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Explore every episode of the podcast Heads In Beds Show

Dive into the complete episode list for Heads In Beds Show. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.

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TitlePub. DateDuration
The 60-Day Booking Window Is Dead - Here's What To Do About It15 Apr 202600:35:28

In this episode Conrad and Paul talk all about the death of the standard 60 day or 90 day booking windows and instead tell you what you need to work on inside of your vacation rental business to drive more demand and appropriately market your properties for maximum revenue and occupancy. 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Events Are Huge Vacation Rental Marketing Opportunities - Do You Take Advantage? 08 Apr 202600:33:22

In this episode Conrad and Paul break down building marketing opportunities with events. The duo specifically focuses on how to leverage landing pages, search volume trends, and other signals in your local community to take advantage of people traveling for these events. Drive more bookings with these tips.

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Are You Making Real or Fake Progress With AI?01 Apr 202600:41:01

In this episode Conrad and Paul talk about the realities of AI slop, how you know if you’re making real progress or fake progress, being fooled by hallucinations in AI data, and a lot more! 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

What Is The Future Of Direct Bookings (With Arthur Colker)25 Mar 202600:51:23

Welcome to our second-ever guest episode! We're joined by Arthur Colker to chat all things direct bookings, OTAs vs direct booking "sourcing", what percent of Airbnb listings are direct bookable and a LOT more topics.

A special thanks to Arthur for reaching out and joining us.

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Here's The Problems With Vacation Rental Marketing Attribution18 Mar 202600:37:29

In this episode Conrad and Paul talk "All About Attribution" including how ads platforms track "bookings made", limits of pixels, how to proceed when you get conflicting data, Meta vs Google and a LOT more... 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

How To Run A GEO/LLM Search Audit On Your Vacation Rental Website11 Mar 202600:34:30

In this episode Conrad and Paul take a crack at defining what a LLM / GEO / AEO whatever ya wanna call it audit should look like. 

Want a copy of the audit? Email conrad@buildupbookings.com with subject line "LLM Audit doc" and you'll get it! 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Every Section You Need On Your Landing Page To Get More Homeowner Leads04 Mar 202600:44:05

In this episode Conrad and Paul break down ALL of the sections you need to build a killer, lead-generating machine of a homeowner landing page.

From the episode:

1. Hero The first thing a homeowner sees. A bold, benefit-driven headline, a subheadline with your USP, a compelling property photo, and a CTA (form or button). The entire job of this section is to get them to keep scrolling — or fill out the form immediately.


2. Trust Bar
A slim strip of logos and proof points directly below the hero: Google rating, Airbnb/VRBO partner badges, VRMA membership, BBB, years in business, properties managed. Builds instant credibility before the homeowner has read a single word of copy.


3. Pain Point / Problem Agitation
Addresses the homeowner's frustration before pitching solutions. Speaks to the stress of self-managing, the underwhelming results from big-box managers, or the fear of leaving money on the table. Creates emotional resonance and makes everything that follows feel relevant.


4. Earnings Estimator / Revenue Calculator
An interactive tool where the owner enters their address or property details and gets a projected annual income range. One of the highest-converting elements on any owner page — makes the value immediately personal and tangible.

5. What Makes Us Different / USP Explains the core differentiators vs. competitors and self-managing. Boutique vs. national, local vs. generic, hands-on vs. automated. Should answer "why you specifically?" not just "why a manager?"

6. How It Works / Onboarding Process A 3–5 step visual walkthrough of what happens after a homeowner signs up — from evaluation to first booking. Reduces fear of the unknown and lowers the psychological friction of committing.

7. Full-Service Checklist / Everything Included An exhaustive breakdown of every service covered under management: dynamic pricing, professional photography, guest screening, 24/7 support, maintenance coordination, tax remittance, owner reporting, etc. Homeowners need to feel like every detail is handled.

8. Channel Distribution / Where You'll Be Listed A logo wall showing all the platforms their property will appear on — Airbnb, VRBO, Booking.com, direct site, Google Vacation Rentals. Reassures owners their home gets maximum market exposure.


9. Technology & Tools
Showcases the software stack: PMS, dynamic pricing tool, channel manager, housekeeping platform, owner portal. Signals that you run a modern, professional operation — not a spreadsheet-based mom-and-pop.


10. Owner Portal Preview
A screenshot or short UI demo of the owner dashboard. "See your bookings, earnings, and maintenance requests anytime." Transparency about visibility is one of the top concerns prospective owners have.

11. Explainer Video A 60–90 second video walking through the owner value prop — ideally featuring the founder or a real owner story. Vintory's research shows this alone can lift conversions by ~34%.

12. Owner Testimonials Full-name quotes from real homeowners, ideally with photo, property type, and location. Best if mixed between long-form narrative quotes and short punchy pull-quotes. Video testimonials are even better.

13. Owner Success Story / Case Study A single deep-dive narrative: one real owner, specific numbers, before/after comparison. "Sarah had a 2BR in Pacific Beach. Year one with us: $58,000 — 37% more than she earned solo." Makes results feel concrete and achievable.


14. Star Ratings & Review Count
A standalone visual callout of your aggregate Google/Airbnb rating and review volume. Deserves its own moment rather than being buried in the trust bar.

15. Side-by-Side Comparison Table Self-managing vs. big national manager vs. you. One of the most persuasive conversion tools on the page. Directly neutralizes the "why not just list it myself?" objection with a visual, scannable answer.


16. Risk Reversals / Guarantees
Placed near CTAs to eliminate commitment fear. No long-term contracts, no startup fees, satisfaction guarantee, 30-day out clause, performance guarantee — whatever you actually offer. Reduces the perceived risk of saying yes.

17. Local Market Expertise / Market Data Average nightly rates, occupancy benchmarks, peak season data, demand trends for your specific market. Positions your company as the local authority, not just a vendor. Especially powerful against national competitors.

18. About the Team / Company Story A brief, human section with founder photo and origin story. Builds emotional connection and trust — particularly important for boutique operators competing against faceless national brands.


19. FAQ / Objection Crusher
An accordion of the real questions homeowners ask during the sales process: fees, personal use, damage protection, revenue reporting, how long to get started. Each answer should resolve a specific objection.

20. Press / Awards / Recognition Any local media coverage, industry awards, or "As Featured In" mentions. Even modest recognition adds a layer of legitimacy that social proof alone doesn't cover.

21. Property Types We Manage A visual grid showing the range of properties in your portfolio — condos, single-family homes, beach cottages, luxury homes. Helps different owner types self-identify and feel like you can handle their specific situation.

22. Final Lead Capture Form / CTA Section The conversion close at the bottom of the page. Mirrors the hero but with a softer, benefit-forward framing: "Discover Your Property's True Potential." Should include risk reversals nearby ("No obligation. No contracts.").

23. Sticky / Floating CTA A persistent bar or button that follows the user as they scroll — "Get Your Free Rental Estimate →". Critical on mobile where the hero form scrolls out of view almost immediately.

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Here's Why Hotels Can Be Better Than Vacation Rentals25 Feb 202600:41:08

In this episode Conrad and Paul flip the script and break down WHY a hotel often is a better stay than a vacation rental. 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Your Vacation Rental Website Traffic Is Up, But Your Bookings Are Down - Why?18 Feb 202600:37:53

In this episode Conrad and Paul dive into a 2026 trend: your website traffic is up, but your bookings are down - why? 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

AI Update: Q1 of 2026: OpenClaw, "Prompt Tracking" Useless?, Current AI Tools We're Using 11 Feb 202600:52:20

In this episode Conrad and Paul give their regular update on AI: what tools they're using, what's changing, and how you can use it to grow and scale your vacation rental business. They talk ClawdBot (aka OpenClaw), traffic from LLMs going down month over month, prompt tracking value (it's useless?!), and what tools they're using MORE and LESS of... 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Looking Back On Marketing Changes From 2020 to 2025...04 Feb 202600:38:24

In this episode Conrad and Paul take a (not too far back) look into memory lane and see what's changed from 2020 to 2025 in marketing, brand, the Covid boom and bust and a LOT more. A casual chat! 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Direct Bookings Aren't Free... Here's How To Understand Your Marketing Costs28 Jan 202600:40:05

In this episode Conrad and Paul talk all about how much it actually costs to get direct bookings and scale your bookings with paid ads. 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Expanding Into NEW Vacation Rental Marketing Channels In 2026? Here's How To Make It Work...21 Jan 202600:37:13

In this episode Conrad and Paul talk about when and how to consider expanding your marketing and advertising into new channels you may not have used before like TikTok, Pinterest, native, Digital TV ads and more...

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

How To Spend: $3k, $5k or $10k In Marketing Budget For Your Vacation Rental Company (Part 2) 14 Jan 202600:23:58

In this episode Conrad and Paul finish in part two their chat on how to best spend budget if you have between $3k and $10k a month in marketing budget. 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

How To Spend: $3k, $5k or $10k In Marketing Budget For Your Vacation Rental Company (Part 1) 07 Jan 202600:29:11

In this episode Conrad and Paul break into 2026 with a two-part podcast series on what to spend if you have between $3k and $10k a month in marketing budget. Part two next week!

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

ALL The Ways You Can Run Promotions For Your Vacation Rental Business 24 Dec 202500:36:54

In this episode Conrad and Paul talk about all of the different ways you can run promos that are not just "cutting rates lower" to drive more bookings.

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings



🚀 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.

Multiple Vacation Rental Markets? It's Super Hard: And Here's Why....17 Dec 202500:31:53

In this episode Conrad and Paul break down why targeting many markets at the same time is HARD (but not impossible) and explaining why this can be a harder path to success. 

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Mobile vs Desktop Traffic Trends For 2026: Here's What To Work On10 Dec 202500:41:57

In this episode Conrad and Paul go back to an "old" topic that we often ignore: mobile vs desktop traffic, how the site works on mobile, data on Google Analytics conversions and more...

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Here's How To Level Up Your Marketing With JUST 4 Hours Per Week26 Nov 202501:00:55

In this episode Conrad goes solo on this audio-only version of a LIVE training on "The 4 Hour Vacation Rental Marketing Workweek".

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

Enjoy!


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Compelling Vacation Rental Marketing Messages Have Common Traits19 Nov 202500:37:11

In this episode of The Heads In Beds Show, we break down a recent VRM Intel article from Conrad O'Connell talking all about messaging and what homeowners act on vs ignore. 


⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.


What To Consider When Building A New Vacation Rental Website 12 Nov 202500:40:34

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


🔗 Connect With BuildUp Bookings


🚀 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.


The Four Part Process To Build A Guest Marketing Plan05 Nov 202500:33:37

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


🔗 Connect With BuildUp Bookings


🚀 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.


Is This The KEY To Getting More Bookings? 29 Oct 202500:26:27

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


🔗 Connect With BuildUp Bookings


🚀 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.


VRMA 2025 Recap: The Hot Seat Session, Industry Trends & More!22 Oct 202500:45:37

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


🔗 Connect With BuildUp Bookings


🚀 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.


The Four Part Process To Build A Homeowner Marketing Plan15 Oct 202500:36:30

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


🔗 Connect With BuildUp Bookings


🚀 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.


The "Do's" and "Don'ts" Of Using AI With Your Vacation Rental Marketing08 Oct 202500:36:00

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


🔗 Connect With BuildUp Bookings


🚀 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.

Replay: The Vacation Rental Marketing Fundamentals You Need To Have In Place01 Oct 202500:57:24

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


🔗 Connect With BuildUp Bookings


🚀 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.

10 Things You Can Do To Sign More Vacation Rental Properties This Fall24 Sep 202500:33:03

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


🔗 Connect With BuildUp Bookings


🚀 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.


Revisiting Meta Ads vs Google Ads17 Sep 202500:41:38

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


🔗 Connect With BuildUp Bookings


🚀 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.


Can You Really Compete With Airbnb? Nope...10 Sep 202500:35:11

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


🔗 Connect With BuildUp Bookings


🚀 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.


How Are Direct Bookings Trending According To Industry Research Experts? 03 Sep 202500:45:15

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


🔗 Connect With BuildUp Bookings


🚀 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.


Here's What Trust Building Is Needed In The Vacation Rental Industry27 Aug 202500:51:46

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


🔗 Connect With BuildUp Bookings


🚀 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.


Here's What To Look For When Selling Your Vacation Rental Business 20 Aug 202500:34:14

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


🔗 Connect With BuildUp Bookings


🚀 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.


The MOST Important Question To Ask Before Investing In Growth (Part II)13 Aug 202500:43:33

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


🔗 Connect With BuildUp Bookings


🚀 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.


The MOST Important Question To Ask Before Investing In Growth (Part I)06 Aug 202500:41:05

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


🔗 Connect With BuildUp Bookings


🚀 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.


Is Creating Content Even Worth It Anymore? A Debate30 Jul 202500:33:45

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


🔗 Connect With BuildUp Bookings


🚀 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.


Breaking Down The Reasons WHY Guest Choose Vacation Rentals vs Hotels23 Jul 202500:39:56

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


🔗 Connect With BuildUp Bookings


🚀 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.


How To Launch New Vacation Rental Listings And Get Them BOOKED16 Jul 202500:59:41

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


🔗 Connect With BuildUp Bookings


🚀 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.


Build The Demand Formula For Your Vacation Rental Marketing09 Jul 202500:32:51

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


🔗 Connect With BuildUp Bookings


🚀 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.


SEO, AEO, GEO, Oh My! What's The New Search Trend In Vacation Rental Marketing?02 Jul 202500:38:19

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


🔗 Connect With BuildUp Bookings


🚀 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.


Here's ALL You Need To Know About Hiring A Marketing Team For Your Vacation Rental Business25 Jun 202500:53:06

In this episode of The Heads In Beds Show, we replay a webinar between Conrad and Steve Trover - CEO of Better Talent - of all things hiring, agency vs freelancer, marketing teams, margins of your business and more. 

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.


The Success Framework: How To KNOW A Vacation Rental Will Work Well18 Jun 202500:29:52

In this episode of The Heads In Beds Show, Paul and Conrad recap build the "Success Framework" for vacation rental properties to KNOW if a property will be successful. 

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.


Recapping Google Marketing Live 2025 For Vacation Rental Managers 11 Jun 202500:50:33

In this episode of The Heads In Beds Show, Paul and Conrad recap Google Marketing Live from May of 2025. 

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Last Minute Marketing Tips To Boost Summer Occupancy04 Jun 202500:43:59

In this episode of The Heads In Beds Show, Paul and Conrad dive into tips and tricks on getting more bookings this summer, driving last-minute demand and boosting the number of bookings you get to fill in open dates.

⭐️ Links & Show Notes



🔗 Connect With BuildUp Bookings


🚀 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.


Photo & Video Assets: What Do You Need To Succeed? 28 May 202500:41:12

In this episode of The Heads In Beds Show, Paul and Conrad give a TON of ideas on photo and video assets that you need to build your vacation rental brand.

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Video ideas:

📍 Property Showcase Videos (25 Ideas)


Core Property Tours

  1. 60-Second Property Highlight Reel – Wide-angle shots of living areas, bedrooms, kitchen, outdoor spaces ending with dramatic drone pullback
  2. POV Guest Arrival Experience – GoPro-style journey from parking to front door to best view in the house
  3. Follow-Me Guided Tour – Host-led walkthrough highlighting unique features and amenities
  4. Before & After Renovation Reveal – Split-screen transformation showcasing property improvements
  5. Room-by-Room Flash Tour – 3-second clips of each space with text overlays (Master Suite, Chef's Kitchen, Game Room)


Amenity Spotlights

  1. Unique Feature Deep Dive – 30-second focus on standout amenities (infinity pool, wine cellar, home theater)
  2. Chef's Kitchen in Action – Professional cooking demonstration showcasing high-end appliances
  3. Outdoor Living Paradise – Pool, hot tub, fire pit, BBQ area montage with lifestyle shots
  4. Master Suite Experience – Morning coffee in bed with sunrise view through floor-to-ceiling windows
  5. Smart Home Technology – Voice-controlled lighting, automated blinds, keyless entry demonstration


Advanced Visual Content

  1. Aerial Property Overview – Drone 360° orbit at golden hour with distance markers to beaches/attractions
  2. Day-to-Night Transformation – Time-lapse showing property from sunrise to illuminated evening
  3. Seasonal Property Evolution – Same view across all four seasons (great for year-round bookings)
  4. Virtual Tour Teaser – 360° bedroom pan encouraging full Matterport tour viewing
  5. Cinematic Property Film – Slow motion, professional lighting, and music telling the property's story


Practical Demonstrations

  1. Guest Arrival Guide – Step-by-step check-in process from parking to settling in
  2. Amenity How-To Series – Hot tub operation, smart TV setup, grill instructions
  3. Property Navigation Map – Animated overlay showing routes to beach, downtown, parking
  4. Wi-Fi Speed Test – Real-time demonstration for remote workers
  5. Storage & Space Solutions – Closet space, luggage storage, family organization tips


Maintenance & Updates

  1. Turnover Time-Lapse – Professional cleaning team preparing property in fast-forward
  2. Recent Upgrades Showcase – New furniture, technology, or amenity additions
  3. Quality Assurance Check – Host's pre-arrival inspection ensuring everything is perfect
  4. Seasonal Maintenance – HVAC service, pool opening, landscape updates
  5. Accessibility Features – Ramps, grab bars, accessible bathrooms for inclusive marketing


🎯 Lifestyle & Guest Experience (15 Ideas)


Daily Experiences

  1. Perfect Morning Routine – Coffee brewing, sunrise yoga on deck, fresh pastries
  2. Cozy Evening Ritual – Fireplace crackling, wine pour, city lights twinkling
  3. Family Fun Montage – Game night laughter, pool splashing, movie night setup
  4. Couples Retreat Moments – Hot tub under stars, breakfast in bed, sunset dinner
  5. Remote Work Paradise – Home office setup, video call with beach backdrop


Entertainment & Recreation

  1. Game Room Championships – Pool table trick shots, arcade game highlights, competition laughs
  2. Outdoor Adventure Prep – Packing beach bags, loading kayaks, hiking gear organization
  3. Spa Day at Home – Bubble bath setup, face masks by the pool, massage table ready
  4. Celebration Central – Birthday party setup, anniversary dinner, graduation toast
  5. Pet-Friendly Features – Dog bed setup, fenced yard, nearby dog park walkthrough


Culinary Experiences

  1. Gourmet Cooking Experience – Using high-end appliances to create restaurant-quality meals
  2. Local Grocery Haul – Shopping at nearby markets, unpacking fresh ingredients
  3. BBQ Master Class – Grilling techniques, outdoor dining setup, sunset feast
  4. Coffee Connoisseur Corner – Espresso machine tutorial, morning coffee ritual
  5. Wine & Dine Experience – Cellar selection, proper glassware, tasting notes


🗺️ Local Area & Activities (10 Ideas)


Attraction Showcases

  1. Top 5 Local Attractions Countdown – Quick-cut tour of must-visit spots with distances
  2. Hidden Gems Revealed – Secret beaches, local favorite restaurants, insider tips
  3. Seasonal Activity Guide – Skiing in winter, beach days in summer, foliage tours in fall
  4. Foodie Adventure Map – Farmers markets, food trucks, fine dining recommendations
  5. Family-Friendly Itinerary – Zoo, adventure parks, kid-friendly restaurants


Experience Documentation

  1. Day Trip Inspiration – POV drive to wine country, mountain hikes, city exploration
  2. Local Event Calendar – Festivals, concerts, seasonal celebrations nearby
  3. Weather-Proof Activities – Rainy day museums, indoor entertainment, covered markets
  4. Transportation Options – Rental car pickup, public transit, ride-share availability
  5. Shopping & Services – Grocery stores, pharmacies, urgent care locations


⭐ Social Proof & Reviews (8 Ideas)

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Foundational Planning For Vacation Rental Business Success21 May 202500:46:34

In this episode of The Heads In Beds Show, Paul and Conrad cover all things Foundational Planning for a vacation rental management company to thrive and grow. 

We cover:

Strategy & Foundational Planning

 • Mission, Vision & Values statements

 • Company origin story

 • Unique Value Proposition (UVP) — guests & owners

 • Geographic focus / service‑territory map

 • Ideal guest personas

 • Ideal property‑owner personas

 • SMART business goals & high‑level KPIs

 • SWOT & competitive analysis report

 • Growth & expansion strategy + market‑entry playbook

 • Succession / leadership‑transition plan

 • Service scope & business‑model definition

 • Market‑research repository (demand, seasonality, ADR benchmarks)

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.


Grab Bag Show: Vacasa, Growth, Inventory Churn, Data, May Thoughts & More... 14 May 202500:28:29

In this episode of The Heads In Beds Show, Paul and Conrad try something new: a grab bag show with news and notes from around the world of vacation rentals and all growth and the Vacasa - Casago merger. Like this style of episode? Let us know! 

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Designing for Conversion: Best Practices For Vacation Rental Websites30 Apr 202500:32:17

In this episode of The Heads In Beds Show, Paul and Conrad talk all things conversions: getting more bookings, driving more leads and reviewing your website to find the friction points that stop direct bookings from growing. 

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Breaking Down The Ideal Marketing Audit For Vacation Rental Businesses 23 Apr 202500:38:15

In this episode of The Heads In Beds Show, Paul and Conrad cover the concept of a marketing audit for vacation rental businesses, discussing what a good audit entails from both the consultant's and the client's perspectives. They explore quantitative (data-driven) and qualitative (opinion and goal-based) aspects of audits for attracting both guests and homeowners. They also touch upon the challenges of conducting free audits, the potential for bias when sales are involved, and the importance of an audit leading to actionable improvements for the business.

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

Breaking Down The Way The "Guest Booking Journey" Actually Works In 2025... (Part 2)16 Apr 202500:31:15

In this episode of The Heads In Beds Show (Part Two), Paul and Conrad dive into the early stages of the vacation rental guest journey — where interest is sparked and decisions begin to form. 

They explore how true inspiration often comes from unexpected, memorable experiences and how smart property managers can tap into that moment before a guest is even planning a trip. From the role of local tourism boards to leveraging blog content and “pattern interrupts,” they unpack why this top-of-funnel phase is often overlooked—and how to make your brand unforgettable.

As guests shift into research mode, the pressure’s on. The hosts break down what travelers are really looking for when comparing destinations and rentals—and why your website needs to stand toe-to-toe with the likes of Airbnb. If your site leaks trust, design, or information, you’ll lose them fast. Tune in to learn how to optimize your marketing for these make-or-break early stages and build demand that puts your properties in high demand (waitlist, anyone?).

⭐️ Links & Show Notes


🔗 Connect With BuildUp Bookings


🚀 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.

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