Direct Booking Channels Hiding in Your Guest Messages with Jeff Iloulian

Summary and Highlights

🎙️ Direct Booking Channels Hiding in Your Guest Messages with Jeff Iloulian

“You have to ask. You have to read.”

Most operators go looking for direct booking channels in the same three places: ads, social, and an email list. Jeff Iloulian found his somewhere far less glamorous. He found them buried in guest inquiries he almost did not read. This episode is part cautionary furnishing story, part masterclass in noticing what your own inbox is already telling you.

👤 Meet Jeff Iloulian

Jeff Iloulian is the cofounder and CEO of HostGPO, a community buying group built for the short term rental industry. Before that, he was an operator. He started with a single Los Angeles property in 2015 and grew to roughly 150 doors over five years through lease arbitrage, property management, and a mix of creative deal structures.

His background is unusual for the space. Jeff studied Economics and Philosophy at Columbia, earned a JD from UCLA School of Law, and practiced business and intellectual property litigation for three years before the entrepreneurial itch took over. He describes himself as a person who refuses to accept that something has to work a certain way until he has tested it himself. He also loves music, tacos, and travel.

🛒 The 48 Cart IKEA Run

Jeff’s origin story starts across the street from his own home. A developer bought a great property and planned to demolish it, but Los Angeles permitting takes 12 to 18 months. The house sat empty for weeks. Jeff had just read a New York Times DealBook piece about lease arbitrage, so he knocked on the door and proposed a deal: pay a small amount, furnish it, run it, and hand it back with 30 days notice.

They said yes. He set his booking window to 30 days out and started welcoming guests personally.

Then came the scaling problem. Four adjacent units to furnish at once. Jeff brought his entire 12 person team to IKEA, rented a U Haul, and checked out with 48 shopping carts. The line wrapped back into the store. Checkout alone took two and a half hours, long enough that the cashier’s shift changed mid scan. The bill landed around $40,000. He asked for a discount and they laughed.

🛏️ Why Cheap Furniture Is the Most Expensive Thing You Can Buy

The units were terrible. Everything broke, chipped, or peeled. But Jeff’s point is not about IKEA specifically. It is about the real math of a broken bed frame in a live rental.

You block the calendar. You order a replacement. You lose a day or two of revenue. You pay for junk removal. You build the new bed. Then you refund the guest it broke on. Do that a few times and the “savings” evaporate.

Linens compound the same way. Buy sheets from one store, restock at another when the line gets discontinued, then patch in something from a third. Now a bed has a cream pillowcase, a bright white flat sheet, and a duvet that matches neither. Guests notice immediately. So do your cleaners, who are now sorting mismatched inventory on every turn. This is the same logic behind data driven design decisions and why designers like Courtney Petrovich treat furnishing as a revenue decision rather than a taste decision.

🧵 The Hotel Standard Nobody Told You About

Jeff has been in the industry 11 years and says he is still learning. His example: a 60/40 cotton polyester sheet behaves completely differently depending on how it is woven. If the synthetic yarn sits inside and cotton wraps the outside, dirt binds to the cotton and releases in the wash. That is what stain release actually means.

Other details he had never considered until vendors walked him through them. Fitted sheets without hem lines, so they go on in either direction. Color coded thread inside the seam so cleaners can tell kings from queens from twins at a glance. Case packs, so you order 72 pillowcases directly instead of breaking apart 20 full sets to find the pieces that actually wear out.

The best operators Jeff sees do one thing consistently: they set standards, then plan replacement cycles 16 to 18 months ahead and phase inventory in. Boring, and it works. It is the same operational discipline Ishita Lalan and Lisa Roads have both described from different angles.

🎬 The Direct Booking Channel That Started With One Email

Here is where the conversation turns. Jeff’s property management company was never brand forward. Luxury homes, cabins, apartments, studios, all under one roof with no single consumer facing identity. Paid ads made no sense, because there was no unified brand to send traffic to.

So he asked a different question. Not “how do we market our brand,” but “where do the people who want these specific homes already live?”

The answer arrived as inbound. A trickle of emails asking whether a home was available for a commercial shoot. One booking became a signal. Jeff reached out proactively to Warner Brothers, built a relationship with Netflix, and mapped which of his homes sat near which studios and offices. Location scouts started emailing him at the start of every search: you have a couple hundred properties, do you have anything that fits this?

One of those became the apartment in Marriage Story with Adam Driver. Production redressed the unit, then rented the rest of the building so cast and crew could work out of the other apartments instead of parking 20 trailers on the street. That single month long booking covered eight to nine months of annual revenue.

📍 Proximity Is a Channel You Are Probably Ignoring

The film work was not a fluke. It was a pattern Jeff kept applying.

Properties in Westwood kept drawing visiting faculty and academic groups. So he contacted UCLA departments directly and told them: if you have adjunct faculty, students, or anyone needing housing, come to us. That became a channel. Another large home sat five minutes from the Lakers practice facility. Over time, roughly a dozen players stayed there during summer workouts and tryouts, calling directly.

Gil shared his own version. He bought a Gatlinburg cabin without realizing it sat three minutes from a major competitive sports stadium. Guests started asking about tournaments. He listened, then got listed in the housing directory coaches use to book entire teams. It performs enormously well, and he only found it because guests told him first.

Jeff’s framing is sharp here. It is one thing to say you get a lot of nurse bookings. It is another to say you have a property near a specific hospital, then go build a relationship with that hospital. The first is an observation. The second is a channel. Jennifer Barbee made a similar case about tapping your local tourism office for the same reason.

🤖 The AI Warning Buried in the Advice

Jeff describes himself as aggressively pro AI. He still flagged a real risk.

If you hand every guest conversation to a chatbot and never read the transcripts yourself, you lose the pattern. The 14 nurses who mentioned their shifts in a preliminary message. The parent who explained which tournament brought them to town. That context is the raw material for your entire guest avatar and your niche positioning. Automate the reply if you want. Read the thread anyway.

Gil connected this to how the CraftedStays AI site editor works. It scans guest reviews alongside your own property descriptions and search data, because how you describe your place matters less than why people actually chose it. If you are still collecting guest contact details as an afterthought, this is a good reason to fix that first.

⚡ Rapid Fire With Jeff

📚 Book Recommendation: This Is Not a T Shirt by Bobby Hundreds. Jeff knows Bobby personally and watched the brand get built. He calls it a quick, deeply authentic read about what founders are actually selling, which is rarely the product itself. People do not buy the t shirt. They buy into the community around it.

🧠 Mindset Advice: Ask yourself one threshold question before you start anything. Are you solving a problem, or are you solving an inconvenience? Both deserve to exist. But the answer determines whether you raise money, go full time, or let the thing grow organically on its own. Jeff has watched founders go all in on an inconvenience and half in on a real problem. Gil’s shorthand for it: painkiller or vitamin.

🎯 One Tactical Tip: Read your guest messages. All of them. Add an intake question after booking that asks what brings them to town, framed alongside your check in instructions so it feels like hospitality rather than a survey. Then look for the repeat. You do not need to rebuild your property for one demographic, but if you are not asking who is already there and why, you are leaving a channel on the table.

🤝 Connect With Jeff Iloulian

💼 LinkedIn: Jeff Iloulian
📸 Instagram: @hostgpo
🌐 Web: HostGPO
🏓 Jeff also runs the HostGPOpen, an annual pickleball tournament at VRMA with proceeds going to short term rental advocacy through the VRMA advocacy fund and Rent Responsibly. It is expanding beyond VRMA in 2026 with events planned in Palm Springs, Austin, and Atlanta.

🚀 Start Building Your Own Channels

Jeff’s best bookings never came from a funnel. They came from paying attention, then having somewhere legitimate to send people once he found them. That second half matters. A studio location scout, a university housing coordinator, or a tournament organizer needs to land on something that looks like a real business, not a listing link.

That is exactly what CraftedStays was built for. Purpose built for short term rentals, mobile first, SEO native, and live in under 15 minutes once your PMS is connected. If you are ready to start taking direct bookings without giving up your OTA presence, see how it works and start your free trial at CraftedStays.co.

🎧 Listen to the full conversation with Jeff Iloulian on the Booked Solid Show, and join the community of operators building independent booking brands. Every week we share one conversation like this one, plus the strategies behind it. Subscribe at CraftedStays.co and browse more episodes and guides while you are there.

Transcription

Gil: Hey Jeff, welcome to the show.

Jeff: Hey, thanks so much for having me. Really excited to be here.

Gil: Jeff, to kick us off, I want you to give us a rundown on who you are, what your journey has been, and why you decided to start HostGPO.

Jeff: I’m Jeff Iloulian, cofounder and CEO of HostGPO. How did I get here? I’ve been in the vacation rental industry for about 11 years. I was a lawyer before that. I started with one property in 2015 and grew my portfolio doing property management and a couple of other deal structures, which we can get into if you’re curious. I got to about 150 properties over a five year span.

I was doing a little bit of lease arbitrage and some other types of deals, and ultimately one of the biggest problems I had was figuring out how to furnish these places and where to buy and restock all my supplies. HostGPO came from that. It was me as an operator trying to figure out what the best linens were, where to get mattresses, how to get a discount on furniture, what types of furniture to buy. Then banding people together into a buying group, a GPO, a group purchasing organization, to negotiate the guaranteed best pricing with all the different brands we work with. So that’s a quick background on how HostGPO started and what it is.

Gil: Talk to me a bit about the early days. You mentioned you started this 11 years ago, so that was back in 2015?

Jeff: 2015, yeah.

Gil: What was that growth like? How did you start off, what was that trajectory like growing the portfolio, and what were some of the things you learned that started to seed the idea of HostGPO?

Jeff: Out of the gate, the beginning of my vacation rental business was this. I was living across the street from a great property in a really good neighborhood in Los Angeles that a construction company and developer had bought and were going to flip. In Los Angeles, the permit cycle takes about 12 to 18 months to get a permit for a full demolition and rebuild.

It was a great location and a great property, but there was a lot more value in building a bigger house. So the developer bought this property and was just going to leave it. It sat empty for the first couple of weeks, then the first month. Eventually I started talking to them and asked what they were doing with the house in the meantime. They were just going to leave it empty until demolition.

I had just read an article in DealBook from the New York Times that a friend posted in 2015. It was about lease arbitrage, people in New York renting places and re renting them. Really it was about the rise of Airbnb and short term rentals. I hadn’t thought about it before, but this was right across the street from me. I thought, if this is just going to sit empty, I wonder if I could make a deal with them where they’d let me pay a very small amount, put furniture in, and rent it out for the 18 months until they were ready to take it back. And they were thrilled to do this.

I told them, give me 30 days notice when you’re ready to move back in. I set my booking window to 30 days out. That’s how my short term rental journey began. Furnishing the property across the street from mine, welcoming every guest, shaking their hand when they arrived, and telling them all the places in my neighborhood I like to go.

Gil: That’s a very interesting story, and very creative. I’m also thinking about it logistically. The most painful part of managing a rental is getting it all set up, and you were doing this for such a short window.

Jeff: A hundred percent. And honestly, to jump to the end, that’s how I got really good at doing this. I managed a portfolio of 150 properties at its biggest, but I set up maybe 300 properties over that period of time, because so many of them were one year or 18 months. A lot lasted the whole time, but most were very quick setup, teardown, setup, teardown.

So I got really good at having a checklist of everything that needs to be in there and what the right things are to put in there. There’s a lot of wear and tear from moving, too. I did eventually get into property management once I had a big enough team, when we were around 30 or 40 properties. Then we took on a bunch of other assets, like managing entire buildings, and we got into the luxury space doing very large homes. But that’s how I got started.

Gil: You have a story where you had to buy furniture from IKEA and other places that aren’t traditionally where you’d buy furniture in bulk. Tell me about some of those.

Jeff: I was young and hustling and trying to be really smart with the pennies, trying to figure out the cheapest stuff I could put in there. To be fair, this is me throwing myself under the bus, because I have learned, and I’m on a mission to reform people from doing stuff like this. It was a terrible thing to do.

I had four units side by side, duplexes up to fourplexes, and I was furnishing all four at the same time. Again it was a construction company that had bought these units and was going to build one big apartment building, so it was an 18 to 24 month window I’d have access to. It was right by a hospital and it was all vacant.

So I went to IKEA with my entire team. We were pretty big at that point, probably 12 of us. I brought some friends, anybody who would give me the time of day. We rented a U Haul truck, went to IKEA, and checked out with 48 shopping carts. The line of shopping carts wrapped all the way back into the store. The checkout process where they scan items took two and a half hours. They had to clock somebody in and out. It was a shift change during the checkout.

Gil: What was that bill? Do you remember how much it was?

Jeff: It was big. I want to say it was 30 or 40 thousand, something like that. Which is a lot of IKEA stuff.

Gil: Okay. You didn’t break six figures.

Jeff: I didn’t break six figures, but it wasn’t everything either. It was just a lot of essentials. The craziest part was that on a roughly $40,000 bill, I asked if I could get a discount and they laughed so hard. They said, what are you talking about, this isn’t even close to enough to warrant having a conversation about a discount.

All that being said, we threw everything into a U Haul. I don’t know what I was thinking. I was an operations guy, but definitely not good enough. Side note, one of my employees who was driving the U Haul crashed into a car, so that became a whole nightmare.

But then there’s this moment of arriving at the house. The sun has gone down, it’s 7:30 at night, and we open the back of the truck and it’s filled from the back all the way to the front. Just this overwhelming feeling of, my gosh, unpacking this, getting it into the units, and building all the furniture is going to take a week at least.

And then we did it, and the units were awful. They were terrible, so bad. All the furniture broke, it chipped, everything peeled up. That was a really big learning experience, among others. Going to outlets, driving and filling cars, going to flea markets, Facebook Marketplace. I did all of it at the beginning.

What I learned is that the amount of time it takes to do that is fine if you have it, but you must be sitting on a lot of free time. If you don’t, you’re wasting your time, you’re actually spending a lot of money paying people for their time, and you’re not setting up the best product that’s going to give you the best return.

There are a lot of reasons why those units did okay, but a lot of it had to do with the fact that it was 2016. Airbnb was really booming as a booking channel, and the short term rental industry, especially in a place like Los Angeles, was on fire. So you could do stuff like that. You could set up a real bootleg unit and charge 30 percent less than you should have been getting and undercut the market. It was a strategy. It wasn’t the best strategy, but that’s how I got started in the space.

Gil: I imagine if you started that even five years later, you couldn’t pull off what you did. Well, five years later was during the pandemic, but pandemic aside, it would have been really challenging.

Jeff: No shot. Seven years later I would have been okay for a minute, but that’s not the world it is anymore.

Gil: Now it’s a very different world, and probably one you thrive in, because of the quality standard you’ve learned along the way. Just hearing that story of opening the truck, even before you got to that moment, I was imagining your thumb and index finger and how much pain there was from that Allen wrench.

Jeff: There’s an adapter set of IKEA power tools you can get, there’s a whole IKEA kit you can use with a power tool. But it’s not worth it, and it’s just not the right way to do things, for a million reasons I’m happy to get into. I wanted to find a better way. I wanted more cost effective ways to get better quality furniture and better quality items. That’s how HostGPO started to become an idea.

Gil: I imagine IKEA was a combination of cost and accessibility. It was something you could walk into and say, we’re going to do one trip and knock it all out at once. Cheaper, but also local to you, and it has everything you could possibly need. All your dishes, all your linens, everything in one place.

Jeff: Yeah. The hard part is that I learned it’s cheaper up front but way more expensive in the long run, for a thousand reasons. Breakage is brutal. Replacing a bed frame that breaks in a short term rental unit requires blocking off the day, ordering a new bed, losing a day or two of revenue, paying for junk removal, building the new bed, and refunding the guest the bed broke on. That is way more expensive than buying the right bed frame at the beginning.

Not to mention it’ll look better, your photos will look better, and your unit will perform better because it books at higher ADRs when you have a better designed, higher quality property. That’s just furniture, and you can apply the same logic to every single thing.

You start buying sheets from IKEA and you realize, one, they’re terrible quality and guests aren’t going to be happy. If you try to charge a high rate they’re going to ask what they’re paying for. Two, you go back to IKEA down the road to replace your sheets and you have to figure out if they still carry them. Did they discontinue that line? Did they change it? So you mix in some Sam’s Club, some Target, some Costco, and now your bed has a cream pillowcase, a bright white sheet, and a duvet that doesn’t match. That creates a really terrible experience for a guest who shows up and thinks, there are no standards here. It doesn’t create a high level property.

Gil: On the host or property management side, it’s also hard to maintain. Your cleaners have to juggle and make sure they’re matching sheets to bedding. When we overhauled and changed our look, we had to overhaul everything. We basically dumped what we had and refreshed it.

Jeff: Totally. The right way to do it, which took a lot of time to learn, is what I’ve seen from the best operators. We now work with over three hundred thousand properties that have signed up to be part of HostGPO, so I’ve seen a lot of the best operators and how they do it.

They have set standards. They’ve decided what they’re buying and they buy the same thing. If they’re going to do a big overhaul, they say, we’re going to cycle out and change linens 16 to 18 months from now. They plan it in advance, start buying inventory, and start cycling it in. That’s really complicated to do.

But you figure out that there is contract grade furniture, and there are commercial grade hospitality sheets, and they do things like resist stains and dry quickly. It’s what Marriott uses, and it’s meant to go through the type of use a short term rental will have. Whereas you have so much more turnover, and so much more of an operational headache around furniture and linens and everything else, by doing it the wrong way or not being intentional early on.

Gil: You’re leading me down several different paths of what I want to ask you. But one thing I’m starting to recognize is that you’re allowing folks to have that hotel standard. Cycling things out, planning 18 months in advance. These are the operations of mature property managers with a lot of doors, and it’s basically the status quo for any hotel.

So on your side, is there education you have to do to help folks? Or are people already coming to you saying, I need to step things up and I need your help executing? How much of it is convincing them that they’ve been doing it a certain way and don’t realize how bad it is, versus them coming to you already knowing they need to fix it?

Jeff: It’s a good question. The only pushback I’ll give is that I don’t think I or anybody on our team feels like we have to do this. We look at it like we get to do it. We get to help people.

We’re so excited that when you sign up for HostGPO, even if you’re just starting out with a free trial, you get to talk to somebody on our team. We really encourage people to take that time. Our team is full of experts. This is all they talk about and do all day. They’ve all been in the industry before. They’ve set up thousands of properties, or helped people set up thousands of properties.

We get to work with people on these questions. What are your pain points? What are you running into? How are you doing things? And we get the privilege of being able to educate and help the industry, which is something I’m super passionate about, and our team is too.

I’ve been in the industry for 11 years and I’m still learning things. We’ll talk to the linen company we work with and they’ll bring up things I’ve never even considered. I don’t think of myself as a sheet expert, but I can tell you that something that’s a 60/40 cotton polyester blend might behave differently depending on whether it’s all woven together, which is more inexpensive, or whether the polyester synthetic yarn is on the inside and wrapped with cotton. Because that means if it gets soiled, the cotton is getting soiled, and it’ll release the dirt when you wash it. That’s stain resistant, stain release sheets. That’s something I could never have imagined existed.

And all the little things too. Not having hem lines so you can put fitted sheets on in both directions, so there’s no issue of the tag being on the wrong end. Having a color coded thread line on the inside so your cleaning crew can tell queens, kings, and twins apart, and they know what to replace and what to grab from inventory instead of shoving things away in closets.

Or knowing you can order case packs of certain things. That was such a breakthrough for me when I realized I don’t have to order the two pillowcases plus the flat and fitted, order 20 of those, and then break them up. I thought, wait, I can order a box of 24 flat sheets because that’s what I want. Or a box of 72 pillowcases, because that’s where the mascara is going. And then, well, mascara, how do you stop that? Makeup towels.

There’s such a long line of education that we’re fortunate enough to be able to help this industry with, and to help people succeed in their businesses. Not just to compete with hotels that have those standards, which is what people expect when they show up, but also with some of the biggest players in the space who have figured this out. We’re unlocking deals for them and deals for us overall as an industry.

Gil: From a deal perspective, there are great economies of scale in the way you do it. That’s probably the origin behind the GPO in the first place. You have significantly more buying power than an individual consumer could possibly have.

Jeff: We’ve done hundreds of millions of dollars through our GPO, which we’re really excited about. But it doesn’t mean somebody who joins has to buy 25 dishwashers to get a discount. We partner with Lowe’s so you get better than Lowe’s pro pricing on one. We partner with Amazon, Samsung, GE, Schlage, Yale, and others so you can buy directly from them or buy certain things at a discount. We take a lot of pride in helping people get samples, educating them on the right things to buy, and talking through operations and systems to help people run better businesses.

Gil: As you think through building out HostGPO, it’s been a number of years now and it’s gone through many generations and evolutions. What have been some of the hardest lessons at each milestone?

Jeff: There have been a ton. The biggest one, the albatross, has been building the ordering portal and figuring out how people want to place orders.

For any HostGPO members listening who have been with us for five years, they’ll remember how it used to be. Do you want to purchase a couch? Do you want to purchase a mattress? Email us and type out what you want. Type out the SKUs. Here’s a spreadsheet, download it, fill in the SKUs, type them in, put the quantities, put the shipping address. We’ll send you a quote in 48 hours. That’s how it started.

Slowly we’ve worked on making the ordering portal better. We’re pulling in catalogs from Crate and Barrel, from Helix mattresses, from linen companies and amenity companies and Public Goods. We’re pulling all of that in and making it shoppable in one place. That’s been a real challenge to iterate through and to understand what people want.

Gil: I’m guessing there might already be solutions out there, warehouses and resellers and so on. Did you build it yourself? Did you end up using an off the shelf platform, or go one way and have to learn the other?

Jeff: From a technical perspective it was a mix. We did everything custom at the beginning, then we tried to find some off the rack solutions that existed and build custom integrations on top of that. We’ve gone through so many iterations of how the platform works to get it where it is today and in the direction it’s going.

Gil: We talked about this a little before the call, Jeff. I come from the ecommerce world and spent quite a bit of time in logistics as well, and that is not a fun operation. It’s an orchestration more than anything else.

Jeff: It is wild out there. I don’t want to throw any of our vendor partners under the bus by name, the suppliers on the other side of our site. But what I will say is that we are making things accessible.

For example, if you wanted to buy certain soaps and shampoos from certain brands, we have everything from Aesop to Malin and Goetz to Grown Alchemist, Aveda, Beekman, all the way down to entry level options like Terra Pure and Public Goods.

Some of these companies have operated for years logistically by selling to hotels. What that means is when a hotel wants to buy something, they’re usually buying $250,000 at a time, and they’ll send an email that starts a long back and forth conversation. Some of them will even fax an order in. A fax machine. That’s how orders are getting placed.

So we have to go to a lot of these brands and say, we want to digitize what you’re doing and make it work for the short term rental industry. And by the way, our members might want to buy 12 soaps and shampoos and ship them somewhere. They’re also going to want a 50 or 60 percent discount, because together we create a lot of volume.

Solving that problem, then ingesting the tracking, surfacing it, and having uniform order history in one place, is a decent amount of tech lift.

Gil: I imagine you do a handshake deal and say, we’d love to have you in our catalog, and then find out weeks later that this is how they want the order submitted. There must be a few cases where you walked into it, it made a lot of sense on paper, but operationally they just weren’t set up for it.

Jeff: Totally. And it’s one of the factors in why we’re really picky about which vendors we work with. A big part of HostGPO is that we don’t want people to have decision fatigue. We have a list we give everybody for free with about 650 items you need to set up a vacation rental from the ground up. That’s already a lot of decisions to make.

So we partner with one luxury furniture company, one mid level furniture company, one or two basic entry level companies. Those are companies we’ve vetted, and not only do they make the ordering process as easy as it can be, they’re willing to work on these solutions together. In our opinion, we’ve tested the products and they’re the right products for the space. So we curate the assortment of vendors we work with.

We’ve had to say no to vendors who don’t want to be flexible, who say they only want to work with companies that call in and get on the phone with one of their reps. That’s not how people operate and that’s not how our businesses operate. So we’re very cautious about who we partner with.

Gil: Did you take on some partnerships early where you thought, this is the wrong one, but you were growing and felt you had to? And then over time your quality standard rose to where you could say, your product quality doesn’t meet the standard, or your operational quality doesn’t meet our standard. Which is something you couldn’t say in those first years when you needed that logo or that product in there.

Jeff: A hundred percent, and we learned the hard way. We partner with a lot of physical goods companies, mattresses, rugs, art, decor. But we also have service partners. Through HostGPO you get a free Instacart business account, and a discount with DirecTV if you’re putting a package together for your homes.

We also tried to partner with national services. HostGPO members who’ve been around a few years will remember when we launched a pest control discount three or four years ago. We worked with a national pest control company so that if you had 40 properties and needed routine spraying, here’s 40 percent off at the national account level.

The problem is we had to pull it. The program was great, but it was really a franchise of pest control companies. You could live in Palm Springs and have the best pest control guy, but you could be in Chicago or Florida and the pest control in that area wasn’t good. We didn’t think that spoke to our brand standard for recommending it, so we decided to pull it. That was something we didn’t have the luxury of doing earlier, and it’s something we’re really cautious about now.

Gil: Your origin was on the short term rental side. I’m curious whether you have any hotels, boutique or larger, using you, and whether that’s a core focus of your growth.

Jeff: Absolutely. I don’t know if it’s over a hundred, but we’ve set up a decent number of boutique hotels, anything from 12 to 60 or 70 units. Our team are experts at doing it. We’ll do ground up furniture, ground up supplies, and work with interior designers staffed on those projects.

We have a free interior design program, which is pretty cool for smaller or medium sized projects, where we’ll work with the brands and get a design in front of you. But we’ve done boutique hotels, we’ve done some corporate housing, so mid term stays and mid term rentals. Anything that’s a furnished property, we’ve started dabbling in. But short term rentals are really our roots.

Gil: Talk to me a little about your early days. Right before the call we talked about when you were a property manager and some of the things you invested in, and how you captured the right audiences specifically for direct bookings. You had a very different way of approaching direct bookings than the traditional email marketing and social media route. Tell me about that.

Jeff: It was a different time and we had a different business. In 2015, 2016, 2017, we were not brand forward as a company. We had luxury properties, cabins, apartments, studios, homes. We didn’t have one public facing brand across the board. What we did have was a bunch of unique properties that were good fits for certain things.

So our direct booking strategy for the property management company was, we can’t really buy ads sending people to our brand, because it’s not one thing. Where are we going to find people for these specific homes? We learned a little from who was booking the homes, and took that knowledge and asked, how do we get more of these people?

An example. We were in Los Angeles. Most of our homes were in Southern California with a heavy concentration in Los Angeles, which means Hollywood. People wanted to book for commercials, for movies, for whatever. We started getting a trickle of inbound saying, hey, is this home available, we’re filming a commercial for a shoe company and this home would be perfect, this backyard would be great.

We booked one, and that sparked it. This is a direct booking channel for us. Bookings for commercial shoots and movies in Los Angeles. That’s a real channel. So we proactively reached out to Warner Brothers. We had a relationship with Netflix. We had relationships across different industries because we had properties close to their offices or that were good fits for what they were doing.

Then, all of a sudden, there were individuals at those companies in charge of finding properties, and they would email us at the beginning of a search and say, hey, you have a couple hundred properties, do you have anything that fits this criteria? That was our direct booking channel. It was them emailing and asking, because we had built relationships.

And those bookings were significant. We filmed a major motion picture in one of our properties. I don’t know if you ever saw Marriage Story with Adam Driver.

Gil: I have.

Jeff: It was good. I think he won an award for it. It was a great movie, and his apartment in the movie was one of our units. It was a really creative use. They took this one apartment, made it his apartment in the movie, redid it a little, and put new furniture in. Then they rented the rest of the building. Rather than park 20 trailers outside for hair and makeup and sound and the director, they emptied all the units and put everybody in different units in that one building to film the movie for a month. That revenue paid for eight or nine months of our year with one booking. Which was amazing.

Or, we were getting a lot of bookings near UCLA for our properties in Westwood. It was teachers coming with their families to teach in different groups. So what did we do? We went to UCLA, reached out to the different departments and said, if you have any adjunct faculty, students, or people who need homes, reach out to us directly, we have a lot of homes in this area. That became a channel for us.

It was really grassroots and really need based. But if you’re near a big hospital and there are outpatients, or you’re near a school, it’s one thing to say we do a lot of nurse bookings or a lot of whatever. It’s another thing to say, I have a property that’s really close to this thing, and I’m going to go talk to them about building a relationship. That worked really well for us.

Gil: I have something similar. One of my Gatlinburg properties, I didn’t know this when I bought it, is about a three minute drive from one of the biggest competitive sports stadiums in Tennessee. We found out they have housing associations for when coaches need to house their entire team. So we’re listed in their directory, and if someone is coming to compete, they can book with us and we give them a small cut. It works enormously well.

Had we not done that local search, and we didn’t really know it when we bought the property, we wouldn’t have found it. We started getting multifamily groups asking, we’re competing at this place, can we have some friends over? We just started hearing it more and more.

Jeff: But that’s what I’m saying. You have to ask, and you have to read. I’m a very big advocate of AI in general, so aggressively pro. But this is one of those things where if you’re just going to have a chatbot do all your messaging and you’re not going to look at what people are saying, you might miss things like this.

We had a similar one. One of our large homes was really close to the Lakers practice facility. Whenever they were working out new players or doing summer workouts, I probably had a dozen basketball players at one point or another stay in that house, because it was five minutes from the practice facility and perfect for what they needed. They started calling us directly. It was that kind of relationship. And if you’re not asking who’s staying here, or reading, you’re going to miss it.

Gil: That’s amazing. I’ve learned so much about different tactics on this call. One thing I’ve learned about you, Jeff, is that you have this mind for finding opportunities that are almost nonlinear, not the status quo. I wouldn’t have gone to IKEA and bought a truckload and 48 carts of things. Or even before that, identifying that there’s this property across the street, there’s this new concept called arbitrage, could I pick up that home, rent it out for a period, and give it back? That’s unique, and it’s only sustainable to a point, but it was the stepping stone that let you do the next thing.

Jeff: A hundred percent. I don’t want to say I pride myself on it, but it’s a big part of my personality. I refuse to accept that things are a certain way until you try it out. Solve your own problems. Figure it out. Just because this is the social norm, or because this is the way things are, doesn’t mean it’s the way they have to be.

That solutioning and problem solving mindset is honestly why I loved being a lawyer. I really did like it, and it was that type of problem solving where you’re constantly thinking, is this the only way, or what else can we consider? It’s the same itch that gets scratched when you’re trying to figure out how to furnish 16 apartments overnight, or 28 bedrooms, or whatever it is. What’s the fastest way? What’s the longest pole in the tent? How do you solve your own problem?

Gil: I love that. Jeff, that’s a good segue to the last section of the show where I ask you three questions. First question, what’s a book that has inspired you and made an impact on your life?

Jeff: I will always recommend and shout out this book. It’s called This Is Not a T Shirt, and it’s by Bobby Hundreds. It’s a phenomenal book. I have the pleasure and fortune of knowing Bobby and having a chance to watch his journey building a clothing and fashion company.

The book is great if you’re a founder or somebody who’s building something. He talks through, in a very authentic way, what his journey to building the company was, and he focuses on the fact that people aren’t just buying a t shirt. I’m not giving anything away here, but it’s really about community building. They want to be part of a community, and what does that really mean? He talks about building The Hundreds as a clothing brand. I think it’s a phenomenal quick read, and it’s really insightful to see somebody talk about the inner workings behind the scenes of how things really happen in their business. It’s very authentic.

Gil: You’re intriguing me to pick that one up. I have a ton of partially finished books I’m in the middle of.

Jeff: It’s a quick read, but a good one.

Gil: The unfortunate thing about this podcast is that I ask that question every single time and I always get inspired, so I end up in this loop of not finishing a book and then buying another one. I’ve now learned that maybe I should just do Audible and consume a lot of it that way.

Jeff: You’ve got to do a little of both. I’ve started mixing, which is a terrible habit. I’ll read four chapters, then listen to another five, then read the next three. You’ve got to get it however you can.

Gil: Second question. What’s one piece of mindset advice you’d give to someone starting something completely new? I’m excited about this one for you.

Jeff: By this, do you mean starting a new business, or just starting anything new?

Gil: It can be either. If you want, you can go into parenthood and being a new parent and how you tackle that.

Jeff: All right, I’ll keep it business oriented.

I’d say there’s a question that doesn’t get asked enough, and I really believe it’s a threshold question for what you’re solving when you’re starting your business. Are you solving a problem, or are you solving an inconvenience?

A lot of people have great ideas, but they attack them without thinking through that question. I’ve started a lot of businesses other than HostGPO. I had a doggy daycare. I was part of a pharmaceutical consulting company. A bunch of others.

When you’re starting something, you have to be okay with failing, which is just part of this. But you also have to think through whether this is a problem people are having that they need your solution for, or an inconvenience you’re helping people with. That question is preliminary to determining which direction you should go, not just whether you should do it at all.

There are a lot of convenience products and convenience solutions out there, and those deserve a place. But people often get mixed up by going all in on trying to solve an inconvenience, or going half in on trying to solve a problem. Thinking through what your business is a solution for helps you determine, do I want to raise money for this? Do I want to go full time into this? Or is this an inconvenience thing where I should just let it grow organically? I think that’s a real question for founders to think through.

Gil: There’s another saying about whether you have a painkiller or a vitamin. A lot of folks focus on the vitamin side when they really should be focused on the painkiller side.

Jeff: Yeah.

Gil: Last question, Jeff. What’s one piece of tactical advice someone can put into practice today to either get started with direct bookings or amplify their direct bookings?

Jeff: I think we uncovered one here today together, which I wouldn’t even have said before as a tactic. Read through your messages. Honestly, you can even have AI do it and put it together. Read through the messaging to figure out why people are coming to stay at your properties, and learn from that which direction to go.

Maybe that’s, I somehow got 14 nurses and I didn’t even know that, because I haven’t been reading the messages, but their preliminary messages talk about being a nurse. Or maybe you add an intake question like, really excited to host you, what are you in town for? Along with the instructions and what’s going to happen. Pull that data from them.

One of the best ways to learn who to market to, who to reach out to, or who to build a relationship with, is from who’s actually staying there. I don’t think you need to custom build places out of the gate for one demographic. But if you’re not iterating on your place and thinking through who is currently here, what they’re doing, and whether you can find more of these people, you’re missing out.

Gil: That’s exactly why our AI site editor scans through all the reviews, because that’s one of the data points. Yes, we want to know how you describe your properties. We want to know what people are searching for on Google and ChatGPT. But we also want to hear who’s staying at your property, what they like, and why they choose your place over others. We’ve learned through many iterations what types of information you need as inputs for how you market yourself.

Jeff: A hundred percent. And that doesn’t just start there. People think you have to manifest and create this whole thing from the ground up and know exactly how it’s going to perform and what it’s going to do. Yes, you should think through those things and be intentional, and you could probably get pretty close. But if you really want to go from good to great, that requires taking a hard look at the information in front of you and constantly pivoting and readjusting.

Gil: Jeff, it was a huge pleasure to have you on here. I’m so happy we went down the little rabbit holes we did throughout the conversation. I appreciate you sharing your experience and why you chose to go down this path the way you did.

Jeff: I really enjoyed being here, and I appreciate you taking the time to talk about this and help educate the industry overall. I’m a big advocate for people doing podcasts and educational content like this. A rising tide lifts the whole industry up. It makes everybody’s properties better and makes this industry stronger. So thanks for what you’re doing.

Gil: Where can folks find out more about you? How can they keep in touch?

Jeff: I’m pretty active on LinkedIn, so that’s a big one for me. Otherwise HostGPO, H O S T G P O, on all social media. Instagram, Facebook, X, the rest of it. It’s all over, and it’s all us.

Gil: You own that brand, you own that name, everything.

Jeff: Those are the best ways. Or feel free to reach out if you have a question or want to chat. I’m always happy to connect with people and happy to help people out on their journeys.

Gil: And you’re going to be hosting your annual pickleball competition at VRMA, right?

Jeff: Yeah, VRMA this year, international VRMA in Nashville, which I think is the first week of October. This is our third annual pickleball tournament. If you’re coming to VRMA, and if you’re not coming to VRMA you should be, it’s a couple thousand people and it’s great to connect with other operators. If you’re there, on the first day of registration, the afternoon before registration, we do a pickleball tournament where all the proceeds go to short term rental advocacy, the VRMA advocacy fund, and to Rent Responsibly, who do a phenomenal job advocating for fair legislation and making sure the hotel lobbies aren’t having their way with our regulations. It’s an important thing for the industry, and we love doing it. So that’ll be happening and I’ll be there, pickleball paddle in hand.

Gil: I love it. If I were a pickleball player I’d join in, but I’ll definitely be there just to watch.

Jeff: All levels are welcome, and there’s usually a lot of beer too, if you’re into that.

Gil: There’s something about embarrassing myself in front of all my peers.

Jeff: Now I’m going to make sure you play. You’re on my team. We’ll have some fun.

Gil: Okay, we’ll make it happen then.

Jeff: Awesome.

Gil: Awesome, Jeff. Till next time.

Jeff: All right, take care.