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Show Summary
In this episode of the Real Estate Pros podcast, host Michelle Kesil interviews Tim Ensmann, a real estate investor specializing in unique hotel experiences. Tim shares his journey from traditional real estate investments to creating boutique hotels that offer one-of-a-kind experiences. He discusses the challenges of acquiring undervalued properties, the importance of branding, and the strategies that have led to his success in the hospitality industry. Tim emphasizes the need for education and adaptability in this evolving market, providing valuable insights for aspiring investors.
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Investor Fuel Show Transcript:
Tim Ensmann (00:00)
Yes, similar to most, so my career before this, I was in sales and I had a really good role, really good career. As you start moving up the ladder, as you start earning some additional income, you start, okay, what am I going to invest my money in? And then you also start seeing how much you’re paying in taxes. So you’re like, okay, there needs to be a strategy here. So early on, I started probably similar to most, I bought my first house. I purchased some single family homes and you know was learninglearning a lot about hey, how do you make cash flow and take advantage of depreciation and all this stuff. So quickly realized that when I did some back of the napkin math, the single family homes, was it gonna get us to the place where there was a reasonable amount of cash flow? So I pivoted and I went into multifamily investing, more on the limited partner side. And really liked that because I liked that the ability to, if you run the business well, you’re able to actually increase the value of that property.
Michelle Kesil (02:25)
Hey everybody, welcome to the Real Estate Pros podcast. I’m your host, Michelle Kesil. Today I’m joined by someone I’m looking forward to chatting with, Tim Ensmann, who is a real estate investor, specifically targeting unique hotel experiences. So, excited to have you here today, Tim.Tim Ensmann (02:43)
Thanks for having me, Michelle. Appreciate you having me on.Michelle Kesil (02:45)
Yeah, absolutely. I think our listeners are really going to take something away from how you’re approaching creating these one of a kind experiences for people. So let’s dive in.Tim Ensmann (02:55)
Yeah, let’s do it.Michelle Kesil (02:56)
First off, for those not yet familiar with you and your work, can you share what your main focus is?Tim Ensmann (03:02)
Yes. So we go and acquire these undervalued overlooked assets and we turn them into destination escapes where they’re super unique. ⁓ You know, they’re brand led, brand driven, and they’re one of a kind in their markets, right? So they’re not just your run of the mill economy hotel. They’re not really luxury, but they’re places that you want to go hang out with your friends and family. They have the amenities, the wellness, you know, the saunas andand cold plunges, the pickleball courts, it’s very communal, you feel connected and all of them have a nature component, right? So you’re outside, you’re disconnecting and you’re able to spend time and do activities with your friends and family.
Michelle Kesil (03:48)
I love that. How did you get started in that creation?Tim Ensmann (04:40)
Yes, similar to most, so my career before this, I was in sales and I had a really good role, really good career. As you start moving up the ladder, as you start earning some additional income, you start, okay, what am I going to invest my money in? And then you also start seeing how much you’re paying in taxes. So you’re like, okay, there needs to be a strategy here. So early on, I started probably similar to most, I bought my first house. I purchased some single family homes and you know was learninglearning a lot about hey, how do you make cash flow and take advantage of depreciation and all this stuff. So quickly realized that when I did some back of the napkin math, the single family homes, was it gonna get us to the place where there was a reasonable amount of cash flow? So I pivoted and I went into multifamily investing, more on the limited partner side. And really liked that because I liked that the ability to, if you run the business well, you’re able to actually increase the value of that property.
So did a ton with that as well. then came to a point, it was about six years ago where I had stayed in Airbnbs. I love travel. I had been reading a lot about short term rentals, things like that, and said, you know what, I think I want a more active approach and I want to be able to actually experience the places that I’m investing in. I thought that was a cool component of it. It wasn’t just, okay, you put your money in this investment and then you’ll see it again in five years when it sells and all that. Maybe if we get to use it once.
a year. So that really prompted my interest in short-term rentals. Purchased my first short-term rental in Park City, Utah, because I love skiing. And I was like, oh, this is a great investment. It’s something that some place I actually like to go. And that paid for my mortgage for half the year, my first booking. So I was like, wow, there’s something here. I’m actually able to increase the roof on what you can get each month. You look at most real estate, a single family home, apartment building, self-storage, whatever you’re
looking
at, there’s really a cap on what you can get monthly, right? You’re not going to three, four X your rent of your neighbor. You can’t really do that. What I noticed in hospitality, you can, if you build a brand, if you build an experience, if you build a place that people want to go and you can create that exclusivity, you can actually increase two, three, four, five X of what your neighbors are getting. And you can dramatically improve the, you know, the operations and value of your business. So, early on, that’s kind of what we realized was short.
short term rentals, scaled that business up, you know, had with myself and my partner, we personally owned over 20 across the United States and then realized like, hey, how do we take this and go bigger, go more efficient, go more quality and personalize into one experience, which led us to boutique hotels. You know, now we are, like I mentioned, acquiring these undervalued assets. So these places where like the Pine Tree Hotel, and I’ll drop some information on us, but we got this property
from a mom and pop seller. They were super nice people. We’d built a great relationship with them, but they were doing things. mean, the pool was like a cistern. Like they had collected water in the pool to save money on the water bill. It’s like you guys are paying 500 bucks for water. Just open the pool up and now you have a year-round pool in the mountains that’s gonna be a massive revenue driver. So little things like that. There’s a lot of these properties that are on great land, have great space. Like it’s a great vibe there.
need some love and attention and they need the ability to go execute this plan to make it a place that people want to come to. So that’s what we’re doing. And then as you know, when you’re able to take
a business like that, you’re able to build a brand and then now you put that on real estate, the ways that that is valued is completely different now, right? So now you’re going from just a media company or just a normal business that’s traded at three to five X and now you’re at 10, 12 X of what that value could be because now you’re on the property. So that’s what we’re doing. We’re acquiring properties in Blue Ridge and expansions in California. But yeah, that’s the long story.
Michelle Kesil (08:40)
Yeah, that’s amazing that you’re able to upgrade kind of these places. What do you feel has been like the biggest hurdle in navigating like these hotels and making them to the kind of tier that you desire?Tim Ensmann (09:30)
Yeah, the biggest challenges in this space are acquisitions.It’s financing and then it’s the operations of it. So to start with the first one, acquisitions, it’s tough because like I said, you can’t just go buy a Motel 6, put some paint on it, flip the rooms and say, Hey, this is going to be a great you know property. You really need to have properties that have a unique component. Does it have mountain views? Does it have a nice pool area? Does it have a place where you can add some communal space for events or things like that? So it can’t just be every property. You need to really look.
at, hey, does this have the potential to turn into a real destination spot and that Instagrammable moment or that moment where, you know, when people come, they’re like, wow, like, I need to show my friends this, this is something that I want to promote. So that’s really the most important thing. So acquisitions of finding those properties is tough. And then also getting the deal across the line, because a lot of these sellers think about it, they’ve been there for 10 years, they’re probably on property, living there, doing a lot of this stuff, or maybe they’re a
They’re not a hospitality operator, which is one of the reasons why they’re selling they bought it They had a couple multifamily deals and they thought it was going to be similar and it’s completely different so it’s it’s the disconnect between us as the buyers and buying this property at a reasonable price because of what the value is now and then being able to You know put the right investment put the strategy behind it to go make it what it’s worth today So I think that’s a challenge on the acquisitions front
And then financing too, right? A lot of these properties, like from our previous owner.
at the pine tree, we 7x’d revenue in the first year from what they had been doing. So you can’t just go tell a bank, hey, we’re going to go 7x revenue. They just don’t, that’s not how they underwrite, right? They’re going to be very conservative. They’re going to see maybe you guys double it, maybe you triple it, whatever, but like that, that’s just, it doesn’t fit in their buy box. So the financing side of it and the way you go do that is also a challenge. And then the operational component, right? I think a lot of people post on social, they think, there’s some like some social strategy, but it is a
a full on strategy. You need to be very focused on how do you actually go do this? Because there’s a massive advantage from building your own personal brand for each of these properties. You’re removing, think about it. If you book over 90 % direct, you’re saving 15 % that’s going straight to your bottom line from OTA fees from Airbnb and VRBO. Like that’s insane. So every dollar you put towards building that brand out is actually saving you a ton of money and overall improving the value.
you the property. So I think those are, you know, we simplify those things and how we go execute, but those are challenges in the space right now. Just, you know, finding the right properties, being able to actually go get the deals done, finance them, and then operate them and like build these places that people are going to want to come and book direct and come back to.
Michelle Kesil (12:32)
Yeah, definitely that makes sense. What do feel has been like some of the main keys that have made the biggest difference in allowing the business to be able to grow and to continue to run smoothly?Tim Ensmann (12:46)
Yeah, so it was an aha moment when I got my first short-term rental. The first booking covered our debt service for half the year. First hotel.Our first booking covered our monthly debt service in four days. So it was like, whoa, wait a minute. So all we, got a story about what we were building. We got some renderings that were on the website of our wellness area, our heated year round pool, and just like a layout of what the property is going to look like. They were renderings. They were not real photos. Got a booking direct 50 % deposit, you know, cash in the bank for four days that covered our debt service. And we’re like, wow, there is something here. If you’re able to create a place.
where people want to host a retreat, people want to host their wedding, people want to host their birthday party, and you have the accommodation, you have a major advantage. So since then, we’ve, we’ve, in, I think it was like 30 days, we covered over, close to 70 % of our debt service for year one. And then this year we’re already 70 % of the way to what we booked last year for group booking. So point being is creating predictability within your business.
is huge. Whether or not we get high demand or low demand, we actually know we have these bookings coming up.
non-refundable deposits, so like we know they’re happening each month, that at least covers us, we’re safe, we’re good to go, we can operate. And then if we do a good job on everything else with the marketing, the promotions, all that stuff, we’re gonna be able to really outperform and cashflow really well and all of that. So I think that’s something we’ve done really well in our thinking about just reshaping how we operate, right? And like how we actually are segmenting those types of bookings and holding
those dates and we’re just going to continue to refine and improve on that moving forward.
Michelle Kesil (14:39)
Yeah, amazing. Sounds like you’re scaling and working on some exciting things.Tim Ensmann (14:45)
Yeah, it’s been fun. It’s cool. It’s cool too, because I mean, it’s it’sYou know, it’s a benefit to the groups because it’s like you’re kind of a one stop shop. got everything. You’re where your venue where your accommodation, you have the whole place. You’re not dealing with other events or other people or other groups there. So you can really host. They can be intimate. You know, the pricing is really good compared to a lot of other options. And then it’s fragmented. You’re going to a venue and then you’re finding accommodation and all this stuff. So I think it’s a it’s a really good niche and it’s been a lot of fun. And they’re also just like short
term rentals on steroids. It’s like you get all the benefits from short term rentals and commercial real estate and now you’re able to you know just kind of pick and choose the best parts of each.
Michelle Kesil (15:28)
Definitely. What are you most focusing on solving or scaling to next?Tim Ensmann (15:33)
Yeah, think that’s it. The brand side of it is really important. Building that brand and then building more of that predictability with how do you create more predictable revenue within your year through these hospitality assets. So making sure that we are putting out the right content to attract those types of people, making sure we’re reaching out to the right groups to attract those types of people, and focusing on building that. Because once we have that done, then we can justand iterate. And like I said, now you’re almost running this brand media on top of the real estate and that can be really powerful. So that’s our full focus for 2026.
Michelle Kesil (16:13)
Yeah, amazing. What advice would you give to investors that are looking to expand into this market?Tim Ensmann (16:21)
Yeah, so this I think like anything else, education is really important. You can click on my LinkedIn, join our newsletter. We send updates like this. I was before this call was sending our Q4 update to investors and scheduling our distribution andknow, breaking down what we’re seeing, hey, what’s working, here’s what’s not working, here’s the strategies that we invested in this corner that are paying off well. So I think education is really important, right? It is, like I said, it’s not just a…
traditional real estate where it’s a little bit more focused on hey, how do you manage expenses to make sure that you’re, you know, preserving the NOI? Whereas sometimes like we’re actually gonna spend money on marketing and that’s gonna give us an even bigger boost, right? So I think it’s a little bit of a mindset shift and education and then yeah, think listening to podcasts like this, getting an idea of some of the folks in the space that are doing it, more than happy to connect with me. I’ve had a ton of really good conversations with people that are looking to get in the space and actually today
All the advantages you get from multi-family, if you’re doing cost segregation and stuff, we’re able to do that.
even more aggressively because a lot of the times our renovations they’re so heavy in the beginning that we just have this massive depreciation we can take from cost eggs. So a lot of people like that. yeah, education, podcasts like this, joining the newsletters to learn more about it. And then yeah, we have a ton of resources on our fund, the type of deals we do myself and our team and what we’re focused on now and yeah, more than happy to help.
Michelle Kesil (17:56)
Yeah, amazing. Are you looking to continue to expand and work with more hotels or what does that look like for you?Tim Ensmann (18:04)
Yeah, like I said, just to give rough math, we’re buying these really underutilized assets.We’re getting them at significant discounts because they’re not operating well. Every hundred grand NOI we’re adding to the bottom line is a million bucks. So we’re able to like two, three, four X these property values in a couple of years pretty quickly. And then we’re able to take advantage of blending, of being able to go refinance, get stabilized debt and hold these things for a long time and cashflow very well. So we are, we are expanding. We’re being thoughtful about the types of part. don’t bring in every property. It needs to be experiential. needs to be unique in five,
years
we need to say hey this is still going to be a staple of this market and that’s what we’re focused on. So Blue Ridge we’re very focused on in Georgia, great market, drivable from Atlanta, we can go replicate what we’ve done at the pine tree expansions in California and pine tree and really hyper focused there to just build that moat with our brands and with our strategy.
Michelle Kesil
So as you’ve been transitioning and learning how to operate these hotels, what are some of the changes and the learning curves that you’ve had to overcome through that?Tim Ensmann
my gosh, everything. There’s always something new. I’ll tell you though, AI is getting really good and I think AI is gonna change.a lot of how all of us live and work. think for the better, but I think there’s going to be some challenges. But anyway, I say that because I think in the space I’m in, I know that there’s some things that AI can’t do. When you’re selling experiences and dealing with humans and all of that, at the end of the day, a lot of people do want to speak to someone. They do want someone there. yeah, think that’s never a, I think it’s kind of like health. That’s never something you get perfect. It’s just consistent. You stay at. And it’s the same thing with operations with somebody.
Like you’re always going to have something that comes up, whether that’s a weather event, whether that’s something, know, a tree falls and goes into the roof and there’s like a whole thing. So I think, I think just, you know, managing the teams, empowering the teams, constantly thinking of ways of, okay, because we do have really amazing tools, really amazing tech, how do we implement that to just further personalize a guest experience? So we can have more touch points to guests and get better feedback so then we can
make sure that they want to come back and all of that. I think operations has been the continuous learning curve, right, with all of this. ⁓ You know, how to create that really great group experience, how to create that really great individual experience, how to take feedback, ⁓ how to add these like little, ⁓ you know, little moments, like when people come in and they feel, my gosh, like they thought of me and that like I, you know, now I really like this place. Now I really want to post about it and it just improves the experience. So ⁓ yeah.
I think the operations has been the biggest learning and then there’s always surprises. I mean, there’s always little things that are coming up. I think just empowering the team to be able to manage and to handle those as well.
Michelle Kesil
Absolutely, can imagine all of that.Tim Ensmann
Yeah, always fun. Always interesting.Michelle Kesil
Finally.Yeah. Well, before we wrap up here, if somebody wants to reach out, connect, learn more about what you’re up to, where can people find you and connect with you?
Tim Ensmann
Yeah, so you can find me on LinkedIn, Tim Ensmann. ⁓ You can go to our website, boutiquehotelfund.com. ⁓ We have, like I said, we have the newsletter, we have a mini course there, we have a lot of resources for you. More than welcome to connect with me. And just learn more about your investment goals, learn more about what we’re doing. And yeah, those are the best paths. And my phone number and email’s on our website too.Michelle Kesil
Perfect. Appreciate your time and your story. Thank you for coming on here.Tim Ensmann
Yeah, of course. Thanks for having me on.Michelle Kesil
Yes, and for those listeners tuning in, if you got value, make sure you have subscribed. We’ve got more conversations with operators like Tim who are building real businesses and we’ll see you on our next episode.
