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Heads In Beds Show
Conrad O'Connell
165 episodes
21 hours ago
The Heads In Beds Show is your vacation rental & accommodations marketing podcast co-hosted by Conrad O'Connell and Paul Manzey. Learn how to double your direct bookings with search, social & email marketing strategies and tactics.
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Places & Travel,
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Society & Culture
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All content for Heads In Beds Show is the property of Conrad O'Connell and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
The Heads In Beds Show is your vacation rental & accommodations marketing podcast co-hosted by Conrad O'Connell and Paul Manzey. Learn how to double your direct bookings with search, social & email marketing strategies and tactics.
Show more...
Marketing
Places & Travel,
Business,
Society & Culture
Episodes (20/165)
Heads In Beds Show
What To Consider When Building A New Vacation Rental Website

In this episode of The Heads In Beds Show, we break down the questions to ask when building a vacation rental website in 2025 and beyond. Scope, pricing, vendors to work with and a LOT more...


⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
21 hours ago
40 minutes

Heads In Beds Show
The Four Part Process To Build A Guest Marketing Plan

In this episode of The Heads In Beds Show, we come back and talk the four-part marketing for guest focused campaigns. Enjoy! 


⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
1 week ago
33 minutes

Heads In Beds Show
Is This The KEY To Getting More Bookings?

In this episode of The Heads In Beds Show, we talk about the youth and how they are the strategy to getting more bookings by catering and designing your properties along with what Paul and Conrad look for when booking for their family. 


⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101
  • Link To The Report


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
2 weeks ago
26 minutes

Heads In Beds Show
VRMA 2025 Recap: The Hot Seat Session, Industry Trends & More!

In this episode of The Heads In Beds Show, we recap the VRMA 2025 show! We talk all things about The Hot Seat Session, industry trends, marketing ideas and more...

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
3 weeks ago
45 minutes

Heads In Beds Show
The Four Part Process To Build A Homeowner Marketing Plan

In this episode of The Heads In Beds Show, we share our four-part framework to get a homeowner marketing plan in place. 

We discuss: 

  • Targeting
  • Positioning
  • Messaging
  • Channels

And how you can build a winning strategy in each area.

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
4 weeks ago
36 minutes

Heads In Beds Show
The "Do's" and "Don'ts" Of Using AI With Your Vacation Rental Marketing

In this episode, we dive into AI at a deep level: how SHOULD you use it and NOT use it to market your vacation rental business?

Enjoy!


⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram
  • Twitter


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.

Show more...
1 month ago
36 minutes

Heads In Beds Show
Replay: The Vacation Rental Marketing Fundamentals You Need To Have In Place

Note: this is a replay of an episode from last year!

In this episode Conrad goes solo on this audio-only version of a LIVE training on "Building Your Vacation Rental Marketing Fundamentals".

Want to get the video too? Tap the link below.

Enjoy!


⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Recording: Building Your Vacation Rental Marketing Fundamentals
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram
  • Twitter


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.

Show more...
1 month ago
57 minutes

Heads In Beds Show
10 Things You Can Do To Sign More Vacation Rental Properties This Fall

In this episode of The Heads In Beds Show, we dive into 10 actionable steps you can take now to get more homes for 2026!

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
1 month ago
33 minutes

Heads In Beds Show
Revisiting Meta Ads vs Google Ads

In this episode of The Heads In Beds Show, we revisit our chat on Meta Ads vs Google Ads: what we're using them now to get more bookings and more homeowners.

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
1 month ago
41 minutes

Heads In Beds Show
Can You Really Compete With Airbnb? Nope...

In this episode of The Heads In Beds Show, we chat on Conrad's LinkedIn post "can you really compete with Airbnb" to talk strategy, marketing, goals, profits and a LOT more...


NOTE: this was recorded BEFORE the Airbnb 15.5% price increase move -> non-PMS connected price increase for hosts. So we didn't mention that...

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101
  • Conrad's LinkedIn Post


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
2 months ago
35 minutes

Heads In Beds Show
How Are Direct Bookings Trending According To Industry Research Experts?

In this episode of The Heads In Beds Show, we break down the Key Data Dashboard report on trends of market share by direct vs major OTAs, trends of marketing for direct bookings and a LOT more...


⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101
  • KDD Report - Download Here


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
2 months ago
45 minutes

Heads In Beds Show
Here's What Trust Building Is Needed In The Vacation Rental Industry

In this episode of The Heads In Beds Show, we're talking all things TRUST and what stakeholders can do in the industry to build or destroy that trust. 


⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
2 months ago
51 minutes

Heads In Beds Show
Here's What To Look For When Selling Your Vacation Rental Business

In this episode of The Heads In Beds Show, we're inspired by the list from Xavier Helgesen on "what to look for when buying a business" and adapt it to the vacation rental industry.

Full list credit: via Xavier Helgesen

  1. Owner operated businesses are super efficient. Owner does six jobs. You will probably spend more to professionalize.
  2. Only buy from people who have demonstrated values of honesty and integrity throughout the process.
  3. Stock purchases should be at least 25 % cheaper than asset purchases. You can’t write off the acquisition price plus you assume historical liabilities.
  4. Adjusted EBITDA ≠ EBITDA ≠ cash flow. Look for cash flow.
  5. Look for rich owners.
  6. Look for businesses that have survived multiple economic cycles.
  7. Make sure you are not in a commodity business.
  8. Everything is negotiable. We have done 90 % seller financing three times.
  9. Everyone wants a raise after you take over.
  10. Make sure management only gets paid bonuses when they distribute cash flow to owners.
  11. Pay for a really good, but very efficient, lawyer.
  12. Pay for Quality of Earnings even on small deals.
  13. The best way to find a CEO for a business is to ask the seller who has asked about buying it in the past.
  14. Look for the smallest, weirdest niches. Less competition, greater margins.
  15. If you find a good enough deal, the capital will find you.
  16. Don’t underestimate how little you know about any given industry. Find an expert to help you.
  17. Businesses with real estate offer lots of creative financing opportunities.
  18. An owner who works “10 hours a week” is still doing five people’s jobs. They are the world expert in their business.
  19. Professionalizing a business with no management in place is probably too hard unless you are running it.
  20. Understand the working capital situation deeply and as a first order of business. The working capital adjustment can be a huge adjustment in price.
  21. Don’t incentivize anyone to close deals. You want them more excited to kill a deal – this means they will speak up if something feels wrong.
  22. Look at duration of employment of employees. Lots of turnover indicates a toxic environment.
  23. Don’t take single-channel risk (e.g., Meta marketing).
  24. Share customer concentration risk with the seller through revenue shares or forgiveable notes.
  25. Underwrite your downside like a lender. Could you sell the business or its assets to at least pay back the debt if you need to?
  26. Don’t fall too in love with the business. You’ve always got to be ready to walk away.
  27. Honor your word even if it costs you money. Once trust is lost with a seller, it’s over.
  28. Honor the owner/founder’s legacy after you close.


⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
2 months ago
34 minutes

Heads In Beds Show
The MOST Important Question To Ask Before Investing In Growth (Part II)

In this episode of The Heads In Beds Show, the duo asks this question: what is the #1 thing holding my vacation rental company back from growth? 

Part II of this episode series. Go back 1 episode to find part I!

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
3 months ago
43 minutes

Heads In Beds Show
The MOST Important Question To Ask Before Investing In Growth (Part I)

In this episode of The Heads In Beds Show, the duo asks this question: what is the #1 thing holding my vacation rental company back from growth? 

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
3 months ago
41 minutes

Heads In Beds Show
Is Creating Content Even Worth It Anymore? A Debate

In this episode of The Heads In Beds Show, the guys DEBATE the content creation benefits. With AI overviews stealing a ton of your traffic, does it even make sense to take the crumbs of clicks that are left?

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
3 months ago
33 minutes

Heads In Beds Show
Breaking Down The Reasons WHY Guest Choose Vacation Rentals vs Hotels

In this episode of The Heads In Beds Show, we ask what most don't: why in the world do guests even CHOOSE to book a vacation rental over a hotel in the first place? How can you use this information to your advantage and let guests pick your property (and pay a premium to do it)? 

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
3 months ago
39 minutes

Heads In Beds Show
How To Launch New Vacation Rental Listings And Get Them BOOKED

In this episode of The Heads In Beds Show, we replay a webinar between Conrad and Ben Day of Jetstream to talk all things direct bookings vs new OTA listings for bookings, launching, how to fix dead/zombie listings and a LOT more.

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101
  • YouTube Webinar Replay Video
  • Ben Day
  • Jetstream


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
3 months ago
59 minutes

Heads In Beds Show
Build The Demand Formula For Your Vacation Rental Marketing

In this episode of The Heads In Beds Show, we dive into the factors that drive DEMAND in your markets and attempt to break apart what creates and drives demand. 

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
4 months ago
32 minutes

Heads In Beds Show
SEO, AEO, GEO, Oh My! What's The New Search Trend In Vacation Rental Marketing?

In this episode of The Heads In Beds Show, we dive into the "new world" of AI Search trends and all of the new terms popping up. Is there a shift ongoing with your SEO efforts to nail down AI powered LLM searches? If so, listen in for all of the details. 

⭐️ Links & Show Notes

  • Paul Manzey 
  • Conrad O'Connell
  • Conrad's Book: Mastering Vacation Rental Marketing
  • Conrad's Course: Mastering Vacation Rental Marketing 101
  • Rand Fishkin Podcast


🔗 Connect With BuildUp Bookings

  • Website
  • Facebook Page
  • Instagram


🚀 About BuildUp Bookings

BuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.


Show more...
4 months ago
38 minutes

Heads In Beds Show
The Heads In Beds Show is your vacation rental & accommodations marketing podcast co-hosted by Conrad O'Connell and Paul Manzey. Learn how to double your direct bookings with search, social & email marketing strategies and tactics.