking Powerhouse for Vacation Rentals 00:00:56 Meet Katie Besant: Social Media Expert for Holiday Rentals 00:04:44 Instagram's Power for Direct Bookings 00:06:40 Types of Instagram Content for Booking Success 00:13:48 Balancing Instagram Content and Posting Frequency 00:16:03 Hashtags and Instagram Trends 00:20:17 Effective Use of Call-to-Actions (CTAs) 00:22:34 Getting Started with Instagram for Direct Bookings 00:24:54 Instagram Course for Holiday Cottage Owners —----------------------------------------------------------------------------------- Show notes are available at: https://directbookingsuccess.com/podcast/ Simplify your STR Marketing this 2025! Join the DBS AI Content Sprint Workshop! In this live, hands-on workshop, I will guide you through creating a 3-month content calendar targeted to your ideal...

    27 min
  8. How Hosts Can Thrive in the Future with Caitlin Cassady

    12/09/2024

    How Hosts Can Thrive in the Future with Caitlin Cassady

    Are you prepared for the future of the vacation rental industry?  In this episode, I sit down with Caitlin Cassady, VP of Marketing at Beyond, to explore the evolving landscape of short-term rentals and how data-driven insights can propel your business forward.  In this episode, you’ll learn how to: Discover why thinking beyond “short-term rentals” and embracing the broader “stays industry” is crucial for successLearn how to use real-time search data to make informed decisions about pricing, marketing, and amenitiesUnderstand the impact of events like concerts and major sports competitions on booking patterns “Don't just rely on historical pacing data. That is not going to help your direct booking website really start to shine and really start to be as impactful as it probably could be.” - Caitlin Cassady About Caitlin Cassady Caitlin Cassady is the VP of Marketing at Beyond, where she spearheads the company's marketing strategy and cross-functional initiatives, transforming data into compelling narratives that deliver measurable business results. With 15 years of experience as a communications and content marketing leader in enterprise tech, Caitlin brings a wealth of expertise to the table. She’s also an avid reader, a recovering journalist, and a self-proclaimed mac & cheese connoisseur. Connect with Caitlin and Beyond: Caitlin’s LinkedIn: https://www.linkedin.com/in/caitlincassady/ Website: https://www.beyondpricing.com/ Whether you're new to data analytics or looking to refine your approach, this episode offers valuable insights to help your vacation rental business thrive in the evolving stays industry. The key moments on this episode are: 00:00:00 The Future of Travel: Trends Reshaping the Vacation Rental Industry 00:00:51 Meet Caitlin Cassidy: VP of Marketing at Beyond 00:02:51 The Evolving Short-Term Rental Market: Data-Driven Insights 00:07:07 Leveraging Data for Direct Bookings 00:13:13 Beyond Pricing: Data-Driven Strategies Beyond Just Pricing 00:15:50 Event-Based Pricing Strategies: The Taylor Swift Effect 00:23:21 Leveraging Data for Amenity Offerings 00:26:09 Data Democratization: Leveling the Playing Field for Small Property Managers 00:27:30 Key Advice for Growing Direct Bookings —------------------------------------------------------------------------------------------------------------------ Show notes are available at: https://directbookingsuccess.com/podcast/ Work with Jenn to maintain consistency in your marketing and boost your direct bookings without spending so much money on it: https://directbookingsuccess.com/apply/ The ULTIMATE all-in-one marketing platform for short term rental is finally here! Check it out: https://bookdirectpro.com/ FREE GUIDE: 10 Ways to Drive Guests to your Website instead of Airbnb: https://directbookingsuccess.com/10-ways-to-drive-guests-to-your-website-instead-of-airbnb/ Follow Jenn on Instagram: https://www.instagram.com/directbookingsuccess Join Jenn’s...

    31 min
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The Direct Booking Success Podcast is your go-to show for honest, actionable marketing advice tailored for short-term rental hosts. Hosted by Jenn Boyles — vacation rental marketer, former host, and founder of Direct Booking Success — this podcast is all about helping you break free from OTA dependency and build a business you actually enjoy. Each episode delivers down-to-earth insights, from guest interviews to solo episodes packed with proven strategies that boost visibility, increase guest loyalty, and bring in more direct bookings. No fluff. No burnout. Just clear, kind guidance to help you grow with confidence. Whether you’re brand new to direct bookings or looking to refine your marketing game, this podcast is your place to feel empowered, supported, and inspired to take the next step in your business — without the overwhelm.

Information

  • Creator
    Direct Booking Success
  • Years Active
    2022 - 2025
  • Episodes
    135
  • Rating
    Clean
  • Copyright
    © Copyright 2025 Direct Booking Success
  • Show Website
    Direct Booking Success Podcast