From aerospace engineer to acquiring four boutique hotels in just 12 months—Harshad Lalan’s journey proves that systems thinking and strategic boldness can transform your short-term rental business.
In this episode of the Booked Solid podcast, Harshad shares how he and his wife Ishita scaled from zero properties to a thriving portfolio by combining her design brilliance with his analytical systems approach. He reveals how they jumped from less than 1% direct bookings last year to over 30% this year, his framework for using AI to streamline everything from listing creation to hotel underwriting, and why surrounding yourself with the right people accelerates growth faster than any spreadsheet analysis ever could.
Whether you’re just getting started or ready to scale aggressively, Harshad’s honest take on overcoming “analysis paralysis” and building delegatable systems will give you a new perspective on what’s possible.
Summary and Highlights
👤 Meet Harshad Lalan
Harshad Lalan is a hospitality entrepreneur, boutique hotel investor, and co-founder of 5 Seasons Homestays and Ishita Interiors alongside his wife, Ishita. With a professional background in aerospace engineering and systems design—plus experience as a licensed pilot—Harshad brings a unique analytical perspective to the short-term rental space.
Together, the couple has built a portfolio of high-performing, amenity-rich properties across the U.S., transforming ordinary homes into what Harshad calls “Super Properties.” His engineering mindset drives everything from operational systems to guest experience optimization, while Ishita brings the creative soul that makes their properties stand out in competitive markets.
Connect with Harshad:
- Instagram: @harshad.lalan
- Company: 5 Seasons Homestays
- Ishita Interiors: @ishita.interiors
🚀 The Journey: From One Property to Four Hotels in 12 Months
Harshad’s path into short-term rentals wasn’t overnight success—it was methodical growth built on deliberate systems.
Starting in 2017-2018, he and Ishita acquired just one property per year for the first two years. The process was cautious: Harshad spent nine months searching for their Destin, Florida property, meticulously checking ROI goals, distance from the beach, and amenities before pulling the trigger.
By 2022, everything changed. With systems in place, confidence built through experience, and a team supporting operations, they accelerated dramatically. This year alone, they’re acquiring four boutique hotels—large investments that would have seemed impossible just a few years ago.
What made the difference? According to Harshad, three critical shifts:
Risk tolerance evolved. Early on, limited resources meant every decision carried enormous weight. Now, a diversified portfolio provides cushion for bolder moves.
Experience compounds. Multiple iterations taught them what success looks like—and more importantly, what warning signs to catch early.
Community accelerates growth. Joining a boutique hotel mastermind connected them with lending options, partners, and expertise that shortened their learning curve dramatically. As Harshad noted, the mastermind fee felt steep initially but proved to be the best investment they ever made.
If you’re considering joining a mastermind or coaching community, Harshad’s experience validates that surrounding yourself with people who’ve already achieved what you’re pursuing can collapse years of trial and error into months.
📈 From Less Than 1% to 30% Direct Bookings
Perhaps the most striking transformation in Harshad’s business this year has been his direct booking strategy. Last year, direct bookings accounted for less than 1% of revenue—essentially just the occasional repeat guest who happened to remember their website.
This year? They’re sitting at 25-30% direct bookings.
The shift required a complete mindset change. Rather than treating direct bookings as a passive bonus, Harshad built a cohesive strategy around two distinct approaches:
Capturing OTA Traffic Through Brand Recognition
Every listing title now follows a specific format: property name + “by 5 Seasons Homestays.” Instead of cramming amenities into the title like most hosts, Harshad prioritizes brand visibility.
Here’s why this works: Airbnb titles become H1 headers on property pages, which means they get indexed by search engines. Over time, guests searching for unique property names or “5 Seasons Homestays” find the direct booking site instead of returning to Airbnb.
The descriptions reinforce this branding—mentioning the management company name throughout. It’s subtle, but these small nudges add up.
When guests do land on the direct booking website, they immediately see how much they’re saving. Right beneath the booking total, a direct comparison shows savings versus Airbnb pricing—often $700 or more. That visual confirmation removes hesitation.
Acquiring New Guests Through Influencer Marketing
The second strategy targets people who haven’t discovered them through OTAs at all. Harshad works with regional influencers near their properties, inviting them to stay and create content.
But here’s the key: the goal isn’t immediate bookings. Instead, influencer content drives traffic to landing pages designed for email capture. From there, they nurture leads through targeted campaigns.
When local events approach—like Oktoberfest in Asheville—they email their list with available properties for those specific dates. Since many guests book last-minute (especially post-flood in Asheville), these timely triggers fill occupancy gaps without requiring price drops.
This approach mirrors what successful hosts like Lindsey Rodriguez recommend: building email lists as assets that generate bookings on demand, rather than relying entirely on OTA algorithms.
🤖 Using AI to Systemize Everything
If there’s one theme running through Harshad’s operations, it’s systematization—and AI has become his most powerful tool for achieving it.
Listing Creation in Minutes
Creating property listings used to consume hours of careful writing and formatting. Now, Harshad uses a custom GPT trained on his preferred format, word counts, and platform requirements (Airbnb, VRBO, Booking.com, and Hostfully).
His process? Open the custom GPT, dictate a voice note describing the property—bedroom count, location, design inspiration, key highlights—and receive a complete, formatted listing within seconds.
As he explained during our conversation: rather than thinking about structure and content simultaneously, he separates the creative stream of consciousness from the formatting process. The outcome? Better listings, faster.
Hotel Underwriting With AI Assistance
Boutique hotel underwriting involves complex spreadsheets projecting multiple years across multiple units. Traditional tools are often buggy, with macros that fail unpredictably.
Harshad’s solution: upload the underwriting format to AI, provide prompts, and let it perform initial checks and balances. This doesn’t replace due diligence—it accelerates the screening phase so he can quickly identify which deals deserve deeper analysis.
This mirrors the approach many experienced investors use: AI handles the middle step between initial interest and detailed evaluation, filtering opportunities worth serious attention.
Review Responses and Guest Communication
Custom GPTs handle review responses, while Host Buddy AI manages guest messaging. VAs review AI-generated responses before sending, maintaining quality control while dramatically reducing time spent on repetitive communication.
At night, when no one is available, the system switches to auto-mode—ensuring guests receive prompt responses regardless of time zone.
Training Teams to Think AI-First
Perhaps most importantly, Harshad trains his entire team to approach problems with AI as the first resource. Their framework:
- Search Notion (where all SOPs and property knowledge live)
- If nothing exists, ask ChatGPT
- Only then escalate to the operations manager
This reduces interruptions, builds team independence, and creates a culture of resourcefulness rather than task-following.
🧠 Overcoming Engineering Brain: The Mindset Shift
Here’s something Harshad shared that surprised me: his engineering background has actually been a hindrance in some ways.
Engineers are trained to analyze exhaustively, verify everything, and avoid uncertainty. But entrepreneurship often requires acting before you have complete information. The “analysis paralysis” that plagues many new investors? Harshad lived it.
His solution: actively unlearning that analytical default. Instead of requiring certainty before taking action, he now commits to decisions faster and trusts that problems can be solved as they arise.
The engineering mindset still helps—once a decision is made, he knows exactly how to systematize execution, track KPIs, and optimize performance. But getting to the decision point required embracing calculated uncertainty.
For hosts stuck in endless research cycles, Harshad’s advice resonates: “Getting in the game is more important than getting it right.”
🛠️ The Tech Stack Behind the Systems
For those wondering what tools power Harshad’s operations:
- PMS: Hostfully
- Documentation: Notion (all SOPs, property details, knowledge base)
- Project Management: Motion (AI-powered, with automatic meeting notes and action items)
- AI Tools: Custom GPTs for listing creation, review responses, and underwriting analysis
- Direct Booking: CraftedStays for their direct booking website
- Guest Messaging: Host Buddy AI
His philosophy on tech: document everything now, because AI integration will only deepen. The operators who’ve captured their processes, property details, and guest interactions in structured formats will be best positioned to leverage future AI capabilities.
❓ Rapid Fire Questions
What’s a good book recommendation?
Harshad admits he doesn’t read many full books—instead, he uses Shortform to get summaries each morning. His recent favorite: The One Thing, which reinforces focusing on single priorities rather than spreading attention across ten competing tasks.
What’s one mindset tip for someone starting something new?
“Don’t chase perfection. Getting in the game is more important than getting it right.” Harshad reflects on his early days spending nine months searching for the “perfect” property. While that caution made sense with limited resources, he now recognizes that speed of execution often matters more than perfection.
What’s one tactical tip for direct bookings?
“Don’t waste time building a WordPress site from scratch. Tools like CraftedStays let you set up a direct booking site in seconds. Focus your energy on lead generation and marketing—not technical website development.”
🎧 Ready to Scale Your Direct Bookings?
Harshad’s journey from analysis paralysis to acquiring four boutique hotels in 12 months proves that systems, community, and strategic boldness can transform your short-term rental business.
The direct booking strategies he shared—brand visibility in OTA titles, price comparison displays, influencer-driven email capture, and event-triggered campaigns—offer a practical framework whether you’re managing one property or one hundred.
🎧 Listen to the full episode to hear Harshad’s complete story, including how he and Ishita balance their complementary skills and what they’re planning for 2026.
Ready to build your direct booking website? Start your free trial with CraftedStays and launch a professional, mobile-optimized site in minutes—no coding required. Join thousands of hosts building independent booking brands and taking control of their guest relationships.
Transcription
Harshad: Short-term rental underwriting can be a lot more straightforward when you’re talking about boutique hotels. The underwriting is a lot more intensive, projecting over multiple years. You have like multiple units that you can add on. So the underwriting spreadsheet, if you have looked at like these commercial assets, it’s super complicated.
Harshad: Very buggy too, with macro, sometimes not working, sometimes not working out very well. So we are highly using AI for underwriting deals, so we upload. A format of the underwriting tool, give it some prompts and let AI sort of do the checks and balances and tell us what’s going on. Just as an introductory step, you still have to go later on and do your due diligence so you feel confident, but the underwriting has improved considerably.
Harshad: Wanting to use AI and building. G PT is just for analyzing properties.
Gil: Before we bring on our guests, I wanted to talk just a little bit about something that I’ve been hearing a lot from Host. I keep on 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 letting all these marketing strategies, you’re driving traffic and you’re putting it all to work.
Gil: 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 iterate, you can’t test, and you really can improve on things.
Gil: 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 build craft estates. 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 booking.
Gil: And you can keep on testing and improving. As you learn, you can make changes all on the platform. You don’t need to learn something new. So if you need some help or you wanna get started, go ahead and go to craft stays.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing.
Gil: Hey folks. Welcome back to the Booked Solid Show, the podcast we’re bringing top operations, discuss hospitality, operations, and digital marketing. On today’s show, I have Harshad Lain. He is a phenomenal person. I highly respect him and his wife, and how he’s able to grow his portfolio. Their portfolio.
Gil: They’ve started in the beginning of the pandemic and now this year they’re acquiring four boutique hotels in a span of 12 months. He’s also. Ramped up from going 1% direct bookings last year to 30% direct bookings this year. So he has a wealth of knowledge. He shares how he’s using ai, how he scales and train his team, some of the direct booking strategies that he has.
Gil: So I’m just thrilled to have him on. So without further ado, let’s bring him in.
Gil: Hey, Harshad, welcome to the show.
Harshad : Hello, how are you? Good to be
Gil: doing, I’m fantastic right now. It’s, it’s, it’s been really good this, this whole year, and I think Airbnb has helped us a little bit on ad craft this days that a lot of folks have been kind of gearing up and they’re looking at direct bookings a lot more now that Airbnb has kind of put a lot of pressure on hose.
Gil: So it’s been, that’s been kind of good for us from a silver lining perspective. Um, but yeah. How, how have you been?
Harshad : Uh, we’ve been very, we’ve been very, very good. Uh, 20, 25 has been thankfully, and b Blessfully a a, a great year to grow the portfolio quite a bit, uh, on, on various fronts. Would love to talk more about each of those.
Gil: Yeah, so maybe you could kick us off Harshad, give us a little bit of background on who you are, what do you do, where you came from?
Harshad : Absolutely. Well, uh, Harshad la uh, you know, my background is, uh, an engineer and even going back. It, I think, can resonate with a lot of people. I’m an immigrant in the country. Came here with a dream of wanting to study engineering, become an astronaut, uh, go through the rads of studying and, and education, and then finding a job, enjoying that nine to five and basically my enrollment into, into the wheel.
Harshad : And without even realizing that that’s what was happening, I was happy and comfortable in it. Uh, uh, had a pretty good life going up to it. And, uh, in about 20 15, 20 16, got married, tota. And that had a bit different trajectory to, to, to, to our life. And until then, I didn’t really have a lot of financial education.
Harshad : I wasn’t really thinking about it. It was like money in, money out, having fun with life, uh, going on trips and uh, and we were like, well, we start up. We need to have a plan for our life. And that’s when we started looking at. The nine to five, the, the salary is just not going to cut it. Uh, we, we, we spend so much time doing this, we need to do something else beyond that.
Harshad : That not only just helps us with our financial goals, but something fun too for both of us to do together. And this is back when short term rentals was just picking up Ista. She has the design background. I’m a very systems analytical person, so you’re trying to figure out what is a good match for the two.
Harshad : And short term rentals just felt like the right fit. It has that design and the creative element to it. There’s the analysis side of it, like where do you find property? Where do you invest, how, you know, how much money do you put into it? And systemizing all of it. So it just clicked for us. And, uh, we didn’t have a lot to start with, but we, we started with just partnering with a local realtor with one of, uh, uh, her long-term rentals and then doing short term rental.
Harshad : Management agreement on it, and we split the profits half and half. And uh, that allowed us to go in with confidence and see this is going to work for us. Save the money, reinvest it to the next property. It always takes a long time when you’re just starting when you don’t have a lot of capital to work with.
Harshad : But then it starts spit balling slowly and slowly. And, uh, going from one to two to three was hard, and then three to four to five gets a little bit easier and then it gets faster as well. So that’s, that’s kind of been the journey. Kind of where we are today is we have a good portfolio of short term rentals.
Harshad : Ishita branched out doing her own interior design, and she’s probably one of the best in the industry today.
Gil: All right, so Harshad, how, so you’ve grown your portfolio, it sounds like in the very beginning you had these one or three properties and those were like the hardest ones, and then thereafter it was a lot easier. What was that trajectory like? When did you start investing and when was like the first acquisition, second acquisition, like how slow was in the beginning and then how fast was it towards kind of the, the, the, the end or now?
Harshad : Yeah, absolutely. You know, it’s like. Every bold move looks risky until it works. It’s kinda like that mindset. So what happens is, in the beginning, we don’t know what we are doing. So we were not as bold. We’re like, okay, let’s take one step, make sure everything is okay, check like a hundred different boxes, and you, you’re limited with your resources too.
Harshad : So we started with our first short term rental in like, I believe 2017. Uh uh, 20 17, 20 18. I think it’s, it’s probably just just around COVID, whenever COVID was. So that’s when we got our first short term rental and we were just doing one short term rental every year for the first two years. And we were like, we want to be, you know.
Harshad : Making sure it’s the right property. I remember when we were looking for a property in Destin, north Carol, uh, Destin, Florida, that was like the location. We decided, I spent nine months looking for that perfect property that, that met the ROI goals that had the right distance from the beach, that had the right amenities and just very, very calculative on doing that.
Harshad : And that makes sense to do. Absolutely. If you’re just starting out and you wanna make sure that you have very limited resources. So it took a while to do that adding one or two properties every year worked until 2022. And then we said like, this is just going too slow. Life is not that long and you gain a lot more experience to, you have a bit more resources.
Harshad : So that’s where that boldness comes in. And the confidence also comes in with the systems that we had in play. We have done this a couple times. We have systems set up now, so then we started getting into like two or three short term rentals. In, in any one year. Uh, we also started partnering with people to kinda accelerate that quite a bit too. You learn through your process. Everything that we did earlier on was just, I want to figure it out myself. There was, there, was there, we were not part of any mastermind. We were not part of any coaching programs. Just being on social media, seeing what was happening, we were learning and doing, which was great, but it’s a slow process.
Harshad : I really feel joining the right group, the right and surrounding yourself with the right people, um, really helps. It becomes like a shortcut. So when we wanted to get into the Boutique hotel, I knew that I had to surround myself with people who want to invest in boutique hotels. So we looked at like two or three masterminds in the ne in, in the space, in the boutique hotel space, and we joined one.
Harshad : And that alone completely accelerated our trajectory. It may feel like a steep price to get in, but it is, it’s if you, in hindsight, is the best investment ever, I don’t think we would’ve gotten into four hotels in one year. And, and these are talking large investments in four hotels in one year, and we found lending options through the Mastermind.
Harshad : We found our partners excellent, amazing partners, uh, through those masterminds and just connections. So.
Gil: Wow. So I didn’t realize that you started pretty much at the beginning of the pandemic. So like, we’re thinking 20, 20 19, Feb, February, March
Harshad : 18, 20 19, I think when it was, yeah,
Gil: Wow. And you acquire, you’re acquiring four hotels in a span of 12 months. That’s That’s insane.
Harshad : it, it does feel insane. You know, when you look at just the numbers on surface, but you have to keep in mind it’s over the past few years, we now have a team behind us too. It’s just not me and she, so we have a entire design team, like know 10, 12 designers on the co-hosting side. I have multiple VAs.
Harshad : Pretty much everything is automated. So the goal wasn’t to like build another job for me, it’s, I’ve always had that system mindset, how can I offload it? So find something. Can we delegate it? Can we find someone else to do it? I have not been the best at doing it because of that control thing, and I’m not good at it.
Harshad : But the mindset is still there. So there are aspects of the business that we have been able to systemize or delegate, and there have been aspects of it that I still struggle with. Like, I, I really shouldn’t be doing this. I need to find a way to get it off my chest. But the point is that we have a team now, we have the systems in place, so taking on four hotels at and at at one point might seem like, holy cow, that’s, that’s too much.
Harshad : But when me and she can talk about it, like, I think this is doable. I think given the resources we now have, uh, in, in know, uh, with us, this doesn’t seem as bad, uh, to undertake all that at the same time.
Gil: Yeah. I think about this a lot when I had a very similar situation with you where when we acquired our first property, we took basically almost a full year in until we acquired our second property. But then it was maybe six months, five months until we acquired our third property. So it was like, it was shortened.
Gil: And I think when I went into it, I had the mindset that we had to have this feedback loop to help validate what we’re doing is right. And we wanted that full cycle in order for us to scale. But we got to a point where we’re like, oh, I know how to run the numbers. I know what to look for. I already built the team.
Gil: I already built the system in place. That third one was very, very easy for us. We knew who we wanted to hire to bring in to design the place, to stage the place. We had all of that kind of written up. And I, I imagine it’s somewhat similar for, for you, where in the very beginning you’re doing everything yourself and you’re like, oh, like I need to make sure that this is working because we put our life savings in
Harshad : Mm-hmm. Absolutely.
Gil: don’t want to double down on something that could not be working. I’m, I’m interested in you, like, did you have the same kind of feeling where like you had that feedback loop in the very beginning in order for you to trust the system. And it seems like almost you’re now at a point where. You’re acquiring four hotels, you have a very different frame of mind of deciding whether or not this is the right investment vehicle.
Gil: Are we doing the right things there? Is that, is that right?
Harshad : Yeah, absolutely. So it, it, it’s, it’s the risk scale, right? So, like you said, when you’re big, when you’re starting out, you have limited resources. So you are on the higher spectrum. If, if something goes. Not like you plan it and you’re risking everything into it, so you’re really afraid. It’s like the fear of doing meaningful, meaningful work at the time.
Harshad : So you’re really afraid of taking those bold steps. When you start then having a portfolio, the mindset automatically shifts where it becomes easy to take on these bold steps. What happens is like, okay, I’m gonna go into this, but I don’t have to spend six months trying to make sure this is going to exactly work.
Harshad : Because even if it doesn’t work, I’m okay. I can float it for a while and, and take an action. Uh, and there’s always that exit strategy in mind. If it’s, if it’s not gonna work, I can also sell it. I can do something else with it. But more than anything else, the confidence really comes in. You know, people say, like, when people look at it, it’s, it’s success.
Harshad : It’s, it’s, it’s in luck, success is in luck. It’s like reputation, it’s reflection. It’s like system that have been built over time and then. When it all kind of combines together, it starts looking like, wow, this, these guys are just getting lucky with more and more deals, you know, but people don’t see the backward that has gone to get to that point.
Gil: Yeah, there’s a few things I, it, it sounds like the more recent I would say like quote, quote unquote, success is really around like your risk tolerance Now you’re not banking your life savings on this is a much smaller amount in terms of your overall. Net worth at
Harshad : Net worth. Mm-hmm.
Gil: Um, two, you’re, you’re talking about many different iterations there.
Gil: Um, which, which you can think of it as like many different experiences of things you learned, things that went well, things that didn’t go well, so you have a much higher sensitivity to knowing what, what, what, what looks sour very early on. And then three, it sounds like you also are surrounding yourself with folks that will help you take risks because you know that they’ve done it.
Gil: They’re guide, they’re guiding you along the way, so you don’t feel like you have to have this 12 month of analysis and figuring out, like, okay, this first year was good. We can repeat this year after year. No, you, you can reach out to your peers in this space and they’re guiding you on it. If that feels like, kinda like the, the three pieces that I’m picking up of, like, what allowed you to scale so quickly in the more recent time.
Harshad : Yeah, you Absolutely. I think you touched on all three. Exactly. The fourth thing I don’t think really talked about, but I, I was thinking about, I just said it is the. The growth in technology as well. Like for example, like creating a direct booking website even five years ago would’ve been like going on WordPress, trying to start from scratch, trying to figure out how I’m gonna get my reservation data and all that figured out.
Harshad : And I know, I’m sure we’ll talk more about it, but like today, if I wanna create a direct booking website, I can just go to crafted space one click and I have it set up. So I’m just talking the time savings of it too. And we haven’t talked about everything that’s happening with AI today. So our systems have like anything that we wanna build today, it takes one 10th the time it used to take doing few years ago.
Harshad : And not only just doing the process, but the thought process behind it too. So it just like letting this new technology and absorbing it. Try to implement and incorporate that in the day to day. That is that fourth component as well. That’s like, okay, I can do the same things that I used to take me days doing.
Harshad : I can get them done in one 10th at a time,
Gil: Yeah. Yeah, yeah. And, and that, I think that that’s more of like, like an external factor. Nothing like you personally went through to kind of put this in yourself, but we’re now at a really great place to be alive and to be able to see how AI is changing. And we’re almost creating this separation of what I’m seeing kind of in, in both the workforce, but also out in the wild where you have these really skilled people that are thinking about how to leverage AI in very effective ways.
Gil: And even people that are like being very innovative and thinking about how do I stitch multiple things together so I’m not just using some chat interface. And then you also have folks that. Are kind of at the status quo. So you’re starting to see this divide, and I think that a lot of folks now that are investing into like growing learning and really trying to utilize AI to grow their business, those are the ones that are really starting to separate themselves.
Harshad : Absolutely. Yep.
Gil: Given, given that I, I, I am interested in hearing some of the use cases that you guys, you folks have utilized AI in, in your business and how it has helped you scale.
Harshad : Yeah. So, uh, we are starting slow, I think, you know, in terms of what all AI can do. Uh, I’ll talk a little bit on the co-hosting side of things. So everything from responding to reviews, everyth, we have a custom GPT that’s been created. So every time we have to respond to review our VAs, just plug it in, they know exactly what to respond and goes back out.
Harshad : We use the host buddy for host buddy AI for responding to messages and even though we have someone. Actually physically replying the host body creates the messaging, and then they make sure everything is still okay. We wanna still make sure that AI responses are not completely invalid either, so you’re still gaining that trust, building the knowledge base so that it’s, it gets better and better over time.
Harshad : So, uh, and then in the nighttime, if someone’s not available, it’s set up on auto mode, uh, listing creation as well. So we have a custom GPT created that we have put in all the restrictions in terms of the word count, the type of format that we like to see for the short description, the long description, the note section on Airbnb, and it’s combining restrictions from VRBO Airbnb booking.com for each of those fields.
Harshad : Uh, I use hostful as my property management system, so I just, that custom GPT just has those requirements in so. I’m actually, if see in my background, I’m working on a new listing. We are going on live today, so the time it takes to create the listing description has gone down considerably. Today I just open up my GPT, I literally say, just voice note, this is a eight bedroom, five bedroom property in actual, these are the amenities.
Harshad : I think this listing has a, um, has been inspired by the Biltmore. It’s got an electric forest background, and these are the highlights that I want to have just overall notes of as I know about the property. And that’s my one sentence that I put in and it generates the entire listing in the format that I like so
Gil: you, right? I’m gonna pause you right there because I think that’s really interesting. I find that the way that you’re using AI is probably one of the most powerful. Ways to use AI where you’re having a almost a stream of consciousness, thought about what you want to say, how you want it to be represented, but you’re not thinking about how to write that in the format.
Gil: That’s a separate process altogether. So you’re having that conversation and then it takes your custom GPT and it knows the format and how you want things to be structured there. And it bridges that because if you probably remember back before, maybe like a year ago or maybe a year and a half ago when you had to write that, you’re writing it out, uh, and you’re writing it out very carefully, both thinking about structure and the amenities at the same time.
Gil: And I bet you now probably the outcome is better using this new method than it was before.
Harshad : A hundred percent. Yeah. And, and that is just one aspect of just co thing that most people can relate to as well. Right? So, uh, even on the underwriting side, the hotel underwriting or short-term rental underwriting can be like, I remember using spreadsheets where we have to go in, plug in a bunch of things.
Harshad : Short-term rental underwriting can be a lot more straightforward. When you’re talking about boutique hotels. The underwriting is a lot more intensive. You are, you know, projecting over multiple years. You are, you have like multiple units that you can add on. So the underwriting spreadsheets, if you have looked at like these commercial assets, it’s super complicated.
Harshad : Very buggy too. With macro, sometimes not working, sometimes not something. You know, working out very well. So we are highly using AI for underwriting deals. So we upload a format of the underwriting tool, give it some prompts, and let AI sort of do the checks and balances and tell us what’s going on. Just as an introductory step, you still have to go later on and do your due diligence so you feel confident, but the underwriting has improved considerably wanting to use AI and building those, um, gpt just for analyzing properties.
Gil: The way I think about, it’s like when we’re doing a long-term acquisition, you have like the 1% rule, does it pass the 1% rule? Then you start to move into like the in-depth analysis and then you go into your long form, multiple tabs, spreadsheets, you’re, you’re thinking about what the upgrades can be, how much that’s gonna change your rent and all that stuff like that.
Gil: Then you go that, but it sounds like that middle portion there where it passes your sniff test, this is something that’s worth diving a little bit deeper. You’re having AI do this and then you have a follow up step afterwards where you’re still doing the manual parts yourself, maybe using some sort of augmented like AI to help augment the process there.
Gil: But that second middle step there is like now completely given to an AI to, to do. Is that right?
Harshad : Yeah. I, I mean, you know, it’s just, I, the steps you mentioned are exactly right. Is, is where, what I wanna touch base on is the mindset of it and just, I feel like if businesses today are not going to incorporate AI in their processes, they’re gonna be left behind. And it’s not only the mindset of the owners and the people that are leading, but like trying to impose that, not impose that, but encourage your employees to also do it.
Harshad : So when it, for, for My VAs, we literally went through this training last week where I. Any problem you’re approaching, anything that comes up first, everything is in notion for us and Notion AI as well. So anything comes, they type in in notion they search for it. If there’s an existing standard operating procedure for it, that’s also then coming up through Notion ai.
Harshad : If they don’t find something, then they go on to Chad GPT and they try to find, how do I fix an HVAC for this model number and something comes up or not. And then if those of both of those things don’t show an answer, then reach out to your operational manager. So that has reduced the number of interruptions turn to make them be more independent and not just be like task drivers, but bringing about that mindset change where you have to use AI for everything that you do today.
Gil: Yeah, it’s almost like a, a part, like one, knowing the tool sets and really training up the team, but also creating this culture of this ownership mentality where people are owning the problem. They’re not just like cog in the wheel spinning things and, and processing things or trying to figure out like how do you solve these things and being more resourceful with it.
Harshad : Absolutely. Yep.
Gil: Yeah. That, that’s, that’s, that’s super interesting. Y you mentioned some tools that you’re using open ai, you’re using Notion. I haven’t used Notion too much. I might want to kind of dive a little bit deeper into kind of how you’re, you’re structuring that. Have you used. Comet or or perplexity Comet recently at all.
Harshad : I have not, I’ve heard of those, but I have not. So I feel like today, I, uh, every individual software is coming up with their own AI version, like QuickBooks, ai and then, you know, host, host body had its own ai. Every little thing, they’re incorporating AI into it, and I feel it. It’s all like segmented in their own separate thing.
Harshad : And I don’t know if you, I just heard, uh, open AI’s recent announcement where they could look through all the apps on your phone and they can talk to each other under the umbrella of OpenAI and, and like, holy cow, if I can just go in and say, do this one thing, it’ll go on Google and find something, it’ll go to host Hostfully or whichever app and find something and connect all of it together.
Harshad : I don’t know where that’s going to go. So my intention is to dump as much as I can and document as much as I can. So notion is where we document all our process, the knowledge about all of the properties, you know, everything from how many bedrooms to like. Small, little quirky things. Where is the, uh, the safety, safety box kept in this particular home?
Harshad : Every single system is in notion, uh, for project management. On the design side, we are using something called Motion with, with an M, and that is also completely built on ai. Every meeting gets recorded. The, the action items are created automatically. The notes are created automatically. Uh, so we are, we are trying to make sure that everything that we do is captured today, because I can envision a world where it’s going to be where you just say what you wanna do and it’s going to integrate with all these different apps and figure it out faster than you can.
Gil: Yeah, I, I definitely see that coming. I think with one, I think that there’s like two framework pieces that I think that that’s gonna start to come together and we’ll see more and more of that. It’s like, one is the integration where now these LLMs can talk to different systems more fluently. There’s this concept of MCP.
Gil: I don’t know if the, our listeners here are, are quite geeking out at that level, but MCP allows basically an LLM to get access to information. So there’s like a chat, GPT notion, MCP, where in chat GPT, you can ask it things about notion and it’s able to go draw
Harshad : Go ahead and pull this in.
Gil: And that’s basically MCP. And I think OpenAI just announced their app framework, their SDK, that allows people to build experience apps inside chat, GPT.
Gil: So that’s interesting. I think that layer on top of context and data about your business, all your different, think about all your clients that you’re working with, all the properties that you, all of that you’re doing a very, very, very good thing of like documenting everything. Because if you have all the integrations, but you don’t have your SOPs, you don’t have all the details of your properties, your clients and all that stuff, it’s not gonna be able to answer things at the depth that you want it to.
Harshad : Yep. Yep.
Gil: I think, yeah, I think that those things are, are really gonna, like you’re setting yourself up for lots of good successes in in
Harshad : yeah. And, and, you know, documenting today has become so easy. It’s, it’s so easy to capture every meeting. You don’t have to do anything. You just have to have a note taker, go in and record everything you are doing every single meeting and voice notes, just, just talk what you wanna do and it’ll create the notes for you.
Harshad : So I just feel like it’s made life so much easy to capture everything.
Gil: Yeah, there’s a, there’s been a few times where I would have an idea ideation session, uh, with either a client of ours or a team member of ours. And, we’ll, we use Fathom to do our recordings and I’ll take the entire transcript and I’ll, I use Claude as my LLM, um, and I’ll put it into Claude and I’ll ask it like, let’s come up with the first version.
Gil: And usually in these conversations we’re very like fast, we’re very fluid. And we will think about from the user journey, from the very beginning to the very end, how we wanted to do, what the requirements are, what the tech stack is and all that stuff. And then we have it create these. Long form documentation.
Gil: And before we actually do that, we actually ask it, like, ask us any clarify questions. Are there things that we did not discuss that you need in order to perform a task? And so we, we ask it and it’ll ask it one at a time. And usually they’re not that long. It’ll probably take us like maybe another 15 minutes to answer those questions.
Gil: And we use voice to, to answer them. Uh, we, I use Super Whisper to help like dictate. Um, and then it’s able to produce these like requirement documents that with great detail there where we’re actually just reviewing back. But like, yeah, actually that captured everything we wanted to do. Um, so it was like recording your meeting notes, not just for your own memory, but to be able to like act on it immediately is just amazing.
Gil: It’s just amazing.
Harshad : Yep. Absolutely.
Gil: Yeah. Um, the, the thing I was gonna ask you on, like, try this after the show, um, I think this is now public where everybody has access to it, but if you’re Perplexity user, you can download a browser called Comet. Uh. Comment, like the space comment. Um, and it’s basically Chrome. It’s based on chromium.
Gil: Um, so you can use all the extensions that Chrome has, password keepers, all that stuff, but it’s able to do things for you. So if you’re having to fill out a document, if you’re having to do certain things, it’s able to read what’s on the page and then fill in things for you. So
Harshad : I have to try that and thanks. Thanks for mentioning that. What was it called? I wanna look that
Gil: C Yeah. C-O-M-E-T. So any of our listeners here, take pause this episode and look up. Comment. One of the things that we did recently, you mentioned the use case of you responding back to reviews. So what I did is I, I went on our Airbnb page, uh, and it listed out all of our reviews and I had it respond back to, um, all the five star reviews.
Gil: And I gave it a very structured on how I wanted to respond back. So what I did is you basically opened up the assistant and say, uh. On this page, we have all of our reviews. We wanna make sure that we’re responding back to every one of those reviews. This is how I want to respond back. This is typically with the things I say on, I wanna respond back.
Gil: So I give it structure or guidance, and I say, go through and read the first 10 reviews. Give me a response on how you think I should respond back to it. And so it will go through, it’ll probably take like five minutes and it’ll go through each one of those, and then it’ll gimme a summary of how it wants to respond.
Gil: And all I have to do is say yes, and then it goes through and acts and actually does those reviews for me. It’s amazing.
Harshad : Oh really? So it would like click on that reply button, put it at where it needs to go.
Gil: it will, it’ll click on. It’ll click on it. Uh, we did this for VRBO as well too. So VRBO has like this little notice that says you don’t have any personal information inside the review as well too. So if someone says like, oh, this is someone’s birthday, you’re not supposed to say that because you’re exposing like the date.
Gil: Um, so there’s this checkbox that you have to click and it knows to click that checkbox saying that I did not disclose any personal
Harshad : I have to try that. That is gonna save so much more time, which copying, pasting stuff too.
Gil: Yeah, so comment has been amazing for us. Before I was using that, I was using playwright, which is a more advanced version of that, but perplexity comment has been amazing. When we’re filling out forms, we’re filling out like legal documents and I was like, I’m trying to fill out like this document and I don’t have all the information.
Gil: I don’t know what to do. And it would guide me through how to respond back to it. It’s just amazing. Yeah.
Harshad : I love it. That’s, I think that’s the first thing I’m doing after this call is like signing up for it. I love it. Just the thought of it. I love it.
Gil: Yeah. Um, moving on to like the, the second segment there. Um, I know that you have your portfolio of folks that don’t know you have an amazing portfolio of some of the, the most well-designed properties for very, very good reasons. Like she has done an amazing
Harshad : I don’t think she can do anything that is not well designed, so that’s what happens.
Gil: and it’s interesting, like when I talked to her, when I had her on our show, uh, previously, she doesn’t, she has this really strong eye for figuring out like how do we add value to the property?
Gil: So like, going back to what you were saying earlier about like the exit strategy, because you guys are designing the way you design it and what you’re thinking about is not just how do I get more rent into there, but how do I raise the equity in the property? It gives you more paths to, to exit if, if something doesn’t work out, um.
Gil: So like, all in all, like you guys have an amazing portfolio, very beautiful properties. I would love kind of your take on how you folks have approached direct bookings and digital marketing and really your portfolio and how they like, make sure you maximize that, uh, on and off the OTAs.
Harshad : Yeah, so I, I’ll, you know, uh, absolutely I would love to dive more into it and if we are getting more and more on maximizing our direct booking percentage, starting even this year and going into the future. So just, but touching base on what you just talked about, Ishita, you know, between the two of us, it’s like she brings the soul.
Harshad : I cannot bring the framework behind it, and then hopefully that combination creates the rhythm for our portfolio. So, uh, and that’s combination of not just it visually looking good, that’s great to attract the people, but then on the back end. Having those right systems in place is what makes sure the returns are coming in at the same time too.
Harshad : So that’s that collaboration that happens. And, and with the, with direct booking, when we started, we were just doing the, the, the, the built in page that Hostly my property management system provides. And only thing we used to do is for the guest that was booking with us, we were like, Hey, if you ever wanna come back to us, this is a discount code for you.
Harshad : You can go on our website and then go do it. And we had this automated message set up and we used to post on our Instagram page all the time. I think my total direct booking coming through that method was less than 1%. I barely, like, maybe out of the hundred stays a year or whatever we used to do, maybe one person was like a repeat booker, uh, coming through that channel.
Harshad : People, if, if they were coming back to book, they might have, they were just booking back on Airbnb. It was not set up with the direct booking mindset at all. Um, and then this year was, I think the first year where we have really engaged on having a cohesive strategy around direct booking. So when it comes down to it, we have two different avenues for direct booking.
Harshad : Um, we have people that we want to be able to, that are coming to us, like finding us on Airbnb, V-V-R-P-O and all these sites. So one of the trick that has been working fantastic for us is that all our titles today are, are. Basically, let’s say it’s called electric Vortex by five seasons, home stays. So I know the, the governing principle that people talk about, like put in like your highlights in your title, you know, hot tub, sauna, whatever.
Harshad : But this year we are focused on direct booking. So my intention is to not say that because the first five photos hopefully are showing what the property has. Um, but my title is the name of the property, which is something very unique that can be searched and can be SEO maximized for, from SEO standpoint too.
Harshad : So I’ll give an example. Electric Vortex, or sorry, let’s just say electric. Uh, the one in Sedona, it’s like modern vortex by five seasons. Home stays, and the name of the property management company is right there. Again, the description, we mentioned it managed by five seasons, home stays. So it’s all, it’s, it’s the, the, the, the little nudges are in there. What’s happening with Airbnb is that the title is getting H one title on the pages as well. So after a while when your listing has been out there, if people search for it, that’s the thing that shows up. So they’re able to find us directly by Five Seasons, home stays, and it’s really increasing the credibility.
Harshad : So now more and more people are actually going on Five Seasons, home stays, and then finding the property and then booking. The second piece of it is not only just finding a way to people to get to the direct booking website, but when they get there, they wanna be able to quickly see how much money am I saving without having to go back and forth.
Harshad : So on our direct booking website, whenever you put in your dates and you put in what your stay is, right underneath the total, it’s doing a direct comparison with Airbnb and it’ll show you you’re saving $700. Compared to if you were to book on Airbnb right there, it’s just like a second prompt for them.
Harshad : So that is what’s really engaging people to go in and not only go off, off platform and then actually book, uh, on that thing. So I can continue on a little bit, but like basically this is all of the people that are coming in just organically finding us on Airbnb, VRB or so on and so forth. On the other side of it, this is where we are trying to grab people, is by doing more of influencer mi.
Harshad : My, uh, marketing, we are finding regional influencers in and around the properties, having them post reviews about it and then collaborating with our, uh, profile, giving them a discount code. All we want for those people to do is just to go on our landing page, sign up for our email, if at all, or if not, we are just collecting it and then retargeting them.
Harshad : So over time. That’s really increased our direct booking ratio. Um, this year we went from having like less than 1% direct booking, so I think we are like about 25 to 30% this year in direct bookings, just this year alone. And, and, and seeing the return on that marketing investment or direct booking, creating that infrastructure investment, especially at a larger portfolio.
Harshad : Now, it didn’t make sense when you just had like one or two properties to invest in it as much because you have to have all that fallback systems in place.
Gil: Yeah, it sounds like you’ve now built a pretty robust framework and it, there’s a few things that I, I, I took on is like one. There’s this energy that’s now put into direct bookings where you’re now thinking of it not only as like, okay, I can get a few more bookings for anyone. It’s more passive, it sounds like, in the past.
Gil: And now it’s more like deliberate. Deliberate. But that’s too is then thinking that, thinking about the entire funnel there, you’re thinking through how do you get people in the first place, whether or not that’s the billboard effect on the OTAs where you’re showing, you’re encouraging to search for you on Google, where your direct book insights should be the first one that comes up.
Gil: Um, but you’re also working on, okay, how do I acquire folks that may not organically search for us? How do I get them in front of new eyes, new discoverability there. And that’s where you’re working on the influencer side. And you have this, I, I caught this. You mentioned that you’re. You’re not always looking to have them book right away, you’re thinking about the entire funnel.
Gil: With the nurture portion of that funnel there is that league magnet and being able to retarget them, so you’re nurturing them maybe for a little while there. Because a lot of times, especially a lot, a lot of people don’t understand this. When you’re looking at your social media, a lot of times people will discover you and they’ll like your content, they like your property, but they’re not ready to book right then and there.
Gil: It might not be the season, it might not work out with their school schedules or whatever it may be. They’re just not in that mindset to, to book. Um, but they’re interested in, in you. So they may follow you, they may visit your page, but what you’re doing is you’re capturing their email and I’m guessing like you’re, when you’re delivering emails, you’re delivering something of value to them.
Gil: You’re consistently giving value to them. And maybe every once in a while you maybe you’ll, you’ll give a discount code or you’ll say you have opening, but you’re really enforcing you as a trusted person if they ever want to visit. But you’re also doing something pretty clever where you’re using those emails to do retargeting as well too.
Gil: Um, I don’t know if you’re doing any lookalike audiences, but that that can even, um, supercharge things quite a bit too.
Harshad : Uh, so we have experimented with lookalike audiences. Uh, and I think maybe we didn’t know exactly how to do it exactly right, but I think we have had more success with just building up and warming up the people that are signing up on our page and, and, and sending them emails about events in the area. So, for example, when we are in Asheville, a lot of our properties are in Asheville.
Harshad : So now what we are doing in a, in a, in a emailing is like if something, some events are coming through, Hey, by the way, this event is happening on 15th to the 14th. Here is the list of properties with available dates. It’s not just one property. Now we have a collection of properties that we own and manage for other people too.
Harshad : So it might not work out for one property for the right fit, the, the number of people, the guests, but. It’s going to trigger them to book one of the other ones, uh, and then come back for it. And it’s also coming down to where we are seeing a lot less, uh, lead like, you know, lead time for bookings, especially in Nashville after the floods, people are not booking 30, 60 days out as much.
Harshad : It’s very last minute. So they just need that trigger like, Hey, what am I doing in two weekends from now? So just being in front of them at that time. By the way, October Fest is happening this weekend or this weekend. These are the three more properties that are still open and we are getting a lot of people respond to those, those emails then go to a direct and book something.
Harshad : So it’s helping us like fill in that occupancy gaps that we have across our portfolio. Quite a bit
Gil: I, I think that’s really, really important. Um, I think folks, that this is probably you last year, if you wanted to fill that weekend day. The biggest lever that you had to pull was dropping your prices. Yeah. Drop, raise on, on, on the OTAs. And that will, that, that will give you visibility. But now you actually have a different lever where you may not need to drop rates at all, and you’re able to get the dollar that you, that you, the market value that you set out for and you’re just basically using marketing and it’s cost you almost nothing
Harshad : Yep.
Gil: because you’ve already had all the infrastructure already in place.
Harshad : Yeah.
Gil: Do you, um, on, when you provide the links, do you provide them with a dynamic link that they can see all the properties that are available for that period? Yeah.
Harshad : Yeah. So it, it allows us to create this, uh, hopefully allows you to create this link that shows you the list of properties that are available for a specific date. And that’s the link that they can click on. And if they put, put it in a date, they can see these are the ones that are available. Um, but when we are sending out emails, we are kind of curating that.
Harshad : And in our emails we are curating the properties and we do it by I pet friendly state properties and then we write down to two or three properties, like more than 20% occupancy. We write down the two or three, and those are like more manually curated right now. It’s not like automated as much as I would like to.
Harshad : Not yet, so,
Gil: yeah, yeah. Well, maybe, maybe one, one day. We’ll, we’ll help you out with that because on our, on our side, we, we have not many people know about this and use it to this extent, but all of our search URLs are dynamic. So you can actually go in there as a property manager and you can say, I want to go.
Gil: Filter my properties by Asheville between these two dates and maybe even leave the occupancy open, like just leave it at one and whatever. If you hit search, we will fill in the URL and you can take that URL and add it to it so you can curate the properties that are available. But you can also have a button, say CL properties, and it’ll, it’ll be a dynamic list.
Gil: So if properties fill up, you’ll only show, you will show only show. And you could even have it by collections. So we also have like properties with pools or whatever, and that could be part of the collection there so people can curate.
Harshad : That’s really powerful.
Gil: Yeah, we, most of our more advanced, those are more advanced users, use some of those functionalities within our platforms, but it’s, it’s amazing.
Gil: It’s just kinda like what you were saying earlier that like these are some of the capabilities that you, that are enabled now that you couldn’t do before. Um, so it’s, it’s just an amazing time to just give hosts a lot of power to just manage and operate their business. In ways they couldn’t have before.
Harshad : Right. Right, right. No, and I think that, you know, there’s more and more focus on it now in terms of like the whole direct booking motion, especially with the rule changes coming in with the commission structure with Airbnb. I feel like it’s going to push more people to find a way to get more direct booking revenue coming in versus the 15% or whatever it’s going to change to.
Harshad : But, you know, the big, the big difference that I see in, in my journey with direct booking was the mindset was always, I don’t need it. I’m getting enough leads coming in from Airbnb, VRBO, it’s less work. And I was like, if I am not gonna beat Airbnb’s marketing, and that’s true, they have a, I’m not gonna beat Airbnb’s.
Harshad : Reach out there with, with the smaller company across the board, but with the very niche area, very targeted audience. I think I can beat that with the email list that we have. And then the following, that you grow, the brand presence that you grow and, and what’s working well is like if someone’s had a good experience with us and having, using them to become your wealth issue, to push it out to their friends.
Harshad : So the emails that we are sending out now also are like, Hey, by the way, if you were to send this link to your friends and they book with you, we’ll give you a kickback. So that is also something that we are trying out to see, well, how well that’s going to work? Are people actually going to use it? So.
Gil: Rashad, I, I, I feel like, uh, 12 months from now, I had to bring you back on the show and have you teach us, uh, some of the tactics that you tried out. I, I, I love just, you mentioned this already, but like the mentality of, of going direct, um, and spending a lot more energy towards it. But you also have this like very iterative, and maybe this is kind of the, your engineering side of things, like,
Harshad : Probably.
Gil: like with engineering.
Gil: You things usually don’t go out exactly how you planned it the first time. It takes many different iterations and many hypotheses on like how things will work out. And some do, some, some don’t. Um, but you kind of have this like thing like, okay, I’m gonna try this next and see if it actually moves the needle.
Gil: And if you’re really good, like a lot of folks like, and I’m sure you are, like you’re measuring your successes, you’re looking at that direct booking rate on, on a regular basis. You may have Google Analytics where you’re looking at the numbers and seeing if it actually impacts things. And that really helps you shorten the cycle where you’re not depending on like, oh, are my bookings going up?
Gil: But you can see like, oh, is my traffic going up? Is my conversion going up? You can see at a more micro level and that way you can really contain how you’re running these tests effectively.
Harshad : Yeah. Angela, you know, I, I, I sort of agree and sort of disagree with you with one thing that you mentioned. So what happens is, when it comes to engineering, engineering, kind of the engineering background helps me how I’m gonna do something like the steps and the process and verification. But the mindset, the engineering mindset for me has actually backfired because as an engineer, I was trained to be very analytical, have to check everything, make sure everything is like.
Harshad : Planned out and a little bit of like analysis paralysis, probably that’s part of the personality too. So I have to actively unlearn that side of my engineering brain of like trying different things out. So I’m like, I don’t know if this is going to work and I’m, I’m still wanna do it. I don’t know. This is gonna pan out.
Harshad : That mindset shift is unfortunately not like the engineering brain stops that. Like, how is this going to work? What’s step two? What’s step three? What happens? What’s the feedback loop? So the mindset comes from just having to learn, looking at other people in terms of the speed of execution. If I have that mindset, it’ll not get done.
Harshad : But when we decide to do something, then that engineering brain takes over, okay, what are the steps that I want to put in play? What are my KPIs that I wanna monitor? Let’s move on. I don’t have everything put together, but it’ll come in place. So.
Gil: Uh, I, I absolutely love your story and just your overall mindset. Um, are you going to any other conferences later on later on this year?
Harshad : I don’t think we have any other conferences left this year, but we all, uh, you know, one of my initiative’s goals is just like, try to be out there more and more in public. So 2026, we’ll have a whole bunch of conferences. I would love to go, we love to network and meet with people. I think both our journeys have been very siloed in our own world, so to speak.
Harshad : I think initiative is more out there and more in the backseat, but I think that I’m hoping to change that maybe next year. So.
Gil: I, I think I, I think you will. I mean. We didn’t talk about this on the show, but like being behind the scenes, you, you have a setup that is much more equipped to, to do more with. Like, I, we, we kid just before the show, it was like, Harshad, are you, are you like a full-time podcaster because you have a pretty nice setup.
Gil: I said,
Harshad : Yeah, absolutely. I mean, you know, one of the things, uh, the beginning of 2025, me and she said like, we gotta do our own podcast. We have to get outselves out out there more and more. So I get very excited, like, okay, let me find out the best setup, find the right bike. And I went and bought all the gadgets. I love gadgets.
Harshad : You see my, my setup, I’m a game, I’m a gamer by nature. You know, I like buying like cool tech. So like, so I’m like, okay, lemme go buy all this stuff. I did. But when it came down to actually doing the podcast, I think all our projects that were coming our way just kind of took priority and we never committed the time for it.
Harshad : So we’re like, okay. And it’s also a little bit of a collaboration too. I feel like this year it was in. For us to make sure that Ishita was getting a bit more, um, coverage out there and being out there to grow our design business as, as well as it was growing. And that required for me to also just support the backend stuff as much as I can.
Harshad : Um, and it’s also part personality too. I’m a bit more of a shy guy and I like to be in my weeds and in the numbers and, uh, and just stay behind the screen. But, uh, I think we do really wanna start, uh, our own podcast and share our stories and, um, not only just real estate in general, there are a lot of things that we can talk about there too, but, uh, we haven’t figured out and we don’t, we don’t know what, uh, the audience are gonna relate to.
Harshad : There are so many stories to share.
Gil: Yeah, yeah. I, I, I, I absolutely love podcasting and I think. I’m not one to like love being on stage and being in front of a big audience, even though I, I do speak every once in a while. These type of conversations are, to me, the most fulfilling because it’s a lot more intimate. I like the more one-on-one stuff.
Gil: So like, I kind of like just being on the podcast and I can kinda reach my audience more authentically to, to me. And I feel like that’s somewhat the same for you, where like one-on-one you’re very comfortable. Like you, you’re not withholding kind of your thoughts. Um, and it’s pretty fluid on your side.
Gil: So I think like, when, when you’re ready to do it, I think you’ll do a fantastic job.
Harshad : Oh, thank you. Yeah,
Gil: Yeah. And you definitely, you have the setup to do it, so you’re wasting, you’re wasting those efforts right now.
Harshad : absolutely. Absolutely.
Gil: Isha, we usually end the show with three questions. Uh, first question for you, what’s a good book recommendation from you? I, I, I am always searching for a good, good book re recommendation, like after every single episode, like usually I, I jump right on Amazon. I’ll, I’ll pick up whatever one I don’t already have.
Harshad : Uh, you know, I, I, I, I feel like, uh, I’m, I’m, I’m very lazy when it comes to reading books, so I, I’ll acknowledge that. Like, I have not read a book in a very long time.
Gil: What’s a good audible recommendation?
Harshad : but I am a, I’m definitely want, I just like to look at quick, uh, I forget this app. I have to look it up, but it’s, it’s, it’s this app that I use that just goes in and just gives you the summary
Gil: Is it short form?
Harshad : like the short form, I think it’s what it’s called, and you just get the tips from it.
Harshad : I’m like, okay, this is great. So every morning. I’m, I’m going through one single book like today, morning, I think it was, uh, one, one thing. I think it’s called The One Thing. So just like focus on the one thing at a time. That’s the quick little tidbit that I got today. Morning. Okay. Makes sense. I, I got the summary and I that that’s great.
Harshad : Let’s me pick one thing that I wanna work on today rather than being stressed in 10 different things and focus on that one thing. So just got the summary out, but I don’t know if that really helps, but that’s, that’s the honest answer
Gil: Yeah, I, I used to subscribe to, to Shortform and I, I didn’t pick up the habit of checking it very often, so I, I, I think I went like four or five months without ever like, logging on or like going onto the website or going to the app and like looking at it. Um, I used to use it as a hack for when I’m thinking about a book, I’ll look on short form for the summary and say, okay,
Harshad : the summary.
Gil: is this interesting?
Gil: And then also gives me a, it primes me on like what the, the, the thesis is so that when I do read the book, I kind of know, because a lot of times, like books will drag out for a long time. You’re like, come on, gimme the juicy stuff. Like, I like. Give me what I’m looking to define, and it just takes a while.
Gil: But if you know what the framework is, it just kind of helps you, like, okay, they’re gonna get, they’re gonna build up to this.
Harshad : Yes, exactly. That’s, and for me it just becomes like, tell me, tell me the core point. I understand the stories are helpful and that’s great for a lot of people to understand and relate to the content for me, just, just gimme the context. Let me, tell me, tell me the main point that you’re trying to get across.
Gil: Yeah. Yeah. Reading has been my, uh, my relaxing, uh, outlet. Um, I’ve been gaming a little bit more, not as much. Um, I think probably gaming, you probably game to, to, to release any stresses from your day.
Harshad : That I, I look forward to it. Uh, it’s, uh, uh, the days when I’m able to put my VR headset on and then play some games for an hour, it’s the best, um, stress reducer ever.
Gil: I, I find that I go into it trying to reduce my stress and I go to bed like all amped up. Maybe I need a buffer.
Harshad : Yeah.
Gil: all right, Harshad, second question. Uh, this is a good one for you. What’s one piece of mindset advice that you would give to someone that’s starting something completely new?
Harshad : Yeah. I, I think the biggest thing that I see with most people that are studying, and I totally get where they come from, is just like, don’t chase perfection. And that’s coming from my own thing. Like I, when we were starting out, as I mentioned earlier, I wanted everything to be right, like when I’m selling, taking property, it has to be the right area.
Harshad : It has to be the right thing. And if, and I get where it comes from because the fear of losing and fear of it just comes from that. But, and I see a lot of people get stuck in that analysis paralysis. So when you’re trying to get into that short term rental game, you are not trying to hit a home run the first property you get, hopefully you do, but don’t get stuck that you have to hit a home run the very first property that you get.
Gil: I.
Harshad : Getting in, getting in the game is more important than getting it right. So that’s, that’s kinda what I would recommend.
Gil: Yeah, I, I bet you, you were a huge BiggerPockets listener because I, I recognize that that mindset, I, I don’t know if that’s where you picked it up, but
Harshad : I actually, not the pick really. Yeah.
Gil: I, I, back in the day, back in like 2019 when I first started my hosting, um, and we were, we’re ramping up our investments. David Green and Brandon Turner all used to say almost every single episode, like everything, it doesn’t need to be a home run.
Gil: That first one you’re about to, you just need to get a base hit so that you can get yourself comfortable with it. And that’s where the second and third one, that’s where you start to ramp things up because you’ve done it, you made all the mistakes the first time. Um, but it sounds like if you didn’t listen to the podcast, you learned that the hard way.
Harshad : And I’m, I’m just saying that based on my experience, because like, you know, it’s all about. In the beginning, you have the time and you don’t have the resources as much. And then just kind of where we are right now, time is the, the, the, the resource that I fight for the most. So now the mindsets shifted where like it’s all about like, how do I get things done fast?
Harshad : Uh, and it’s okay if they’re not the most efficient all the way to the top. So, uh, it’s, that’s based off that. But, you know, BiggerPockets has been great. It’s not like I was not exposed to them, but my focus was short-term rentals and BiggerPockets focuses on all kinds of real estate. So I was following more podcasts and people out there that were more focused on the short term rental industry.
Harshad : So I just never heard Brian Green and all as much.
Gil: yeah, yeah. All right, Harshad, last question. What’s one tactical advice that you would give to our listeners that are either looking to get started in direct bookings or amplify their direct bookings?
Harshad : yeah, if you’re getting, looking to get started in direct booking, don’t waste your time trying to create your WordPress. Don’t waste of whatever the website you have to create. There’s just so many tools right now, even like craft estate, what you guys have. I love it. I, I remember we set that up for our properties in Nashville, uh, for Savvy Realty, and I remember how simple it was.
Harshad : It’s like, tell me the property management system you are using and it was like 15 seconds and you had a direct booking site set up. If we can set up a, a direct booking page to begin with for that amount of time, that’s the way to go. Don’t waste your time trying to get the, the most perfect direct booking site if you don’t have everything else in place in terms of your lead gen and marketing to funnel things to that direct marketing page.
Gil: Yeah. Yeah, and, and what I love about it’s that a lot of times people come to us because they hear about us as being like the easiest solution and then they start to dig into it like, oh, I didn’t know that you guys had x, Y, or Z feature. That allowed me to do retargeting, allows me to put my pixel in there, allows me to capture emails and all these different things that we add on to the platform to make it almost like we almost try to teach people how to build their stack as they’re onboarding there.
Harshad : I They going? Yeah.
Gil: So like for any of our listeners here that haven’t gone through the onboarding process for KA days, when you log in, we have a checklist of things that you should be filling. One of those checklists is do you have FAQs on your, on your, on your site? Do you have reviews on your website? Do you have your social profiles on there?
Gil: And what we find is a lot of times when people are guests getting started, they’re like, oh, I should have a Facebook page. Oh, I, I should have my FAQs in there. And so they have to think about those things and they’re, and they’re trying to build it. Um, so, and it’s super rewarding because at the very end of it, we now have learned through so many different iterations of these websites that like, okay, this is, these are the, the minimal set of things that you should have everybody should have on there.
Gil: And I can’t wait until like the next generation where like I’m encouraging people to like set up their analytics, set up pixels and all those different things. Like that’s, that’s the next big step for us is to like, help, help folks kind of get to, like, not just launching, but like how do you get to the more advanced tools that, like some of the stuff that you talked about, like retargeting.
Harshad : Yeah. I, I, I think your platform set up right, it’s, if you can walk someone through step by step, that’s a great way to get going because I feel like there’s so many different paths you can take with direct booking and you can get actually lost. What should I do? What should I do next? So this helps to kind of go step by step by step.
Gil: Yeah, Rashad, it was a huge pleasure. It seems like, I mean, we’ve met earlier this year at Level Up and you guys have just grown phenomenally and it sounds like you folks are scaling in a way that feels natural to your trajectory as well too. You’re putting the right systems in place. You’re thinking about how to leverage your team, how to train your team.
Gil: You’re in surrounded by the right folks to help you grow like I am. I’m inspired by your story, so definitely I hope our listeners like walk away, like just feeling like, oh, you started 5, 6, 7 years ago. With just one property, and now you’re scaling to acquiring four boutique hotels at this point, scaling up a team, thinking about how to maximize it so that you still get to enjoy the things that you, you folks do.
Gil: So that’s, that’s an amazing story. And I don’t know, actually this is, this is already public for our listeners here. is actually going to be on an upcoming book, um, later on.
Harshad : Yeah, I’m very excited that, yeah, doing it with you
Gil: Yeah. So Harshad and I, were, we’re going to be in the hospital hosts, um, a couples edition book that is going to be released next year.
Gil: I can’t wait to reach your story in there. I, I feel like I’ve gotten so much of the chapter already and kind of feel how, like, what your story is all about, but I’m, you just have an amazing story and I think you and Ashita have this really elegant balance there where you folks are leaning on each other’s strengths really, really well.
Gil: So kudos to the both of you.
Harshad : Oh, thank you. Thank you. I’m super excited about the book too. And I think there’s some amazing couple authors in that book, including, including you, Joe, and I’m, I’m excited for that book to come out too. Uh, and thank you for saying that. Yeah. Me and Sheta have been blessed. We have a good. She’s the soul, as I said, and then I bring in the, the structure and hopefully things have been working,
Gil: Yeah, it, it certainly has, and I, I think it sounds like you’re, you’re trying to detach yourself from the, the engineering mindset and encapsulating the soul yourself as well too. So, so you, so she’s, she’s stretching you as well.
Harshad : Yeah, we are learning from each other every day, so
Gil: Awesome, Harshad. Well, it’s great to have you on and I can’t wait to, to see you again maybe multiple times next year.
Gil: All the conferences will probably be at.
Harshad : Absolutely. I’m looking forward to 2026 and what that’s gonna bring.
Gil: Awesome. Thanks again. Bye.
Harshad : a good one. Bye.