How to Replace a Six-Figure Job with Boutique Hotel Investing | Tim Ensmann E55

Ever dreamed of quitting your six-figure job to build real wealth through hotels? This episode shows you what it actually takes.

Tim Ensmann, founder of the T.C. Hotel Fund, shares how he went from tech sales to owning a multi-million-dollar boutique hotel portfolio in under five years. He reveals the sacrifices, systems, and strategies behind turning a $1.5M property into a $4.5M success story. He then shares how you can follow the same path without losing your sanity.

You’ll learn:

• The real moment he knew he couldn’t stay in corporate anymore
• How he used short-term rentals to bridge the gap from W2 to full-time investor
• What it costs (financially and emotionally) to leave a secure job for entrepreneurship
• How to identify the right first project for your goals

This is a step-by-step blueprint from someone who’s actually done what so many people dream of.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Tim

Tim Ensmann is the founder and managing partner of Boutique Hotel Fund, an investment platform that acquires and repositions boutique hotels across the United States. With a background in corporate sales and strategy, Tim transitioned from tech leadership roles into hospitality investing, where he now helps accredited investors build wealth through experiential real estate. His firm focuses on transforming underperforming properties into design-driven, story-led destinations that deliver both emotional impact and strong financial returns. Through his content and education platforms, Tim is redefining what modern hotel ownership looks like for a new generation of investors.

Connect with Tim

Email: tim@boutiquehotelfund.com

LinkedIn: www.linkedin.com/in/tim-ensmann/

Website: boutiquehotelfund.com/

Instagram: @tim_ensmann and @boutiquehotelguy

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

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Transcript

Michael Russell 0:00

If you're still working at W2 but dreaming about owning a boutique hotel, this episode is your roadmap. You'll hear how Tim Ensman traded the safety and comfort of a high-paying corporate job for the chaos and uncertainty of entrepreneurship, and how that leap led to a multi-million dollar portfolio of boutique hotels. It's a real look at when to make your move and what it takes to find your zone of genius along the way. Let's dive in. Welcome to the Hotel Investor Playbook, your guide to building wealth and freedom through boutique hotel ownership, hosted by Mike and Nate. Get in the game. On this podcast, we talk story about everything you need to know to make money investing in hotels and hospitality assets. Now, today's episode hits pretty close to home. It's about making the leap so many of us dream about, which is leaving a six-figure job to build wealth through boutique hotels. And our guest did it and built a multi-million dollar portfolio in under five years. Tim Ensman, founder of Boutique Hotel Fund, welcome to the show.

Tim Ensmann 1:23

What's going on, Michael? Thank you so much for having me, man.

Michael Russell 1:26

So, Tim, you left a secure, high-paying job to build something completely on your own. So I want to know what was the exact moment when you knew you couldn't keep doing the corporate thing anymore?

Tim Ensmann 1:36

The thing that really prompted me was finally, you know, getting that asset uh under contract. There was a deal that we had, the Pine Tree Hotel. It really hit a lot of the check marks of what we're looking for now and taking on investor capital. We knew the scope of the project uh project and what we needed to do to deliver. We needed to be absolutely full focus. There was no other option but success. And that's really what prompted the move from uh my W-2. We went into that um with some really good systems teams uh properties and a vacation rental management company. So Second Home Stays had already been operating. We'd already been managing other owners' properties. So it wasn't like I just went, you know, completely, hey, I'm completely done. I'm now fully in the boutique hotels. Um we had still, you know, had a lot of expertise and been managing other clients on the vacation rental management side, which gave me a little bit more security and confidence. And hey, this is something that at least is going to be consistent versus, as you know, with boutique hotels, you're really not getting compensated in a lot of areas. It's the income's rather lumpy.

Michael Russell 2:47

All right. Well, let me unpack a little bit. You recognize that you had an obligation to protect your investors' capital. And while working a full-time job, I presume that must have been extremely difficult to be laser focused, especially when you're buying a property that needs a major renovation. So you made the sacrifice, you made the leap. And you know, I think a lot of people romanticize the idea of leaving a six-figure job, but I imagine those first few months were a little messy, and um, especially mentally and possibly financially. I I'm curious to know like where were you in life, like from your status as far as your income? Did you have a nest egg put away that gave you some comfort to be able to um step away?

Tim Ensmann 3:28

Yeah, I had been so I'd been in high a high tech sales role for close to eight years. Um, so really good income, investing in everything, you know, single family, multifamily syndications, all of this stuff. And that's what got me into short-term rentals, which I really like, the aspect of having more control over it. We had been building this business on the side too, along with very strong income roles. So I we were able to sort somewhat stack up our short-term rental portfolio, manage the short-term rental portfolio, and then start to manage others. So we're slowly accruing this other, you know, active in income stream that was very tailored and focused on what we were doing in Boutique Cospitality as well. The focus was hey, build up a business that's very focused on things that are gonna help the success of the deals that you're doing. So that was, you know, through Second Home Stays that we really said, hey, like we're building up this portfolio. This pairs really nicely with the next deal that we do. And then because the next deal that we do is gonna be managed by us, that's always that's also gonna activate another uh income stream for the business that gives us a little bit more confidence to uh to focus and to put our focus there.

Michael Russell 4:42

How did you first discover or determine that there was an opportunity for you to start investing in short-term rentals?

Tim Ensmann 4:50

A bunch of now experience because I had gone through acquiring single families, I'd gone through diligence of multifamily syndications. And it said, okay, well, uh to your point. One, if I can be more actively involved in real estate, specifically around short-term rentals, there are tax benefits. And then two, uh, I have more control over my cash flow with short-term rentals. Um, because you know, a single family home, you you can only charge so much for market rent. Short-term rentals, um, very similarly, demand's only going to support so much, but you're not gonna be getting, you know, three, four, five X of your rent each month on a single family for short-term rentals, like you can get your mortgage payment in a weekend. So I like the idea of that. And I said, hey, if I can even, you know, make any anywhere near more cash flow, I have these tax benefits. And it was the personal, the passion project. I my first short-term rental I purchased in Park City. Um, I said, and if I break even, I can stay here, you know, once a year with friends and family and go skiing and all that stuff. Uh, so that's a win for me. And then appreciation is going to do its thing over time.

Michael Russell 6:00

Where when you reflect back on your arc and you were to give advice to someone who is currently working before they quit, what are some of the financial markers that they should have? Let's say liquidity or passive income or something else. Um, can you lend some advice on that?

Tim Ensmann 6:19

So I think it really comes down to your goals, right? If their goals are strictly to, hey, I want to leave my corporate job because I really don't like my corporate job and I'm looking to create over a six-figure business that's in real estate. Um, I think my advice to them is going to be look at how you can get as active as possible for the least cost of capital getting into that, right? So here's an example. Um, you can purchase your first short-term rental, but that's going to be, you know, 10, 20% down, right? And then you're going to own that asset straight up, or you can partner with someone to purchase that short-term rental, or you can, you know, um manage it for someone. And the reason for that is because short-term rentals do have that tax advantage, right? If you participate the most in that property, um, you're going to be able to use a pretty significant, I think it's like there's a $25,000 um limit, but you're going to be able to use some of that depreciation against your normal income. So things like that are actually going to help you get closer to leaving that nine to five. So I think short-term rentals as of right now is a great um vehicle to go do that. So what's important is if the goal is for people to leave their job, I think I'm saying something different. Whereas if the goal is for someone to like go purchase a boutique hotel and they want to become this like hospitality operator, um, I think I would recommend something different. You'd almost want to partner with someone who's doing boutique hotels versus having to learn all this stuff, do all this stuff to support your W-2 income. And you'll say, hey, Michael, you're very good at you know finding deals. And we have a really good operations guy here. There's a very good capital raiser here. Like I think that's how you build those partnerships, and that's what can help you get access to those types of deals. But if you're comfortable with creating businesses that provide value to real estate, these ancillary businesses, that's a very clear path to um making money as you're building your investments. Yeah.

Michael Russell 8:24

I want to connect the dots here a little bit because I think what you're saying is gonna ring home, ring true for a lot of people. So, but the reality is uh to be able to replace your active income, you gotta get up to a certain scale. And you can get up to that certain scale by owning um enough short-term rentals, or you can go the hotel route and you grew a short-term rental management company. You had, I believe it was 20 different rentals spread across all throughout the United States. And we owned all of them. But one of the challenges of running an Airbnb or short-term rental portfolio like that is you have created a full-time job for yourself. So the idea of investing in hotels to be able to gain freedom, I think it really needs to be acknowledged that you're you're hurting cats a little bit there with all those individual properties. And when you're managing short-term rentals that are spread out like that, you don't have the same degree of operational scale where you can assign uh roles and positions to people, and there's enough revenue from the business or the operation or the asset to be able to support permanent support roles. So you found payday with short-term rentals, but then recognize, well, operationally speaking, this is a full-time job and then made the pivot to hotels. So for someone that is thinking, yeah, I want to not only replace my income, but I want my own sanity. I don't want to be working all the time. How realistic is it that someone can find that freedom and still be an active real estate investor? And if so, what route would you recommend that they go knowing what you know now based on all the different opportunities you've experienced so far?

Tim Ensmann 10:12

There's two routes knowing that I know now. One, if you're like, hey, I don't completely hate my job, I'm I'm okay with this for the next five to 10 years. I think doing what we're talking about, like having a really boutique, like curated experience, um, you leaning in with a partner or another friend or something like that, that you can go purchase these, you know, luxury short-term rentals, smaller ins, something like that, is probably a very like, you know, the old single family adage where you just, you know, buy one every year and that stacks up over 10 years and now you have all this wealth or appreciation. I do see that being an option, right? If you and your spouse are able to manage the asset, now you're getting all these tax benefits, you still have the income from your job. It's one property, maybe even local. Um, I think there's still a path where you can say, hey, I'm gonna go a little bit slower, stack up some really unique properties, some really solid, solid uh places that we're passionate about. You can use a lot of tactics from short-term rentals, but it's more like you driving it. The second part of that is once again, we talked about is like leaning into what are my strengths and what is the value, finding that deal that's gonna gross over a million bucks a year. That that's one thing that I would absolutely look for. Like, because the reality is, is when you cover debt service, when you cover your teams, all of that stuff, it's probably not gonna be producing cash flow, and most likely you're taking on investors. It's not gonna be hitting the returns you want. And then you're back to square one. You're like, hey, this isn't actually the thing that I wanted to replace my job. I would say finding the right partners is pretty important. Like identifying that. Here's what I'm good at, here's what I can bring to the table. If you don't have another business or if you don't have another area to support that other income, probably doesn't make sense for you to say, hey, I'm going all in, right? So making sure that um if you can tag up with partners, that's that's how I would have done it in hindsight.

Michael Russell 12:07

Yeah. No, I think that's really sound advice. I mean, basically to unpack that and what you're saying is so from a tactical perspective, it's like, look, if you've got income that you can support yourself and you can participate as part of a team, you don't have to be responsible for everything. So you could be hyper-focused on your highest and best use and go and attack that and maybe hold off on quitting your job until you've got enough cash flow from the business to be able to replace your existing income. So let's talk about this Pine Tree Hotel. From a high level, you took a property and you increased its value by about $3 million in less than a year and a half. And you did that through strategic investment in intentional features, wellness, um, you know, a sense of community. You were very design-oriented. So all of that has really played a role. But I want to start with at the beginning, how did you find and underwrite the Pine Tree Hotel?

Tim Ensmann 13:06

Great question. We so we had um done quite a few short-term rental, well, short-term rental and medium-term rental projects in Palm Springs, California. Palm Springs is a super high vacation rental market, um, but very, very strict. And so doing deals there, you know, a lot of our properties were medium-term rentals. Um, we would have a few short-term and uh and we we saw, oh my gosh, these properties are they do very well. If we had the ability to have a hotel, they would probably do much, much better. So that's what really prompted our interest in moving to okay, we know the experiential properties, crush it. We said, okay, if we're able to do that at a larger scale, we're probably gonna be able to get the best of both worlds. We're probably gonna be able to get, you know, we have a commercial property now. We're spending money on one pool instead of you know 10 pools, and um, and you can build a brand behind that. So we had started seeing that, hey, this may be an option. So we were very, very active, actively looking in Palm Springs, California, um, for quite some time. And we could not find anything. We walked so many properties, the pricing just did not make sense. Um, the revenue didn't support it. Um, if you're familiar with Palm Springs, like Palm Springs is a really, I'd say, like high-end design forward market. So, like some of these sellers that were selling were just it was more pride than anything than justifying the actual financials. So after a few years of disappointment of trying to find something, um, we came across Idlewild, California. And um, we weren't really familiar uh because it's interesting. It's like literally 45 minutes up the mountain. It's such a cool town. It's uh it's the only place in Southern California that gets snow. So you can be in Mexico in two hours, two hours, and it snows in Idawild. So you really get this like nature, you got the mountains. Um, it's it, you know, it smells like you're in a like uh a different country. Smells like you're in Blue Ridge, Georgia when you go up there because you got all the pine trees around and everything. It's it's a it's a super neat town, and they have a a really solid town as well. And um, it's so close to everything that we thought, man, this there there could be something here. So the Fern Valley Inn was actually on Zillow, so it popped up on our Zillow feed, and we knew what we were looking for. We were looking for um, you know, multiple units on a decent amount of land so it could be like somewhat communal. We had the same concept that we wanted to do in Blue Ridge, Georgia, that we wanted to build multiple cabins there um that we weren't able to uh actually execute on because there's a lot of work there to get it approved by the county um and then to get the funding for new construction. So we we just that that dream kind of died a little bit. Um so when we came across the Fern Valley Inn, we said, oh my gosh, like there was the first time we walked a property, it had all the things we were looking for. It had multiple units, it had really good, good land, good space to create the type of experience we were looking to do. Uh, it had a pool that had been uh converted to a uh a place that was just collecting rainwater. So the owners didn't want to take care of it. So they just put like a lid over it and we had a pool. So we're like, oh my gosh, so now we can be one of the only pools up here. It's heated year-round. People, people love it, it's a huge hit. But um, this property had all these just really um unique advantages that no one else in this town really had. Um, and with our experience, we said we know we can we we can make something here because we had we had done a lot of work in Palm Springs.

Michael Russell 16:52

Well, let me let me just hold on just for a second here. So this is a 13-unit hotel or zoned hotel. It's you know a property that has 13 separate rooms and 13 separate bathrooms, right? They're independent of each other, kind of like a micro resort basically.

Tim Ensmann 17:11

Yep, it's it's 11 rentable units, but yeah, 13 bedrooms, 13 bathrooms.

Michael Russell 17:16

Okay. And it's a couple hours from Los Angeles, is that right?

Tim Ensmann 17:20

Two hours from LA, two hours from San Diego.

Michael Russell 17:23

So you got a major metropolitan source there of people that want to do weekend getaways. And what was it about this thing that you felt like, okay, there's an opportunity, there's there's a gem here, there's a feature here where you know we can differentiate ourselves from the market. Because when I think LA, or at least that market, um first off, a million and a half bucks for 11 units, I mean, in LA, like the region of LA, that that seems like a pretty low price point. And obviously you created tremendous uh upside through some of the improvements you made. But what what were some of the things that you recognize? Like, let's talk about who's gonna be staying there. What did you identify like who this would appeal to? Are these weekend getaway couples? Are these groups? Um, what was it about this property that you identified? Hey, there's an opportunity to really generate extra revenue.

Tim Ensmann 18:22

That's a great question because a lot of the properties that we walked prior just didn't work. The topography was really important. Each property that we do, we wanted to have some form of wow factor, right? So when we came on this property, all the cabins were almost, I'd say perfectly arranged. There's some topography where it's there's a little bit of a slope, so it feels a little bit bigger than it is. There's massive pine trees all through the property. Um, you had different sections. So you have the courtyard that's just a little bit outside, the pool area that's just a little bit outside where we have the pickleball court and the coal plunge and and saunas, the wellness area. So as we're walking it, we could feel and we could see okay, it's it's small enough to be intimate, but it's big enough where you can have groups there. It really is the perfect place for a micro wedding, birthday party, family reunion, you know, friends get together, and you could feel that walking on the property. It just truthfully, it needed so much love. I mean, it literally needed everything. So, um, so yeah, that that's what it excited us because we were thinking, okay, obviously you're traditional travel traveler, right? Couples get away, or someone just looking to get up, get up for a few days, get out of the heat in Palm Palm Springs, or get away from LA and get away from the noise. Um, so that was obviously our target uh avatar of folks coming up of guests. But what what we significantly uh conservatively underwrote was the amount of interest from the group booking. So we had had in our initial underwriting that hey, maybe we get one group booking for. Six grand a month, that would be awesome. Right. And um, assuming a weekend getaway or something like that. And we were just so, so far off on what the actual demand and interest was for something like that.

Michael Russell 20:13

What do you mean by that? You were off. Like you uh you received more demand than you originally expected?

Tim Ensmann 20:19

Absolutely. Yeah. So we were initially underwriting, you know, six grand if that for one weekend a month, that was just going to be, hey, this is gonna be, you know, a birthday party or something like that. We've significantly pushed our pricing for for weekends, but our first booking was $20,000. So that was, you know, significant when you look at that, that booking, that $20,000 booking covered our debt service in one weekend. So if you're able to do that, hey, how do we go do that again? How do we really create a brand behind it? Create just this um buzz and this loyalty and this it's it's unique. It's there's no other places up there like this doing that. Um, and it's so close and accessible from LA and San Diego that it makes a ton of sense. It's actually pretty reasonable, right? It's a couple hundred bucks a person for the weekend.

Michael Russell 21:08

Well, let's double-click on that a little bit though, because I think the main takeaway is what you recognized is with its proximity to Los Angeles and the way that the footprint of the property was set up, it was really well suited for group bookings. And if you go and you like looking at your website, by the way, there's a lot of wow factor. Like this is not just an ordinary place you can tell there's clear design intention, but intention for a specific avatar, you recognize that your creative niche is going to be group bookings. And sure you can still accept individuals, but when you go to your website and you try to book, from what I can tell, anything 60 days out is is required of group booking. Is that correct?

Tim Ensmann 21:52

Yeah, that that's a great observation. Yeah. So what we noticed was there's this happy balance between last minute couples. So our pricing showed this too, but less than 10% of our web website bookings were booking more than 90 days out. And what that that while they were better bookings, the ADRs were much higher because they're planning and they're booking further out. We were okay giving up that 10% to focus on strictly outbound marketing to attract groups because our group premium is so is significantly higher than what we would get on a normal weekend. So that's why our, you know, anything over 90 days, you can only book full property buyouts. And anything under 90 days, if we're not booked, um, you you can book individual accounts.

Michael Russell 22:38

Okay, so that's a really important point there. You've just carved out this specialty product to stand out, to separate yourselves from the competition. You provide a product that works really well for groups and you charge a premium for it. So if there are levers that you can pull where you can generate more revenue, then ultimately property is gonna be worth more if the bottom line, the NOI is higher. And your capacity to recognize this property is suited for groups and charge a premium. I've experienced that in Maui with my own vacation rentals. When you look at a like cost per room basis for like a one or a two-bedroom condo, there's a ton of supply in Maui, for example, tons and tons of individual condos. And so there is price competition for those uh smaller units, but there are very few four bedrooms. Now, I'm just providing this example for you know, for context. I know we're talking about hotels, but but the idea here is there's not that many hotels in that market that provide the capacity for large groups to get together and spend time in nature all together in a really cool, hip, fun design forward spot with like a pickleball court and like, you know, I think the the the wellness features. If you might have a sauna, I'm not sure, but you've got really nice things. So it's like, who wouldn't be excited to go there? And so when you think about the premium that you're charging, people don't really compare, like, well, it's cheaper to go stay down the road. They're thinking about whoa, this is one of a kind. We can stay with our whole family, and so they're willing to pay a lot more. And that is a huge lever, I think you're tapping into in your business model.

Tim Ensmann 24:19

You're spot on. And I I'll make an important note too. It's more than just some amenities that make the property, right? And I think like the ability to have a good piece of land, and you know, it's not always easy to articulate what that means, but like when you walk on a property, does it have the flow, right? Like if you have your whole group of people there, is it easy to move in and out, to be either playing games or be sitting around a fire? Like we've all been on properties where it's like, okay, you just have a parking lot and then the space is over there, and it's kind of weird and kind of awkward. You really have to get creative to lean into that because you're exactly right. I mean, people want to be able to have all of that stuff with just your group. There's and there's a ton of value to that. We found that niche, and um, we've just been really leaning into that because it's it's in such high demand.

Michael Russell 25:13

So million and a half dollar purchase. Today it's worth around four and a half million dollars. Can you walk us through specifically what has driven that three million dollar jump in value?

Tim Ensmann 25:22

Yeah. So I would say um, I mean, the NOI obviously helps prove that out, right? So I think that's an amazing just takeaway for anyone thinking about this is commercial real estate, especially when you think about going to get debt to the lender is evaluating the property based off the DSCR, they're gonna be able to get paid back and obviously the appraisal, but that's massive, right? So that's the debt service coverage ratio.

Michael Russell 25:47

So, in simple terms, what does that mean?

Tim Ensmann 25:50

In simple terms, that's just making sure that your debt service can be covered each month through the income of the property. So a lender's gonna look, and that's that's why after you're stabilized as a commercial asset, it's much easier to get much better terms on debt on lending. So when you're able to increase the property value, you're therefore able to most cases increase the type of debt that you can secure on the property.

Michael Russell 26:15

Yeah. So I think yeah, heard you say, hey, look, we had like a $18,000 all-in mortgage and one booking brought in 20 grand. And so right there, we've covered our mortgage. So from a lender's perspective, anything on top of that is gravy. So that gives you the ability to um qualify for, I guess like a refi. Is that kind of the intent? Or how what's the relationship there?

Tim Ensmann 26:39

Exactly. Yeah. So um, so typically, I mean, so just any in any boutique hotel acquisition, there's a few ways to go secure debt on the acquisition side. It's going to be SBA or or bridge debt or private, private lending. Um, but then once you're stabilized, there's a lot of conventional options that you have access to that are pretty decent terms. I just spoke with a lender the other day, like 7% interest, you can pay a little bit more if you want interest-only payments, which reduces you know, your mortgage payment, um, improves your cash flow. So on a 25 to 30 year note, so like these are pretty decent terms that you can get once you're stabilized. And what stabilized means is having you know a solid track record, usually 12 months, to show that the property's been producing income to support the debt that you're looking to uh go take out on the property. So my point in sharing that is being able to turn around the income for that property that we bought for 1.5 million um showed that, hey, this property can support a much, much higher valuation for the lender to loan us money, um, but also for a potential buyer to say, hey, you can purchase this property and you're producing uh, you know, quite quite a quite a bit of income to cover any sort of debt that you may have on the property um and support that valuation.

Michael Russell 28:02

Yeah, I I think I heard you say on a previous podcast that after you stabilize this property after year one, your net operating income was around $300,000, $350,000. Am I in the ballpark? Is that accurate?

Tim Ensmann 28:15

Yes. Yep.

Michael Russell 28:16

Okay, so let's do this. So for that part of California, cap rates are more compressed than you're gonna find in other parts of the country where you're gonna have higher cap rates. So a lower cap rate typically means higher value. What's the cap rate in Idawild, more or less?

Tim Ensmann 28:31

Yes, tip typically it's gonna be seven to eight. We should be able to get lower than that, but yeah, I would say seven to eight.

Michael Russell 28:37

Okay, so $350,000 of net income, and you divide that by seven percent cap rate, and there's there's five million bucks. So they there you go. That this thing tracks. So yeah, you went and an increase. What do you do you mind sharing what was the net income then?

Tim Ensmann 28:52

So our first our first year. Oh, the net income prior to when we yeah, when you bought yeah, when you bought it. Was was 118, and then we we went from 118 with the previous owners were doing their net operating income was I can't even remember because it was it was irrelevant. It was like maybe 40 grand, I think.

Michael Russell 29:12

I see. So they weren't even valuing this thing off of NOI. It was basically just replacement cost.

Tim Ensmann 29:17

Yeah, spot on. Yeah, the owners lived there, they were a nice older couple, they uh they did all the cleanings, they you know, did everything. So they were just kind of living in the main house and then they were um cleaning, you know, the like they they managed the property. Yeah. So the first year we had quite frank, like literally 6x the the income on the property, and then boosted up a pretty decent, you know, margin on with our NOI. We were we were around 300, uh, but now this year we're pacing for four. And uh and in California, Southern California, I mean, that's that's pretty significant. So um, yeah, we're just we're we're trending upward. And I think it's it's been amazing to even see like the brand increase too. You know, we went to I think we have like 25,000 followers now, but uh that's been in a year. So now we're gonna keep building on that, you know. So if we even track remotely close to the same, um, you know, 50,000 followers in a few years and um pretty decent NOI, like uh, you know, it's a great property.

Michael Russell 30:15

Yeah, well, that didn't happen on accident. So obviously you guys are doing something correct. You're as operating doing extremely well, and you guys have a lot to be proud of. I feel like this is important to highlight that, especially starting out, right? I want to kind of keep on the theme of like, what's it like to go from working a W-2 job? I think you were living in Tampa at the time. You said, Hey, we got this deal under contract, we're gonna renovate this thing, I'm gonna go all in. You you packed up your bags, right? You moved into this property, right? And yes, it from what I understand, it was not so glorious. Like there were spiders there and it was just like kind of run down. Can you walk us through some of the sacrifice, some of the stress, like the sweat equity? I mean, changing like moving your entire life and putting it all into this renovation. What was that experience actually like day to day?

Tim Ensmann 31:05

I think when you do, when you when you believe in something, especially like this, and keep in mind like all the things we talked about earlier, there was there were steps to get there. So it wasn't like, oh, tomorrow I'm gonna buy a hotel. It was like, okay, we've been really interested in this for all the reasons that we talked about. Um, but especially when you're gonna take on you know people's money, when you're gonna, you know, bet on something like this. That is, I would say speculative, right? Like how many other of these micro resorts were in the area? Not a lot. So it is speculative because it's like if you want outsized returns, you got to do something different. And that was the bet that we were making. And when we're making that bet, we wanted to make sure that, hey, there's people that put their trust in us. We have something here that we believe is the future of travel, right? Like the the way that trends are moving. This is what people want. We we need to do this.

Michael Russell 31:57

But I want to know boots on the ground. I want to know when you were there. Like, was there ever a moment when you're like, oh my gosh, what have I done? You know?

Tim Ensmann 32:07

You mean we're getting woken up by contractors at 6 a.m. in the morning every day? Yeah. There's a lot of days I'm like, what am I doing? Um, no, so yeah, when we had, you know, moved out there and living there. My fiance will tell you, I mean, there's spiders in the place. It was like an old place. It was an old thing. Um, and it was it was scary at night because it's like we didn't have all the lighting in, you know, it was just like you're just up there in the mountains, it's pitch black, it's dark. Um, but there was so much going on. I mean, we we literally had um you know renovated each of the cabins, you know, we had the county out there for electric upgrades and permitting, and we had um, you know, contractors with pickleball court, we had contractors for the pool, we had like a million different things going on, and it was it was a lot, man. It was uh it was definitely um, you know, every single day you're focused on a lot of different types of tasks too, which I will say we had we had had the experience. So myself and Isaac had both done projects in Palm Springs. So we were familiar with Riverside County, we were familiar with our team, we had teams out there, so it wasn't like we were just going from scratch. Um, but yeah, it was definitely a larger project. And when things run run over, right? I mean, think about oh my gosh, man, the amount of sleepless nights over missing timelines, going over a little bit over budget, securing SVA debt. I think you know, all of that is just a testament to I'm very glad I was fully in, right? Like I'm very glad I was there every day. I'm very glad I was completely invested to make sure that um, one, we knew everything and we had everything, we got it done. But two, uh just making sure that as we scale and as we do this, we have these teams and systems in place to say, hey, like we we understand we we're preparing for this three steps ahead now, right? Like there's no more surprises. There's always surprises and hospitality and projects, but there's less surprises because you have a little bit more familiarity, right? So um, so yeah, man, it was painful. I mean, we spent the holidays out there, uh, we were across the country. It was like myself and my fiance just dialed in on and my business partner Isaac, but he lived in LA. So yeah, it was uh it was quite the experience. I would do it again, but uh I'm very happy we're having this call and it went so well, you know. I think it was like definitely a lot of sleepless nights and stress that uh that that went into that property to make it is what it what it is today.

Michael Russell 34:33

Yeah, I think that part of the stress comes from uncertainty in the beginning. But as you go through this the first time, you learn, hey, look, it's gonna be okay. You you get through a lot of these moments, and then that gives you the confidence to continue to move forward and you also start to recognize the signals, like the things to look out for. And there's just there's really no way to prepare yourself for everything that you're gonna learn other than just diving in and doing it. And so I think that that was the right call, you know, for you and your team at that point was to move from where you were, to be immersed in the project, to protect your investors' capital, to make sure you set up all the systems. And you know, the success speaks for itself, right? Success leaves clues. You've you've proven this model, you've got a valuation that you you 3x the the property value and a year and a half. You're now moving on to your next property, which uh I think it's a two-property combo, right? Maybe you can kind of walk us through what's what's next, what's in the pipeline for you? What are you working on currently?

Tim Ensmann 35:32

Yeah, so um the the vision of the pine tree actually started in Blue Ridge, Georgia, when we were going to try building a little cabin community with 10 units and in it with a communal space and all that stuff. So it's kind of surreal to be able to be back in Blue Ridge. That's that's where kind of this all started. We had some Airbnbs there and short-term rentals there. We managed short-term rentals there too, and it's an amazing market. We really like it. Are you familiar? Have you been to Blue Ridge before?

Michael Russell 36:00

I haven't. No, I've seen some of your marketing collateral, and it looks really amazing. I think that it it um aligns well with what you've done previously at the Pine Tree. It seems like it's a nice transition. You can definitely take that group booking model and apply it to what you're working on over there.

Tim Ensmann 36:16

Absolutely. Yep, and that's why we like you too. It's less or it's about an hour away from Atlanta. So short drive up, massive city, huge hub, right? Like one of the largest airports in the world. Um, and we can we have two incredible assets. Uh, you know, so one of them is called Willow Falls. It's already got an existing wedding wedding business. It's on its own private lake, 20 acres, just like super immersed in nature, beautiful place. You feel very calm when you you walk in there. And um, that property we're very excited about. We got some very good seller financing terms on it. Um, it is 15 minutes down the road from the other property, which is also a benefit. As we think about scale, it's like, okay, we're gonna have cleaners, we're gonna have you know maintenance teams, we're gonna have operations teams. So, how can we continue to you know improve those efficiencies through scale? So, this property right down the road, it's a 15-unit boutique hotel. It's on the 10th hole of a golf course, it's got panoramic mountain views, it's got a beautiful pool, and we're gonna put some sports courts in there, and that's gonna be sort of a country club vibe. And Willow is gonna be your you know wedding vibe more because we already have a solid wedding business there. So those two are gonna pair really nicely. They'll have their own unique brands as we build them. But the benefit is because we're building both, we're gonna get the learnings from each other, right? So if we're running certain ads or marketing strategies or or things on Willow that are working that maybe aren't on the other one, it's the same team. So now we can tweak certain things. Same thing with operations, same things with you think about group sales. Now we can have someone dedicated on the group sales front to be selling weddings, to be selling some of these group buyouts, to be building partnerships with uh um companies based out of Atlanta, right? Companies have corporate events. How cool would it be to do your sales kickoff at one of these properties? Um, so I think those are avenues we're pursuing that get us really excited. The price we're getting them both at, the location, the landscape, um, the the brands that we're gonna be able to build, and then the success we've seen at the pine tree to keep digging in and and um nailing that group sales strategy, just make these really, really incredible deals and also just legacy assets. There's like a $20 million development going up, very, very similar area. And by the time they open, we're gonna be up and running, stabilized, like ready to roll. So I think there's a that you're already seeing this from some larger players that are that are coming in the space, and we're we're really gonna be there first.

Michael Russell 38:50

I I want to know now that you're working on your next set of properties, you've still got the Idaho property that is operational, you're no longer sleeping at the resort, you've got presumably some management in place. Like if the goal is to be free of operations, which it sounds like you've gained some of that freedom now, yeah. How should someone start? What's step one? What's step two, and what's step three in terms of acquiring your first asset, getting someone to operate it, and then number three, being able to scale and and operate multiple properties simultaneously.

Tim Ensmann 39:29

Yeah. So um I I would first think education is gonna be very important to sort of understand how to underwrite deals, how to evaluate deals, like how to really understand what good looks like, like what you're looking for in a deal. Um, and then you can start to map that things backwards. So I I said the million dollar income mark for these hotels, because if you think about it, right, if your management fee is typically 10%, right? 10% Percent on even 700 is like the pine tree is too small. So so we're even a little bit tight there, which is why the deals that we're looking for moving forward are well over a million. But you're looking for things where, hey, if your management fee on you know a million dollar uh income is a hundred thousand dollars, you definitely have room to pay someone to cover that. So that would be the first thing is is look, understand the underwriting, like understand the business. Um, you don't need to be, you know, a 10-year experienced asset manager, but like look at enough of these deals to understand, okay, here's what the actual cash flow is going to look like. Um, here's what the cash flow is gonna look like after debt service and paying investors back. Um, and here's what the bucket is for the team. So that would be my first recommendation is like um educate yourself on what these deals look like, what the cash flow looks like, what you know, and and understand the economics of it. Then from there, really, really hone in on what is my real goal with this? Do I want to do multiple deals or am I looking for just doing one boutique hotel and I want to, you know, own that and operate that, and that's gonna be a legacy asset, gets me out of my my W-2. And I don't mind, you know, managing a little bit or you know, being a little bit closer to the asset. Because if it's that one, there's a very, very real path forward where you can leave your W-2 by buying one of these boutique hotels. If you're like, hey, you want to live in or near that market, right? You want to manage it. Like if it's doing over a million, there's a very real chance that, hey, this can be your business. You oversee it, you hire some outside management and can be very hands-off, but you're still a little bit involved. So that is a is a uh a different example than hey, I I really like the concept that we're both doing. I want to be a part of multiple deals because then your value can be, hey, maybe I'm one thing instead of everything. And I think that's really important, right? Because um you can do that, hey, I'm gonna do everything route. And that is definitely one option. My where I was looking was, hey, I don't want to do everything. I want to focus on a few key areas and be able to provide value in those few key areas, and that's a way to get compensation, whether that's through equity, um, through knowledge, through um actual, you know, fees and things like that. Um, and I think, I think so. To answer your question, if you're looking to purchase the boutique hotel, own that, operate it, manage it, you need to understand what the deal economics look like, what your goals look like. Is it gonna be one deal or multiple deals? And then from there you can make your decision on, okay, if it's gonna be one deal, I'm identifying my market, I'm identifying my concept, and I'm full focused on building that list of sellers or building that list of owners in that market, building the list of broker relationships and really focusing on, hey, how can I get in touch and and um negotiate some of these really amazing seller financing terms that we've been able to get? Really negotiate, hey, how can we actually, you know, maybe even do a JV with the seller? How can we um build those relationships with some of these brokers and maybe you are able to secure some bridge debt or something like that to actually uh do these things on your own, um, versus when you can partner up with someone and say, hey, Michael, I really like this concept. You're awesome at operations and asset management, I'm awesome at investor relations and marketing. Why don't we partner up and say, hey, we're gonna go do this deal? I think there's another avenue with that as well.

Michael Russell 43:48

So if someone wanted to figure out what are the tactical steps to be able to pursue a you know, pivot from their current career into investing in hotels, what you're sharing is number one, identify your personal goals. What is it that you're trying to accomplish? Start there and then educate yourself on what is required to be able to achieve those goals. Then number two, go and learn by doing. And often in the beginning, maybe you have to be a generalist. Like you've done, you had to be boots on the ground originally, which meant you were wearing a lot of hats. And then number three, once you progress to a point where you have enough revenue to be able to assign uh roles to position players, then think about from a collaborative stance, what you want to really refine and specialize in. And that's how you can scale. We if you're going to really be hyper focused on one aspect of the business and you know and you trust that other folks within your team are gonna be working on what they're specialist in, that's when you can really gain some momentum. But those three steps, like you don't become an expert at something until you've started as a generalist, in my mind, on what I'm hearing. And so, you know, start with the vision, get to a point where you have enough revenue to hire out, to pay people, to take over the things that you were doing, and then from there become a specialist, a hyper focused in, you know, your highest and best use, your skill set, which uh can move the needle. And and not just that, but also I think it's important to find something that you enjoy doing. And that is something that probably isn't spoken about often enough, is the reality of entrepreneurship versus what you see on Instagram, right? They don't always align. And I think you got to be prepared for that mentally, that if you're gonna be transitioning out of your job, your your your current job, the grass isn't always greener on the other side. You got to make sure that you truly want that entrepreneurship, it's risky, there's hard work, and it takes a tremendous amount of life sacrifice. All things you got to be willing to do if you want to reach success. But if your goal and your vision is clear, like I believe you have a clear vision on what you're working on, then it just takes execution and you got to go and get the reps and you got to start somewhere. And you've proven that from what you've done from starting with investing in short-term rentals to scaling up to your first boutique hotel, which um I think I, you know, I think you would agree that you learned that you need to have more revenue, but you started somewhere. And so starting with that first hotel now gives you the confidence to go and buy a two-set hotel package, which is presumably significantly more costly than your original. So there's a clear sequence here. You're not an inventor here. Getting into this business, one of the things that I teach all the time is learn from others. If you can learn from others, you're gonna avoid so many of the mistakes by trying to just tackle this on your own. So I think it really rings true. And you said the education, gain the experience, and then specialize is essentially, I think, kind of the three-step approach to being able to be successful in this.

Tim Ensmann 47:11

Absolutely. Yeah, I think you summed that up really, really, really well.

Michael Russell 47:15

Yeah. So what you've done with the Pine Tree Hotel is really impressive. Um, where can someone go and view that? Is it just the pintreehotel.com? They do a quick Google search and they'll find it.

Tim Ensmann 47:26

Yeah, check us out on Instagram. Um, but yeah, the Pine Tree Hotel is our website and then uh thepine treehotel.com and Instagram, it's just the Handles Pine Tree Hotel.

Michael Russell 47:36

Okay. And if I understand correctly, you're raising money currently for your next project, right? Is that something where investors, you're you're still actively open to taking on investment capital?

Tim Ensmann 47:46

Yep. So our boutique hotel fund, um, so we re raise capital for deals exactly like the pine tree. So we love, you know, overlooked, undervalued assets, um, coming in there, creating the experience, and um so and then just you know delivering exceptional returns and experiences for guests. And so we will do our own deals as we've done the pine tree. We will also partner with folks to do these types of deals. And um, these two deals in Blue Ridge, Georgia, we are super excited about. That brings us back to where it all started. And uh, and yeah, you can learn more at the boutiquehotelfund.com. Uh, my name's Tim Ensman, so you connect with me on LinkedIn. Um, more than happy to do that. And then I think you maybe will share my email in the the show notes or clients.

Michael Russell 48:35

Absolutely. Yeah, we'll put all your information so that our followers, our listeners can connect with you uh either on LinkedIn or Instagram or wherever uh you want them to reach you. But yeah, we'll put all that in the show notes. So, Tim, uh look, I really appreciate this. This has been a great uh discussion on you know, you've exemplified how folks can transition from working a uh regular W-2 job into entrepreneurship. And I think you've demonstrated it's not all it's not all glitz and glory. There is some hard work and sweat equity that goes into it, but you're the epitome of success. And I wish you the best. So thanks so much for being on the show.

Tim Ensmann 49:14

Amazing, man. Thank you so much for having me.

Michael Russell 49:17

Yep. And to everyone listening, look, if this episode has opened your eyes in any way to the possibility of maybe making a career pivot, making a career pivot into entrepreneurship or hotel ownership, look, share this episode with someone who might appreciate it. Maybe it's a friend still who's on the fence about making their next move. Um, and also one other favor here before you go, I'd like you to scroll down and use those nimble thumbs of yours and reach your phone and drop us a five-star rating or a quick review. Because I'm aiming for 10 new ratings this week and I need you to help me accomplish this. So if you can do that, I appreciate it. In fact, I appreciate y'all. We'll catch you again next week. Aloha