Vacation Rental Brand Strategy I Learned the Hard Way with Ali Haney

Summary and Highlights

👩‍💼 Meet Ali Haney

Ali Haney is the Founder and CEO of Brand & Market, a marketing agency building independent legacy hospitality brands. She owns and operates two short term rentals, cohosts a third, and has been in the industry in some form since 2019.

Ali is a former high school English teacher who never lost her love of learning. She is also a former wedding photographer who knows how to tell a compelling visual story, and a current superhost who knows the STR industry from the inside out. She hosts The Brand & Market Podcast, now more than 115 episodes in.

Outside the agency, you’ll usually find Ali, her husband Caleb, and their three kids covered in paint and plaster dust while they work on their latest boutique hospitality property. 🏡

🔑 Key Takeaways

• Brand strategy comes before any marketing plan, content calendar or ad spend
• Your messaging should attract the right guest and repel the wrong one
• In a group stay, one person makes the booking decision, so speak to her directly
• Guests need many touchpoints before they book, so build a spider web, not a straight funnel
• Founder videos filmed on a phone can outperform polished professional content
• Your email list is the middle of the web, and it’s a channel you actually own
• Your past reviews already hold the words your ideal guests use

🏡 Two Plans Fell Through, and Rentals Took Their Place

Ali’s first rental started as a last effort to keep a house. Her husband was active duty military, and orders moved the family to a new duty station. They tried a year as long term landlords and didn’t love it. So they turned their first home, about half a mile from the Intracoastal Waterway in North Carolina, into a short term rental. The first booking came in over Thanksgiving 2019, just before COVID changed everything.

After the military, the family chose Kentucky and moved to 90 acres on the Bourbon Trail. Ali’s dream was a wedding venue. Zoning offices and neighbors pushed back, and even with the permit approved, the restrictions meant she couldn’t deliver the experience she wanted. So the property became a short term rental in 2022, and it still runs strong today.

In 2025 the family added Luna, a 30 year old geodesic concrete dome in the mountains of Virginia. 🌙 Ali is honest that none of it was easy. There were natural disasters, tough guests and two road washouts on check in days.

🌙 Every Property Needs a Story

Before Ali buys, she looks for a story she can tell. Luna came to her as “The Toasted Marshmallow,” and the name felt a little kitschy for where she wanted to go. She renamed it Luna as phase one of a planned micro resort. A mirror house called Sol would follow, giving guests the sun and the moon on one property and a reason to come back to collect every experience.

The road washouts mean that expansion is on hold at Luna. The idea itself is not. Ali learned that the more you share a vision out loud, the more opportunities find you. She recently submitted an LOI on an assisted living facility she hopes to turn into a boutique hotel in her hometown.

If you love the idea of a destination brand with many units, Steph Weber’s story of building a 12 cabin micro resort with 30 to 50% direct bookings is a great companion listen.

🧱 Vacation Rental Brand Strategy Comes Before Marketing

Ali admits this is the unsexy answer. Direct bookings used to feel optional. Since Airbnb’s host fee change, she says, they don’t anymore, and you can read more about that shift in our breakdown of Airbnb’s simplified pricing. Her advice is still to start with brand strategy, not tactics.

Here is what she means by brand strategy:

1. Core values. What do you stand for, and what do you want guests to feel when they walk through your front door?
2. Ideal guest. Who is coming through that door, and why? A five bedroom house and a studio attract very different people.
3. Differentiator. What makes your stay different from every other property with the same specs in your market?
4. Messaging and content pillars. What will you say on social, on your website and in your emails?

The goal is to attract the right guest and also repel the wrong one. Without this foundation, Ali says, content creation turns into frustration. We explore the same idea in why your values matter more than your amenities and the power of defining your perfect guest.

👩‍👧 Market to the Person Who Makes the Booking

Ali shared a Joshua Tree micro resort she worked with. It had three very different units: a studio, a party house with a pickleball court and outdoor movies, and a wellness house with saunas and cold plunges. The question was how to brand them as one.

Her answer was two layers. The primary avatar is a multigenerational family from Southern California celebrating a milestone. Grandparents retreat to the studio, parents enjoy the party house, and the youngest generation sings karaoke at midnight. 🎤

Then she went one level deeper and asked who actually books. Most likely it’s someone in the middle generation, probably a woman around 35. So the messaging spoke to her: all you have to do is say yes, and everyone can plan their own experience once they arrive. That message lifts the planning weight off her shoulders.

Terri-Leigh Huleis takes a similar approach in her episode on how guest avatars shape profitable rentals.

🕸️ Think Spider Web, Not Funnel

One of Ali’s favorite books, Oversubscribed, describes the 7/11/4 rule. Before someone buys, they spend seven hours with you across 11 touchpoints on four channels. That’s not a straight line.

So Ali asks clients to picture a spider web:

• The outer edge is awareness, where a guest first meets your brand
• The middle is nurture, usually your email list
• The center is the decision, which in hospitality is your direct booking site

The job is to speak to the same guest in many ways until they reach their next easy yes. Repurposing reels across Instagram, Facebook and TikTok can widen the web without tripling your workload. For projects raising capital, PR and podcast appearances help people find you when they search your name. Paul Anderson shares more on this in turning Instagram into a funnel.

🎥 Founders Belong on Camera

One of Ali’s clients runs a boutique hotel in Sevierville, Tennessee, with deep ties to the local community. The property already had beautiful professional photos and video. Ali compared those against simple phone videos of the owner telling the story behind each unit. The founder videos earned four times more engagement. 📱

Gil sees the same thing in his own content. In a feed full of AI generated posts, a real person telling a real story is hard to fake. Ali’s advice is short: founder, get in front of the camera and tell your story.

It takes patience, though. Content can feel like talking into a void for months. Gil shared that one client listened to 40 episodes of the podcast before reaching out. By the time the call happened, there was nothing left to sell. Amber Hurdle covers this well in building an authentic personal brand that converts.

📬 Own the Middle of the Web

Ali’s favorite middle channel is email. Social platforms are like OTAs: you don’t own them, and they can go down or change the rules. An email list is yours.

Gil adds that the emails that work aren’t about your properties at all. Skip the coupon blasts. Be the local guide instead: what to do, where to eat, what guests might miss. Ali points to Building a StoryBrand here. Position yourself as the guide and let the guest be the hero. Every so often, mention a project or a win so people remember what you offer.

Start with our complete guide to collecting guest emails and why your email list belongs on your direct booking website. Damian Sheridan’s story of a local bar guide that booked a 16 month stay shows what local content can do.

🗓️ Plan Content Around the Booking Window

Ali uses AI to pull booking window and seasonality data for each market, never for design. That tells her when to record what. For her Sevierville client, guests booking December stays are searching in September. So content about the area’s Christmas events has to be ready well before then. 🎄 Jamey King’s episode on strategic seasonal marketing pairs well with this.

⚡ Rapid Fire with Ali

📚 Book recommendations: Oversubscribed by Daniel Priestley, which she recommends to every business owner. Also Big Magic by Elizabeth Gilbert, which she read during her last Christmas break as a teacher and which pushed her toward entrepreneurship. Building a StoryBrand by Donald Miller came up too.

🧠 Mindset advice for starting something new: Create an alter ego. Ali learned this from a mindset coach in her mastermind. Instead of listing habits, picture the person you want to be and start acting like her. Hers is named “All In Ali.” You’ll want the full episode for how she uses it. 🃏

🎯 One tactical takeaway for today: Paste your existing reviews into AI. Ask what your guests have in common and which five phrases they use most. Then mirror those words in your website copy, emails and social posts. Gil notes that Aria, the AI inside CraftedStays, was built to do exactly this with reviews pulled from your PMS. Learn more about Aria, the AI website builder.

🤝 Connect with Ali Haney

🌐 Website: Brand & Market
📸 Instagram: @brandandmarket.co
👍 Facebook: Brand & Market
💼 LinkedIn: Ali Haney
🎙️ Podcast: The Brand & Market Podcast
📧 Email: ali@brandandmarket.co
🎁 Free resources: B Roll Content Checklist and STR Acquisition Checklist

🚀 Listen, Connect, and Start Booking Direct

This recap covers the highlights. The full conversation has more, including the analog micro resort Ali is helping launch and the printed morning brief she and Gil both swear by. 🎧 Listen to the full episode on Spotify, YouTube, or wherever you get your podcasts.

Once your brand strategy is clear, your website is where it comes to life. CraftedStays gives you a fast, mobile first, SEO ready direct booking site that syncs with your PMS and is built to convert the guests your brand attracts. Build your brand. Start booking direct. ✨

Transcription

Ali: I would absolutely encourage anyone starting out in this business to start with brand strategy. That’s a really unsexy thing to say, and it’s a really intangible thing to say, because people don’t know what I mean when I say brand strategy. What are your core values? What do you want people to feel when they come in through the front door of your property?

What type of guest is going to come in through that front door? It could be based on the specs of the house, right? A five bed, five bath house is a lot different than a studio apartment. So let’s look deeper at who that person is, why they’re coming to your place, and how we can make them feel really, really seen.

Gil: Before we bring on our guest, I want to talk a little bit about something I’ve been hearing a lot from hosts. I keep hearing the same thing: “I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it.” Here’s the thing. You’re learning all these marketing strategies, you’re driving traffic, and you’re putting it all to work, but if your site isn’t really built to convert, you’re basically lighting your energy and money on fire.

And even if you could afford an agency build, every time you want to test something or make a change, you have to pay them again. You can’t iterate, you can’t test, and you really can’t improve on things. You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform.

That’s why I built CraftedStays. It’s purpose built for short term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings, and you can keep testing and improving as you learn. You can make changes all on the platform. You don’t need to learn something new.

So if you need some help or you want to get started, go to craftedstays.co and start your free trial. Now, let’s bring on our guest and get into hospitality and marketing.

Hey, folks. Welcome back to the Booked Solid Show, the show where we bring in top operators to discuss hospitality, operations, and direct bookings.

On today’s show, I have Ali Haney. She’s the founder of Brand & Market, a brand and marketing agency built for hospitality, and she’s a host herself across multiple states. Ali never planned to get into the industry. Twice, a plan fell through, and short term rentals took its place. Today, we talk about the thing most hosts skip: brand strategy.

We cover how to find the guest who actually makes the booking decision, why marketing should feel more like a spider web than a funnel, and how your reviews can write your brand messaging for you. So without further ado, let’s bring her in.

Gil: Ali, welcome to the show.

Ali: Thank you for having me. I appreciate the opportunity.

Gil: It’s always good to have another podcaster on the show. I love the mic. I appreciate you showing off your mic there, and I’m sure our listeners like that intimate radio voice as well.

Ali: Thank you. I’ve been told I have a face for podcasting, so I’ll make the mic as good as I can. The audio can be great.

Gil: Well, Ali, to get us started, do you mind introducing yourself?

Ali: Of course. I’m Ali Haney. I’m the founder of Brand & Market, a branding and marketing agency for the hospitality industry. I also own and operate two short term rentals and cohost a third, in multiple different states, and I’ve been in the short term rental industry in some way, shape, or form since 2019.

I’ve gotten to see the peaks and the valleys during COVID, post COVID, all of the things. I’m also a podcast host, as you know, with the awesome mic I’ve got here. The Brand & Market Podcast has been on air for 115 episodes. And outside of work, because everybody has that personal life, I’m a wife and mother of three young children: eight, six, and four.

So I like to move and groove, I like big projects, and I like bringing other people’s dreams to life through branding and marketing.

Gil: I love that. We have overlap on the kids. I don’t know if yours are boys and girls, but I also have an eight year old girl and a six year old boy. I stopped there, so I don’t have a four year old.

Ali: Our eight year old’s a girl, our six year old’s a boy, and then the finale, as I like to call him, is also a boy. He’s the baby, and he will be the last.

Gil: My kids recently started asking us, “Are we going to get another sibling?” I’m like, “No, we’re not. You guys are enough.” But they’ve been asking. At this point the gap is so wide, and I know you can have wider gaps, but I’m not quite ready to hit that reset button again.

Ali: Maybe a pet would suffice.

Gil: We have plenty of those in the house too. My daughter does want some sort of small animal she can carry around in her hands, so we might.

Ali: I guess a guinea pig is in your future.

Gil: Yeah, a guinea pig, a hamster, something like that. My wife had one, so my daughter knows it’s possible for her. If mommy had one when she was a kid, she should have one too. That’s the story she’s telling us.

Ali: I think there should be some sort of project attached to it. Like, you have to bring me a presentation on why the guinea pig should become part of the family.

Gil: Well, the project right now is: take care of our dog first.

Ali: That’s good.

Gil: And she’s actually done quite well. She’ll pick up the droppings, and I’m like, “Okay, you’re showing that you care,” because that’s not something she’d want to do if she wasn’t motivated.

Ali: That’s good. That’s a good stepping stone.

Gil: Ali, talk to me a little bit about how you got into the properties you have right now. Was it intentional, or did it happen by accident? What’s the story behind that?

Ali: I like to say that I never got into short term rentals on purpose, but after the second one, I realized the universe was trying to tell me something. Back in 2019, my husband was active duty military. We got orders to go from one duty station to the next, and we had our first home that we bought together as a married couple.

We had it as a long term rental for one year. We ended up not loving the landlord life, so once those tenants moved out, we converted it into a short term rental, almost as a last ditch effort to keep the house. That house is what got our toes wet in the short term rental industry.

We were about half a mile from the Intracoastal Waterway in North Carolina. We did not know what we were sitting on at the time. That one did well for about two years, and we weathered COVID with it. Our first booking was Thanksgiving of 2019, so we got thrown into it almost immediately.

We had some hard fought lessons there, just because everybody was navigating COVID and had never done anything like it before. But that one performed very well. We ended up selling it in 2021 when we moved to Kentucky after my husband got out of the military. A lot of people ask, “Why in the world would you move to Kentucky?”

Well, it was the first time in our adult lives that we got to choose where we wanted to live, because the military had been telling us where to move for the last seven years. And my husband said, “I like bourbon and I like horses. Let’s go to Kentucky.”

Gil: There’s no better combo for those two.

Ali: So we moved to the Bourbon Trail on 90 acres.

Gil: Do you have a horse yourself, then?

Ali: We did not have any horses. That was in the 10 year plan that never came to life. His family in Virginia had a couple of horses over the years, but once we got down there, we never brought to life the project we had purchased that property for.

I told him, “If you get your dream of moving to Kentucky, I’m going to get my dream of owning a wedding venue.” So we moved there to start a new business. About two months into that journey, we ran into a lot of issues with local zoning offices and neighbors who didn’t want us bringing our business ideas to a very rural place.

Although we ended up getting the permit we needed to run weddings on the property, I knew the experience I wanted to deliver to the bride and groom wasn’t going to be possible with the restrictions placed on the permit.

So yet again, we transitioned an idea that didn’t work into a short term rental. That was the second time I thought, “Maybe I should stop refusing these signs from the universe that we need to be in the short term rental and hospitality world, and really embrace it.” We converted that property into a short term rental in 2022, and it’s been running strong for over four years now.

Once I got out of my own way, we acquired another short term rental last year, in 2025. It’s a cute little geodesic concrete dome in the mountains of Virginia. Her name is Luna, and she is adorable.

Gil: I love the imagery there. I’m sure we’ll get into that later. I’m guessing it was very intentional that you describe it that way.

Ali: Yes, absolutely. I’m happy to talk about the brand behind that property. But in case anybody out there is thinking, “She’s making it all sound so easy,” trust me, there were years and sets of guests and natural disasters all wrapped up into that story. It’s never the easiest path, but it certainly is a rewarding one.

Gil: Talk to me a little bit about Luna. I’m assuming that when you got that property, you started on Airbnb or the OTAs in general, and over time shifted toward going direct. What was that journey like for you?

Ali: Anytime we’re looking at purchasing a new property, I try to find some sort of story I know I can tell. Luna was actually a short term rental before we purchased her. I keep calling her “her.” We were lucky enough to live only about three hours from the property.

So instead of a traditional showing, I rented it, and we stayed overnight at the place, which was then called The Toasted Marshmallow. You can imagine: it’s a white geodesic dome. It’s concrete, about 1,600 square feet, two bed, one bath, with a loft.

It’s a big dome. I think when a lot of people think of a dome, they picture a nonpermanent structure. But this girl is about 30 years old, and she ain’t going nowhere. When we purchased it, I thought, “The Toasted Marshmallow just doesn’t feel right for this.”

It felt a little kitschy. We actually purchased the property to add more unique stays to it, so I wanted to build the brand around something that could evolve and grow into what was going to be a micro resort.

Luna was phase one. The next unit we planned to add was a mirror house. I’m not sure if you or your listeners are familiar with ÖÖD houses, but they’re the really cool reflective glass mirror homes. They’re basically a studio, anywhere from about 250 to maybe 400 or 450 square feet.

So guests could first come to Luna as a family, in the bigger dome, and the next time they returned, the mirror house could be a parents’ getaway. It would be a “collect every experience on this property” type of idea. The name of that mirror house was going to be Sol, S O L.

So we’d have the sun and the moon on the same property and be able to build that celestial, whimsical brand as we added units. Now, again, every single property we’ve ever owned has had some sort of challenge. Since we purchased that property in November, we’ve had two road washouts, both on days guests were supposed to check in. That’s not something we caught during due diligence.

So that’s another hard earned lesson in the real estate world. We don’t plan on expanding into more units at that property, because the infrastructure isn’t going to support it right now. But we do still want to pursue that unique stay micro resort vision as a whole.

Gil: That was going to be my follow up. You mentioned you’ve always had this vision of a wedding venue or a micro resort. While you were talking, I had the sense that this wasn’t the final one, and it’s not the one you’re going to be building on. So what does that look like next for you? Are you already looking at areas and spots you want to build on, or just starting that process?

Ali: I think the more you put the idea out into the world, the more the opportunities find you. That’s something I learned the hard way too. I’ve had a lot of hard lessons. I would always create these beautiful visions or brands in my own head, maybe in a conversation between me and my husband, but I never spoke them out loud publicly, for whatever limiting belief or mindset reason.

All that to say, if the right property presented itself, I would absolutely jump on it. We haven’t created a new buy box since Luna, because we still have capital wrapped up in that property. But other projects have come my way since then. We haven’t even talked about this offline yet, but I just submitted an LOI on Monday on a potential conversion of an assisted living facility into a boutique hotel in my hometown.

It would be our first step into commercial real estate, and something a little bigger for ourselves outside of single family short term rentals. So if it’s in the hospitality realm, I’m open to the idea. I love building a brand and a vision around an idea and bringing it to life.

Gil: I see a theme of multiple units. Rather than collecting different properties across a region, you’re looking to build a portfolio around one specific area and then create a brand for it. That’s the sense I’m getting.

Ali: Yes. You’re picking up what I’m putting down. Yes, sir.

Gil: Talk to me a little bit about the consultancy side, the business you run. What’s it like? Who are your ideal clients, and how do you serve them?

Ali: Absolutely. I love working with hospitality founders who are willing to be on camera, be visible, and be present in the marketing of their properties, assets, and projects. Especially those with a very unique stay or guest experience that’s easy to differentiate. For example, one of my clients is about to break ground on a micro resort focused entirely around the analog experience.

Basically, you check your phone in when you check in. Everything you’d normally use your phone for, whether that’s a map, music, a phone, a book, or reading material, is taken care of in an analog way when you arrive, so you have no reason to even touch your phone.

It’s sad how revolutionary that sounds, but to me that’s a really easily marketable guest experience we can put out into the world. Anytime someone comes to me with that kind of individualized, differentiated experience, it makes me excited.

Gil: Slight tangent. I work a lot with AI, and my mind feels like it’s all over the place because I’m juggling so many different things, so I’ve been looking for that analog experience myself. I saw something that piqued my interest, started playing around with my own Claude, and basically produced my own paper newspaper about my day. It prints out every single morning.

Ali: Me too.

Gil: It’s amazing. It prints automatically on my printer on a schedule. It reads my emails. It reads all my deals. It has follow ups on my team. It basically knows me very intimately, and I get this thorough report, because every morning I wake up and think…

Ali: Where do I start?

Gil: Exactly. It’s very easy to derail me. So I’m trying to get some distance from technology while still leveraging it in the most useful way.

Ali: Oh my gosh, we’re kindred spirits. I do the same thing. Mine tells me my number one revenue generating task, my two supporting tasks that will move the business forward even if they don’t generate revenue, any follow ups or deadlines coming up, and the content I need to record.

That’s literally what I have. I don’t have it set to print automatically. I don’t know how to do that, so I’ll have to ask you. But I print the report that gets sent to my email every day, because I need to write notes and highlight things, and I need something physical in my hands.

Even if it leads me back to the screen, like “follow up with this person,” it still gives me something tangible I can throw away at the end of the day, and it actually feels like my to do list got shorter.

Gil: I do feel a little bad from a sustainability standpoint, printing something every single day. That feels icky to me. Being a San Franciscan, it’s very against San Franciscan ways. But in terms of business impact, it feels well worth it.

Ali: My one way around that is printing two pages on one sheet.

Gil: I don’t have duplex printing on this machine, so I’d have to physically turn the paper over.

Ali: Oh, I shrink it down. It’s two pages on one side.

Gil: Okay. That’s helpful. Sorry, slight tangent, folks. Bringing it back: I’m guessing you use AI quite a bit?

Ali: We do use AI. Not for any of our actual brand designs, but I use a lot of AI to pull large sets of data and distill them into digestible pieces, especially when creating a marketing plan for someone. For example, the booking window for each market is slightly different.

So I’ll use AI to source that, so we can build a marketing plan around their high season, shoulder season, and off season. Then we decide what content to sprinkle in throughout each quarter of content creation, so we know what to record and when, based on the seasonality and booking window that market sees most often.

Gil: Got it. So, for instance, if your booking window is typically 90 days in the winter, someone booking for Christmas comes in closer to September. That means you have to create content possibly in August to prepare for publishing.

Ali: Correct. You mentioned you have properties in Gatlinburg. We have a client in Sevierville, right next to Dollywood, and Dollywood puts on a lot of events for Christmas. There are the lights and so many smaller events. We make sure we know that far in advance, so the people booking December in September are aware of those events.

Gil: I think that brings us to the meat of the show, and something I want to talk to you about. If you look at any traditional company and its marketing team, they typically have a marketing calendar. A lot of us on the hospitality side who don’t come from that world are starting to learn that these are things we have to do.

Most businesses that depend on marketing already do these things, and there are frameworks in place that help us understand this. On a rudimentary level, people have to learn what a funnel is and how to drive people to it. It’s not just putting something in front of guests and expecting them to book.

It takes work, and work in the right places, to make sure that lands. I think we’ve been spoiled as an industry, because it’s so easy to land that first property, put it on Airbnb, discount the first three stays, and we’re off to the races.

Before you know it, you’ve hit your revenue numbers, everything is good, and you keep riding that. So we’ve been conditioned in many ways to feed the OTAs. Now we’re at a point where there have been so many changes in how Airbnb shows up for guests and for us, and how bifurcated that may feel.

Property managers are now feeling, “I need to do direct bookings.” Sometimes it feels like, “I’ll just put up a website and start getting bookings.” But a lot more goes into generating the volume of bookings that gives you the same independence you feel when you rely on the OTAs.

So talk to me about some of the foundational pieces you feel need to happen before you start any of this.

Ali: I’ll start with this. Previously, there was some optionality around direct booking sites. Ever since October of last year, when they started switching over the service fee percentages for hosts, it’s felt a lot more like pressure. It’s not an option anymore, because that was such a drastic change, from 3% to 15.5%, that people are feeling it in their bank accounts.

So I agree with you. It felt optional two years ago. It doesn’t feel optional anymore. To answer your question directly about where I’d recommend anyone start: I’ve worked across many industries. I had a wedding photography business before this.

I’ve worked with online digital creators who sell courses, and now I’m in the hospitality industry. It doesn’t matter which industry it is. Having a business or marketing plan without brand strategy as the foundation takes away specific direction and messaging, so you’re essentially talking to everyone.

You don’t have an ideal client, you don’t have an ideal guest, and when that’s the case, you’re talking to everyone, and therefore you’re talking to no one. People get a lot of frustration wrapped up in content creation when they don’t have a specific guest avatar they’re talking to.

All that to say, I would absolutely encourage anyone starting out in this business to start with brand strategy. That’s a really unsexy thing to say, and a really intangible thing to say, because people don’t know what I mean by brand strategy. What I mean is: what are your core values?

What do you want people to feel when they come through the front door of your property? What type of guest is going to come through that front door? It could be based on the specs of the house. A five bed, five bath house is a lot different than a studio apartment. So let’s look deeper at who that person is, why they’re coming to your place, and how we can make them feel really, really seen.

Next up is your differentiator. What’s going to differentiate you from the other properties with the same specs in your market? How are we going to make that guest experience different from everyone else with a property in your market? And finally, your messaging and your content pillars.

The purpose of brand strategy is not only to attract the right guest, but also to repel the wrong one. So what are we going to say specifically in our social media content, website copy, and email newsletters that brings in and speaks directly to the guest you want coming through your front door, and pushes away the ones you don’t?

So that’s where I would start: brand strategy.

Gil: Let’s put that into practice. Walk me through a client you worked with: the before state, and how you went through some of these questions. Pick a client where, at the end, you felt, “Oh, this is really, really good,” so our audience can picture what the end state could look like.

Ali: Absolutely. I worked with a micro resort in Joshua Tree. When the owner came to me, I believe they had two units open and were opening a third. They were trying to decide whether to brand each unit individually or give the entire micro resort its own brand. We had to work out the guest experience for each unit.

One was a studio, one bed, one bath. One was, to use general terms, a party house. It had a pickleball court, a DJ stand, and an outdoor movie area. And the newest unit was meant to be a wellness house.

It had saunas, cold plunges, and an outdoor yoga area guests could use. So it was like segmented pieces of a puzzle we had to bring together into one. I said, “Let me put myself in the shoes of somebody renting this property as a whole,” because that’s what the owner said his end goal was.

And I said, “I see two different guest avatars. We’ll have a primary avatar and a secondary avatar. The primary avatar is multigenerational families coming from Southern California up to Joshua Tree, most likely for a large celebration or life event.”

I’m not necessarily talking about hosting a wedding, although maybe that’s the case. I’m thinking more about milestone birthdays or an engagement party. The kind of moment where you want to pause, celebrate, and be with your people: the grandparents, the parents, the grandkids.

This property specifically allows the matriarch and patriarch, the ones who probably aren’t the booking guests but who call the shots behind the scenes, to have their own studio to retreat to, while the parents enjoy the party house.

Or maybe the parents are in the wellness house, and the youngest generation is out singing karaoke at midnight. You know what I mean? So that would be the primary guest avatar we market to directly. But then I break that primary avatar down into something even more granular: who’s going to be the booking guest?

We know who’s going to come and enjoy the experience, but who’s leading the booking decision? Probably the middle generation, probably female, probably around 35 years old. So how do we appeal to that person in our messaging? Because she’s the one choosing the property.

That’s how I break it down in a real life scenario.

Gil: So what was the end state? What was the positioning statement, and how did you present it at the end?

Ali: I’m sorry, I’m not sure I understand your question.

Gil: Given that your ideal booking avatar was a woman of about 35 in the group, what was the end messaging to that guest?

Ali: Oh, okay, I understand now. The end messaging was: all you have to do is make the decision to say yes, and everybody else can plan their own experience once they get here. The weight of the booking decision was on her shoulders, but once you actually get to the property, each grandkid and each person in each generation can do their own thing.

That took the pressure off the person making all the planning decisions before the trip, so she didn’t have to suffer decision fatigue once they arrived.

Gil: That’s very interesting, and it makes a lot of sense in this scenario. Usually, when you’re planning a trip in a house with a multigenerational group, it’s the mom stuck in the middle, appeasing the top and the bottom. She has to keep the grandparents and the kids happy and make sure everything is situated.

But you took a slightly different angle: you don’t have to be the one who organizes everything. I can also see the spinoff as resources she could hand off to other people in the family, or landing pages and parts of the website that help each person know where to go to plan their own experiences.

Ali: Yeah, we would have that live within the blog for sure.

Gil: That’s interesting. We touched a little on the funnel and why it’s important. We talked about one of the most fundamental things before you start any type of marketing: understanding who your ideal guest is, who you want to attract, how you message them, what words you use, and how you use that across all your channels.

Then there are the different activities you do. As we mentioned, those activities aren’t random. There’s a logical flow you want to focus on, thinking about the entire user journey, where someone may discover you on multiple channels, get more familiar with you, and start to build trust.

Walk me through how you think about that overall funnel and how you guide your clients through it.

Ali: One of my favorite books is called Oversubscribed. It’s a business book, but mostly focused on marketing. There was a statistic in that book that blew my mind. It’s called the 7/11/4 rule. Essentially, before someone makes any type of purchasing decision, regardless of industry, they have to spend seven hours with you across 11 different touchpoints on four different channels.

How overwhelming does that sound?

Gil: Sounds like a lot.

Ali: Sounds like a lot. The transition I see in consumer psychology today is this. Anyone familiar with marketing has heard of the funnel: top of funnel, middle of funnel, bottom of funnel. It’s a very linear path, and I think consumer psychology is changing, because people are no longer taking a linear path.

Think about the 7/11/4 rule, where people have to be touched 11 times on four different channels. There’s no way that’s a single straight line from, “I found out about this company for the first time,” to, “Now I’m ready to book a stay with them directly 10 days later.”

So I encourage all my clients to think of their marketing as a spider web. We want that spider web to be sticky. To go along with the funnel analogy, imagine the outer edge of the spider web as your old top of funnel. That’s where people start to become aware of your brand.

That’s the first time they enter the brand’s ecosystem. The middle of the spider web is the middle of the funnel, where you can nurture them on a more permanent basis, like an email newsletter list. And the very center of the spider web, the old bottom of funnel, is where they actually make a purchasing decision. In hospitality, that’s your direct booking site.

So I want people to think, “How can I talk to this same guest avatar in multiple ways with multiple messages, so they can make their way around the outside of the spider web and get touched, let’s say, seven times before they finally take the next yes, which is signing up for the email newsletter list?”

Then we touch them, let’s say, three more times. Now we’re up to 10, and we finally get them to our website, where they can make the booking decision. That’s the 11th touchpoint.

Gil: To put that into practice, talk to me about one of the clients you’re working with right now and the channels they’re using. It sounds like it’s not simply Instagram, a pop up form, and a website. There are other things in play as well.

Ali: It depends on each individual property and each founder. But there are easy ways to repurpose content these days, between Meta, Instagram, and Facebook, and even TikTok, using the reels you created on Instagram over on TikTok as well.

So there are ways to expand across channels without doubling or tripling the work. Then there are other clients in the capital raise phase of a ground up micro resort development. In that case, we explore other channels like traditional PR, getting them a local spot on television.

I don’t specialize in PR, but I can create the strategy to figure out which angles to pitch, as well as podcast appearances like this one. It’s about creating an online ecosystem where, when someone Googles your name or your project’s name, the first page of Google points back to you.

It helps people trust you a little more and become more familiar with you.

Gil: Talk to me a bit about founder led content. We touched on it before the show. For folks trying to grow their direct bookings, what is founder led content, and why have you seen it be so effective?

Ali: One client in particular is my Sevierville client I mentioned, near Dollywood. Their brand story is absolutely incredible. They have a boutique hotel in downtown Sevierville with a lot of ties to the local community, to Dolly, and to the University of Tennessee, and all of that comes to life beautifully in the interior design of the building.

But the interior design in and of itself, to me, doesn’t sell the building. That’s evident because she has the most beautiful professional videography and photography for her listings. We did a case study on that client to see how the professional photos and videos of the space performed versus a regular iPhone video of her talking about the story and inspiration behind the individual units. The founder videos, filmed on an iPhone on a random tripod or propped against a coffee mug, got four times more engagement than any of the professional photo and video content we put out.

Gil: Wow. And we’ve been seeing this…

Ali: Founder, get in front of the camera, please. Tell your story.

Gil: We’re seeing this more and more, not just in your example but across the board. It’s quite humbling to see founders putting themselves out there, especially in an age when so much content is easily generated with AI, and people can see and smell that right away.

When you get in front of the camera, it’s really hard to fake that, and to fake it consistently. Just showing up and putting your iPhone out there. I’ve dedicated more of my own time to it, because the feedback from my team is that when I put myself on camera, even when it feels cringey at first, that’s the content people value and relate to more.

It resonates a lot more than generating carousels, using photos, or talking about a feature. When we talk about the story behind something and why we’re investing in it, it creates an intimacy with the audience. I think that’s probably why you’re seeing that 4x engagement.

You’re creating a space where the founder has a connection with the outside world. No one really connects with photography. People can see it as beautiful, something to aspire to, but it’s different from relating to the founder, the story of why they built it, and the experience they’re trying to create for guests.

Those are the things I feel we’re almost begging for more of on social media, rather than the pretty stuff.

Ali: I see it in my content as well. I’ve forced myself this last quarter to be the person on camera doing the talking head reels and all of those things. I was at a conference in March, I believe, before I started doing that. I introduced myself to someone, and they looked at me a little sideways, like, “I recognize you from somewhere, but I don’t know where.”

Then I said, “I’m the host of The Brand & Market Podcast,” and they said, “I knew I knew your voice.” Now it’s gone to the next level, where people don’t have to cock their heads and figure out where they know me, because they see my face every single day.

I think that says something too. Especially if you’re a founder who’s on property here and there, we’ve had feedback from that client’s guests like, “Oh, I’ve seen Alexis. She’s the owner. That’s so cool.” Connecting the online pieces to the real life experience is such a cool connection.

Gil: I know a property manager with a pretty sizable portfolio, over 100 doors, and he’s gotten into producing content. All he talks about is the market: what he’s seeing, what the booking windows are, whether things are up or down, and anything local happening in the area.

When you look at why he’s creating that content, it’s really to build trust with homeowners. He’s establishing himself as an authority, someone very knowledgeable in the space, so an owner thinks, “I have a home. I can’t do everything he does. For my one or two properties, it may not be worth it.”

So he’s creating that relatability, where if you’re looking to hand off your home to be run as a short term rental, the trust is already there.

Ali: One of the challenges is that you put out all this content, right? That gentleman probably put out content for months before he got any feedback. It feels like you’re talking into a void, into some echo chamber.

Nobody seems to be hearing your message. But that goes back to the 7/11/4 rule. Somebody has to see 11 pieces of content from him before they’re ready to move forward. So it’s an investment in your marketing strategy for the next three months, six months, a year.

You’re accruing social credibility and social trust, so when people are ready to make that decision, which might be in three months or in six, it’s easy. For a property manager, once you get them on a discovery call, you’re not selling them anymore.

You’re just telling them the next steps, and I can tell you, that feels really good.

Gil: It’s kind of odd, but once you pour energy into this, people will come to you as if they know you. When you talk to them for the first time, they know you very well, and you’re just discovering them. We had a client with a sizable portfolio who listened to 40 episodes of our podcast and then reached out and said, “Hey, we want to hire you to help us build our website.”

Ali: Forty episodes. How many hours is that?

Gil: Oh my God. Each episode is about 45 minutes on average. He invested a ton, because he got a lot of value out of it. I think Alex Hormozi talks about this in one of his books, $100M Leads.

He talks about giving value, value, value, and almost never asking for the sale. If you constantly give value, folks will come to you when they eventually need help. I think the same applies in hospitality. Way too often, when people finally get someone on their email nurture list, they spam them with coupons.

They talk about their stays, their properties, and why their properties are the best. That content does not perform well. The content I find performs best comes from people who’ve done the homework to know who they’re trying to get on that email list, so it resonates when it lands.

And they’re not talking about themselves. They’re not talking about their stays or their hospitality. They’re talking about the great things to do in the area, really creating the imagery of what it’s like to be in their space and their environment.

Not necessarily their property, but the market, the things to do, the places you might have missed. The more personal you can make it feel, the better. Like you mentioned, you’ll alienate some folks. If someone got on the list the wrong way, they’ll stumble on it and unsubscribe, and that’s okay.

Ali: It helps your open rates.

Gil: Exactly. And the folks who stay subscribed and resonate with it, you’ll see phenomenal results with. Those are the ones who convert at a higher rate.

Ali: Have you ever read Building a StoryBrand?

Gil: Is that the Donald Miller one?

Ali: Yes.

Gil: I think he has two versions now, right?

Ali: He does. I don’t know that I’ve read the second version. I read the original a long time ago. Essentially, you position yourself as the guide and let the guest or client be the hero.

Like you said, you’re not talking about yourself or all the places you have to stay. You’re literally the tour guide around the market. Then, once they’re ready to make a booking decision, the first thing at the top of their mind will be, “Oh, that guy who sends me those emails from Sevierville.”

Gil: And you have to be subtle about letting people know you do things outside of this. That’s why every so often you drop a CTA, like, “If you need help, feel free to reach out.” I do see that if you go too far to the other end of the spectrum, you become an educator no one knows the services of, and that doesn’t help you either.

So yes, build that trust, but every so often drop a little about the projects you’re working on and the wins you have for your clients. Just don’t make it about yourself.

Ali: Very true. Agreed.

Gil: Ali, any other advice for folks trying to figure out the foundations they need to invest in?

Ali: I’d say double down on brand strategy. I know that was my suggestion earlier, but a lot of times people say they’re going to do it, then they never do, and they feel like they’re spinning their wheels without real progress toward their direct booking ratio.

So do the intangible stuff, the stuff that feels kind of boring. I can assure you that once you build that foundation, it’ll be much easier to build the house you get to make pretty later.

Gil: I’d double down on that, and also add: really figure out what your middle of funnel looks like. I feel the middle of the funnel is very underused. Folks who do well on social media pour their energy into it and watch their follower counts grow slowly over time.

They’ve got a well oiled website, yet they’re constantly losing people, because to your point, it takes 11 touchpoints for someone to book with you or act. If you don’t bring them back, you’ll easily lose them. So find some way to nurture that middle of the funnel.

Ali: My best suggestion there is to use your email list. Much like the dynamic between OTAs and a direct booking site: you don’t own the OTAs. You’re at the mercy of whatever fee or service change they want to make, whereas you own your direct booking site.

The same dynamic exists between Meta or Instagram and an email marketing list. We’ve seen TikTok go down. We’ve seen Meta go down. You don’t own those platforms. Accruing followers there is great brand awareness, but we need to give them an easy next yes to step into the middle of the funnel, so that we, A, own it, and B, can keep nurturing them outside of that one platform.

Gil: That’s a good point. In many ways, Instagram, TikTok, and the other social platforms use some sort of algorithm to put you in front of an audience, so you’re still at the mercy of another platform deciding who you get in front of.

And you’re right about email. I’m surprised it hasn’t shifted, but to this day, it’s the one direct way to reach someone. People are also starting to experiment with phone numbers and SMS. Be careful with that. Don’t spam folks. Those are the two most personal ways to keep in touch with someone.

When you do get someone’s contact information, be respectful, make sure they actually want to see you in their inbox or on their phone, and don’t spam them. Because if you do…

Ali: 100%.

Gil: …you’re going to lose them for good. Even if they’re a great guest, even if they’re your ideal guest, if you don’t message them properly, it’s going to go south.

Ali: Absolutely. I agree with you on that.

Gil: Ali, we usually end the show with three questions. You’ve mentioned a few books, so you may repeat one, but what’s a book that has inspired you or your career?

Ali: Inspired me or my career. Well, Oversubscribed, I’ll recommend that, period. It’s a great business and marketing book for any business owner. But for my career, I read this one while I was still teaching. I was a high school English teacher before I jumped into entrepreneurship, and over Christmas break of my last year teaching, I read Big Magic. It’s all about creativity and ideas, how ideas form, and how to embrace creativity.

That book inspired my entrepreneurial journey.

Gil: I like that. I haven’t come across that book, so I’ll have to check it out.

Ali: It’s a little different. It’s a little more feminine and woo woo, but it’s a good one.

Gil: Would I still like it?

Ali: I think so. One of the main examples I remember from it is how big ideas can hit multiple people at once, and how society shapes the way we think and our creativity. As a creator in general, I think you’d enjoy it.

Gil: I like that. For me, and I don’t know if the book touches on this, the biggest source of creativity is play and experimenting with things. I experiment a lot, and my team probably doesn’t love it, because I’m always playing with different things.

These little side projects, you don’t know where they’ll go, and they’re not meant to be the thing you sell or produce. But they let you try something new and see how the pieces connect, and sometimes they click in different ways later. It may not be on this specific project or in this role, but eventually it turns into something.

Ali: I love that you give yourself the freedom to do that, because a lot of us entrepreneurs put ourselves in a productivity or die mindset. Sometimes things aren’t meant to be productive, and that’s where the ideas come from.

Gil: I think that’s even more important today. With the rise of AI over the last year and a half, we feel like we always have to work and always have to be doing something. We’re in this mass execution mode where we always have to be on.

If you give yourself the freedom to play, it relieves some of that stress. You can play in your own space, in your work, without feeling like you need to hit some end goal. Go experiment and release some stress, whatever that looks like for you.

Ali: I wish it were as easy done as it is said.

Gil: I feel like if I don’t play and experiment, I become a miserable person. I have to force myself to do other things.

Ali: Yeah.

Gil: Ali, next question. What’s one piece of mindset advice you’d give someone starting something completely new?

Ali: I’ve recently done a lot of mindset work. I used to think it was very woo woo and kind of dismissed it. I thought, “If I put the work in, it’ll come to fruition.” But as I’ve told you multiple times today, I’ve learned a lot of lessons the hard way.

After banging my head against the wall for years, I realized the problem might be inside my own head. I was the common denominator, not all the different problems happening around me. And I realized the mindset work is just as important as the hard work.

One recent lesson came from a group I’m in called Action Academy. They have a mindset coach in the mastermind, and he gave an example of a client who basically created an alter ego for himself. Before his mindset shift, the client worked all the time.

He missed his kids’ ball games and wasn’t taking care of his health, and that’s not who he wanted to be anymore. So he created an alter ego of what his ideal life looked like: the habits that person has and the decisions that person makes.

I’d heard advice before like, “Do the things your future self would do.” But for whatever reason, the idea of an alter ego to model yourself after really clicked for me. Instead of just listing the habits of the person you want to be, create that other person.

Create who you want to be in a world without all the outside input about who you should be, and then start being that person. Start embodying that alter ego. That’s the mindset shift I’d give anybody in the entrepreneurial world.

Gil: Nice. Did you come across that yourself? Did you read something that led you down this alter ego path, or was it Action Academy?

Ali: It was the presentation from the mindset coach. His name is Joe Moffitt. He used his client as a case study, with permission of course: here’s what he was doing, and here’s his reality today. I had a lot of confidence issues and imposter syndrome, which I think a lot of us struggle with regularly.

So I asked, what if I didn’t have that? What would that woman look like? What would she do? How would she make decisions? And I literally gave her a name: All In Ali. All In Ali goes all in on herself. She’s confident. She pushes all her chips to the middle of the table when she’s making a big decision, and she takes the bet on herself every day.

That was a huge mindset shift for me.

Gil: I’m thinking about the email summary you get every morning. There could be an All In Ali version of it. If you’re using Claude or whatever produces it, you could give it that persona to help you get your head into the right space. I can see some overlap.

Awesome. Ali, the last question. We talked about a lot of tactics and fundamentals. I want to make sure this episode is tangible for our audience. What’s something they can put into practice this afternoon?

Ali: A great first step: if you have an existing listing with reviews, whether on your direct booking site or an OTA, copy and paste all those reviews into AI and ask, “What are the characteristics of the people already visiting my place? Give me the top five phrases they use over and over again.”

That way you can start figuring out who your ideal guest is, and what your brand messaging should be, by mirroring the phrases and terms people who’ve already stayed and loved it actually use. Then you can work those ideas, frameworks, and words into your social media content, email marketing, website copy, or anywhere else you write for your ideal guest.

Gil: That’s so helpful. We’ve even trained Aria, our AI persona in CraftedStays, to do exactly that, for the reason you mentioned. We pull the reviews from the PMS and analyze them. We look at who’s staying there, what they’re saying, and the words they use.

Ali: Where they’re coming from.

Gil: Yes. You learn so much from your past guests.

Ali: Right. People think they have to start from scratch, and that’s certainly not the case if you’ve been hosting for any amount of time.

Gil: Ali, it’s been a huge pleasure having you on the show and getting deep into brand marketing, brand strategy, and the fundamentals. If folks want to get in touch or learn more about you, where can they find you?

Ali: I practice what I preach, so it’s consistent across every platform. Anywhere you want to find me, it’s brandandmarket.co. My email is ali, A L I, @brandandmarket.co. Website, Instagram, everywhere.

Gil: Awesome, all the channels.

Ali: Yeah.

Gil: Ali, again, it’s been a huge pleasure. I’m sure I’ll see you around, and it’s been great getting to know you.

Ali: Thank you again for the opportunity. I really appreciate it.

Gil: Thank you. Bye.

Ali: Bye.