“You can have a perfect property, listed perfectly, with perfect reviews — but if it’s not priced right, people just won’t book it.” — Tim Hubbard
What does it actually look like to run a short-term rental business from thousands of miles away, across 40+ cities, in multiple countries — and still deliver a five-star guest experience consistently?
That’s not a hypothetical. That’s what Tim Hubbard has built.
In this episode of the Booked Solid Show, Gil sits down with Tim, founder and CEO of Corzly, a remote-first hospitality company managing 220+ properties across dozens of markets. Tim is also the host of the Short Term Rental Riches podcast, and he brings more than 11 years of STR experience to this conversation — from his first light-bulb moment comparing Airbnb rental returns to traditional long-term properties, to building a white-label operations model that gives owners back their brand without sacrificing operational control.
You’ll hear Tim’s perspective on why the property management model is changing, how AI is reshaping guest communications, what every host needs to have in place before chasing direct bookings, and the one tactic he recommends for anyone looking to grow their direct booking rate starting today.
If you’re a host trying to scale without losing the personal connection to your property — or a property manager rethinking how your operations are structured — this one is for you.
Summary and Highlights
👤 About Tim Hubbard
Tim Hubbard is a real estate investor, entrepreneur, and educator who has been operating in the short-term rental space for over 11 years. Originally from California, Tim now lives in Southern Brazil and runs Corzly — a remote-first hospitality company that serves as the core operating center for STR partners across 40+ cities and multiple countries. To date, Corzly has managed 220+ properties and hosted more than 50,000 guests.
Tim is also the host of the Short Term Rental Riches podcast, where he shares quick, actionable solo episodes drawn from his portfolio and the property owners he works with daily. His focus is helping STR operators optimize operations, protect their listing performance, and increase revenue — all without giving up control of their brand.
🔗 Website: www.corzly.com 🎙️ Podcast: www.strriches.com 📘 Facebook: facebook.com/corzly 💼 LinkedIn: linkedin.com/in/tim-hubbard-str
🔑 Key Takeaways From This Episode
Managing 220+ properties remotely isn’t luck — it’s infrastructure. Here are the ideas that stood out most from Tim’s conversation with Gil.
🏗️ The White-Label Model: Operations Without Ownership
Most property management companies take over your listing and your brand along with it. If things go sideways — poor reviews, inconsistent service — those marks stay with your property permanently. And if you ever want out, you’re often starting from scratch.
Corzly works differently. Every listing stays under the partner’s name. Payments flow to the owner. The brand remains theirs. Corzly simply steps in and pulls all the operational levers — guest communications, revenue management, housekeeping coordination, review management — while the owner retains full control of their marketing and their asset.
For hosts who still feel deeply connected to their property but genuinely don’t have the bandwidth to manage it themselves, this model addresses a real tension in the market. As Gil noted, many homeowners who built their sites through CraftedStays are exactly this kind of operator — invested in their brand, proud of their property, but needing the right operational partner to make it sustainable.
This matters especially because listing performance is tied directly to reviews, and reviews are tied directly to who’s managing the guest experience. A traditional PMC can quietly damage your listing’s ranking with no real accountability. A white-label model keeps that risk on the right side of the table.
🤖 How AI Is Actually Being Used at Scale
Tim and his team use AI for guest communications — and the results aren’t just about speed. It’s about consistency.
When multiple team members handle guest messages across different shifts, tone and phrasing naturally drift. That drift is a human thing — not a failure. But for guests expecting a seamless experience, even small inconsistencies can erode trust. AI solves this by maintaining one unified voice throughout every touchpoint of the guest journey.
Corzly currently uses Conduit as their AI infrastructure and has built custom layers on top of it. One example: if a guest mentions a loose door handle in a message, that feedback is automatically pushed into Breezeway as a maintenance task. No manual handoff. No missed follow-up.
This connects to something Gil regularly talks about when it comes to building a direct booking strategy that scales — the systems that remove human error from high-volume operations are the same systems that protect your reviews, your ranking, and ultimately your revenue.
What AI doesn’t do well yet, Tim notes, is handle complex operational workflows with multiple decision layers — like early check-in requests, which require confirming housekeeping availability, owner approval, timing parameters, and payment collection. The promise of “AI handles everything” is still a long way from that level of nuance.
💰 Revenue Management: The Piece Most Hosts Underestimate
Tim is direct about this: even a beautifully staged, perfectly photographed, and consistently well-reviewed property will underperform if it isn’t priced right.
Corzly puts significant effort into revenue management — not just setting rates, but knowing when to offer promotions, which channels to mark up, when to apply discounts for direct bookings, and how to compare performance against the broader market. Tools like PriceLabs play a role, but the strategy behind them is just as important as the tool itself.
For hosts just getting started with direct bookings, pricing is often the last thing they optimize — and that’s backwards. You can drive traffic to a beautifully designed website, but if your pricing isn’t competitive in context, you’re still leaving bookings on the table.
📸 The Fundamentals That Actually Move the Needle
Before any advanced strategy comes into play, Tim always makes sure a few core things are in place for every property Corzly takes on:
Photos first. Professional, high-quality photography isn’t optional. It’s the first impression on every channel.
Maximum distribution early. Corzly lists every property on all primary booking channels — Airbnb, Booking.com, Google — specifically to build momentum and pull guests into a direct relationship over time. The goal from day one is to convert OTA guests into direct bookers later.
In-property touchpoints. QR codes on the fridge, branded magnets, digital guidebooks — all with a direct booking link. Every guest who stays through an OTA should leave knowing they can book directly next time.
Email capture from every touchpoint. This is one Tim feels strongly about. Whether it’s through a rental agreement, a WiFi login tool like Safely, or Charge Automation, Corzly actively builds a guest contact list for every partner. And if the property sleeps twelve people, they’re capturing all twelve emails — not just the lead booker’s.
This last point connects directly to why email collection is one of the highest-leverage activities any STR host can invest time in. A list of people who’ve already stayed with you is the warmest audience you’ll ever have.
🔧 Building Your Own Tech Stack — Carefully
One of the more candid parts of this conversation was Tim’s reflection on building vs. buying. Corzly has built several internal tools — including Smoothly, their housekeeping coordination layer — but Tim has also spent months on builds that didn’t pan out, including a trust accounting system that was eventually scrapped in favor of an invoice-only model.
His takeaway is something Gil echoes from his own experience building CraftedStays: build only where the gap genuinely exists and where no one else is solving the problem well. The rest should be left to tools that have been working on it for years.
Today, Corzly uses their PMS primarily as a channel manager — nothing more. Everything else they’ve either built or sourced from best-of-breed tools. That’s a meaningful departure from how most operators approach their tech stack, and it reflects how quickly the SaaS moats that once seemed permanent are being challenged.
🧱 Protecting Your Listing Performance
Tim’s model is built in part around a hard truth: if you give your listing over to a traditional property manager and they mishandle it, the review damage follows your property — not them.
Maintaining ownership of the Airbnb account, the guest contacts, and the brand means that if you ever need to switch partners or take back control, you can. That portability has real value, especially in a market where review scores directly impact visibility and booking rates.
This is worth thinking about for hosts who use CraftedStays to run their direct booking website alongside their OTA presence — the same principle applies. Your brand, your guest relationships, and your data should always stay with you.
⚡ Rapid-Fire Highlights
📚 Book Recommendation: Rich Dad, Poor Dad by Robert Kiyosaki. Tim credits it as the mindset shift that redirected his entire career from traditional long-term rentals to short-term rentals and real estate investing. He calls it simple, but genuinely life-changing.
He also referenced The Slight Edge by Jeff Olson — a book about the compounding impact of small, consistent actions. Tim’s framing: the difference between hosts who succeed and those who don’t is often just continuing to do the work, even when results feel far off.
🧠 Mindset Advice: “Don’t overlook the small things you’re doing every day. They add up to really big results.” Tim’s advice for anyone starting something new is to trust the process, stay consistent, and not expect overnight results. The slight edge compounds in your favor — or against you.
🎯 One Tactical Tip: Collect every guest’s contact information — from every single stay. If your property sleeps 12 people, work to capture all 12 emails. A guest list of people who’ve already experienced your property is one of the most valuable assets you can build. From there, email marketing becomes your most reliable direct booking engine.
🤝 Connect With Tim Hubbard
🌐 Corzly: www.corzly.com 🎙️ Short Term Rental Riches Podcast: www.strriches.com 📘 Facebook: facebook.com/corzly 💼 LinkedIn: linkedin.com/in/tim-hubbard-str
🚀 Ready to Build Your Direct Booking Brand?
Tim’s story is proof that you don’t have to choose between operational efficiency and brand ownership. The best operators do both — and they build the right infrastructure to make it sustainable.
If you’re ready to stop sending traffic to platforms that don’t work for you and start building a direct booking site that actually converts, CraftedStays was built for exactly this. Purpose-built for short-term rentals, mobile-first, and designed to grow with you.
👉 Start your free trial at craftedstays.co — no agency required, and no technical skills needed.
And if you’re not already following the Booked Solid Show, subscribe on Spotify and YouTube so you never miss a conversation like this one.
Transcription
Gil: Before we bring on our guest, I want to talk just a little bit about something that 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’re having 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, keep testing and improving as you learn, and make changes all on the platform — no need to learn something new.
If you need some help or want to get started, go to craftedstays.co and start your free trial. Now let’s bring on our guest.
Gil: 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 Tim Hubbard on the line. He’s the founder of Corzly — think of it as the white-label property management company. He helps hosts offload their entire operations while maintaining control over their marketing. On today’s show, we talk about how he approaches operations, how he leverages the best technologies in the industry, and how he’s relying less on them as he builds his own tech stack. We also talk about some of the fundamentals he advises homeowners on when they want to build their own direct booking engine. Without further ado, let’s bring Tim on board.
Tim, welcome to the show.
Tim: Great to be here. Thanks for having me.
Gil: I love having another podcaster on — I always appreciate someone with a great mic on the other side. And I don’t know how you feel, but I actually end up loving being on the other side of the mic, where you get to be the guest rather than the host. Just from an enjoyability standpoint — what’s your experience been like?
Tim: I agree. It is refreshing. You don’t have to plan too much out. You just…
Gil: You don’t have to plan anything, do you? You’re just there.
Tim: Exactly. Much easier to be on the interviewee side.
Gil: When you’re the host, you’re constantly thinking about the next set of questions. I’m furiously taking notes as we talk so I don’t forget something — we may go deep on a topic and I don’t want to interrupt, but I want to get back to what we discussed three minutes ago, and my memory’s not that sharp.
Tim: That’s totally right. Yeah.
Gil: So Tim, do you mind giving folks an introduction — who you are, a little about your show, and everything you do?
Tim: Sure. I’m Tim Hubbard. I started in the short-term rental industry about 11 years ago, after quite a bit of time in traditional long-term rentals. I found short-term rentals through my travels — I was traveling a lot and always enjoyed staying in them.
One day I was in a state outside California, looking at long-term rentals to buy, and I had rented an Airbnb. I started running the numbers on the property I was staying in versus the long-term rentals I was considering, and the light bulb went off. I thought, “Why am I buying these long-term rentals?” So I just started focusing on short-term rentals and haven’t really looked back.
I expanded quite a bit outside of California — went to Tennessee, Oklahoma, and eventually outside the US. I started vacationing a lot in South America, which I really liked, and eventually made that permanent. I’ve been living in Brazil for the last eight or nine years. Along the way, I’ve been expanding my portfolio and my team.
I started a podcast called Short Term Rental Riches about six years ago — just talking about my portfolio and how I was managing it. They’re quick, actionable episodes, and a lot of people reached out asking, “Can you help with my property?” or “Can you help with my portfolio?” We had extra capacity to manage more properties, so we started doing that. That led into Corzly, which is the business I run today. The whole idea is that we become the core operating center behind all of our partners’ short-term rentals. We pull the levers, press all the buttons to get the most visibility, price things right, handle the guests — and that’s where we’re at today.
Gil: Would you consider yourself a property management company, or is it slightly different? Because a lot of what you talked about — managing someone’s operations, revenue management — that sounds like a PMC, but I think you look at it a little differently. Is that right?
Tim: Yeah. When we first started, we were more like a property management company than we are today. We’re every day becoming more and more a technology company, because a lot of the operations on the back end are essentially the same no matter what type of property you have or where it’s located.
We’re currently in dozens of markets and multiple countries, and the reality is: you have to set really good expectations, market your property well, deliver a good guest experience, and make sure your property is clean and maintained. Those core functions exist with any type of property.
So we’re on a mission to automate as much of that as we possibly can — and to do it in a way that’s financially viable. A small property manager often doesn’t make sense to hire a big team, especially if they’re seasonal and people are just sitting around in the off-season. Our goal is to make it as cost-effective as possible, so people can use us while the brand and everything stays underneath them — and we help them have consistent, solid operations.
Gil: What does that mean from a day-to-day perspective? If I’m a homeowner or have a small portfolio and you’re managing it — what does my day look like versus what does your day look like?
Tim: Most of our interaction with partners is really just in the very beginning. We get all the information from the property — we have some great ways to do that now, including pulling your entire Airbnb history and analyzing everything. Then we need an on-the-ground contact, so we need someone for housekeeping and maintenance.
With all that initial onboarding out of the way, we handle all the guest questions. The only time we’re really interacting with our partner is if a question comes up that we don’t have the answer to yet. When that happens, we save the answer so we don’t have to ask again.
Another area where they’d be involved is a major maintenance item. We don’t handle the expense side of our partners’ properties — we’re not paying housekeeping, maintenance expenses, or utilities. That’s a difference from a traditional property manager, so that’s where we’d ask them to jump in.
We use Slack on the back end to communicate with all our partners. We have a private channel for every property, with everyone on our team plus the partner in it, so they can reach out to us 24/7 — there’s always someone there.
Gil: It’s a very interesting model. One of the key differences is that you get to keep your brand. A lot of times when a PMC takes over your property, you lose that ability. The brand gets engulfed into their company and you’re like, “I don’t have a direct booking website anymore. I’m completely disconnected.” But I’m hearing something slightly different here — the homeowner still owns the asset and still owns the brand. There’s still that connectiveness where they can still drive their own bookings if they want to.
Tim: Exactly. And it’s actually a big difference. There are a lot of great property management companies out there, but there are also a lot of bad ones. If you give your listing to a PMC and they start getting poor reviews, those stick with your property forever. And if they own your listing, your only way out is to basically start over.
You can see that pretty clearly with some of the national property managers that grew really quickly — they don’t have great reviews, and a lot of them are trending down. We know the lower your reviews, the lower your visibility, which means lower revenue. It has a significant impact.
So yes — everything stays under our partners’ names. Their brand stays with them. Someone could walk away after we set everything up, and we’re not concerned about that. There’s a lot of work in running a short-term rental, and it’s been a really good fit.
Gil: Does that mean the Airbnb listing stays in their name as well, not under Corzly?
Tim: Correct. Everything is under our partners’ names, but we connect directly into all their accounts and take over full control. We change the contact phone number, we change the email — so reservations and guest questions come to us. If we needed to file a resolution, for example, that’s something you can only do with full account access. So we do take over full control operationally, but ultimately it’s under the partner’s name. Payments go to them. Ownership stays with them.
Gil: This is very interesting because I have quite a few property management companies that built their websites with CraftedStays, and every so often one of their customers will reach out and say, “Hey, we actually want to build our own website.” There’s this tension where you now have one property under two different brands. You’re almost leaning into that more — empowering them to own their own book of business, but giving them the benefits of operational efficiency.
Tim: Exactly. And there are certainly some owners who want to be much more involved with their property. That’s one of the challenges with a traditional property manager — you basically give everything over to them. If they have all this great social media content and stories, and they want to build out some marketing, but the property manager isn’t doing that, they don’t really have the option.
We give them full control. They can market as much as they want. But when the reservation comes in, we take over and handle that part.
Gil: That’s interesting because that’s why folks do come to us. There’s almost a connectiveness to it — especially on the smaller side, when you have a homeowner who spent a significant amount on a down payment, did the renovations, has a W2, and doesn’t have the capacity to run it all on their own after the first year or so. But they’re still pretty invested in that property. They might use it themselves. There’s a big affinity toward it — “Yes, I want someone to manage it, but I don’t want to lose that connection.”
Tim: Yeah, for sure. For a lot of people, it’s the biggest investment of their lifetime. It’s nice to have some of that control while not having to handle the back-end operations.
The industry has also changed a lot. You used to be able to put up a short-term rental and it just got booked. Guest expectations were also lower, so it was easier. Today, if you’re just getting started, you can do a great job with your reviews, but that doesn’t necessarily mean you’re optimizing revenue. You might not have had the experience to look for certain pieces of data, compare the market properly, or charge upsells where you can. The more marketing, the better — for any property.
Gil: You mentioned technology and thinking of yourselves as a platform with a lot of tech behind the scenes. What are some of the things you’ve been investing in to help with operational efficiency?
Tim: We’ve done a whole bunch of things. We didn’t start out wanting to recreate something like PriceLabs — that’s a tool that’s been working at this for over a decade. But software is getting much easier and much quicker to build.
The way we’re currently set up is that we use a handful of the industry’s leading tools, and then we have our own software that sits on top of them. One of the challenges in operating a short-term rental is that there’s no single perfect software solution today. Maybe you use PriceLabs for pricing and Hostaway or Guesty for your channel manager, but you don’t want to use them for messaging — maybe you prefer HostBuddy or one of the AI tools.
In our case, the only real thing we use our property management software for is as a channel manager — the connections to Airbnb and Booking.com, which aren’t easily accessible otherwise. Everything else we do outside of it.
We use a lot of AI for guest communications, and that’s one of the areas where AI has really excelled — in support. It knows every single detail about your property. It doesn’t matter if it’s been rented for a year or ten years — it has all the history, never forgets anything, never gets mad, doesn’t get sick.
In our case, managing hundreds of properties, one challenge was having receptionists respond in slightly different ways. Not bad ways — just different voices on different shifts. Now with AI, we can maintain one consistent tone throughout the entire guest experience.
Some of the things we’ve built that don’t currently exist have to do with operations. We use Breezeway — one of the industry-leading tools for operations and task management. But there’s a lot it doesn’t do. A big one is two-way feedback with housekeepers.
Here’s an example: a guest had a great stay but left private feedback saying, “There were some cobwebs on the front entryway — you might want to check next time.” That kind of thing often gets overlooked, especially as a portfolio grows. So we take all feedback — from the housekeeper, from private or public guest reviews, from checklists — and push it onto the upcoming turnover checklist so it never gets missed. We also share all reviews with our housekeepers, both positive and negative.
We’ve even built AI calling for housekeeper confirmations. We’ve gone a long way on operations in the areas where we know technology does a better job. But we also have clear escalation points to a human — having that built in is really important. In a guest experience, you don’t get many opportunities to drop the ball.
Gil: You mentioned guest comms and using AI for consistency. When you have multiple people running guest communications, it’s hard for any one person — it’s a human thing. You have to retain a lot of memory, read back the conversation, figure out next steps, stitch everything together. That’s actually a very easy problem for a computer to handle, especially one with a lot of property knowledge. Are you building your own guest comms tool internally, or are you leveraging existing platforms?
Tim: We’re currently using Conduit as our AI tool, but we’ve built a lot on top of it. We’re also housing all our guest communication in our own internal database, because it’s looking like we’ll probably bring that in-house at some point.
For now, we use Conduit as infrastructure, and we have a whole layer integrated on top of it. For example, it’s integrated with Breezeway — if a guest mentions that a door knob feels loose, we take that input and automatically create a task in Breezeway for that property. That’s not something Conduit does on its own. So we’ve built a lot of things on top. The short answer is: we’re preparing to bring it all in-house sometime in the future.
Gil: It seems like the natural trend — and almost a principle — of how you operate. You use tools for what they’re good at, identify the gaps, and either build from scratch or repurpose those tools for just their core value.
Tim: Yeah, that’s exactly right. We basically have the ability to customize things like we’ve never had before. It’s pretty exciting. We find opportunities to improve — whether it’s revenue, operations, guest experience, or owner transparency through reporting. We’ve built custom reports to keep our partners much more in the loop. Exciting times.
Gil: What’s been on the flip side? Any projects where you went all in, spent a lot of time, and it still didn’t feel right — and you ended up reverting?
Tim: We have. I spent probably six months with a developer building out an accounting system. We do multiple accounting methods in our business, and we’re actually moving to an invoice-only model as of this recording — because trust accounting across a whole bunch of different markets and countries gets complicated.
We spent a lot of time trying to build that out, and we ultimately started using a tool in the industry called Clearing, which had been working on the same problem for a few years. And now we’re actually moving away from that too, going to a simpler invoice-only model. That was definitely one of those rabbit holes.
Gil: Yeah, I’ve gone down many of those myself — trying to optimize certain parts of the business, and two weeks in thinking, “Why did I do this?” I think it’s especially true when it’s not core to your business, and when the underlying platforms keep changing. I’m trying to find the balance between building internally versus leveraging third-party tools. For instance, we could build our own LinkedIn API integration for posting — but things change so fast on their side that it’s just too much to maintain. And I’m never going to replace Stripe. Even if we could save 3%, it doesn’t make sense.
Tim: Yeah. It’s like shiny object syndrome. You think, “I could automate this in two weeks,” and then two weeks later you realize there were a few things you overlooked.
And you’re right — if you’re working in one segment of the industry, like direct booking websites, it’s a little different than our position. We handle the whole operation. We can’t do a bad job at one piece, because if we do, the whole job suffers. So we spend a lot of time on quality control and testing before we release anything. But we’re never going to replace PriceLabs — although, never say never. It’s so much easier to get data scraped these days than it’s ever been.
Gil: I’m seeing the whole SaaS industry getting turned upside down. Companies that thought they had moats — those moats have eroded over the last six months.
Tim: For sure. I look at property management software companies, and the reality is we’re only using them as a channel manager right now. That’s it. They offer all the other pieces, but they’re not doing them as well as other solutions. It’ll be interesting to see what the next couple of years look like.
Gil: I wonder if there’s going to be some PMS that becomes more of a headless system — less about the interface and more about how it connects with the rest of your stack. I don’t know if anyone’s building it that way, thinking about connectiveness rather than the GUI.
Tim: Yeah. There are programs out there — BoomNow, Journey — that are promising some version of an all-in-one AI done-for-you management software. But the reality is you still have to set them up, and you still have to monitor them.
Just to give you an example: we create workflows for things like early check-in requests — which everyone knows is a common ask and a good upsell opportunity. But there are a lot of things you have to check before you can offer that. You need to confirm the property’s clean, confirm with the housekeeper, make sure the owner is okay with it, know how early is too early, know when you start charging, send a payment link, then confirm. A lot of the AI programs coming out promise this, but they don’t actually handle all those layers. What they do well is general communication — someone asks for the Wi-Fi password, that’s easy to automate. But the deeper operational workflows are where it gets tricky.
Gil: Since your portfolio is so large, it’s a lot easier for you to make the investments to even figure out whether something is worth pursuing. For a smaller operator, you might not get those economies of scale — and the distraction cost is real.
Tim: For sure. That’s how we look at ourselves — like consultants when we bring a new partner on. We say, “We’ve been working on this for years. We have tons of data from dozens of markets.” When someone joins us, we can offer things right away and say, “This has worked for properties like yours.” It’s refreshing that we can do that, and that building software is so accessible now.
Gil: You take on all the operations and empower the homeowner to keep their brand. What are some of the foundations you set them up on? What do you invest into, and what do you want them to invest into so they can thrive on the direct booking side of things?
Tim: When someone starts with us, we have some general recommendations about the property itself after we look through it — furnishings and things like that — but we really leave that up to them.
Obviously, photos and getting your property to stand out online are huge. You want to have the best photos. We always put every property on all the primary booking sites — with the goal of pulling as many of those guests off and having them book directly afterwards. But getting as much exposure as possible in the beginning just increases the likelihood of booking. So Booking.com, Google, all of it — and playing with promotions on different channels while marking things up appropriately on the back end so we’re not giving properties away.
We spend a lot of time on revenue management. You can have a perfect property, listed perfectly, with perfect reviews — but if it’s not priced right, people just won’t book it. So we make sure it’s priced right at the right time on the right channels.
For direct bookings, we give a small discount when someone comes back to us directly.
When it comes to housekeeping and operations — also fundamental. We can’t have dirty properties. We’ve invested a lot in the organization with housekeepers we work with. We use Breezeway as a core tool, and we’ve also built an internal tool called Smoothly that does a whole bunch of additional things — making sure there’s never a missed turnover, making sure every note a housekeeper gives us doesn’t get overlooked.
On the marketing side, we’re just getting into it. We’ve been focused on core operations, and we know there’s a ton of opportunity to improve — with sites like the ones you guys create and other marketing to drive direct bookings.
Gil: You mentioned before the show some of the physical assets inside the property you invest in to help build the brand. Talk a little about that.
Tim: We want to make sure every guest who came from an OTA knows they can book with us directly next time. So we do things like magnets on the fridge with a QR code — “Book with us next time” — somewhere visible that they won’t overlook.
We capture guest information through several methods. Quite a lot of properties use Safely, where we can build a customer list and do email marketing on the back end. We’re also saving guest contacts through Stripe and Charge Automation for all our contacts.
We get rental agreements signed digitally. We have digital guidebooks. Our direct booking link is in all of those pieces. We have custom messages that go out after the stay — “Hope you had a fabulous stay. Just so you know, you can book with us directly next time.”
Those are core base fundamentals.
Gil: On the marketing side — are there any projects you’ve been itching to explore to help property owners gain traction?
Tim: There are certainly a lot of things we’d like to be doing that we haven’t got to yet. We currently leave marketing up to our partners. We have direct booking website options for them — and they could also use something like CraftedStays, as long as it integrates with our PMS. Once the reservation comes in, we handle everything from there.
Gil: I like that sharp focus. On our side at CraftedStays — we talked about this before the show — we can do a lot of different things to help drive direct bookings. Social media management, ads, all of it. But our core is building the highest-converting, best-performing sites. More recently, we’ve been doing a lot with SEO, AEO, and GEO. That’s ultimately why people come to us. And I think you have a similar ethos: “This is the core thing people come to us for, and this is where I want to obsess over perfecting.”
Tim: Yeah, for sure. If we get our core operation wrong, the property’s not going to be successful. Direct booking websites are super important, but if someone doesn’t book directly, they still have the opportunity to book through another channel. We want to do all the things — but we’re focused on core operations for right now.
Gil: Love that sharp focus. Tim, we usually end the show with three questions.
First: What’s a book that has inspired you — doesn’t have to be recent?
Tim: Rich Dad, Poor Dad. I’m sure you hear that one a lot, but it really was a game changer for me. I started my real estate career basically my whole life ago, and I’m really fortunate I came across it. It’s just a different mindset.
Gil: I empathize with that one completely. At one point I had three or four copies on my bookshelf, and when I’d meet someone who needed a light shined on how they were handling their assets, I’d grab a copy and give it to them the next day. The people I’ve handed it to — it’s been a game changer. I read it back in 2019 and the way I was spending money back then… the next year, my wife and I started acquiring properties and completely changed our lifestyle. I’m so glad we made those shifts.
Tim: It’s pretty simple concepts, but definitely life-changing.
Gil: I even tried paying my niece $100 to read it — she read it, but didn’t appreciate it yet. Maybe in a couple of years.
Gil: Second question: What’s one piece of mindset advice you’d give to someone starting something completely new?
Tim: There’s another book I’d pull from — The Slight Edge by Jeff Olson. The core principle is that doing small things that seem insignificant add up to really big results. A lot of times, the difference between someone who succeeds and someone who doesn’t is simply continuing to do it. Starting a business is hard. There are a lot of pieces to it. But if you don’t continue, you’ll never succeed. Don’t overlook the small things you’re doing every day — they add up to really big results.
Gil: Last question: We talked about a lot of tactics and strategies on the operational side, the hospitality side, and the direct booking side. What’s one tactical piece of advice for someone either getting started in direct bookings or trying to amplify what they already have?
Tim: Make sure you’re getting the guest contacts — whether through in-property materials, an external guidebook link, a digital agreement, whatever it happens to be. Having a list of people who have already stayed with you is really, really valuable. Do everything you can to get every guest contact, including the other people staying in the property. If you have a bigger property that sleeps 12 people, do everything you can to get all 12 guest emails.
Gil: This is one of the biggest fundamentals — and why I see folks with really phenomenal direct booking rates after that first or second year. They deliver exceptional service, they set the right expectations, they answer questions promptly. Guests want that high-level service consistently. And if you stay in contact and keep nurturing those guests, you build this really strong book of business where after a couple of years, you have the same guests coming back. You don’t really need to rely on the OTAs because you have folks who love staying with you and love recommending you.
Tim: For sure.
Gil: Tim, it was a huge pleasure having you on the show. Where can folks learn more about you and get connected?
Tim: Our company is Corzly — C-O-R-Z-L-Y — at corzly.com. I’d love to connect, or someone from our team would love to talk with you about your properties and see if they might be a good fit. And then I also have the Short Term Rental Riches podcast — you can find it on all podcast platforms and on YouTube. Quick, actionable, mainly solo episodes — 10 to 15 minutes — with real-world advice from our portfolio and the property owners we work with daily.
Gil: Awesome, Tim. It was a huge pleasure. Thank you for being on the show — chat next time. Bye.
Tim: Thanks for having me.