Jacobo Hernandez - Specializing In Short Term Rentals & Boutique Hotels

Jacobo Hernandez, a dynamic entrepreneur and accomplished author of Short Term Rental Secrets, has demonstrated exceptional prowess in real estate investing. With a background in scaling a seven-figure Amazon brand and establishing a $10 million short-term rental portfolio, Jacobo's expertise and strategic acumen offer invaluable guidance for individuals navigating the real estate landscape. His transition from e-commerce to short-term rentals underscores his adaptability and forward-thinking approach, making him an influential figure in the industry.

In this episode, you will be able to:

• Learn how Jacobo was able to Master the Art of Transitioning from Amazon to Real Estate Investing: Uncover the secrets to seamlessly shift your investment focus and boost your real estate success.
• Crafting a Lucrative Short-Term Rental Business: Discover how to maximize profits and create a thriving short-term rental portfolio that works for you.
• Scaling Strategies for Boutique Hotels: Unlock the tactics to expand and elevate your boutique hotel business to new heights of success.
• Unleashing the Power of Digital Marketing in Real Estate: Harness the potential of digital marketing to skyrocket your real estate ventures and attract high-value leads.
• Profiting from Commercial Airbnb Investments: Learn how to leverage the benefits of commercial Airbnb properties for a rewarding investment journey.

The key moments in this episode are:
00:00:00 - Similarities between E Commerce and Short Term Rentals
00:07:41 - Applying E Commerce Strategies to Short Term Rentals
00:10:08 - Creating Unique Short Term Rental Experiences
00:15:32 - Scaling Challenges in Short Term Rentals
00:18:22 - Transition to Boutique Hotels
00:21:47 - The Opportunity of Boutique Hotels
00:24:19 - Short Term Rental Secrets Book
00:26:29 - Connecting with Jacobo

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Full transcript here:

Jacobo Hernandez
The similarities between E Commerce and short term rentals, it's like absolutely everything. So I started applying the exact same strategies I used when I started identifying what product to sell on Amazon. This time it was for short term rentals. So I went on air DNA and I started looking at the listing distribution. So first it was identifying the market. Right. And I was already in Florida, so I knew anything in Florida was, was booming at that point. So I started looking at that market. But what I found was that there was a lot of saturation, but not for every property.

Mike Swenson
Welcome to the Real Freedom show where we inspire you to pursue your passion to gain time and financial freedom through opportunities in real estate. I'm your host, Mike Swenson. Let's get some real freedom together. Hello everybody. Welcome to another episode of Real Freedom, Real Estate Leverage Freedom, where we talk about different ways that people build time and financial freedom through different opportunities in real estate. I'm your host, Mike Swenson. If you want to get started on your real estate investing journey, check out our website, Freedom through Real Estate. Com. Lots of great content, articles, podcast episodes like this for you to really kind of figure out what's going to be the best path for you and what do you want to do. And one of the things that I really love about people that are finding success in real estate is they have transferable skills, they have a background that they can bring inside of real estate, bring their passions and their, their energy to the real estate space. And that's certainly what we've got today with our guest, Jacobo Hernandez. He's a serial entrepreneur, scaled a seven figure Amazon brand in college, has spent over $1 million on pay per click ads and then successfully transitioned into short term rentals. Built a $10 million short term rental portfolio and now focusing on boutique hotels. Also the author of the book Short Term Rental Secrets. You've done a lot in the few years that you've had here. You're certainly a younger guy and certainly accomplished a lot. So congrats on your success, Jacob, and excited to hear your story.

Jacobo Hernandez
Hey, thanks for having me, Mike. I'm excited to be here on your show today.

Mike Swenson
Well, why don't we just start, just talk a little bit about kind of your background, you know, getting into your Amazon business and we'll go from there.

Jacobo Hernandez
Awesome. Yeah, so basically I was in College. I was 22 years old at that time. I was going to the University of Miami. And for me it's, I've always wanted to have freedom. Freedom of time, freedom of location. So for me, the traditional 9 to 5 job was never a thing for me. My dad worked incredibly hard all his life, but that meant I really couldn't see him much. Like weekends. He was always traveling. He was all around the world as working for a multinational, high earning guy, super hardworking. But for me, like I didn't want that. Like I didn't want to follow his footsteps after seeing how much sacrifice he had to do for his family. So for me it was looking at like what kind of businesses I could do where I could actually leverage the Internet and be and work from anywhere in the world. So that same summer, I'm still a freshman, I fly out to China for an internship and I quit like three days into it because they were just making me serve their coffee and do all this stuff that was not related to what I had signed up for. It was actually an E commerce based company so I thought I was going to learn a lot from them. It didn't work out so I ended up quitting and I actually spent those two months in China just traveling around by train checking out different cities, different marketplaces. And I landed upon YIWU Marketplace and that's where my mind just exploded. I was seeing how everything was being manufactured there from scissors, gifts, like anything you could think of. It was crazy. Like they had every single reference and this went on for miles. So like it would take you a couple days to walk through this kind of like a shopping mall filled with suppliers. And yeah, basically I come back from that internship. I couldn't. I just knew I had to do business with China. I knew what was there. I just needed to figure out a way how to do it. And I started going to different meetups for E commerce and Amazon selling. And that's when I stumbled upon this really good friend of mine who became my mentor. He was a couple years older. He was already being what I, what I was thinking was really successful. He was selling 10k a month and he was about to quit his, his nine to five. So for me he's like, this is the guy I want to follow. And he just started showing me the ways. From there I paid a high level course. I invested like 5k into a course that I had saved up for my money and the rest is history. That year I ended up launching a wedding gift brand, scaling it to seven figures. And then of course I had all these different issues. I stumbled upon cash flow problems because I didn't really know what I was doing. I had this warehouse in Doral in Miami and I would drive back and forth from the warehouse and to school. And I actually had virtual assistants at that point, so in the Philippines. And I would have them helping me out not only with like, yes, customer service and all this different stuff, but I also had them doing some of my schoolwork so that I could focus on scaling the business. Right. So I was really going to college for my parents. They had already invested all this money into me and like, they wanted me to go to college. So I just, I'm like, all right, I'm going to stick through it. But at that point, I didn't really need to go to school. Like, I was already doing pretty well with the business. But of course, all businesses have their challenges. I started having, like I said, cash flow issues. My Chinese competitors copied my exact same products. They basically ripped apart what I was selling. And that just forced me to become really good at digital marketing, SEO, listing optimization to try and compete. However, I didn't really see this as a sustainable business venture. And that's when I started looking into real estate, more specifically short term rentals, as a way that I could unlock both cash flow, but also being in a business where you have a tangible asset. Because the problem with what I was doing at that point, it was just to give you an example, I had say 20,000 Mr. And Mrs. Aprons. If Amazon suspended me, if my product got copied, if anything happened, I'm stuck with a warehouse full of aprons that have no value. When I looked at real estate, I'm like, okay, say Airbnb kicks me out of their platform, I can still live in that asset. I can long term rent it, medium term rent it, I can sell it. If I am stuck with 20,000 aprons, if I try and sell them on Etsy because it's just such a smaller marketplace, like I would die before I would be able to actually liquidate all that stock. So that was kind of my transition from E commerce into short term rentals.

Mike Swenson
Yeah, it's interesting that you say that. You know, one of the things that we talk about is it being a tangible asset, you know, in real estate, comparing it to stocks or mutual funds or cryptocurrency, things like that, where I think a lot of people that like investing real estate, like the fact that I can go touch it, right, I can go drive by that house or whatever that property is if I need to. Hadn't really thought about a tangible asset in the, the sense of, you know, wedding aprons or, you know, things like that, where, yeah, the value is just much different. And so Now I will have that example to share with people when I talk about real estate being a great investment from a tangible asset standpoint.

Jacobo Hernandez
Absolutely. And another way that you know it, that it's a real asset as you can get a loan or a HELOC against your asset. Like I can't get anything against 20,000 aprons. Like it's, it's just, you're not getting financing for that. Right.

Mike Swenson
So banks have hoops for you to jump through. In real estate, I'd imagine it'd be a lot more for aprons. So.

Jacobo Hernandez
Right.

Mike Swenson
So talk a little bit about. Yeah, that, that journey, getting into the short term rental space, building and scaling, selecting properties, kind of some of that stuff that you've learned along the way.

Jacobo Hernandez
Yeah. So basically I started applying. It's crazy because the similarities between E Commerce and short term rentals, it's like absolutely everything. So I started applying the exact same strategies I used when I started identifying what product to sell on Amazon. This time it was for short term rentals. So I went on Air DNA and I started looking at the listing distribution. So first it was identifying the market. Right. And I was already in Florida, so I knew anything in Florida was, was booming at that point. So I started looking at that market. But what I found was that there was a lot of saturation, but not for every property type. So it's not only identifying the right market but also identifying the right property for that market. And what I found was that anything above five bedrooms plus there was only 2% of all the listings. Yet these big properties that allowed you to host 16 plus guest had huge, huge demand. And I started looking at comparable properties. They were doing 300 to $500,000 a year. Right. So from there I validated the thesis that limited supply. It was also really hard to find these six bedroom properties. And then from there I went on to purchasing. So I had saved up some money for my E Comm business. I was already trying to sell this business, which later I successfully sold. And again that same mentor was now a business partner in this venture. So we acquired our first property. It was a six bedroom property with a pool, a garage that we could convert into a game room. What we basically focused on was this thesis of creating many resorts. So after that first property, our second property was actually waterfront, not oceanfront lakefront, because oceanfront would be millions of millions of dollars. It could be two, three million dollars. We could charge just as much for a property that was lakefront than an oceanfront. But our basis was just so much Lower that. Our returns were incredible. So our thesis just to sum that up is it was six bedroom properties, garage that we would convert into a game room, lots of space so that we could add amenities. Backyard with the, with a lakefront pool. Pool and then space to add a fake beach. We would add a volleyball court, we would add mini golf, we would add an outdoor sauna, we would add a cinema. We would, we would add, we would just deck out these properties and we just found massive success. So all our properties were 90% plus occupied. Our ADRs were 90010001200 bucks per property. And yeah, that was our experience with, with short term rentals. We also applied the exact same digital marketing principles which that's pillar number three. So number one, it's the right market, number two, it's the right property. Number three is marketing. And that's where a lot of people get hang up on is like they just launch, they just throw the property in Airbnb and are just praying for it to get booked. But if you don't know how to talk to the algorithm, then you're not going to get the visibility that you need. So from there we basically had a launch strategy. We would leverage influencers to stay at our properties and then they would ask their audience to go onto Airbnb, wish list our property and contact the host. This would give Airbnb massive signals from the get go that there was so many people trying to book, which wasn't the reality, but it gives the algorithm, it feeds the algorithm what it wants. And that would boost us to page number one from there since we had a really optimized listing with a really great main image, really good price and title. Then the organic wheel wheel, the flywheel of organic bookings start flowing in and then from there the rest is just history. You start getting more reviews. You do proper revenue management, which that's pillar number four is obviously you need the right operations in place, cleaning the fundamentals. But also revenue management, which I think not a lot of people talk about. But it's having the automated repricing tool like Price Labs. But on top of that you want to manually be changing those prices because sometimes what ends up happening is you can either have an overbooked calendar or an under booked calendar. So sometimes you might be leaving money on the table, other times you might not have that occupancy that you want. So we manually will override whatever Price Lab is giving us based on our 7, 14, 30, 60 and 90 day occupancy. So lots of Data I can really say E Commerce was the basis to really building out this short term rental business.

Mike Swenson
Just to back up a little bit, you had talked about, you know, finding this, this niche here in 6 bedroom plus what are the types of folks that are going there for six bedroom because like you said it's finding that right mix. I'm in Minneapolis St. Paul, we have some short term rentals. A lot of it's coming to Mall of America but there's also visiting friends and family, that sort of stuff. You've got a summer season, a winter season, Minnesota, just totally different. But talk about for people looking in those types of areas, like what are they looking for and why is that six bedrooms so lucrative?

Jacobo Hernandez
Lots of bachelorettes. It's Miami after all. So lots of bachelor, bachelor, bachelorettes, but lots of people coming to say weddings. So family members trying to get a property where they can all be close to each other. You know, funerals happen as well and families travel from all around. So there's just so many different groups. There's also business groups that will stay at our properties. They're coming for work and they all just stay at a house, all of them together and they have everything, all the amenities plus space to work. So I mean it's always been different. The good thing about market like South Florida is that there's just so many people coming in that it's, if you, you have a good property like it, the end you don't have too much competition, you're going to get booked.

Mike Swenson
That was the thing. Surprising to me. You know we, we've got a handful of short term rentals. Like people come for all sorts of reasons. You know like you mentioned funerals, that stuff happens. It's last minute funerals, it's funerals A month or two from now, it's you know, college graduations. Yeah, there's all sorts of reasons why people travel and I think people probably have a limited mindset of thinking, well why do people book an Airbnb? It's pretty much anything, you know. And for somebody like me, in my, my shoes, we've got three kids booking a hotel room can't fit five people. Well, because you've got, you know, the two bedrooms and then you've got the pull out couch. Well, as our kids get older the pullout couch is a lot less exciting. They used to fight over sleeping on the pullout couch but now it's like I don't want that. So an Airbnb just for going to stay somewhere makes a lot more sense. Because you just have more space and you have the bedrooms that you want. So even something as simple as that is important for people to book an Airbnb versus Hotels.

Jacobo Hernandez
Yeah, no, absolutely. And you got your own private amenities as well. And when they end up doing the math per bedroom, they end up probably spending less than they would. If 16 people were to book say six or seven different hotel bedrooms. They're going to be saving money. So it's good for us, good for the guests as well.

Mike Swenson
So talk about scaling that up and then kind of your journey moving towards, you know, looking at boutique hotels.

Jacobo Hernandez
Yeah, so we ended up scaling and then that's when the issues start coming in. We had properties all across spread out, say 30, 20 minutes apart. So our maintenance guy, if there was check ins on the same day, our maintenance guy couldn't be on both properties at the same time. We didn't really have like a centralized place and it was just so expensive. There was no really real economies to scale. It was hard to scale finding these six bedroom properties. And we were limiting ourselves to this radius because we couldn't go and buy in another market because now we had to set up a new team and now you only have one property. You don't have the economies of scale to set up a property manager, a maintenance guy, a cleaner. You need to pay them by the hour or per project. So it just became a complete hassle. When you have 10, 12 properties now you have 12 pools to take care of. They all have different maintenance issues, different pool heater, you need to cut the grass in all of them in different dates and different schedules. And it just became a nightmare to scale. So I ended up exiting that. A private equity company came in and acquired the whole portfolio. And at that point I was starting to look into boutique hotels, AKA I call them commercial Airbnbs, because that's all they are. They run pretty much on the same systems, but they have the economies of scale. So we can go in any market because what we're looking for is hotels that when we project them, we can at least do 500 to 700k a year in revenue. With that sort of revenue, we're able to basically hire a property manager. We're basically able to hire everybody on site, so we're not really buying a job. And there's the economies of scale to have just a bigger, more scalable business and we can buy in any market. Another limitation of residential is that you can't force appreciation. So when you go to sell, unless you find the right investor, if it's your regular investor wanting to buy your property. When they go to the bank, the bank's not going to appraise the value of the asset based on the income. It's going to take the asset and look at comparable properties, which adds a huge limitation. I don't ever want to be in a business where I'm tied to just the market going up. I want to be able to force appreciation. The good thing with boutique hotels is that your value is tied to the income. So you buy an asset that's cash flowing, $100,000 in net operating income. If that market's cap rates 10% that assets worth a million, you take that asset, improve operations, renovate it. Ad revenue management, digital marketing, which a lot of these hotels or motels are owned by baby boomers. They might not even have an online website. So you're able to double or triple the net operating income, which means you double or triple the value within, say, two years. Right. And then you can cash out, refi sell. So it gives you just a lot more flexibility, a lot more growth, and a lot more scale. And then finally, regulations, if you look across the board, they're starting to regulate Airbnbs heavily in a lot of places. So I want to be in the side of the law and I want to actually take advantage of regulations and not be the one hurting because of regulations. We had one property that we owned where the county just came back and said, you can't have 16 guests. You can have maximum of eight people out of nowhere. Now our property bookings and revenue slash in, in pretty much half because we can't charge as much as we can charge for bigger groups. So, I mean, it just makes a lot more sense from everything I've, I've been doing that this was just the next step in, in just this whole puzzle.

Mike Swenson
So now, size wise, you had mentioned kind of the, the revenue you're looking for, but is this, you're looking for motels where they have exterior entrances so you can put keypads on doors or kind of like what are maybe some of those things that you're looking for that create a good opportunity? You mentioned the baby boomer boomers. Obviously, that makes sense. They're looking to get out. But yeah, what, what's kind of some of those features?

Jacobo Hernandez
Basically, we want to be able to apply the exact same strategies that we learned during our Airbnb days, which is design and amenities. And if you look at this trend nowadays, there's a lot of trends towards wellness and experiential Stuff people want Instagramable spots. Right. So what we're doing is we're finding the bones. So if we find a motel that just has this really cool looking like structure that, you know, you can renovate and it already has a pool, but it also has a lot of grass area or space for you to add a sauna and wellness and cold plunge. And maybe you're adding a wedding venue and you're adding all these extra revenue sources like food and beverage. And at the moment I started thinking I was going to just do a smaller deal, but at the moment we're actually looking at a pretty large deal that we ended up finding. The owner is a baby boomer. He's willing to sell or finance this deal. So he's giving us excellent terms and it's got the scale. At the moment they're doing a million dollars in revenue. We think we can easily get this to four or five million dollars in revenue. And, and we're going to be taking this asset from say 5 million acquisition to over 15 million by the time we exit. You can't, you're not going to get that ever with the residential asset, like with short term rentals. Right. You're not, you're never going to see 3, 4x the value of your asset unless you hold it for 20, 30 years. But in, in hotels or boutique hotels, you can take a motel and triple or quadruple its value within a couple years through Force Appreciation. But the thesis remains the same. Cool experiential design stuff. That's going to be different.

Mike Swenson
Yeah. And you mentioned, you know, with the Force appreciation. That's awesome. You know, that's why I moved from small multifamily into regular multifamily just because you, you get control over that. Right. And that's what I often tell people is you don't have to worry about what's happening in your neighborhood or what's happening with the house next door to you because it's all dependent on, you know, income and expenses and what's that spread. And you know, to your point, yeah. Being able to really ratchet up the income really fast gives you an incredible opportunity that even, you know, for us long term rentals, we're moving, you know, let's say $800 a month rent to $1,100 a month rent. That's awesome. And yet at the same time, you can do that on steroids much faster than long term tenants can. So there's, there's an incredible opportunity there for you guys.

Jacobo Hernandez
Yeah, no, absolutely. Last thing to mention is obviously you're trying to find these motels that are in prime destinations that have been mismanaged, that have no marketing, no online presence, they probably haven't been updated in years. And these boomers are just ready to hand them off to you because they've owned them for 20, 30 years and there's a big chance they're going to be able to sell or finance. Now in residential, it's so easy for people to exit. They'll just put it on Zillow and sell it. So you don't have a lot of these opportunities to actually get a seller finance opportunity. So we're seeing a lot more opportunity to do really creative deals. And it's a win win for both because now the boomer has this monthly check. He's not paying taxes up front. So it's a win win scenario. And they're business owners first. So I just find it also better to be dealing with other business owners that sometimes residential, there's a lot of emotional attachment to their house or their primary residence. In this case, it's just business. You're selling a business to somebody else.

Mike Swenson
Yeah, for sure. I mean, one of the reasons we love the commercial side too, because yeah, I think there's so many probably mindset roadblocks that people have about what the unknown is. And I tell people on the commercial side, for multifamily, yes, sellers are much more interested in a seller finance deal. You get on the residential side, like trying to buy a single family home with seller financing, well, they're probably wanting to use that cash for their next house. So they're not willing to finance that. But if you're talking to somebody that owns, you know, let's just say in this example, you know, five apartment buildings, they're looking to sell one where they're more willing to take something like that on Somebody like you, a baby boomer, they've been owning this property for years and years and years. It's 100% paid off. Like you said, they can afford to do that. They want to take some, some sure income every month. They're willing to handle that. With interest rates being higher, you guys can probably get a good deal on that as well. So there's just, there's so much more willingness to be open to those types of conversations where some people, their limiting beliefs think like, oh my gosh, how can you do something like that? Well, it's a lot easier because you have a flexible seller than a bank with all their regulations.

Jacobo Hernandez
It's like you Said a limiting belief and I had to get over that. It's like I'm going to buy a hotel. Like it's just a hard thing to get over it, but it's actually easier, more scalable. Obviously you're not going to go and buy a hotel if you've never even bought a single house. So obviously buy a house, two houses, get the ropes of real estate, but then go commercial because it's, it's, it's literally just a limiting belief that you just got to get past.

Mike Swenson
Are you looking to get started or scale in real estate investing but don't know your next step? Are you overwhelmed thinking about finding deals, analyzing deals, doing due diligence and managing properties on top of it? Go ahead and push the easy button and invest with us. Real estate investing is what we do full time. We've done dozens of deals with hundreds of doors. We have the knowledge and experience to hand pick the best deals that most investors can't find. We've at large off market deals all the time where you, you can hopefully find returns and economies of scale that you just can't find on your own. The best thing is it's 100% passive to you for less capital than you put down trying to acquire a property on your own. Don't let this year go by where you don't make the leap, add to your portfolio or you just sit in analysis by paralysis. To find out more, visit freedomthroughrealestate.com and click on Invest. You can book a call and learn more there. So get to scaling your portfolio portfolio now with us by your side now just for, for a couple minutes here, talk about your book Short Term Rental Secrets. Kind of what was the, the reason for wanting to do that and kind of the process for that. Would love to hear your story on it.

Jacobo Hernandez
Yeah. So Short Term Rental Secrets is literally it's just a book that I put together with all my SOPs and everything I learned throughout the years of scaling a large Airbnb portfolio. And I teach you everything I learned basically how to identify a market, how to find the right property within that market like we discussed from there, how to do the right marketing. And I go deep into the Airbnb algorithm, how to talk to the algorithm, how to feed it, everything at once. From there we go over operations and those are the four pillars of short term rental success. From there, at the end of the book I talk about why once you're ready to take the big leap, you should go into commercial Airbnb AKA Boutique Hotels. And I show you how and basically everything, the four pillars of short term rentals can be applied into boutique hotels as well. So it's, it's all just transferable skills that you can take either if you're doing residential or commercial. Boutique hotels.

Mike Swenson
Yeah, that's such a great thing. It's cool to see. You know, I talked about this at the beginning of the episode. You know, taking those transferable skills into real estate, a lot of people think like, oh, real estate, like it's, it's new. I don't understand it. And it's like, well, what did you do? Well, before that, what were you excited about? And what can you bring into real estate? And everybody has different skills and abilities and passions that they can bring into real estate. And it's so obvious to see your background, how it prepared you for what you're doing today.

Jacobo Hernandez
Yep, my background was digital marketing and data, but I knew nothing about real estate. But you can learn the real estate side or you can partner up with somebody that's, or hire somebody that's really good at the finance part and the spreadsheets. But you can always add value. Like one of my partners right now in the boutique hotel, he's, he's the design guy, he's the vision guy. So he's not the numbers guy. So you just look for, maybe you look for two partners and data guy, a digital marketing guy and a design guy, and you guys go and take down bigger deals. So I love real estate because it's also a lot of networking, a lot of you're not doing this alone. Like you since you're taking down bigger and bigger deals like in commercial, now you're doing it with others. And that's something I've enjoyed a lot.

Mike Swenson
Well, thank you so much, Jacob, for coming on the show, sharing your experience for people that want to reach out to you and learn more about what you're doing. How can they do that?

Jacobo Hernandez
Yeah, they can go to my website, freedomvestcapital.com and then you can just add all my social media to the show notes. But it's my first and last name, so you can find me on LinkedIn, Facebook, Instagram.

Mike Swenson
Well, thank you so much for coming on and sharing. Excited to see what the future holds for you with boutique hotels and excited to see where it goes.