I sat down with Akshay Bajaj, a former AI engineer who spent over a decade building systems for self-driving cars and aircraft autopilot before turning that same expertise toward his own short-term rental portfolio. Akshay walks through the exact moment he realized property management had the same core problem as the robotics he’d spent his career solving, and how that insight led him to build an AI system that handles guest messages, vendor coordination, and dynamic pricing while knowing exactly when to hand a decision back to a human. We get into why most property management AI is really just glorified auto-replies, how his platform’s “ask before act” approach protects the guest experience, and where he thinks the short-term rental industry is actually headed over the next few years. If you’ve ever felt like self-managing a rental gave you cash flow but took away your time, this conversation gives you a real framework for getting both back.
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I’m Adrienne Green, and today we’re here with Akshay Bajaj. Akshay is a great example of someone who broke free of the grind, and he’s made a tool to help everybody else do that too. So I’m excited here. Akshay, thank you for joining me.
Thank you for having me, Adrienne.
Before we get into the tech stuff, can you start by giving listeners a quick picture of your real estate background? Because you’re not just a tech founder, you’re an investor yourself.
Yes, that’s how I actually started. I was in tech building AI for more than ten years for robotic systems, not for real estate at all. But while I was doing that, I also started my own Airbnb, because in my own journey I found that freedom is the most important thing to me. And the first way I could actually start comprehending how to get freedom was financial freedom. So I started investing in real estate, living in Las Vegas, the hospitality mecca of the world. Thought it’d be great, and actually it went as planned: 92% occupancy and more. I kept increasing prices, things were going good. And then I scaled up to quite a few listings to actually get my freedom back. That’s how I experienced it, because when you start as a new Airbnb short-term rental owner, it’s deceptively taxing. We don’t realize how many small things go into not just the day to day, but also the setup of the listings and finding the listings. So I found all of that out myself, learned the hard way.
Also, just for background, my dad, although being a doctor, has been in real estate his whole life. He’s a developer, and growing up as a kid I helped him out a lot with his real estate business. So I know how the entire thing is built and all the small things that go into a property. And I’m a big believer that there’s a difference between a house and a home, and making every house a home.
And of course all the other things that go with it.
And I think we’ll get into a lot of it as we go through here. I had the pleasure of actually meeting and speaking with Akshay last week, so I know he’s got a lot that he thinks about, kind of like me. I think you think about every piece of the puzzle and it all fits together nicely. But if we get back to the cool thing you developed here: you were in your W-2 job working for someone else, working on the software for self-driving cars, for aircraft autopilot, and you applied it to vacation rentals. But as a vacation rental or short-term rental owner, what were you seeing on the operation side that made you think this is the same problem I’ve been solving on the tech side, and I could solve it here in the short-term rental side?
Absolutely. I actually gave a talk at UNLV, and the title of the talk was basically the same, which is “Are We Living Inside a Robot?” Fun fact, we still have not come up with a perfect definition of a robot that everyone agrees on. But in a way, the way we describe a robot is that it has actuators, which is like motors, arms, legs, whatever. It has a brain and intelligence, and it also has a way to sense things, which is what we call the sensing unit.
So I realized, okay, for aircraft, for self-driving cars, the things we’re controlling with the intelligence I’m creating are the final position of the wheels of a car, or a steering wheel. In this case, we have the same thing, but what we’re actually trying to manipulate or get control of is the people moving inside. Which is: when does a turnover happen? When does a guest come? What is it that we’re telling the guests that will allow them to have an experience like we want them to have? In our case, the intelligence was missing. There’s no real estate platform which has any kind of built-in intelligence that allows this to happen autonomously. We have workflows, which is what we try in our stack: hey, at this time do this, at this time do this. But whenever you have anything that’s workflow-based, you’ve lost the human touch. It’s not organic anymore. It’s not calibrated to you anymore.
That’s what I found: in a way, it’s the same problem, just the actuators are different. If I build an intelligence layer that has control over the things, it would be great. And the other examples of actuators would be the house temperature, the lock codes, the jacuzzi being on or off, the recommendations we give guests. And that is how, when I thought about the problem like that, all of a sudden a new world opened up.
Which is what now has become Host Easy.
So Host Easy is the name of the SaaS system you built. For people who are familiar with SaaS, but I know you like to call it something else.
Yes, it’s not SaaS, it’s FAS: Freedom as a Service. We are not software as a service.
Because you’re really about what you’re providing people, and that is freedom.
Exactly, because that’s what happened to me. Imagine, at one point I had about twelve listings. Eight to twelve, some were owned, and then I was controlling and managing about thirty-eight. Even at six to eight listings I realized I had no freedom at all. Because I wanted to treat my guests as God, as we say in India. I really wanted to give them a great hospitality experience. I wanted to be available at three a.m. when they wanted to get in the jacuzzi at night.
But also, it was taking away from everything I thought I would want. And that’s when I realized: I do not want to compromise on giving my guests an immaculate experience, but I also don’t want to give up on having my own freedom back. How do I come up with something that allows for both? And that’s why we call ourselves Freedom as a Service.
I love it, and that’s such a common challenge in the short-term rental space. People do short-term rentals because they want increased cash flow, so they’ve got financial freedom. But then they find that if you self-manage to get that cash flow, you don’t necessarily have time freedom, because you now have to provide a lot of service, and that could be twenty-four hours a day. So you came up with Host Easy, Freedom as a Service, to help solve that problem. You can self-manage and keep that financial freedom, but it helps with a lot of the time pieces so you can get the time freedom you’re not often getting with self-managing. Is that a good summary? Am I understanding that right?
Yes, that’s one part of it. We do take over all the operations, end to end. So ninety-one percent of the work is done by AI.
But you don’t just get an AI platform like any other PMS. First of all, it’s a different PMS altogether. AI is literally doing the work for you, not just following orders. But you also get a team of people available twenty-four-seven, not just for the guests but for you as well, within five minutes, taking care of the nuances whenever something goes wrong. So you really can be hands-off if you want to. But the other thing is, because AI is so good at data collection and processing data at a tenacity humans can’t, it also gives you financial freedom in the sense that sometimes listings aren’t going to make as much money. So Alfred also changes your strategy for pricing, for minimum stay, everything, like a revenue manager does. On top of that, it gives you a prediction of what you’re going to make in the future or not. So when you look at it, you really know whether this listing is going to give you financial freedom or not, while it’s managing it. And then it also takes over the operations to give you the time freedom, both in a single package.
Okay, so walk us through what a well-automated short-term rental operation actually looks like day to day. If somebody’s using Host Easy, they’ve got Alfred, who’s not a real human, but they also have VAs who are real humans on the back end. What’s the AI handling, and what’s staying with a human?
Alfred is really good at doing anything monotonous. It never sleeps, never forgets. So you don’t need to create a property guide or SOPs or anything like that. Alfred already knows the best ways to manage things. It learns everything from your listing. It actually analyzes every photo and looks at every amenity you have, and when it doesn’t know something, it asks you questions during onboarding. So now it has a full picture of what’s going on. It also talks to the cleaners, talks to the vendors, as well as handling your pricing. The only thing Alfred does not do is handle something that’s an emergency. It will notify you of the emergency, but rather than just handling it, it will message the guest to de-escalate, but it will let you handle everything else. It will give you a suggestion, because we understand that’s when the human touch is needed more. Any kind of nuance where it feels uncertain about information it doesn’t have, it pings the team or you and says, hey, I’m not sure if we have a baby grip. Before I reply, can you confirm?
And either you can reply yourself and Alfred remembers, or you can tell Alfred, yeah, we do have a baby grip, and it remembers forever. So it’s very accurate about knowing what it can do, but more than that, it really knows what it cannot do. And that’s our goal. Ask before act. That’s what it always does.
That’s a really good point, actually, because I know when I use Hospitable on my properties, I’ve used it for a year or two, and I have all their AI tools turned off. Whenever I try the “answer with AI” function and it drafts something, I usually think that’s wrong, so I don’t use it. I’ll use the “improve with AI” function where I write the facts and it makes it sound nice, but that’s still very labor intensive for me or for my VA.
Because if you think about it, you have to be on call. At two a.m., if you still have to improve the message yourself, you’re not hands-off. That was my main problem with these tools as well.
Right, especially when you have thirty-eight doors you’re managing. You could just guarantee something’s going to go wrong every few days with that many doors.
And that’s why we architecturally built it entirely differently. I’ve been building AI for more than a decade, since before AI was a mainstream thing. I know how to build a cutting-edge AI. It needs three things. For an AI to be like Alfred, it always passes tuning tests. A tuning test means you can’t tell whether it’s AI or human, and it’s not by chance. The way it works is that AI can only be as good as its access to three things. One, how much access to real-time information it has about everything.
That’s why we built a unified platform where Alfred knows about the last cleaning that happened, the last maintenance that happened, access to lock codes, access to the knowledge base, listing info, everything. It knows everything about everything, and that’s in real time. The second thing is how good the training is on that particular thing. That’s why we have human in the loop. It’s trained on industry-specific, hospitality-specific data. And then the third thing: now it has all the intelligence, all the training, and all the access to what’s going on. What it can do with that is integrations, and that’s why Alfred has access to the door lock. When a guest is locked out, it looks at the lock code, and if it’s not working, it unlocks the door, creates a new lock code for them, and sends it. This would be impossible for any other system out there, because they’re not unified like that. It actually contacts the cleaner or a handyman, because it can call them.
And message them and say, hey, can you please help out with that, based on the instructions you’re given. That is how it becomes a very different experience altogether. And that’s why when you look at Hospitable or other hosting companies, I see them as more of a glorified quick reply system. You’ve told it, for this situation do this, do this, do this, and then AI is doing “improve,” sending it based on the last thing. I don’t think that’s scalable.
No, and that’s where listeners who have short-term rentals and maybe got burned by the AI built into these other platforms, because they just do auto replies. You set up: when somebody messages about early check-in, send this message, but then it sends it when it’s not appropriate. Yours is a totally different, much smarter system. Now, Akshay, you said if there’s an emergency, it pings you. You also have an option within your program where somebody can have the AI and a VA on your team. Who’s helping with that person piece? What stays with the person piece?
We have something called supervision mode. If you want, you can turn on supervision for guest messages, vendor messages, or any action you want. You have full control. If supervision is on, AI knows what it’s going to respond, it drafts the message, but then waits for you, or our VA team, to accept or decline. When you accept, the message goes out as you, not as Alfred. If you decline, you or the VA rewrites it and sends it from there. That is the idea behind having a VA in the loop, human in the loop. On top of that, there are also actions. We don’t just do messages, we also handle day-to-day tasks, and that’s also our team of people.
We also handle guest disputes. We manage guest disputes for Airbnb and VRBO, and we’ve done it more than 10,000 times now, so our success rate is very high. You get all of that with one subscription, because to be honest, we don’t have the margins to give twenty to twenty-five percent to a property management company. You get all that work done as a flat fee model, like a SaaS software.
So it sounds like, and correct me if I’m missing pieces, Akshay, with Host Easy, whether you have it fully automated or you’ve chosen the human in the loop supervision mode, you’re handling all the day-to-day management of the property. Coordinating the cleaning, maybe a handyman, messaging guests, dealing with disputes. What are some of the other pieces that I as a property manager would still have on my plate? So my personal property manager VA would still be coordinating my twice-yearly HVAC inspection, correct?
Yes. There are certain actions, and the idea is that one action you set up is, say, twice-yearly HVAC inspection. Alfred will still trigger it, but you can assign that action to your VA. So it automatically comes to your VA’s desktop, your property manager. This action needs to be done. And that is how we go about it.
Awesome. So the nice thing being taken off the plate is the revenue management, optimizing the listing, handling all those guest messages, helping problem solve how to use the Roku TVs. Am I the only one where about once a month a guest doesn’t know how to use the TV because they’re used to cable? Those are the kinds of things host handles.
Yes, we also help with guest disputes, damage claims, coordinating with the vendors. When there’s a crisis, that’s the only time we don’t take decisions on your behalf, meaning how you want to handle the crisis. That’s where either a property manager or you would be there a hundred percent. We would still handle the back-end work, like communicating with guests, coordinating with the Airbnb support team. But you have to be the one actually calling the maintenance person and scheduling them. Once the schedule and payment are set, we continue with the coordination.
And what I love about this, Akshay, is I’m all about leveraging technology and a team. What I love is when technology can help a team do a better job or go further faster. So if somebody wants to work with a company like Workergenix and get a virtual assistant to be their property manager, they can partner that VA with something like Host Easy, and Host Easy can handle a lot of the day-to-day communication. The virtual assistant can handle the bigger things. Right now my VA is handling getting quotes on new HVACs, because HVACs on oceanfront houses in Myrtle Beach die in about six to eight years. Ask me how I know. That’s something my VA, the property manager, can handle better, faster, and easier when the day-to-day guest messaging is off his plate with something like Host Easy.
You’re absolutely correct. The nuances would always be there, to be honest. One more thing we’ve done is try to make the VA’s life easier as well, because I realized there would be days where everything across all the listings goes down at once, and that’s when the overwhelm happens and bad reviews come in. The way we’ve addressed that is we created something called Playground. It’s a tool set. So rather than a VA finding, say, an HVAC person manually, they can ask Alfred on the Playground, hey, can you find me HVAC people, and it gives a list of five to ten people. Now they can call, coordinate, and do the same work faster and more accurately. Same goes for finding other collaborators.
I love that.
And then we made inviting those people faster. You click invite, put the information in, and coordinate fast. That’s how we’re trying to streamline every single thing I personally came across as a property manager myself. The other thing is finding a good VA. That’s a very important problem as well, and that’s why we’re doing this partnership where you’ll soon be able to find a vetted VA literally on Host Easy. They’ll be VAs who are vetted by us, highly certified, incredible at what they do. No need to train them or teach them what needs to be done. They already know everything. You just do a vibe check interview if you like, and there you have a VA.
Yes, because if you talk to a few real estate investors, you’re going to run into a VA fail. For every five investors you talk to, you’ll probably hear at least one VA fail story. So as much as I’m passionate about helping investors lessen that, it’s a learned skill.
And also, you would know already how difficult it is to tell one good VA from another, because it’s the culture they have to understand, very intangible, beyond just the skills themselves.
That’s a very good point. There’s a lot that goes into it. Now, thinking about the automation piece, one of the fears people often have when we talk about automation and AI is the loss of guest experience. You’ve got Hannah the host, who thinks there’s no way Alfred the AI can provide the same experience she can, and she’s afraid she’s going to lose her five-star Airbnb rating if she uses this system. How do you think about protecting the human side of hospitality while the AI is handling the operational load?
To be honest, Hannah could be correct, because the way Hannah curates an experience might be very exclusive to her and her property. That’s why we give full control. If Hannah loves guest communication, she can turn that off for Alfred and let Alfred handle everything else. The good thing is, every time she’s doing guest communication, Alfred in the background is always learning. It’s learning how she talks, her communication style, what she says for different things. So if tomorrow she wants to go on vacation and turns it on, she knows Alfred is as in line with her as any system out there could be. Or she can turn it on with supervision mode, and in supervision she can make herself the supervisor instead of our team. Or if she wants more trust built first, she can make our team the supervisor. If she feels comfortable, she can turn off supervision mode. So you can go through it in baby steps, full control, and full transparency, because everything happens on one system, so she can see what happened. That’s how it becomes valuable for anyone getting into it.
And in that answer, even though we’ve spoken before, I learned something new about how your system works. What resonated with me is, as a former teacher who’s also in the virtual assistant world, half of the job is training the client, the employer, how to work with the VA. One of my main frameworks is I do, we do, you do. And that’s really what you’re allowing to happen with your system. I do is like Hannah turns it off and does it herself, but Alfred is monitoring and learning. Then there’s we do, with supervision mode, where Alfred is doing some things and she’s supervising. And then there’s you do, where she has trained Alfred and he can run on his own. That is a standard teaching model for handing off control, and you’ve built that into your system.
Absolutely. That’s why we say we’re not an automation platform, we’re a symbiotic platform. Humans and AI together doing the work for you, end to end, twenty-four-seven. And Hannah might not like numbers, let’s be honest, so give Alfred the dynamic pricing, give Alfred the revenue management, maybe the turnover.
You can hand that to Alfred. Because at the end of the day, what is hospitality? Hospitality is serving the people who are guests. So I want to serve, and I have my own idea of how I want to serve them. I don’t want to take that away from you. That’s the thesis Host Easy is built on. We truly make hosting vacations easy. Host Easy, that’s the idea.
At what point in a portfolio does it make sense to invest in a platform like Host Easy, Akshay? Is this a tool for someone with two properties, twenty, or two hundred?
We don’t look at it in terms of how many properties, we look at how much freedom you want. We have hosts who just don’t want to do anything. Right now their only option is giving fifteen to twenty percent of revenue to a property manager with no transparency, no visibility, no control, because they do it their way. Instead of that, you can use Host Easy, fully managed, and there you go.
Or we have property managers with thirty, fifty, eighty listings. They really need something like that, because they’re running what we call a Franken Stack. Now you have one tool for finding cleaners and paying them, another for ticketing, a PMS for channel management, another for dynamic pricing, another for guest verification, plus Notion, Google Docs.
Yes.
Passwords, training VAs, all of it. Everything is on one platform, and they love that idea, because once you’re past twenty properties, it just makes sense. Everything is here, Alfred is in the center, and I just tell Alfred and it updates everywhere. It’s a different experience.
It’s funny you use the term Franken Stack, because the very first place I ever heard the term “tech stack” was at a short-term rental conference. This guy got up and said, I’m going to share my whole tech stack, and I thought, what’s a tech stack? Then he started sharing all these tools he uses.
That’s a lot. That’s how a lot of short-term rental operators are in this space, and it really is a Franken Stack. Then the connections between tools break and stop working, because one of them updates and you have to redo the connection. I feel like any short-term rental person listening probably has some experience like that.
And not even just the connection. Forget about having ten logins, we can make do with that somehow. But imagine all of a sudden you want to take the pool off your listing because it’s too much hassle. Now you have to change it in your quick replies, on Airbnb, remove the amenity, then in your property guide, then in Notion because that’s what your VAs use. You have to change it everywhere. And still, you don’t know if something is missed. Your VA might say one thing, and something else might be listed elsewhere. Your vendors might know a different thing altogether. It doesn’t scale like that. Here, because everything is in one spot, in our case, Alfred, we don’t do pool anymore, update everywhere. It updates the listing, updates the knowledge base, tells the guest the same thing, tells the vendor the same thing, and it also updates pricing, because now it knows that’s not one of the amenities you provide anymore. It becomes super simple.
I love it. Now I’m curious, Akshay, because you’ve got your ear on the ground in the short-term rental space. With this asset class, what do you envision for how it’s operated and run now? This space has changed a lot since 2019, 2020. It got pretty hot, we’ve had some markets go up and down, but the key question is, three to five years down the road, what do you think the market and the operations ecosystem will look like?
I believe the ecosystem is finally going to look like the way we always imagined it, which is: the more human experience you can create, what we call high touch in hospitality, the more you’re actually going to get the earnings. So it’s not about automation anymore, it’s about how much human experience, how good of a custom curated experience you can create, how tailored you can be.
That’s what we’re doing with Alfred and Host Easy. Because it has full control over every single part of your house and your listing, we want to allow it to create an experience for your guest that would be almost impossible for us to do at scale otherwise. And that’s what I believe the ecosystem is going to move toward. You’re already seeing that. If you look at short-term rentals, there are properties worth 200,000 to 300,000 dollars that are making returns like 5-million-dollar properties, because it’s an experience. It’s a tent in the middle of nowhere that just looks a certain way, with some kind of guidebook. That’s how I see it becoming. And one thing I think a lot of people aren’t talking about, and everyone with a short-term rental should be careful of, is that Airbnb, the biggest marketplace, now also shows hotels. So you’re not isolated anymore. You’re actually competing with fifty-dollar-a-night prices. What can you provide? It’s a very specific kind of customer you’re looking for, so you have to position your property accordingly.
I think we have to point out that the guy who’s here with his AI-forward solution thinks the future of short-term rentals is high-touch, curated human experience. And that so much resonates with what I see across the board, where in all these different industries we’re seeing people crave human interaction, face to face, as real life as possible, so we know it’s not fake, so we know it’s not AI. My kids are better than I am at spotting AI on Instagram, saying that’s AI, that’s AI. It’s tricky now, but people are craving those real, authentic experiences that aren’t contrived, and what I love is how you’re using technology to facilitate that human connection and great human experience.
Yes, absolutely. I truly don’t think you should use technology unless it’s needed. Although I’m a technologist myself, I believe in experience first. We are the most human AI company. It was actually a big deal as a new startup to take a stand and say, we’re going to provide a human team as well. Because the whole point of SaaS is, why would a company run humans? Because humans reduce your profit margins and your scalability. But we’re like, no, if you want to change the world, start by changing a house. You want to make a world that’s more experience centric. Let’s start from where we’re going. And if you can create a great experience through human connection, it will pay dividends. That’s how I believe.
So Akshay, if people would like to connect with you or learn more about Host Easy, what’s the best place for them to reach out?
You can go to our website, which is hosteasy.ai, and you can sign in and onboard your property yourself. Alfred will help you onboard the property because it learns everything about your listing the moment you add it as a co-host. Or you can set up an onboarding call, and we do all white-glove onboarding end to end at no extra cost. If you want to get in touch with me, I’ll share a LinkedIn link. Happy to connect. Any ideas, let us know. We’re always listening first, trying to know what your pain points are and fixing them for good while maintaining the experience. That’s our goal.
Love it. Well, thank you so much, Akshay, for coming on and sharing your experience as a short-term rental investor and how it prompted you to develop Host Easy and solve all the problems you had. And for our listeners, that is a wrap on today’s episode. If you got value from this conversation and you know somebody who needs Host Easy, do me a favor, do Akshay a favor, and send this episode over to them so they can take a listen or a watch. And join me again next week.