Guests Don’t Wake Up Wanting to Be Difficult

Most guests don’t arrive intending to be a problem.

They arrive tired, rushed, juggling information, and already under pressure. And when something small goes wrong, what looks like an attitude issue is often something else entirely: a stress response shaped by uncertainty, automation, and missed moments of orientation.

In this episode of Seen. Booked. Sane., Kay Walten breaks down why guest behavior has felt heavier lately across hotels, vacation rentals, and destinations — and why the real issue often starts long before the front desk, inbox, or check-in message.

This isn’t about excusing bad behavior. It’s about understanding what’s actually happening, so operators can design calmer systems that prevent escalation in the first place.

In this episode, we explore:

• Why guests are arriving more on edge than they used to

• How shorter booking windows and compressed travel plans increase emotional load

• The “invisible escalator” that turns small friction into big reactions

• Why orientation beats explanation — and framing beats enforcement

• How systems shape not just guest behavior, but operator behavior too

A quiet takeaway:

Calm isn’t a personality trait. It’s something you can design for.

Before your next check-in, pre-arrival message, or automated reply, ask yourself:

Where might my system be creating stress without meaning to?

Hosted by: Kay Walten
Founder, Smart Pineapple
Helping small hotels, vacation rentals, and unique stays get seen, get booked, and stay human.

Connect with Kay:

On Linkedin

Website and on Substack

Most operators think trust breaks happen in the inbox.
But 75% of guests never say what went wrong — they disappear quietly.

In this episode, Kay Walten breaks down the five moments that shape every guest’s decision to book, enjoy, return, or vanish. Only one of these moments happens online. The other four happen in the quiet, human parts of hospitality where trust is either reinforced… or eroded.

You’ll learn:

• Why website clarity isn’t design — it’s emotional safety

• How inquiry tone predicts the entire stay

• Why pre-arrival communication is the hinge moment

• What guests really evaluate in the first three minutes on-site

• How the stay actually ends (and why most operators get this wrong)

• A simple, practical test you can run before your next check-in

Kay also shares behind-the-scenes stories from Mexico, the French Riviera, Bobcaygeon, and Sian Ka’an — real moments that reveal how easily trust is broken and how powerfully it can be rebuilt.

Short strategy. Quiet truth. One thing to test before your next guest arrives.

• Smart Pineapple — AI + marketing for hospitality brands
https://www.smartpineapple.ai

• Substack (AI for Hospitality & Tourism)
https://www.aiforhospitality.info

• LinkedIn
https://www.linkedin.com/in/kaywalten/

Why Guests Don’t Reply After You Do

Most bookings aren’t lost on your website.
They’re lost in the first reply.

In this episode, Kay breaks down why response speed is no longer enough and how the emotional safety of your message quietly determines whether a guest moves forward or disappears.

This is not about scripts, automation, or policies.
It’s about the moment a guest decides whether it feels safe to trust you.

What This Episode Covers

• Why the inbox is now a trust signal, not a logistics task
• How guests scan for calm, clarity, and human presence when choosing where to stay
• The difference between hotel and STR guest fears
• A real-world case from Sri Lanka showing how reply tone changed guest behavior
• Why “professional” often sounds cold to guests
• The quiet cost of being fast but emotionally unsafe
• The difference between hosting energy and self-protection energy

Before you hit “send” on your next reply, ask:

“Does this feel like I’m hosting… or protecting myself?”

You don’t need perfect messages.
You just need awareness.

That one moment of awareness changes how you show up.

Key Takeaways

• Speed gets attention
• Safety earns trust
• Trust fills rooms
• Guests don’t ghost bad properties, they ghost unsafe feelings
• Hospitality shows up in the small moments

Invitation

Kay is building a small, intentional system for operators who want their standards of communication to quietly outperform their competitors.

If it feels aligned, you can find it here:
https://smartpineapple.systeme.io/waitlist

Kay Walten is the founder of Smart Pineapple and host of Seen. Booked. Sane.

She works with small hotels, vacation rentals, and destinations that want to grow without losing their soul.

We’re Not in the Attention Economy. We’re in the Mistrust Economy.

Guests aren’t getting pickier.
They’re getting more cautious.

In this episode of Seen. Booked. Sane., Kay Walten breaks down why hospitality shifted from “wow them” to “reassure them” and what that means for small hotels, vacation rentals, and unique stays.

You’ll learn why trust is the new luxury, how guests actually evaluate risk when booking, and one simple test you can run before your next check-in to close the trust gap.

This is a short, sharp reset on how modern guests really think.

𝗘𝗽𝗶𝘀𝗼𝗱𝗲 𝗦𝘂𝗺𝗺𝗮𝗿𝘆

This episode explores the shift from the attention economy to what Kay calls the mistrust economy.

Instead of chasing attention with polished photos and clever descriptions, winning operators are now focused on reducing risk, building trust, and creating calm for hesitant guests.

Key idea:
Guests aren’t comparing you to competitors.
They’re trying not to be fooled again.

𝗪𝗵𝗮𝘁 𝗬𝗼𝘂’𝗹𝗹 𝗟𝗲𝗮𝗿𝗻

• Why guest “pickiness” is actually protection behavior

• How bad experiences have trained guests to verify everything

• Why your listing is now a trust contract, not marketing

• How digital deception (fake reviews, scams, AI listings) changed guest behavior

• The difference between Performers and Protectors in hospitality

• A simple weekly trust audit you can run before your next guest arrives

The Trust Gap Test™

Before your next check-in:

1. Open your listing

2. Find one sentence you cannot physically prove with a photo

3. Delete it

4. Replace it with one honest, informative photo

This one shift builds calm and reduces hesitation.

𝗪𝗵𝗼 𝗧𝗵𝗶𝘀 𝗘𝗽𝗶𝘀𝗼𝗱𝗲 𝗜𝘀 𝗙𝗼𝗿

This episode is especially helpful for:

• Boutique hotels

• Vacation rentals

• Unique stays

• Small hospitality brands

• Owners frustrated by ghosting, abandoned carts, or price-sensitive guests

𝗘𝗽𝗶𝘀𝗼𝗱𝗲 𝗟𝗶𝗻𝗸𝘀

More from Kay Walten:
👉 https://aiforhospitality.info

Smart Pineapple:
👉 https://smartpineapple.ai

𝗦𝗼𝘂𝗿𝗰𝗲𝘀 & 𝗙𝘂𝗿𝘁𝗵𝗲𝗿 𝗥𝗲𝗮𝗱𝗶𝗻𝗴

(Referenced for research. Not named in audio.)

1. SAGE Journal – Negative accommodation experiences and trust loss
   https://journals.sagepub.com/doi/10.1177/21582440251316146

2. MyTrip.ai – Travel industry challenges and trust issues (2025)
   https://mytrip.ai/50-largest-challenges-to-travel-agencies-tour-operators-activity-providers-in-2025/

3. Hotel Link Solutions – Hotel booking scams and consequences
   https://blog.hotellinksolutions.com/the-hotel-booking-scam-crisis-consequences-how-to-avoid-them

4. Geojournal of Tourism & Geosites – Trust spillover in travel
   https://gtg.webhost.uoradea.ro/PDF/GTG-4-2024/gtg.56428-1342.pdf

5. TravelerWP – Fake reviews harming travel brands
   https://travelerwp.com/how-fake-reviews-can-harm-your-travel-business/

6. HospitalityNet – Trauma-informed hospitality post-pandemic
   https://www.hospitalitynet.org/opinion/4109218.html

7. Frontiers in Psychology – Pandemic anxiety and traveler behavior
   https://www.frontiersin.org/journals/psychology/articles/10.3389/fpsyg.2021.769175/full

8. Tourism & Business Affairs – Business travel and mental health
   https://tourismedaffaires.com/actualite/business-travel-taking-toll-on-mental-health-stats-2/

9. Travel Media Group – Fake reviews and reputation damage
   https://www.travelmediagroup.com/fake-hotel-reviews-have-series-consequences/

10. IPX 1031 – 2025 travel hesitation trends
    https://www.ipx1031.com/americans-travel-report-2025/

Ever scroll through ten Airbnb listings and realize they all sound the same?

That’s what being forgettable costs you.

In this episode, Kay Walten — founder of Smart Pineapple — breaks down how brand consistency isn’t just about matching fonts or keeping your logo straight. It’s about staying memorable in a market drowning in sameness.

You’ll learn:

• Why Cornell research shows consistency drives more repeat bookings than location

• How one small boutique hotel turned brand alignment into national expansion

• The emotional ROI of “memory equity” — and how to create it

• The hidden cost of automation that erases your voice

• Simple 5-minute brand checks every host, innkeeper, or destination can run this week

This is Seen. Booked. Sane. — your short, sharp hit of strategy and cheeky truth, with one idea you can test before your next check-in.

If you manage a property, market a destination, or simply want guests to remember your name long after checkout, this episode’s your wake-up call.

Three Takeaways:

1. Consistency beats convenience. Thirty million reviews prove guests rebook based on trust, not location.

2. Memory is money. “Deliberate delight” moments — notes, upgrades, surprises — can lift positive reviews by 20 percent.

3. AI can amplify your originality — or erase it. The choice is in how you train it.

Memorable Quote Highlights:

“You weren’t bad. You just weren’t anyone.”

“Templates kill creativity. Consistency amplifies it.”

“Being remembered is the cheapest marketing you’ll ever do.”

Connect + Contribute:

What’s one tiny detail guests still mention months later?
Share your story in the comments on AI for Hospitality Community or on Substack — your proof might be featured in an upcoming episode.

Subscribe to Smart Pineapple for weekly insights on AI, branding, and hospitality that stays human.

Connect with Kay on Linkedin

Sources & References:

1. Cornell University Hospitality Research Center – Brand Consistency and Guest Loyalty Analysis

2. Grenoble École de Management – Visual Uniqueness and Booking Behavior in Airbnb Listings

3. The BOB Hotels Case Study (Brand Consistency in Boutique Hospitality) — blog.thebobhotels.com

4. Oliver Corrin – LinkedIn Hospitality Leadership Series: Memory Equity and Emotional ROI

5. Behavioral Economics Review – Deliberate Delight Moments and Customer Loyalty Metrics

6. Emersion Wellness – Hotel Branding Case Studies

7. Hospitality Insights (EHL) – Luxury Brand Identity and Guest Experience

8. PhocusWire – The True Cost of Hotel Brand Recognition

AI doesn’t replace hospitality—it redeploys time for connection. In this episode, Kay from Smart Pineapple shares real case studies of small inns, boutique hotels, and independent operators using automation to scale care, not just bookings.

You’ll learn the “Three-Layer Strategy” for adopting AI—Listen Faster, Respond Smarter, Connect Deeper—and a simple action you can take this week to create more meaningful guest experiences.

🧭 Key Takeaways

• Listen Faster: Use AI to monitor and respond to reviews quickly, improving satisfaction and loyalty.

• Respond Smarter: Automate pre-arrival and in-stay messages to save hours while adding personal warmth.

• Connect Deeper: Let technology amplify your local stories, culture, and humanity—not replace them.

Pick one repetitive task—like guest messages or review tracking—and automate it using a simple tool such as HelloShift, GuestRevu, or Tidio.

💡 Listener Challenge
Then use the five minutes you save to do something personal for a guest this week.

🌍 Connect with Kay Walten + Smart Pineapple

• Website: smartpineapple.ai

• Weekly Substack: aiforhospitality.info

• LinkedIn: Kay Walten

• Community: AI for Hospitality Community on Skool

Thanks for listening to Seen. Booked. Sane.
Subscribe wherever you get your podcasts so you never miss an episode, and join us each week on aiforhospitality.info.

You’ll find destination strategies, marketing insights, and weekly workflows for small hotels and vacation rental operators — plus free resources to help you grow smarter, work lighter, and stay human in a world full of automation.

📚 Sources and References

1. HelloShift – Guest Messaging for Independent Hotels
   https://www.helloshift.com/guest-messaging

2. EnsoConnect – Unlocking Scale with AI-Powered Guest Experience in Boutique Hotels
   https://ensoconnect.com/resources/unlocking-scale-with-ai-powered-guest-experience-in-boutique-hotels

3. Marriott International – AI Review Analysis Report (2025)
   https://superagi.com/case-studies-how-leading-brands-are-using-ai-to-revolutionize-customer-review-analysis-in-2025/

4. RENAI.ai – AI-Powered Local Storytelling in Ecuador
   https://renai.ai

5. GuestRevu – Reputation Management Case Studies for Boutique Hotels
   https://www.guestrevu.com/resources/case-studies

6. Revinate – Smarter Guest Feedback with AI Analytics
   https://www.revinate.com/blog/ai-in-hospitality/

7. NetSuite – AI in Hospitality: Global Translation Tools (Ryokan Yoshida-sensō Feature)
   https://www.netsuite.com/portal/resource/articles/business-strategy/ai-hospitality.shtml

You don’t need a marketing budget—you need the courage to start a conversation.

In this episode, Kay Walten, founder of Smart Pineapple and host of Seen. Booked. Sane., shares real stories of small operators who turned everyday neighborly connections into booking-boosting collaborations.

✨ From a West Virginia inn and bakery that built a breakfast ritual guests now travel for…

🍺 To the Corfu Beer Festival in Greece that filled hotels during the off-season…

🍷 To a Canadian wine region where local partnerships reshaped tourism…

You’ll hear how one idea, one conversation, and one small collaboration can transform a business—and a community.

What You’ll Learn:

• How small hotels, vacation rentals, and destinations can partner locally to grow bookings.

• Why 85% of hotels report better guest reviews after local collaborations (HospitalityNet & RTO9).

• The simple “1 neighbor → 1 conversation → 1 offer” formula you can start this week.

Listen if you:

• Run a boutique hotel, vacation rental, or unique stay.

• Want authentic marketing that builds trust, not just clicks.

• Believe hospitality still has heart.

After you listen:
Write down one neighbor you could collaborate with—and tell Kay how it goes.

Get an easy How To go to: How to create your first Stay and Play Offer in an Afternoon.

Tag @SmartPineapple or share your story using #SeenBookedSane so we can feature it in a future episode.

Stay seen. Stay booked. Stay sane.

When guests lose trust, it doesn’t start with a lawsuit — it starts with a small lie. An outdated photo. A broken promise. A silence that lasts too long.

In this episode, Kay Walten of Smart Pineapple breaks down real stories of trust lost and trust rebuilt — from small inns to boutique hotels that turned transparency into loyalty (and profit).

You’ll hear:

• A Michigan Attorney General case that exposed hotel operators running a bait-and-switch scheme.

• How Boar’s Head Resort learned that ignoring reviews can cost more than a refund.

• The Rex Hotel’s wild transformation from a crumbling $242K motel into a $3K-a-night boutique success story.

• What Historic Smithton Inn and Wingate Hotel taught us about communication during crisis.

• The Shores Inn verdict — a $2M lesson in why silence isn’t neutral.

• And how Hotel Crescent Court proved that accurate photos and honest storytelling can double bookings.

Because trust isn’t built online — it’s proven offline, one honest detail at a time.

• Honesty is a competitive advantage.

• Transparency isn’t PR — it’s profit.

• You can rebuild trust faster than you think — but never by hiding.

Trust isn’t built online — but conversations like this are.

👉 Subscribe to Seen, Booked, Sane wherever you get your podcasts,or get the extended notes, links, and tools every week on Substack:🔗 ⁠https://aiforhospitality.info⁠

Like What You Heard? Subscribe wherever you get your podcasts.

Sources:

Mackinaw City Hotels (2022)
Michigan Attorney General Press Release – “AG Nessel Announces Settlement With Mackinaw City Hotels”
FOX 2 Detroit Coverage – “Mackinaw City Hotels Accused of Tricking Guests”
Detroit Free Press – “Michigan Hotels Accused of Duping Guests”

Boar’s Head Resort (2024)
TripAdvisor Reviews & Reddit Threads (r/charlottesville, 2024)

The Rex Hotel (2021–2024)
Realtor.com – “We Transformed an Abandoned Motel Into a $3K-a-Day Boutique Hotel”
Business Insider – “A Couple Bought a $242,000 Motel and Turned It Into a Boutique Getaway”
Finding Promised Land YouTube Channel
🔗 https://www.youtube.com/@FindingPromisedLand

Wingate Hotel, Steubenville, OH (2025)
Herald-Star – “Wingate Hotel Faces Mold, Structural Issues”
The Intelligencer – “Steubenville Wingate Hotel Under Health Department Investigation”
WTOV9 News – “Officials Probe Wingate Hotel for Health, Safety Violations”

Historic Smithton Inn (2020)
eHotelier Case Study – “Major Chains and Small Hotels: Business Recovery During COVID-19”

Shores Inn, Ventura, CA (2020–2025)
Los Angeles Times – “Bed Bugs in Ventura Hotel Lead to $2-Million Jury Ruling”
KFI AM 640 – “California Hotel Guests Win $2M in Bed Bug Lawsuit”
USA Today – “2 Hotel Guests in California Awarded $2 Million in Bed Bug Lawsuit”

Flevy Boutique Hotel Service Case Study (2024)

Hotel Crescent Court, Dallas, TX (2023)
TravelBoom Marketing Case Study – “Hotel Crescent Court: New Site Launch Yields 46% More Bookings”
TripAdvisor Insights – “The Impact of Photos on Traveler Engagement”

Written and narrated by Kay Walten
Produced by Smart Pineapple
Research by Smart Pineapple Editorial Team

How Vacation Rentals & Hotels Turn Guest Feedback into Bookings

You’re losing bookings to properties worse than yours — not because they’re cheaper, but because they sound better.

Here’s the kicker: your guests already wrote your next marketing campaign. You just haven’t stolen it yet.

In this episode of Seen. Booked. Sane., Kay Walten, founder of Smart Pineapple, reveals how to turn guest reviews into marketing copy that drives direct bookings for vacation rentals, boutique hotels, and short-term rentals.

You’ll learn:

• How to use the Review-to-Story Method to write listings that sound human

• Why emotional storytelling outperforms feature lists

• How to sell belonging instead of just location

• Simple ways to use AI tools in hospitality without losing the personal touch

• Quick tips to rewrite your OTA descriptions and automate with empathy

Because great stories get remembered.
Great guest experiences get rebooked.
And the hosts who sound human? They stay sane.

🧾 Episode Resources & Mentions

• Smart Pineapple: https://www.smartpineapple.ai

• AI for Hospitality Substack: https://www.aiforhospitality.info

• Research referenced:

  • Zloteanu et al., 2018 – Digital Identity: The Effect of Trust and Reputation Information on User Judgement in the Sharing Economy.

  • Martinez et al., 2017 – The Impact of an Airbnb Host’s Listing Description “Sentiment” and Length on Occupancy Rates.

  • Hostfully Case Studies, 2024 – Revenue Growth Through Guest-Focused Messaging.

  • Lighthouse, 2024 – Vacation Rental Distribution Trends.

  • AirDNA, 2024 – U.S. Short-Term Rental Outlook.

💡 Listener Challenge

Find one line in your listing or website that sounds robotic.
Rewrite it using your guest’s own words — then tag @SmartPineapple or email hello@smartpineapple.ai to share your before-and-after.

Before you build the next cabin or pour concrete for that dream spa, pause.

Your next big idea might already be hidden in your guest reviews.

In this episode, Kay Walten breaks down how small hotels and vacation rentals can grow smarter—by listening first, building later.

I built one for you — the Property Revenue & Offer Tracker. It’s a plug-and-play spreadsheet that tracks bookings, upsells, and which offers actually make you money.

👉 Get it here

• Subscribe to us on Substack for more useful strategies and tips.
• Visit our website and blog

If your Airbnb listing feels invisible lately, you’re not imagining it.

Airbnb’s ranking system has changed — it now rewards hosts who deliver great guest experiences, not just great listings.

In this short episode of Seen. Booked. Sane. SHORTS, Smart Pineapple founder Kay Walten shares a five-minute “Visibility Audit” designed for busy property owners and managers.
You’ll learn how to spot the key issues that quietly lower your ranking — and how to fix them fast using simple steps (and a little help from AI).

• The real signals Airbnb uses to rank listings (and what they mean for you)

• A five-step “visibility audit” you can do between turnovers

• How to read your own reviews for repeat issues

• Why accurate photos and pricing matter more than ever

• How small listing updates signal quality to the algorithm

• Quick, low-stress ways AI can help you update faster

Run the five-point audit this week:

1. Review your latest guest feedback.

2. Update your photos and descriptions.

3. Fix recurring guest questions or complaints.

4. Check your price against similar listings.

5. Refresh your listing once a month.

Share your results or questions inside the Smart Pineapple Community — we’ll be talking about what changed after hosts ran this audit.

Quick, human-centered insights from Smart Pineapple — where hospitality meets AI and still feels human.
Hosted by Kay Walten, each SHORT gives you one clear action to grow your bookings, delight guests, and keep your sanity intact.

• Join the Smart Pineapple Community for free resources and conversation

• Explore Smart Pineapple’s AI tools, courses, and playbooks at smartpineapple.ai

• Connect with Kay on LinkedIn

What You’ll Learn

• The real signals Airbnb uses to rank listings (and what they mean for you)
• A five-step “visibility audit” you can do between turnovers
• How to read your own reviews for repeat issues
• Why accurate photos and pricing matter more than ever
• How small listing updates signal quality to the algorithm
• Quick, low-stress ways AI can help you update faster

Episode Summary
Big chains sell rooms. Small stays sell stories.
In this episode, Kay Walten shares the Personalize → Prototype → Partner playbook for independent operators who want to boost guest loyalty, drive repeat bookings, and capture more of the $775 guests typically spend outside their rooms. Packed with research, case studies, and cheeky truth, this is your roadmap for turning size into an advantage in 2025.

• Why guests remember ceviche shacks, not thread counts.

• How a simple personal touch can lift repeat bookings.

• The magic of testing micro-experiences (and what success rates to expect).

• Why partnerships with locals outperform glossy brochures.

• How reputation directly impacts revenue.

• A 30-day challenge to get started with personalization, prototyping, or partnering.

• 📬 AI for Hospitality on Substack → Weekly strategies, workflows, and cheeky truths for small operators. Visit AIforHospitality.info

Run one test this month: personalize, prototype, or partner.
Track the results.

And remember: guests aren’t buying rooms. They’re buying moments.

• Industry benchmarks: Hospitality email ROI outpaces paid ads

• Constant Contact data: Small inns boost repeat guests with regular updates

Action Steps This Week:

• How to audit your wins and choose one repeatable

• Simple, proven AI prompts to generate content

• Why it’s okay to miss a month (and how coming back compounds results)

Subscribe for More:
Get weekly tested plays at “AI for Hospitality” (Substack)—the newsletter for operators who want resilience, not stress.

For listener questions, feedback, or guest requests, contact Kay directly at kay@smartpineapple.ai or visit our episode page.

Airbnb is rolling out temporary phone numbers that disappear two days after checkout. On the surface, it’s about privacy. In practice, it’s about control. In this episode of Seen. Booked. Sane. Shorts, Kay Walten breaks down what this means for hosts and hotels, why it kills your follow-up, and the smart ways to build direct guest channels that actually last.

Want more sharp hits of news, truth, and strategy for indie stays and small hotels? Subscribe at aiforhospitality.substack.com.

Episode Summary:

Logos don’t fill beds. Visibility does. In this episode, Kay breaks down why obsessing over brand design is costing operators real money—and what to do instead. With lessons from Iceland, Derby, and Zoku hotels, you’ll learn the “3 V’s of Visibility” framework, see the ROI math in action, and walk away with two simple steps you can do today to boost bookings.

What You’ll Learn

• Why logos = ego, visibility = revenue

• Case studies: Iceland’s volcano stunt, Derby’s mountain biking boom, Zoku’s guest-driven brand

• The 3 V’s of Visibility framework: Guests, Community, Campaigns

• Back-of-the-napkin math that proves one guest photo can out-earn a $5K rebrand

• Two action steps: quick win + stretch play

Stats & Sources

• Iceland tourism arrivals grew nearly 40% and receipts ~40% after 2010 volcanic eruption + Inspired by Icelandcampaign (OECD report)

• Derby, Tasmania attracts ~30,000 visitors annually, generates ~$12M revenue, creates 120 jobs, and added 200 beds thanks to MTB trails (Hans Rey case study)

• MTB tourism in Tasmania grew 11% annually over 5 years, reaching ~27,700 interstate/international visitors by 2020 (Tourism Tasmania report)

Quote to Remember:

“Logos are for your ego. Visibility is for your revenue.”

Try This

• Quick Win: Drop your last 20 reviews into ChatGPT. Ask, “What do guests rave about most?” Use that as your next headline.

• Stretch Play: Pick one guest-loved experience (fire pit, view, Saturday market) and turn it into a 30-second reel today. Post it.

Stay Connected. For cheeky truths and AI-driven hospitality strategies, visit smartpineapple.ai and follow Kay on LinkedIn.

And don’t miss us on Substack: Smart Pineapple’s AI for Hospitality, for weekly insights and resources made for operators like you.

Airbnb just gave every host, manager, and boutique hotel a 15% pay cut.
Here’s the blunt truth: guests don’t save a dime. You lose margin. And unless you build your own direct booking system, it won’t stop at 15.

In this episode of Seen Booked Sane, I break down:

✔️ How Airbnb’s new 15.5% fee structure really works
✔️ The long-term cost (spoiler: $40K over 5 years on $50K annual bookings)
✔️ Why Airbnb isn’t your business — it’s just a channel
✔️ 3 big myths about direct bookings (and the smarter play instead)
✔️ How AI makes “going direct” easier than ever

💡 Plus: I built something to help.
The Smart Pineapple Direct Booking Power Pack is my free bundle with templates, strategies, and AI shortcuts to protect your revenue and build guest loyalty.

👉 Grab your free Power Pack here

Because here’s the truth:

• Airbnb owns the channel.

• You own the guest.

• And when you do? That 15.5% fee doesn’t touch you anymore.

Your bookings aren’t broken. Your strategy is.
Seen. Booked. Sane. is the no-fluff, all-fun show for vacation rental owners, boutique hoteliers, and small-stay pros who want more guests, more profit, and less chaos.

Hosted by Kay Walten of Smart Pineapple, each short, sharp episode tackles the real stuff holding you back—from pricing mistakes to guest experience wins—served with a side of cheeky truth and zero boring jargon.

If you’re ready to outsmart the big chains, cash in on local demand, and still have a life outside check-in day… you’re in the right place.

Download your copy of Turn Events into Bookings

Guests don’t want fancy. They want frictionless.
In 2025, personalization isn’t a perk—it’s the baseline. Whether you run a boutique hotel, a remote Airbnb, or a glamping cabin in the woods, your guests expect seamless, thoughtful touches... and they don’t care how many staff you have.

In this episode, Kay breaks down:
– What “smart stays” are doing to personalize without sounding robotic
– How indie properties are using AI to get more repeat guests (and better reviews)
– Why automation doesn’t mean losing the human touch—it means saving it
– One powerful story about a tiny stay that used an AI trip planner to wow even their regulars

Tech doesn’t replace hospitality. It lets you actually practice it.

Next up: We’re pulling back the curtain on rental software.
That all-in-one solution? Might be quietly sinking your margins.
Don’t miss it.

Connect with Kay on Linkedin

Subscribe on Substack

Smart Pineapple Website

Most hosts are stuck in a cycle: waiting on OTAs, tweaking listings, hoping the algorithm shows them some love. But what if your next booking didn’t come from Airbnb—or Vrbo—or some endless scroll?

In this episode, Kay Walten breaks down why your vacation rental or boutique stay needs a blog in 2025—and how one simple post can work harder than most hosts realize.

You’ll learn:

• Why blogging still works (and why it’s not just a trend from 2012)

• What kind of blog posts build trust and get seen by the right guests

• How one blog can fuel your SEO, social, email, and even future podcasts

• The real ROI—and how skipping just two OTA commissions can pay for it all

This isn’t fluff. It’s strategy for small stays who want visibility before guests ever hit the OTAs.

And the best part? You don’t need to be a writer—you just need to know your guests.

→ Follow Kay on Substack for weekly tips + tools for vacation rentals, small hotels, and indie destinations.

What if AI could give you back 14 hours a week—and help your small property look more polished than the big chains, without hiring a team?

In this episode of Seen. Booked. Sane., Kay Walten breaks down how indie hosts, boutique hoteliers, and small destinations are using AI for messaging, pricing, guest support, and content—without sounding robotic or losing the human touch.

We’ll cover:

• Why AI is your new relief valve (not your replacement)

• Real stats behind the AI wave in hospitality

• Simple ways to start—even if you’re not techy

• One cheeky story about a chatbot that never asks for a raise

Plus: how to fire your inner micromanager and still get the job done.

Grab the free AI Messaging Cheat Sheet: aiforhospitality.info