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A
We are betting on all things that are, like, opposite of AI.
B
Everything sucks, Everything's hard. This is like my flavor of suck. Is this my flavor of heart? Right?
A
51% of the economy is owned by small businesses ages, like 51 to 70 or something.
B
Anybody that says they're like, oh, yeah, I love sba, I'm like, they've never bought a business. I wish I would have just partnered up and done a bigger deal sooner. Blake daily calls me and say, hey, I need a million dollars, like, in 24 hours. All right, Tim. Welcome to the Action Academy podcast, my friend. How are you?
A
What is going on, Brian? Good to be on, man.
B
Dude, good. Good to finally talk. You and I connected over Instagram and I was like, dude, we're just gonna be boys. Like, we need to. We need to hop on the pod. We need to go travel, we need to go build some hotels together, man. I'm excited to hear about your story. What you got going on, how you got there and, you know, what, what kind of, what value we're delivering to the audience today. So for somebody that's unfamiliar with Tim Ensman, who are you? What do you do today? And then we'll reverse engineer it.
A
Yeah, man. So I'm Tim Enseman. I'm actually out of Tampa, Florida right now. But we are betting on all things that are, like, opposite of AI. So experiences getting out with your friends, like, build, you know, building those memories. So that's really what we're. We're focused on in, you know, creating these, like, really unique experiential types of properties, and we're doing that across the United States.
B
Beautiful. So what properties do you guys own and run today? And then which ones are you developing currently?
A
Yeah, so, so we, we. We started out with short term rentals, so that's kind of our natural progression. So myself.
B
The natural story.
A
The natural story. Yeah, man. So you get 20 plus short term rentals. You're like, oh, my gosh, we need to. We need to learn a little bit about.
B
Have we ever considered. Hey, guys, it's like you. You're sitting around a campfire, you're like, what if we had all of these under one roof?
A
Yeah. You're like, oh, my gosh, we're brilliant. Yeah, exactly. So, yeah, so now we have three BO hotels, say boutique hotels, but they're like experiential type of, you know, resorts. And. And then we have our management portfolio, which is we still own a couple Airbnbs, but also manage others as well.
B
Beautiful. So let's let's reverse engineer it a little bit because boutique hotels are the, you know, kind of the hot girl at the bar right now alongside as much of a hot girl as plumbing companies for some reason now and Laundromat. So business buying and boutique hotels. So walk us back. So you were, what were you doing before in your profession? And like walk us through acquiring all of these portfolio of. This portfolio of Airbnbs, because I mean, I would probably venture to assume that getting 20 short term rentals was significantly harder than buying these boutique hotels.
A
Absolutely. Yeah. Bigger is usually a little bit easier. But I started similar to you background in sales. So I was, I actually played soccer and when I got done with the soccer career, that was going to be something. Then it was like, okay, you got to go either to pharmacy school for four years or you're going to take this sales job. So I was like, okay. Like my, one of my best friends is like, hey man, they have this job open. I think you'd be good at it. I go, I get the job. And that the rest was history. Was like, wow. I made more my first year in a selling job than I would have as a pharmacist after four years and a lot of debt and all that. So that kind of got my taste for, you know, sales, entrepreneurship, kind of having a control over your own destiny type deal. So really had had, you know, built a career in sales for the better half of a decade. I think I was like 7ish years before I really left corporate through public companies, smaller AI companies, moved up the ranks and honestly enjoyed a lot of it. But like had always been looking at like, hey, I know that this company isn't gonna always be great, right? I know commission checks aren't always gonna be that great. Like I need to be looking at things that are gonna pay me when I'm not working or things that I have more ownership in. So I pretty much invested in like single family homes, a lot of apartment syndications. I've been looking at a lot of these alternatives and I think you may have realized this too. But short term rentals had that loophole with tax benefits. And I was like, okay, I need, I need something that I could get my hands on more. And similar to you, I love travel. So I'm like, all right. My first short term rental was in Park City, Utah because I love beautiful. So I was like, all right, I'm going to buy this property. If I break even on it, that's a win because I'm getting it paid for it's going to appreciate family and friends can come out there. You know, it's a good investment. Dad ended up crushing it. Like fast forward. I think I doubled my money in like a year and a half just because everything went up. But as we were going through that, really enjoyed just short term rentals and hospitality is a lot like owning a business on top of real estate, which I really like. So yeah, you manage the marketing, you manage all the, you know, guest experience, the sales, the design. Like you can compete, I feel like more than other real estate. Right. Like an apartment building, you're not going to spend 50 grand on the brand because it's like we want to cut all the costs we can. Right. A hotel. Absolutely. Like you're creating a like value through your branding, the aesthetic, the design, the marketing, all that stuff. So that's really what got me hooked on short term rentals and then also the tax benefits as well that you
B
want to talk about the STR loophole real quick for somebody that's unfamiliar.
A
Yeah. So the STR loophole, if you own it, so you own the property, what it allows you to do is really take off $25,000 off of your ordinary income that isn't taxed as ordinary income. So it helps reduce your tax rate pretty significantly.
B
Off of your active income. Yeah.
A
On your active income additionally too, if you things like, you know, a cost segregation. So like they'll come in and they'll do a cost seg, you'll be able to use that depreciation off against other gains you may have. Right. So if you have investments out and you have, you sell a property or you have just general portfolio gains, you're able to leverage that cost seg against some of your active portfolio, which is huge. So you stack up a few of those things and now you're actually getting into that like rep status. So that's really what we saw early on. But the learning from that is if you scale a portfolio in Scottsdale, Blue Ridge, Georgia, Park City, Joshua Tree, Palm Springs, you're like, dude, there's a lot of teams, there's a lot of tech. This is yes, you can manage remote, but as we both know, it's, it's going to run better if you either have like true teams on, on site or you're just a little bit more localized so you get some stale.
B
Yeah. I mean I've learned throughout all of this is everything sucks.
A
Yeah.
B
I mean that's the easiest way to put it. Everything sucks, everything's hard. And if you go into every Investment in every Airbnb and every hotel and every business that you buy and you. You go into with the freight frame of this is gonna suck and it's gonna be hard, comma, now, is it worth it? Is this like my flavor of suck? Is this my flavor of hard? Right, because, like, I think we're all past the, the passive income thing.
A
Yep, yep. That. I love that I'm stealing that, but that's. That's exactly right. So our flavor of suck, we're like, okay, this is too fragmented. We no longer term that. You know, we want larger projects. We want to be able to have more leverage to pull. And that's really where boutique hotels, especially where that natural progression of like, hey, we have the operations down. Now we want to go into something bigger that really has that commercial valuation too. I think that's really important. It's like now you're playing at a totally different game. Like, you're not trying to take out this, like, vacation loan, or you're not trying to do this, like, you know, investment loan on single families. Like, you're actually buying a commercial asset and then it's being valued like a commercial asset. So if you, if you crush it, like we have, that's dramatically impacting your bottom line. So that's what, what got us into. It's like, hey, what if we. To your point, like, what if we had all these Airbnbs on one property and then we could have courts and saunas and cold plugs. Yeah. Management.
B
That was just all.
A
And so that was it, man. So. So now the whole. The whole thesis is just similar as you're seeing. I think I saw something the other day. It's like 51% of the economy is owned by small businesses ages like 51 to 70 or something. So like, that's exactly we. All the hotels that we've. Well, two. Two of the three that we've acquired, like mom and pop seller, they're retiring. They really weren't running it. Well, one guy was a. He was a multi family guy that didn't know what he was doing with, you know, hospitality. So, like, there are some of those. But yeah, so you, you're buying these properties from folks that they just want their retirement. Right. Like, they just want a way to kind of step out of these properties and they, I mean, they're pricing. You go on the website, like, the pricing on a Tuesday is the same as it is in Christmas of, you know, next year. It's like there's zero strategy. You talk about social media, dude. We're, we're talking right now because of social media. Like, it is probably one of the, you know, the biggest sleepers on these properties. Because it's like you can create demand. You can create demand.
B
Crazy wacky idea. Crazy wacky.
A
For free. So it's like there was.
B
Yeah, I bought a freaking Alaska tourism company that does Northern Lights tours. No social media. Wow. They do $2.1 million a year doing Northern Lights tours, Alaska wildlife. Check them out, everybody. But it's just like, dude, no social media. Now we have social media. But I'm like, it's insane, but you would see. But yeah. So to that point, how are you finding the deals? Because I think that's a wonderful point is these are the deals that are the mom and pops, you know, they're off the beaten trail. They've got some love that needs to be given to the properties. They need to be updated. You know, obviously systematized, dynamic pricing, getting off the OTAs or even if they're not even listed on the OTAs. So how do you go about sourcing these deals?
A
Yeah, and dude, that's a great question. In the, in the beginning, as we were like starting out, we really knew that because where our market primarily was was Southern California. So we just knew that area. We had good teams. We knew what we were looking for. We were walking properties in Palm Springs and it was so overpriced. You'd have a property selling for 5 million and their NOI was like 400 grand. And like a shaky 400 grand. You're like, I don't think this is going to trade at that. And we got to put a couple million bucks to turn it around. So the pricing was just very misaligned. And when we came across our, you know, pine tree and I'll get to Blue Ridge as well because we own some properties there. You know exactly what you need. Like a few of the buy box things. You need like one. It, it, it needs to be priced right. Like we're going to put a couple million bucks into these things. So if, back of the napkin math, like if we're, if we're already at cost per door, like we, we can't even look at these. It needs to have that ability to like communal activities. Like you need to be able to host events, needs to be commercially zoned. It needs to be drivable. Like think like major metros, your Austin, your San Diegos, your la's, your Atlantas. Like you need to be able to go attract traffic and then really it needs it needs the ability to, you know, appraise. Like, once we go do all of this, like, it needs to be able to trade as a commercial property. So those are the things that we were looking at. But Southern California, we were already touring deals, we already were familiar with the market, we already had the teams there, and we essentially had this buy box of like, hey, you know, typically this is what we're looking for. And if something like this comes up, we're going to jump on it. So the first, the first couple were just like completely mispriced. And the pine tree, which, you know, we bought today, we got from these mom and pop sellers. We went up there, we saw the whole property. We toured the property. We saw that they had been collecting rainwater and like a cistern because they didn't want to pay the water bills. So we're like, is there a pool under here? They're like, yeah, this is, this is a pool and it can get operate, like it can operate everything. They said, yeah, they, they closed it off. The previous owners had it operating. So things like that, where you can have the amenities, you can like, really enhance the space at the right price. We have friends in Eureka Springs, we're doing deals in Blue Ridge, Georgia. I think really the key is the use of the land. Like, you're able to actually operate it like a commercial property. And then it needs to fit that, that buy box. Right. Like you're. We're not looking at 50 to 100 unit properties. We're looking at these like, smaller boutique type properties. And I'll get into why, like the way we can operate a lot more efficiently versus like a, you know, larger like 100 unit plus type type place.
B
Yeah, for sure. For Southern California. I know you had the, the cruise there, and I think, I think I know what the answer is to this, but I'm curious about your perspective on it. So you guys, a lot of people, especially in commercial will hear California, and they're like, hell, no, you know, I don't want to invest in California. And those are mostly like the multifamily guys and girls because of like the tenant landlord laws, like, they're, they're kind of the laws in California. And the tax strategy to California real estate investors is, is terrible. But so why was, why is that an area that you guys want to target?
A
Yeah, I'll say My, my perspectives change and like, it's, it's interesting you say that. We just had a retreat with 10 hotel operators all based out of California last month, and I think we could all agree with that. Like just some of the things in California people aren't too fond of. But I will say from a perspective, California is incredible. Right. Like if you look at the demographic, like from hospitality hotels, if I look at like the ADRs and the type of brand like value you're going to be able to create and all that, I can't think of two better places in LA and San Diego. So that's helped us a ton.
B
The regulations actually work in your favor too because from what I heard it was, they're so hard on short term rentals and, and residential real estate that they're getting squeezed so badly that people are flown to hotels.
A
There's a. Absolutely 2%. Yeah. And that's in same thing with Blue Ridge where we are in SoCal. There's Palm Springs is the most regulated short term rental market in the world. And then Idlewild, which is just up the mountain where Pine Tree is, has a moratorium on short term rentals. So you can't like, you can't get a short term rental license. It is what it is and that's incredible. So obviously that pushes right to us, right? And we're Airbnb esque in the sense it's a seamless digital check in. You got the pickleball courts. It's like, it feels like it's your own space. But you know, during the weeks and some weekends and stuff, it's, you know, it's individual units that you can rent.
B
So let's talk about Pine Tree first and then we'll move over to the Blue Ridge deal. So you guys, you guys found this deal. Was this through a broker or was it direct outreach?
A
This was direct outreach. Yeah, we reached, we reached, we reached out to the broker actually, and he did the buy and sell side, which I think was actually pretty. I think that was a good thing. I think he held it together. I think we've learned when you have two brokers involved too, that's just, we try to go direct to seller, like that's the best way. But yeah, if there is going to be a broker, like having the one there kind of managing both sides, they want to get it done.
B
Yeah, super cool. So how'd you guys structure the deal? How'd you buy it? And then use that as an opportunity to hit on like why you're in kind of your door range. Is there a door range that's too few doors? Is there a door range that's too many doors? What do you guys kind of target?
A
Yeah, I'LL say what we learned with Pine Tree. And like moving forward, we really, it's less about the doors. I think it's more around the top line revenue.
B
Sure.
A
Because you, you get more, there's more levers you can pull if you have a certain amount. So like anything under a million, we really don't pursue anymore. Pine will get there just because we are running that thing like so efficiently. But we're only at 13 bedrooms, 13 bathrooms. There it's 11 doors. Like, it's just humming. But I will say the smaller properties like that, your margin is just that much better because you, you're, you, you're running a leaner staff. Everyone's 1099. You're people expect more of that like Airbnb esque type of check in and like, yes. Not. It's not super, you know, super hotel. It doesn't feel like a hotel. But, but yeah, anything, anything under a million, top line, we're really not looking at. But when we were underwriting it, when we looked at the property, essentially we, we bought it for like 1 5. We're like, hey, we'll put, you know, 502 million. And. Which is right around what we did. We did just about a million and it recently appraised for like 4, 6, 4 7. And like that's, that's without like us really pumping.
B
That's a million, two million equity.
A
Yeah. Yeah.
B
Okay. Yeah, that's, that's a Tuesday.
A
And it's, that'll do it. And it's. Yeah. So we tripled the property value and we are like, our EBITDA margin last year was like close to 50%. We were like 45%, which is crushing. And the reason for that is exactly what we talked about, like with the, the branding power and then like the marketing side of it and driving group sales. Like, we put our sales hat on and did what we had come from, where we're essentially partnering with influencers. So we have people that, you know, have reach in the demographics that we want to attract. They come, they produce content, that content hits. Then we repurpose that content for groups like you or I. So it's like Brian's hosting his birthday next month. Like, you're getting targeted with our ads. You book a call with us, you book your birthday next month at the Pine Tree. So we're already booked out like, you know, three, four, five months in advance. And then anything we're not booked with, group events will just open up. So we're creating this like, predictable pipeline really, with, with that you're running meta ads for that? Yeah.
B
Super cool. So how do you, how do you target the pixel? So like, do you just target that through the ad creative is you're just speaking to people, looking to do bookings for small groups.
A
Yeah, a hundred percent. So in a go high level, you can set that up where you set up different, you know, different content and then you'll just target certain they have characteristics or like fields where it's like, oh, birthday coming up in June. They have wedding. If you just got engaged. If you have.
B
Dude, that's gnarly.
A
It's insane.
B
Yeah, dude, that's freaking. That's freaking sick.
A
You know, it's a unique product. So it's not like there's a ton of these types of properties that can do that. So it's like you're not competing with Airbnb your commercial so you can host the event and there's not a lot of options. It's like, you know, sold. Yeah, it's like, okay, like, and, and it's reasonable. It's not like we're gouging people like the price is decent. It's. If you were going to go up there with, you know, 12 couples, it's going to be the same amount doing, doing somewhere else. So it just works out beautiful.
B
How'd you guys do the debt on it?
A
Yeah, so we, we actually put out the deal to a ton of people. We were raising capital, so it was just through like emails, friends and family, just like getting the deal out there. And then a person that we thought was going to be an equity investor said, hey, I can actually beat the debt on it. Because we were going to do bridge debt originally. So it was just going to be a lender that we had worked with luxury short term rentals in Palm Springs. They were going to do the debt on it. We had an investor that's like, hey, we'll do the bridge debt for it and do it at better terms. So we had an individual investor, just like private money fund. And then we raised the rest through equity.
B
Super cool. And then what was the purchase?
A
The purchase was 15.
B
Oh, yeah. So probably what raised like 30% equity?
A
Yeah, we raised like close to 700.
B
Cool.
A
Yeah, yeah, yeah. So covered. Covered, you know, majority of the, the reno and everything. And then we refinanced into an SBA loan. Perfect structured. So we, you know, got a little bit better terms. Sba. Have you've done SBA in the past?
B
Oh, yeah.
A
It's a. Dude, it is like, it's the Worst colonoscopy. It's like, I don't even. What do you need?
B
Anybody that. Anybody that says they're like, oh, yeah, I love sba. I'm like, they've never bought a business, dude. It is.
A
It's.
B
It's a lot of red tape, but at the end of the day, it's like, we still do. We still will go the SBA route whenever we. Whenever we can. We're getting into the space now where we're kind of starting to, like, size out of sba, so we'll go more like conventional loans once we're getting up past, like, the 5 million range, but. Yeah, yeah, same thing. Yeah, dude. I mean, debt. I mean, there's one thing that's certain with. It comes to hotels is you're gonna restructure the debt once or twice. We're restructuring the debt for our hotel buyer right now, so it just is what it is. But you and I were.
A
What did you guys acquire it with? What. What?
B
So we did it originally with cpace, and we were doing it kind of like an agriculture loan. And then. Then they came back and they were. They were saying, hey, we don't. We don't really have the risk appetite for this. We actually changed our mind. And, you know, we're going to need this much equity to continue moving forward. And with the new interest rates that they proposed, dude, it's the same thing with every single loan underwriter. They tell you everything that you want to hear. They lie through their freaking teeth. If. If I never talk to another loan originator again, I'd be happy, bro. And then they just pull. They just lie to you, to your face until, you know, Tim, when. When does the loan originator reach back out to you? Six hours before you're closing. That.
A
That's. I'm glad I'm not the only one, because I'm like, am I. Is it me? Am I just like, am I the problem?
B
Yeah, we were doing an sba, dude. Sba, too. Oh, my God, man. We. We retraded debt on two of our businesses within the last week of close. And. And so now it's like, for everything we tell Action Academy, we're like, there's one thing that you can guarantee will happen, that your lender will just screw you at the very last second. Have two to three lenders all the way up until the table. Like, it's insane.
A
Dude, I'm so happy that you're saying that, because I. I thought it was me. I thought. I'm like, yeah, you Just suck, man. You just. I need to figure this out. All right. I'm not the only one, man.
B
But something. Something that you mentioned before that I do want you to hit on is you said if you could go back, you wish you would have done a bigger deal sooner. Why is that?
A
Yeah, so what I've learned, and I'm very happy I did all this, but, like, I honestly think it wouldn't have gone the same way. So when you look at the deal, it. It took longer. It was more money, more stress, more pain than we expected, which is fine. I think you do that, like, you commit to that. As a business owner, if you're going to do something, you burn the boats and, like, you make it happen.
B
You're paying. You're paying the stupid tax.
A
You're paying. That's great. Yeah, you're paying the stupid tax. And I'm. And we're crushing it now. So it's like, okay, everything worked out. That's awesome. I will say, though, as you think about, you know, that, that, that time allocation, it's like, okay, if I really look over the past two and a half, three years, we bought Pine Tree in November 2023. Now, granted, we were buying deals and stuff, so it wasn't like Pine Tree was our only thing going, but, like, that was the. The hotel that. That took the focus for the same amount of time. You're still underwriting the deals, you're still structuring the deal. You're still negotiating with sellers. You're still going through the pain of having the lenders fall out. You're still, you know, having insurance drop off. Like, then you figure that, you know, come back there. You're going through all the same shit you would do if you bought a $10 million deal or a $20 million deal or a $30 million deal. And now, while I wouldn't recommend someone say, oh, I've never bought a hotel before, now I'm going to go buy a $30 million hotel. I think you just partner, right? Like, you. You put yourself in rooms or you create value for people that are doing those things to learn quicker and understand sort of the space, like what you're doing, like your roles, where you can really provide a lot of value without being like, the key operator on it. You'll find is you still get the track. That's another thing. If people are listening and you're looking to buy businesses or do deals, you need track record. That's the same reason that we've gotten crushed on. Oh, you can't do, it's like, dude, you can do 50 Airbnbs. Like, if you property, they don't. You're talking to a bank. You're not talking to guys like us. Like, they don't understand that's not in their underwriting requirements. So, like, you're an Airbnb community or like, you're. What are. You know, you're a time. Like, what are you. So my point is, is you need all that stuff that you don't even know you need. So to be able to like, learn for a fraction of your ownership or stake or whatever you want to call it, but like, to understand, hey, I want to be in boutique hotels or I want to own businesses or whatever you want to do, I would highly recommend leaning into your skill set, like what you're very good at and what you can bring to the table, and then just hitching a ride with someone like a. You some like someone out there that's doing it. Because you're going to learn, man. And it's way better, in my opinion, to like, you can learn from others mistakes while still being in it and then still get saved instead of you're there and you're like, like, this happened to us. Our SBA lender falls out. Lost 10k for committing to them. They're just like, oh, sorry, we already like spent like push date three weeks that. That was in a deposit. So now you're, now you're back to square one doing the same thing for, you know, three more months and we didn't have to do all that. All you need is one partner that's done this. Hey, we already know. We already know the, the ropes. We maybe, you know, their, their balance sheet or something, they can get the deal done a little bit quicker. There's, there's like these little nuances that just partnering with the right people and going larger is going to benefit you long, like so much more long term. Because that's two years, you know, turns into. Well, if you do that over five years, if you do that over 10, it's like it's night and day. So that, that would be my biggest thing. Like, don't just burn the boats on something. You know, I'll say pine tree small, but it is kind of small, right? Like, it's not. It's not. We're.
B
Don't be a hero.
A
Yeah, exactly. So crazy. More focused and bigger with the right people, man.
B
It's just like there's a few fundamental truths that I've gotten from this podcast and just talking to so many hundreds and hundreds and hundreds of people. You know, everybody has their own flavor of doing things and everyone has their own background and all this stuff. But what I've just found to be true over everything is that there's nothing more important than your network and your community. And every single successful person I've ever had on the show invests all of their money into relationships and network and masterminds and coaches, like, totally all of it. And so, you know, I would go as far as to say, I don't think that there's another way, at least not to do it well, to break into commercial than exactly what you just said. Not only is it true, it's exactly what I'm doing right now. My first deal, I'm doing exactly the advice that you just gave today, right now is you said, man, I wish I would have just partnered up and done a bigger deal sooner. My first deal in hospitality, I didn't even buy an Airbnb. I'm doing a $14.2 million hotel.
A
Yep.
B
Via new development, modular 20 key ground up. I don't know how to do that. Beautiful operators that I'm partnered with are amazing. Ben Wolf, Steve Turk, my dude. I'll tell you who the most impressive operator on my team and on my cap table is, is my gc, Bangs Chisholm. He is our most impressive guy. He is just a savant when it comes to, like, grading and commercial and construction. And so the point being is I'm a. I'm. Dude, I'm a tiny little. I got like 10% of the GP, dude. Absolutely, like 10% of the GP. But I'm on the GP and I'm learning. And so I get to do this deal. We raise money so easily for it because it's such a good deal that you have so many good operators that have a piece of the pie. And so everybody's trying to eat the whole pie. I'm like, no, dude, get you a slice of it, but make it a bigger pie. Dude, I wish I could, like, freaking print out what you said. Highlight it. Like, instead of trying to be God's gift to entrepreneurship, they don't care how many airbnbs you've bought. They only care what you've bought in the, like, kind asset for multifamily, for hotels, for storage, for all of it. Thousand percent, dude, I freaking love it. So talk about the transition now from doing this deal to the Blue Ridge deal.
A
Yeah. So I think that was exactly the learning. So Isaac, my other partner with Pine Tree, we kind of had that moment where it was like that, aha. We're sitting around the campfire. We're like, oh, what if this was under one. One roof? And we're like, oh, what if we don't need to do all of this all the time? So I think that's where the more, you know. Yeah. Our relationship with Blake. Because now it's like, okay, it is really important. I think I'm at that stage, too, in my life where I'd rather simple things that, you know, you can create value and, like, deliver a ton of value with and, like, bigger. Like, just bigger things in general. Right. Simple scales, longer term stuff that. Where if you're doing this in 5, 10, 15 years, like, you're enjoying that. So that's where we kind of took a step back and we know we'd seen, okay, pine trees working. That model really works. How do we go replicate that model? Well, Blue ridge, which is 90 minutes from Atlanta, destination we had. It was called the tree house there. It's still, like, one of the top Airbnb. Airbnbs on Airbnb. It still operates today. And we're like, what if we had 10 of these things around a lake? And we know. You know, we know Isaac French, he crushed it. We know that. We know the market. We know the pine tree model works. We're like, we. We need to do this here. Blake, who is, you know, this. The hotel community is, like, really small. So there we had friends that are in Blake's mastermind at Tara Palm Springs, which is in Palm Springs.
B
Oh, dude. I know Tara, too.
A
That's solely. Yeah, yeah, yeah. Solely.
B
I know solely Cayetano. And then Blake was with Blake when he was creating his hotel mastermind, dude. We helped him create Shout Out Blake daily. Dude. I was like, yo, do this, this, this, and this. We have to create a sales team for the freaking hotel mastermind, dude. So it's like, shout out his hotel community. Awesome dudes. And Gideon's Spencer.
A
Yeah, Gideon's a great guy too. Yeah. So. So, yeah. So we got connected with Blake and he, his mastermind, they were touring properties in Blue Ridge. And, like, we're like, we should once again, like, where. Where does your skill set lie? It's like, okay, we know the group sales model. We know the branding. We know this market. Like, we know how to activate these spaces because once again, we really like hospitality because it's a business. You have a business on real estate. So you're not sitting there. You're not like, oh, man. Like, rates are going down or rates are going up, like we're totally screwed. It's like you may, you may be more in trouble, but like you gotta like get someone there. Go find, go find a group that's hosting a wedding, you know, out of Atlanta. Like go post things that are going to attract people that you want there. So, so we own that. But Blake's got the largest short term rental management company in Tennessee. Like he's got the op style. So we're like, let's partner. Why do we need to have 100% of these things? Let's partner. So that's exactly what we did. And we said, look, we know these, we know these deals are going to crush. Like, we know the market is extremely strong. We know there's no other competition. There's 7,000 active short term rental licenses in Blue Ridge, in Fannin Gilmer county. And then there's like 8 inns, there's 8 like properties like ours and none of them are even remotely closed. We're on the 10th hole of a golf course. One of them, one of them's got a private lake. Yeah. So all. And you think about, I think this is something we think about a lot. But like, okay, tell us about the downside. Tell us. Everything goes to like, you know, we, we go into recession. Like people, people tightening their wallets and stuff. You're exactly right. But I'll tell you, there's still going to be 30% of people traveling up to Blue Ridge. So what's going to happen is, is like that top 10% is still going to get business. Like you're. Yeah, top 10%.
B
Emphasis is you have to be in the top 10%. So it's just like you don't want to be economy. You. So it's like you have to choose. It's, it's middle, it's economy or it's luxury. Might as well go high.
A
Go high. And, and I'll, I'll, I'll even say we're not, we're not luxury. But we have way more things that you would prefer.
B
If I think about this top 10% of any market.
A
Yeah, yeah. It's you, you pay for experiences. If you get to have, you know, beers till 9 o', clock, playing pickleball with your buddies at one of these resorts. Like, and it's private, like you're gonna pay. There's not a lot of places, there's no cabins up there that you can do that with. So it's like you're gonna pay for that. You have, you're on the 10th hole of a golf course. You have a speakeasy. Like those are memories that you're gonna pay for. And it's with. It's the same price as some of these other cabins. So it's like heat. So that. That's kind of how that came about. And. And we're breaking ground next week. Man. I'm still. We gotta have you up there. It's gonna. Dude thousand percent insane properties.
B
Yeah, I'd love to. And so what's the deal size for this one? Because you guys are doing A frames I saw am so jealous. If you guys have anything. If you guys just are feeling that you want somebody else on the gp, just give me. Give me a ring. I know that there's no room, but if.
A
If.
B
If there's room. Throw me, throw me in there. Dude. I. I'm ready to come swinging.
A
But dude, I'd say even what. What we've seen too like activating the spaces. Like dude, just. Just coming up there with. With your group with your. Your master.
B
Sure.
A
It's. It's. It's crazy. So anyway. Yeah.
B
Beautiful A frames on the lake. If anybody wants to see. See what it looks like, man. There's this wonderful spot that I stayed at and I don't even think Blake or you know about this, but it's just like it's called Adler written Lodge in the Dolomites and it's by this pond. You have these beautiful A frames around it. And I stayed there and as soon as Blake sent me the. The renderings I was like, oh, dude, that's it.
A
Yeah. No.
B
Why'd you wait, man. But it's freaking awesome. So here talk a little bit about that project real quick.
A
Yeah. So we have. There's two properties. We bought them once again scale. They're 15 minutes down the road. So one of them is going to be. It's the L A J Resort. We purchased it at three. Three and a half million just appraised. Actually. The replacement cost on that property is eight and a half million. And like it's 20,000 square feet. Dude. I'm telling you that it's like buying. You're buying residential assets and you're turning them into commercial assets. It's crazy. So like you're getting like the real today land and property value and then you're turning it into a commerc real estate, which is insane. So that one we got for 3 5. We're putting around 2 million into it. But primarily the bones are good. We're adding Pickleball courts. We're doing the cold plunges, saunas, a cool gym downstairs, speakeasy. We're gonna activate it, activate it. With the cafe. We have like a venue area, a sick resort style pool on the 10th hole of a golf course. So we'll do some partnerships there. And then like a pitch and putt too, like on the side. So that one will be like, go and have fun and play. And then the other one, Willow Falls, which you're talking about, that's a. That's on 20 acres. It's around its own private lake. It's already an operating wedding venue. It already has a wedding venue. It's got three additional cabins on it. And then we're developing seven, like luxury a frames and all different flares. Summer is one's like a. A badass one that like looks out over the lake and. And that one we got for 3.3 million and we got that one on like 80% seller financing terms, which is insane, bro.
B
He called me. He called me like, because what happened? There was a lender or something that went out or a capital partner or something that went out that was on
A
White Path, that was on LJ Ellaj Resort. The let. The. The seller said that they were going to hold 10%. The seller know, and they just completely failed. Like, did not do that.
B
So we called me and he. So this is what happens when in our world. So Blake Daly calls me and say, hey, I need a million dollars like in 24 hours. I was like, oh, okay, well, let me text a few people. And by the time I texted him back, he's like, nevermind, we're good.
A
Yep. Yeah, man. Crazy. But I mean that's. That's a perfect example. That's literally how these deals go. Like pine tree. We. We almost lost it because of insurance stuff. And then I think there was a capital capital situation at the end. Same thing with these. It's like you just.
B
You go.
A
You roll with the punches. We were short and then, you know, raised it and then back, back filled in. Back, back. Raised them out. But yeah, man, they're. They're insane properties. And like looking in where these are going to be in like two, three years, it's just. You can, you can feel, feel already. And the demand too. I think people prefer that over just a room. And there's really nothing like that in Blue Ridge. So I think there's just that sort of unique factor as well.
B
Dude, that's gonna be freaking crazy. I'm so excited. Yeah, I'll for Sure. Come up there. So closing thing, you really care about lifestyle design and making sure that your assets and your investments support the life that you guys want to live. And you don't want to buy an asset or buy any properties or buy anything that takes away and takes you away from the life that you want to live. Can you talk a little bit about how you go about designing your. Your lifestyle and then how that influences the properties and projects that you take on?
A
Yeah, I think, I think this whole kind of journey started a few years back when we went into Pine Tree. Like, hey, we have all these Airbnbs. And like, this isn't really it. Like, this isn't the end goal. Right? So how do we consolidate? And I think that was also learning because it's like, it's okay to consolidate, but then you almost consolidate a little bit more. Like, you keep going bigger, but then more focused.
B
Right?
A
So when I think about that, like, the types of deals I want to do and the types of businesses I want to be a part of, I want to be a part of them for 10 plus years. Because I also realized I'm going to be working forever. Because I like it. Like, I like, I like doing this. Like, I like meeting you, man. Like, I, I hope we have a couple of beers up by the Blue Ridge properties. Like, I like doing this. I like, I like building businesses. So I want to be a part of things that I'm cool with for the next 10 +. So focusing in on that, it's like, if, if I, if I can't do that and it's not big enough, I don't want to focus on those things anymore. Right? So, like, it doesn't excite me to, oh, I don't want to go two
B
or three year exit. You're like, oh, I'm going to buy this hotel, I'm going to renovate it, and then we're going to just dispo.
A
Yeah, no, and I think unfortunately, where we're at today, the way things are structured, we may have to do that just to pay people back and do all that. But still, like, still being in the space, like, we'll still keep doing these types of projects and then that vehicle is, okay, so, like, what's my role in these things? Right? Like, how do you actually create value for the partnership structure? So, for instance, working with Blake and like, okay, hey, we don't need 100% of these deals in Blue Ridge. Let's partner with someone who's got the ops team in Georgia, in Tennessee, that you can partner with and actually scale and scale more effectively longer term. So I think it just comes down to, like, every deal that we're doing is actually like filling a role. Right? So, like, the hotels are dramatically filling that role of. Okay, there's a serious equity play there, a ton of tax benefits when they start operating, like some management fees and stuff like that. And then the Currently too, I'm working with. With Sam Silverman on the paving roll up. So that's.
B
No, you're not. You're going. Wait, what you're doing. So wait, I didn't even know that.
A
Wait. Yeah, so we're doing the, the paving companies that we're working on right now is to roll up all capital markets with Sam and then the private credit side, which is like filling some of these roles, right?
B
I didn't even know that.
A
Oh, really?
B
No. You're doing.
A
Yeah, man.
B
What?
A
Yeah, Sam's one of my best friends. I've known him since like, college brother.
B
I'm going to Italy with him.
A
Yeah, yeah, yeah, yeah. All right, cool.
B
There's a whole other podcast. All right. Yeah, I was just talking to Sam last night about his freaking paving rolls. So what, what role are you playing in that?
A
Head of investor relations.
B
No.
A
Yeah, yeah. Okay, cool.
B
So what, what aren't you doing? Who else do you know? Do you know my family?
A
Yeah. Yeah. Your mom says hi.
B
Holy shit. Well, dude, that's freaking awesome, man. And so in closing, you know, what makes you say no to something? So out of all this stuff that you're doing and all these projects that you see that come across your desk, like, what, what is your kind of frame of reference that you say, not necessarily just like a buy a box, like a financial buy box, but just like a life buy box where you're like, hey, like, if this isn't. If this deal doesn't scratch this itch for me, if this partnership doesn't scratch this itch for me, I'm just out.
A
Dude, I. I think I'm saying no to a lot of stuff right now. Like, I think it's. It's pretty much those three. Those three areas, right? Like, what we're doing and paving is the same thing we're doing at boutique hotels. You're buying these, like, really undervalued, mispriced assets, and then you're completely turning them around. You're professionalizing them and you're operating them like a real business, right? So the boutique hotels, major tax benefits, big long term play, personal play, right? Like being actually able to use the space, the paving roll up. I've known Sam for a long time and this is a very large opportunity and it's also very sound like these are good businesses. It's AI resilient and the team is like rock solid. And then the private credit stuff is just, that just is cash flow and like kind of keep, you know, keeps the, the, the daily, your daily lifestyle going. So it's like those are the three roles and everything else there's really for the next like couple years. I don't really see saying yes to many other things unless it's like, you know, like, I don't know, Elon Musk is like, hey man, we're gonna, yeah, we want to do boutique hotels on Mars or something. But outside of that I think, I think it just comes down and then you roll in that right. Like heading up capital markets and like focusing on the actual strategy and like cap stack of these, of these deals is like really where I enjoy being and just focusing there. Like to your point, I'd rather have 10% of a pie than 100% of a grape. And just working with people that sort of align and have, you know, similar goals.
B
So people want to find out more about you, they want to follow along the journey and they want to potentially invest. Where can they find you?
A
Yeah man, connect with me on LinkedIn just Tim Enseman. That's the best spot. You can drop my, my email below. I'll, I'll put my email here and, and yeah, LinkedIn's probably the best. Tim Ensemb Instagram. I'm, I'm on but more for personal stuff and, and then yeah, I'll drop my email in the comments here.
B
Sweet. Beautiful dude.
A
Awesome.
B
Like we know every single person together so end up doing business in some way shape or form together.
A
Where are you at, Brian? Where, where are you right now?
B
Austin.
A
Okay, cool. Are you there for a little bit?
B
No, we're flying to Europe in two weeks.
A
Okay, cool man. Okay, we're in Europe.
B
We're in Europe for the next 90 days. So we're here. We're going to be in Europe until August and then we're going to cruise with my girlfriend's family and then we're moving into our new home here in Austin in mid August. Then we have three weeks, then we're going to Cancun to host an event and then we come back and I think we're going to Iceland. So dude, we'll plan it out.
A
Oh yeah, I was going to say let's link. We'll link up, like, later in the year.
B
Yeah. Sweet. Well, guys, it's been Brian and Tim with the Action Academy podcast signing off.
Host: Brian Luebben
Guest: Tim Ensmann
Date: May 18, 2026
This episode dives deep into the journey of Tim Ensmann as he transitions from managing a portfolio of 20+ short-term rentals (Airbnbs) to acquiring and developing boutique, experiential hotels and resorts. The conversation is a masterclass in buying, structuring, and scaling hospitality and real estate businesses, focusing on how to create a life and business you love by moving beyond traditional job structures. Along the way, Brian and Tim candidly discuss the realities of business acquisitions, deal sourcing, partnerships, challenges in hospitality, the pitfalls and rewards of SBA loans, and their "flavor of hard" approach to entrepreneurship.
[01:02–05:17]
[05:17–06:30]
[06:56–09:55]
[09:55–13:10]
[13:10–14:47]
[14:47–22:19]
Memorable Moment:
“For every investment...you go into it with the frame of ‘this is gonna suck and it’s gonna be hard, is it worth it, is this my flavor of suck?’”
— Brian [06:34]
[19:00–22:19]
[22:19–28:49]
Memorable Quote:
"I'd rather have 10% of a pie than 100% of a grape."
— Tim [42:40, paraphrased throughout]
[28:49–36:58]
[37:24–41:20]
| Timestamp | Topic | |----------------|------------------------------------------------------------------------------------------------------| | 01:02 | Tim’s background: sales to real estate entrepreneur | | 05:17 | STR loophole explained | | 06:56 | Why move to boutique hotels? | | 09:55 | How to find and buy great boutique hotel deals | | 13:10 | Investing in regulated markets like California | | 14:47 | Deep dive on Pine Tree deal: structure, value-add, and marketing | | 19:00 | Bridge loans, SBA loans, and the pain of funding real estate | | 22:19 | Why partnerships and scaling up matter more than going solo on small deals | | 28:49 | Transition to Blue Ridge boutique resort deals | | 34:29 | Willow Falls and LAJ Resort development details | | 37:24 | Lifestyle design—aligning investments and projects with your ideal life | | 41:20 | Tim’s “life buy box” and how he says no to deals that aren’t aligned | | 42:57 | How to connect with Tim (LinkedIn, Instagram, email) |
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