This Investor Turned Vacation Homes Into $30M Business | Dan Pascone with Shawn Moore | Podcast #18

Posted on June 20, 2025 by Dan Pascone

Answer Box: TL;DR

Short-term rentals can be a powerful wealth engine – if you treat them like a real business, not a side hustle. In this episode, host Dan Pascone and real estate investor/entrepreneur Shawn Moore break down how Shawn turned vacation homes into a multimillion-dollar business. They walk through why STRs are really a hospitality business, the four ways real estate actually pays you (hint: cash flow is the smallest piece), and how high-income professionals can use a focused, “follow-the-recipe” approach to build a small but highly productive portfolio that supports a hybrid retirement.

Key Takeaways

Short-term rentals are not a side hustle. They’re a hospitality and experience business layered on top of real estate. Pretty photos and an Airbnb listing are not enough anymore.
Not every property or market works for STRs. There’s always a highest and best use. Some markets are over-regulated or lack demand; some homes simply don’t make sense as short-term rentals.
Real estate has four main return drivers: cash flow, principal paydown, appreciation, and tax benefits (depreciation/bonus depreciation). Over 5–10 years, cash flow is often the smallest part of the total return.
Short-term rentals can unlock better appreciation and tax treatment. You’re typically buying higher-quality, vacation-area properties, and with the STR “material participation” rules, high earners may be able to use bonus depreciation without being full-time real estate pros.
A small portfolio can replace a big income. Shawn has never owned more than 6–8 homes at a time. For many high earners, 4–5 well-chosen STRs can give them the option to step away from a demanding career.
Time commitment is real but manageable if you follow a blueprint. Expect ~3–5 hours per week for the first year to learn the system and manage your team (designers, managers, CPAs, lenders) – more if you self-manage.
Discipline beats dabbling. The biggest mistake Shawn sees is people jumping between strategies, gurus, and markets. Pick a proven recipe, do your due diligence, then stay on that path.
Use tax savings to accelerate the flywheel. Instead of “spending the refund,” treat bonus depreciation and other savings as if you paid it to the IRS, then pay it to yourself and recycle it into the next property.
Hybrid retirement is a perfect fit. For many executives and business owners, STRs can be the asset class that helps them move from trading time for money to a more flexible, option-rich lifestyle.

Key Moments

00:29 – Meet Shawn Moore & Vodyssey. Shawn shares how he left a salaried job after one wholesale deal replaced two-thirds of his annual income and eventually niched into vacation rentals.
02:18 – First vacation rental back in 2006. Shawn buys a second home pre-Airbnb, rents via classifieds/Craigslist, and realizes it can cash flow even while values are dropping.
02:57 – Covid boom: “Owning an STR was like having toilet paper.” Why the 2020–2021 surge made everyone look like a genius – and taught a lot of people the wrong lessons.
03:48 – Why STRs are not side hustles. Shawn explains why you’re in the experience business now, and why “pretty house + Airbnb listing” is no longer a winning formula.
04:47 – Highest and best use. Not every property or market should be an STR; regulation and demand matter as much as the house itself.
05:39 – Who Shawn really works with. High-income professionals (often 40s–50s) who realize their 401(k) alone won’t support the lifestyle they want in retirement.
06:16 – The four ways real estate pays you. Cash flow, principal paydown, appreciation, and tax benefits – with a detailed walk-through on a hypothetical $500K property with 20% down.
10:29 – Why cash flow is overrated as the only metric. On a 5–10 year horizon, appreciation + leverage + tax benefits often drive most of the total return.
11:35 – STR bonus depreciation for high earners. How material participation rules let W-2 and business-owner clients sometimes use big paper losses against active income.
13:30 – Lifestyle upside: “vacation homes all over the world that someone else is paying for.” Using STRs for both investment and family experiences.
14:37 – Ideal client profile. Typically $250K+ income, hard-working, values experiences, and wants to put capital in quality assets instead of just toys.
15:12 – Dan’s “hybrid retirement” concept. Using STRs as one of the income pillars that allows you to exit intense W-2 roles earlier.
16:34 – Scaling: from first cabin or beach house to a real portfolio. Why properties 4–5 are often the tipping point where you have the option to quit.
18:09 – Tax law & bonus depreciation as accelerators. Treat tax savings like forced savings for the next down payment instead of lifestyle inflation.
19:54 – Time & energy required. Why 3–5 hours per week for the first year is realistic, and how leveraging property managers can trade money for time.
20:43 – The danger of mixing “recipes.” Doing too many strategies at once keeps you stuck; Shawn urges picking one blueprint and sticking with it.
22:31 – Lightning round: steak & potatoes, auto barn doors, Warren Buffett, routines, Alaska trips, and a $30M business goal.
25:18 – Advice to his younger self. Take more chances, accept that you’ll be bad at new things, and care less about what others think.
26:05 – How to work with Shawn & Vodyssey. Resources, trainings, case studies and a path to get on his calendar.

Episode Summary

In this episode of Making Sense of Your Money, host Dan Pascone sits down with Shawn Moore, founder of Vodyssey and a 25-year full-time real estate investor, to unpack how short-term vacation rentals can become a serious wealth-building vehicle – when approached like a business.

Shawn starts by sharing his own story: after wholesaling his first house and making two-thirds of his annual salary in a single deal, he quickly realized the corporate job wasn’t for him. He cycled through asset classes – fix-and-flips, development, build jobs – before buying his first vacation rental in 2006. Even as values slid during the downturn, that property produced strong income, opening his eyes to the power of destination rentals long before Airbnb and Vrbo went mainstream.

From there, Shawn explains why short-term rentals are fundamentally different from long-term rentals. You’re no longer just in the “landlord” business – you’re in hospitality and experiences. That means regulations, market demand, design, systems and guest experience all matter. Not every home or city makes sense as an STR, and trying to force it can be a costly mistake.

Shawn and Dan then break down the four pillars of real estate returns using a $500K property with 20% down as an example:

Cash flow (5% cash-on-cash isn’t sexy, but it’s there to cover capital expenses and avoid negative cash flow);
Principal paydown (guests paying the mortgage, slowly building equity);
Appreciation (averaging 5% annually over long periods, magnified by leverage – a 5% increase on a $500K home is a 25% boost on a $100K down payment);
Tax benefits (with STRs, high-income earners can sometimes use cost segregation and bonus depreciation via the “material participation” rules).

Stacked together, those can result in very meaningful returns over a 5–10 year horizon – often 50–75%+ on invested capital in Shawn’s example – even if the headline cash flow looks modest. That’s why he urges clients not to walk away just because the year-one cash-on-cash is “only” 5%.

For ideal investors – typically high-income professionals earning $250K+ who are realizing their 401(k) alone won’t get them to the lifestyle they want – STRs can be a cornerstone of what Dan calls hybrid retirement. Shawn has never owned more than 6–8 homes at once. In his experience, it’s often around property 4 or 5 that people gain the option to step away from intense W-2 work.

The catch: it’s not passive on day one. Shawn tells clients to expect roughly 3–5 hours a week for the first year to learn the blueprint, work with their team, and make decisions. If they self-manage, that can jump to 15+ hours. His program exists to compress that learning curve with vetted partners and proven systems.

Perhaps the most important theme is discipline. In a world with endless gurus, TikTok clips, and AI-generated advice, the hardest part is picking a strategy and sticking to it. Shawn emphasizes doing deep due diligence on any mentor or program, then committing – instead of hopping between recipes and never gaining momentum.

The episode wraps with a more personal lightning round covering Shawn’s daily routines, his long-running annual Alaska trip with friends, his goal of growing Vodyssey into a $30M company, and the advice he’d give his younger self: take more chances, accept that you’ll be bad at new things at first, and care more about “I’m glad I did” than “I wish I had.”

Full Transcript

Dan: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions. Welcome to episode 18 of the Making Sense of Your Money podcast.

Dan: I’m your host, Dan Pasone. I am the founder and CEO of Tailored Wealth. And as you know, each of our episodes on the Making Sense of Your Money podcast features a trusted voice in the financial world. Someone who works directly with high-level professionals to simplify the complex and turn strategy into action.

Dan: And I’m pretty pumped about this one. Today, we’ve got with us a special guest, Shawn Moore. And Shawn’s got a lot of experience. He’s on a lot of different platforms. And he is the founder of Vodyssey. And Shawn, for his entire career, has been a really successful real estate investor.

Dan: So I’m interested to hear a little bit more about his thoughts on that asset class. So Shawn, thanks for joining the Making Sense of Your Money podcast. Pumped to have you today, brother.

Shawn: Awesome. Thanks, Dan. I really, I really appreciate it. I love having these types of conversations, so I appreciate you having me.

Dan: Likewise. Likewise. I know I have a lot that I want to hear and learn from you. I know our viewers and audience will as well.

Dan: If you don’t mind, let’s jump right in and give us just like a quick 90-second overview of what you do, how you got into that space, and then ultimately what you’re helping your clients to achieve.

Shawn: Yeah, I love it. I appreciate it. And yeah, so I’ve been full-time real estate investor for 25 years now. So, right out of college, I had a job for about six months and wholesaled a house and made two-thirds of my annual income and thought, “Hey, man, this salary job deal is not for me.”

Shawn: So, we jumped into real estate right away. Bounced around a lot of different asset classes. Actually, I spent a lot of my early years in real estate investing in fix-and-flip stuff. Did a lot of fix-and-flip, did development deals, build jobs, and ultimately fast forward started getting involved in second homes and resort-style developments and started to kind of get introduced to the vacation home side of investing back in like 2006 and bought my first vacation rental back then and saw how it performed during the slide and realized, “Holy crap, this – even though this property is losing value, I’m actually making quite a bit of money on it.”

Shawn: That was before Airbnb and Vrbo and everything became really popular. It was just local classifieds, Craigslist, renting it on the weekends and realizing that, man, there might be something to this. After a few years of doing it, back in 2012–13-ish we started getting really serious about this asset class and have been fortunate to watch it grow up and start to become mainstream.

Shawn: Covid hits, it becomes really mainstream and everybody looks like a genius in the short-term rental world for about a two-year period. You know, it was like having – I always tell people having a short-term rental was like having toilet paper during Covid during that time. And while it was a fun ride, it also was never going to last either. And I mean, this is an actual – there are nuances to it. There are pros and cons to short-term rentals.

Shawn: Back in 2017, before Covid, I actually wrote a book that was kind of teaching people our process with it. And because of that, that book kind of took off when short-term rentals became very, very popular after 2020. And Vodyssey was formed and we started teaching people, and I thought I was going to teach about 100 people how to build a portfolio and we’ve got about 3,000 active investors across the country and having a lot of fun with it.

Dan: Very, very cool. Yeah, that’s certainly an interesting ride.

Dan: So, I think most of our viewers and listeners will understand what a short-term rental is, but give us a little bit of a look under the hood as to what does it take to be successful in that space? I’ve got a ton of friends, certainly a ton of clients that have said, “I want to get into this,” or maybe have gotten into this. But what does it take to really make this a career and build a true business out of it?

Shawn: Yeah, it – well, you know what it is? I always tell people, at least our view of short-term rentals, these aren’t side hustles. They’re not second jobs. These are assets that we invest in. And like any other asset that we’re going to invest in, what we do is try to help people take their active income, putting it into certain asset classes. Ours in particular is short-term rentals – the only one that we know very well.

Shawn: I know that, like, you guys help people analyze and look at and maybe diversify that portfolio. For us, we’re saying let’s take some of that active income, put it into something passive, and understand what it takes to succeed.

Shawn: The big misconception with short-term rentals is that, “Well, if you rent it short-term, you’re going to make more than putting it on as a long-term rental.” I’ve been in real estate for a long time and there’s usually a highest and best use for a property and there’s not a lot of plan B’s and C’s when it comes to property usage and investing.

Shawn: People will always say, “Well, if it doesn’t work out as this, you can do this.” That’s not really the case most of the time. There’s usually a highest and best use of that. And there’s no difference with short-term rentals. Not every market works well for short-term rentals. Not every property works well. Some markets are very regulated. Other markets, there’s not a lot of demand.

Shawn: And so what you have to realize is we’re not in the property business. The property is part of what we do – it’s what we’re delivering – but we’re in the experience business. We’re in the hospitality business now. And a lot of people that don’t understand that think that, “I can just go buy a really pretty property, furnish it like a model home, throw it on Airbnb, and I’m going to make money.”

Shawn: That game has changed. It’s not that anymore. You very much have to dial in the hospitality side of it. And it can be a lot more moving parts in the beginning. And when we’re saying, okay, I’m working with high income earners, busy professionals, trying to take that active income, put it into something passively on a 5 to 10-year time horizon – well, that’s a hard sell sometimes, right?

Shawn: And it’s like I know you guys, I’m sure, have tons of conversations with those people saying, “Hey, listen. We need to look 10 years down the line, 20 years down the line.” And when everybody wants this instant gratification, right? And short-term rentals became this shining star of the real estate world for a little while. And it was instant gratification for a couple years for a lot of people.

Shawn: It really introduced a lot of people to the wrong way to play this game. And so right now you hear those stories of the Airbnb bust and the short-term rental game is over. And actually nothing is further from the truth. It’s that there’s a lot of people playing a game that they don’t understand the rules of and they’re getting crushed. But the consumer is spending more money than they’ve ever spent.

Shawn: And so I still believe, you know, we’re super excited about it as an asset class, but it always has pros and cons just like everything else.

Dan: Very cool. Very cool. Great explanation there.

Dan: So I want to dig into that hospitality component for a second, Shawn. I want to see it through the lens of a typical client of ours that’s got a high demand job, whether they be an executive or they own their own business, and they’ve got capital that they want to put to work, right? And so they see an asset class like short-term rentals and the potential upside and the passive income that comes with it.

Dan: But help educate us on what you do and maybe what they would need to understand to really master that hospitality piece where they may not have really any expertise.

Shawn: Yeah. And it’s why we have a business – to try to help people navigate those waters that can be a little bit muddy at times. Because without understanding, first of all, the game you’re going to play… Our goal is always to help people walk into this game with their eyes wide open. That sometimes means it’s not the game they should play.

Shawn: And how much time is it going to take for somebody that is busy and feels like there’s not an extra hour in any day, let alone multiple days? What we try to do is put together a blueprint for them to say, “Hey, listen. We’re going to dedicate 3 to 5 hours a week for the next year or so.” And that’s a commitment.

Shawn: When you really are saying, “I’m going to dedicate an extra hour a day every single day,” we’re having to cut something out. And so, if somebody doesn’t have the time to do that, it’s going to be a difficult game to play, even as we try to compress all the effort that they have to do.

Shawn: I don’t manage any of my own properties. We teach them how to get the teams in place. At this stage, we’ve got a really extensive rolodex, I will say, of the CPAs, the management partners, the finance partners, the designers, everything else. So they’re just plugging into a system, but at the end of the day, they still have to understand the system. And that’s where that 3 to 5 hours a week is going to come in.

Shawn: And what I also – I’m sure you guys have these conversations all the time when somebody is analyzing an investment or what their ultimate financial goals are – because so many of us, like myself included, especially in my younger years, were very financially illiterate. You just don’t learn that stuff in school.

Shawn: I came from a family that – my parents, they worked their 40 hours a week and they contributed to their 401(k)s and they did what they were supposed to do, and at the end of the day they’re looking at it saying, “Holy crap.” You know, my mom and dad are on payroll now, right? And they’re retired, but they can’t live on retirement. And so they’re on my payroll, and – which I love, I love that we can do that – but the old-school way of doing things doesn’t work.

Shawn: And we have to look at different alternatives. This is one alternative. But with real estate, there’s really four ways that you get a return on that asset class. And a lot of people always focus on the one that is the least of your returns in a 5 to 10-year time horizon, which is cash flow.

Shawn: Everybody’s like, “I’m chasing the cash flow. I want X amount of cash flow.” And I’ll give you a quick example of that, Dan. I always say, “Hey, listen. If I’m going to go buy a $500,000 property, and I have to put 20% down, I’m going to put $100,000 in that. So I’ve got $100,000. I’m a busy professional trying to decide what to do with this money. Where should I put it? How am I calculating my returns?”

Shawn: Well, in real estate, you’re going to put that $100,000 down on a $500,000 asset, which is great because we’ve got leverage, right? We’re not over-leveraging. I’m not a huge fan of 100%, 5%, you know, some of those big high-lever properties. But 20%’s a good position to be in, or more.

Shawn: And then, if I – let’s say that’s giving me a 5% cash-on-cash return. Nothing to write home about. I’m not going to retire on that. I’m getting $5,000 a year. Really, most I’m trying to do, Dan, is if I have a big capital expense like an air conditioner or something goes out, I’ve got the capital to pay for it. I don’t like negative cash flow, but I don’t chase really high cash flow.

Shawn: So I get 5% there. The next thing I get is note paydown. Somebody else is paying for this property for me over time, right? So the first couple of years is going to be really modest. Maybe it’s another $5,000 a year on that $500,000 asset that my note gets paid down because somebody else is paying that mortgage for me. So there’s another 5%, right, that’s compounded that year.

Shawn: Then the other two are huge for real estate investors. The third one is appreciation. And this is where I really like short-term rentals, because short-term rentals allow us to buy quality assets in quality areas because they’re vacation areas. They’re the areas people want to be. They’re not places that you’re going to go find a bunch of long-term rentals.

Shawn: And so we’re buying higher-quality assets in higher-quality areas that appreciate at better-than-average clips. But the average clip in America over a 40-year run is 5%. And you have to look back – I always look back at least 20 years because you need to have an upside and a downside in there to average it out, right? You can’t look back at real estate the last five or ten years and say, “Well, it’s averaging 15% or 12%.” That’s not realistic, right? I need to look back at a long time horizon.

Shawn: But let’s say I’m still right at that 5%. Well, that – this is where the big power of leverage comes in – that asset went up 5%, not my $100,000. And so that $500,000 asset is now worth $525K. So now I’ve got a 25% return on my $100,000 that year, because now I’m up to 35% return. I got 25% on appreciation, 5% on note paydown, 5% on cash flow.

Shawn: And then the fourth one, with taxes and depreciation – and with short-term rentals, active income earners don’t have to qualify as a real estate professional to take bonus depreciation. They can qualify with a short-term rental loophole called material participation. It’s different and it allows us to do that.

Shawn: And now all of a sudden I’m able to write off usually somewhere around 25% of the purchase price of my property, depending on the area, after I cost-seg it out. Well, if I’m paying 35% taxes and I get a 25% write-off of my $500K, it’s a $125,000 write-off. I reduce my taxes by another 35–40 grand.

Shawn: And so all of a sudden I’ve got, you know, 40,000, 25,000 – 65. All of a sudden, before I know it, I’ve got a 75% return on my $100,000 when so many new investors will say, “Ah, I’m only getting 5% on the front end. I’m going to put it somewhere else.”

Shawn: And so, I love – that’s why I love real estate. It’s not necessarily right out of the gates for the cash flow. And that’s why I love working with high income earners that are saying, “Hey, listen. I need to put it into quality assets that over a certain time horizon, I’m going to get this nice return on.”

Shawn: And then there’s a, you know, the fifth aspect for short-term rentals that’s not available for other real estate is the personal use. It’s a lifestyle upgrade. You know, it’s pretty fun to have vacation homes all across the world that we can use and somebody else is paying for. That’s – you know, that’s a – it’s not necessarily returning me any money from that. In fact, it costs me when I use my properties typically. But it’s a huge lifestyle upgrade.

Dan: I’ll add another one on for you. You probably have heard of the Augusta rule. So if you’ve got a business owner that can go use it for business purposes, you get the additional tax break there. We’ll get into that another time.

Dan: All right. So, that’s really good. I love sort of understanding the complete picture and not just sort of just chasing that cash flow because there’s a lot more to it than that.

Dan: So, let me ask you this, Shawn. You said you’ve got 3,000 investors, which – congratulations on that. Tell us a little bit about what does your ideal investor look like? How do you find them? And what’s a good candidate for someone that’s going to come and work with you and your team?

Shawn: Yeah, usually like, you know, we’re looking for higher income earners. They’ve got disposable income. They’ve got extra cash. They’re saying, “Hey, listen. I’m…” – they’re buying into the fact – most of my ideal clients, Dan, honestly, come to me and the first conversation we have is they’re in, you know, late 40s, early 50s, and they’re looking at their 401(k) and they’re calculating it out and saying, “Man, I’m going to retire and take a huge step backwards.”

Shawn: And they’re saying, “I need to do something else. I need to take control. I’m interested in real estate.” We always are looking for somebody that’s making at least 250 a year. Not because they need to be accredited, just because the fact of the matter is I teach the ownership model. I teach people how to go buy properties.

Shawn: I don’t teach a no-money-down, all that kind of stuff. We buy properties all the time on seller financing and everything else. But at the end of the day, our ideal client is somebody that is saying, “Hey, listen. I’m working my butt off. I want to enjoy life today. I don’t want to wait forever.”

Shawn: Which is why we like people who – people are attracted to those lifestyle assets because it’s – I always say to somebody, you know, it’s like going and buying that fancy $300,000 wakeboard boat. We do it to create the memories and spend the time with their families and everything else. What if instead of buying that boat, you go buy your cabin or the beach home or whatever else, and you can still kind of, you know, satisfy that need of wanting to create those memories, but you’re buying quality assets.

Shawn: But it’s really just somebody that is saying, “Hey, listen. I’m working too hard for this, and I want to put it somewhere responsibly.” It’s the same people you guys probably talk to, Dan. And they want to know what their options are. And we’re one of many options, right? It’s not like – I always say I don’t – it’s where all my money is at. It doesn’t mean it’s where everybody else’s money should all be at.

Dan: Yeah. You hit on a concept that I talk about all the time and I hear from our clients and prospective clients almost daily – probably daily at this point in time. And it’s a concept that I’ve coined hybrid retirement, which is: I’m in an intense job. I’m earning well, but like, you know, I’m trading my time for money, right?

Dan: And in the future, I’d like to get to a place where I’m not necessarily looking to go hang it up and go sit on the beach somewhere and never do anything again. I want to get to a place where I can get rid of the 9-to-5 – or in many cases, it’s a lot more than 9-to-5, right? – but I can get rid of the intense job but still do something that’s meaningful, that’s purposeful, and where I have a lot more flexibility and control of my time.

Dan: So, we talk to them a lot of times – and this is why I really enjoy this conversation – about how do we supplement the income in some form of way. For some people it’s consulting, for some people it’s fractional work, but this can be a really nice complement to that for the right people, to your point, to be able to build that up.

Dan: So let’s kind of take down the journey of like the first-time short-term rental investor. I go and I buy the beach house or I go and I buy the cabin and I’m getting the experience that you just laid out and that nice sort of compounding return with the four different categories. Where do you go from there? Is it just a matter of just kind of doing the system over and over again? How do you make this, instead of just like a one-time experience, something that’s more scalable?

Shawn: Yeah, I love the question because, you know, one of the things that people are always surprised about is how highly producing a small portfolio can be. Like, I’ve never had more than eight homes. I usually have somewhere between six and eight homes as long as we’ve been doing this. But we continually trade up based on a return on our equity after usually about five years into a home.

Shawn: But what you’re really doing, you really are rinsing and repeating. And you’re using that disciplined – you have to be fairly self-reliant. You have to look in the mirror and say, “Hey, listen. I’m going to have this disciplined approach,” because the first few years, you’re just – those first two or three properties, you’re not quitting on them anyways. You’re not typically replacing your income.

Shawn: But if you’re disciplined enough to take the earnings from those, the savings from those and parlay them into multiple other properties, usually for most people it’s somewhere around that property four or five that they have the option to quit, right? And that’s what we want. We want options. We don’t want to have our back against the wall and say, “Hey, listen. I have to keep working and doing this.”

Shawn: There’s a lot of our clients who love what they do. They’re making good money. It’s also nice to have the options that if you do get tired or you do not want to do it that you don’t have to. But it doesn’t happen overnight. This type of a portfolio, it’s like spinning a flywheel. It’s going to take some time to get it moving, right? And you’re going to put some effort in in the beginning. Once that sucker’s spinning, it’s pretty hard to stop it.

Shawn: And what’s really fun about it is you just – I always tell people, especially high income earners, you would – you know, and likely with the new tax law that’s going to probably pass closely to when this thing airs, bonus depreciation is going to come back and it’s supposed to be permanent is what they’re proposing. And that’s a big, big deal because on that example I gave you, that’s an extra $40,000 now that you’re putting back into the investment kitty.

Shawn: Just pretend you paid it to the IRS. Just pay it to yourself and put it in your investment account. And then you take that 40,000. Now I don’t have to save up 100,000. Just that one saving – I don’t have to save up another $100,000 to go for my next property. I just need to save up 60. And then I do that again. And then I have two of those properties doing that. And I do it again. And before you know it, you’re hitting – and the reason it’s four to five properties for most people is because most of us buy within our earning potential, right?

Shawn: If I’m making a million dollars a year, I’m not usually buying $300,000 properties. I’m buying bigger properties that are going to produce more. If I’m making $200,000 a year, I might be buying $300–500,000 properties. But those properties are going to do a good job of replacing that $200,000 income. Somebody that’s making a million dollars a year, you’re probably going to buy $2–3 million properties. It’s going to be able to produce enough to replace your income.

Shawn: And so the game is saying, am I willing to buy into the fact that after I do this for 3 to 5 years, that’s when the real payoff is? And I always ask my clients to say, “Hey, listen. Be disciplined enough not to live off – not to use this money. Just put it right back into the investment kitty so that you can get to that point where it starts to really produce.”

Dan: Help our audience – that’s great stuff. Help our audience understand – you did a great job of laying out sort of like the financial components here. Help our audience understand – you mentioned the time component. What’s the work that’s involved? Like, what do they need to be prepared to dedicate to really make the system that you have – sounds like really perfected – work? What do they need to be willing to give from their own energy, their own time, etc.?

Shawn: One, I think the hardest thing is mentally being able to follow a recipe. And so I always tell people: do a lot of due diligence on the front end. You know, if you’re going to hire me or anybody else, look at our recipe, look at the blueprint, look at the things that we’ve done, look at the properties we own, look at the people we’ve helped.

Shawn: It’s one thing if I know how to do it, but if I don’t know how to teach anybody to do it, that’s another thing, too. You need to be able to look and say, “Okay, is this the blueprint?” Because I’ll tell you what’s really hard right now, Dan. You don’t need to go put in the work to understand or learn this stuff – it’s been done for you, right?

Shawn: There’s so many people that can just pass the baton, myself included, that say, “Hey, listen. Here’s the road we ran down. I’m going to pass you the baton so you don’t have to run down what I’ve already run down. You can run further and faster and farther.”

Shawn: And so it’s not work trying to figure anything out. It’s – the hard part is the discipline to buy into a recipe. Do a ton of due diligence on the front end so that you feel confident: “This is the right blueprint and recipe I’m going to follow,” because there’s so much noise out there.

Shawn: You’re going to hear me say one thing, somebody else say another thing, and they both might work, but they don’t work together. Does that make sense? There are a lot of paths you can run down, but the people I think that struggle the most are the people that try to run down so many paths at once.

Shawn: And it’s like, “Hey, listen, there’s a lot of things that work.” And I think that the hardest thing right now in the age that we live in is you have a lot of options and there is no shortage of advice. And the due diligence on the front end is what’s important, because there’s a lot of advice that’s just AI-generated.

Shawn: I mean, I can’t tell you – yesterday I found a competitor of ours is literally using my property, one that I own, on their ads with my exact scripting, and they’ve never done this before and they’re just trying to get into the game, but they’re using all of our stuff. That happens all the time.

Shawn: But once you peel back a few layers of the – on the due diligence, you can find that out really quickly. But hire the people – don’t figure it out on your own. There’s no reason, right? For anything you need time, money, knowledge, right? You know what capital you have when you’re investing.

Shawn: The time is going to be 3 to 5 hours a week with our blueprint. Somebody else’s might be different because a lot of people teach you to manage your own homes. That’s going to be another probably 15 hours a week if you’re going to manage your own homes. I don’t do that, but it costs me. I pay for that, right? I pay a management company for the time, for sure.

Shawn: And then the knowledge – it’s like, okay, how do I bridge the knowledge gap? It’s finding the right people to help you with that. But then once you say, “That is the right person or organization or whatever it is, this is the right blueprint,” stay on it. Because I see too many people that run down one road, then they think, “It’s a little harder than I thought, I’m going to run down this road. It’s a little harder than I thought, I’m going to jump over here and try this one.” And they’re never any further ahead when they should have just stayed on the same road.

Dan: I love it. I love it. Really, really good stuff, Shawn.

Dan: All right. We’re going to switch gears a little bit. We’re going to get to know you a little bit better now. We heard all about the business and that concept. So we’re going to head into what we call the lightning round. I never prep anybody – just like to get really authentic answers here. And the only thing we ask is first thing that comes to your mind. Could be a one-word answer. It could be a drawn-out thought. Whatever works best for you.

Dan: You ready?

Shawn: Let’s do it.

Dan: All right, let’s do it. Coffee or tea?

[segment edited – no clear audio answer in transcript]

Dan: If you had to eat one meal every day for the rest of your life, what is it?

Shawn: Steak and potatoes.

Dan: All right. He didn’t hesitate there, ladies and gentlemen. He did not hesitate there. That was good.

Dan: All right. What’s one tool – could be hardware or software – other than your computer or your phone. So, one piece of technology that you can’t live without.

Shawn: Oh, that’s a tough one. Can it be something I have on my farm?

Dan: Sure.

Shawn: I’ve got automatic door openers for my stalls for my cows and my chickens so I don’t have to wake up and go up.

Dan: By the way, that’s technology at its finest right there, brother.

Shawn: I use that every day. Those come in real handy a lot of times for me.

Dan: I love it. Do you have a favorite quote or phrase about money or success?

Shawn: Probably my – one of my favorites is the advice of, “Be fearful when others are greedy and greedy when others are fearful,” and really paying attention to not really following the masses. That’s old Mr. Warren Buffett.

Dan: Love it. Yep. The Oracle himself.

Dan: Do you have a favorite book on business or success?

Shawn: Winning by Tim Grover.

Dan: Yep. Okay, good one. Know that one well.

Dan: Do you have a personal hack you can share with the audience?

Shawn: Oh, mine is routine. I guess – and it’s just a daily routine, morning routine, daily routine. I’m a very routine person. That has allowed me to accomplish a lot more than being kind of at everybody’s beck and call. And so I would say – and I don’t think you follow my routine or Dan’s routine or anybody else’s, right? I think everybody can develop their own routine, but for me that has been a huge hack.

Dan: Love it. Love it.

Dan: What’s one bucket list item that you’ve already accomplished?

Shawn: The trip that I take with my friends every single year. We go to Alaska, disconnect. We decided we were going to do this – this is maybe my 20th year in a row. So, we decided we were going to do this a long time ago. We haven’t missed a year. And I always – I love the outdoors, love Alaska, and we’ve continued that tradition on, and I think that’s a pretty amazing thing for us.

Dan: Very cool. Very cool. How many folks on that trip?

Shawn: Ten of us.

Dan: Very cool. Good for you.

Dan: What is one milestone – whether it be personal or professional – that you’re currently working towards?

Shawn: Yeah, we’re trying to – my milestone that we really want to hit is we want Vodyssey to be a $30 million a year company. And so for us we’ve hit about $18 million and so we’re trying to hit that $30 million mark. And this has been one of those big milestones that we think is real possible.

Dan: Good for you, man. That’s awesome.

Dan: And last one, what’s one piece of advice you would give to your younger self?

Shawn: Don’t be afraid to just take a chance. You’re going to suck at whatever you try first the first time. And don’t worry about who’s looking, who’s doing anything. Be proud of that person that says, “I’m glad I did,” instead of, “I wish I had.”

Dan: Absolutely, man. The power of being in the arena. And we all suck at some point in time. That is for sure.

Shawn: Yeah. If we sat here, we could have a whole podcast on the things that didn’t work, right, versus the…

Dan: But it’s the lessons learned that – I mean, I’ve seen that myself in life – it’s the lessons learned that really drive you to where you want to get to.

Dan: Awesome stuff, Shawn. I’ve really enjoyed this.

Dan: And then lastly, if our listeners want to connect with you, collaborate with you, potentially work with you – which after everything you’ve told me, I don’t know about the listeners, but I’m going to be a client of Shawn – so tell us where they can reach you.

Shawn: Yeah, you can check out vodsy.com – it’s vodsy.com. And we have all kinds of resources there. We’ve got lots of case studies, lots of success stories. I’ve got my book on there. You’ve got free trainings on there, lots of resources. And then if it comes to the point where you want to chat, there’s a way to get ahold of us and jump on my calendar.

Dan: Awesome, man. Well, that’s really, really cool. So we’ll put that in the show notes as well. vodsy.com.

Dan: Shawn, thanks so much for sharing your time and your insights today. Really, really enjoyed this.

Dan: That’s it for the episode. As always, keep your strategy sharp, your goals clear, and your money working as hard as you do. Cheers, everybody.

Resources & Citations

Short-term rental tax basics. IRS and tax-professional resources on material participation rules, depreciation, and how STRs are treated differently from traditional rentals.
Cost segregation & bonus depreciation. Educational materials on how investors accelerate depreciation on residential property and how law changes affect timing.
Due diligence on STR markets. Checklists and guides for evaluating regulations, demand drivers, and seasonality in potential vacation rental markets.
Hybrid retirement & lifestyle design. Planning frameworks for transitioning out of a traditional 9-to-5 into more flexible, portfolio-supported work.
Building STR teams. Practical guides on vetting property managers, cleaners, contractors, and virtual assistants for a short-term rental portfolio.

FAQs

Is a short-term rental really “passive income”?

Not at first. A well-run STR is a real business and usually requires several hours per week in the first year to learn the systems, set up your team, and make decisions. Over time, with good property management and processes in place, your involvement can drop significantly – but it’s more “leveraged effort” than truly passive.

How many properties do I need before I can replace my income?

It depends on your income level and the types of properties you buy. For many high-earning professionals, a focused portfolio of 4–5 quality vacation rentals – bought within their earning capacity and held for several years – can often give them the option to replace a large portion of their W-2 income. The key is disciplined reinvestment of cash flow, equity, and tax savings.

What makes short-term rentals different from long-term rentals?

Short-term rentals layer hospitality and experience on top of the underlying real estate. You’re managing guest expectations, reviews, cleaning, design, and dynamic pricing. Regulations and market demand are also more nuanced. In exchange, you may see higher gross income potential, better appreciation (because you’re in desirable vacation markets), and unique tax opportunities if you materially participate.

Do I need to manage my own STRs to get the tax benefits?

Not necessarily. The “material participation” rules for STRs are different from those for traditional rentals, and there can be ways to qualify even with a professional manager – but the details matter. You should work closely with a tax professional who understands short-term rentals before assuming any specific treatment.

How much time should I expect to spend each week?

Shawn’s framework assumes roughly 3–5 hours per week for the first 12 months if you’re using property managers and a proven blueprint. If you decide to self-manage, that could grow to 10–15+ hours during busy seasons. Over time, as systems and teams solidify, the time demand generally drops.

How do I know if a short-term rental opportunity is actually good?

Start with the fundamentals: local regulations, consistent demand drivers (not just one event), realistic occupancy and nightly rates, and all-in cost (purchase + furnishing + start-up). Then underwrite the deal using conservative assumptions for occupancy, ADR, expenses, and financing. If returns still look compelling after stress-testing, and it fits your broader financial plan, it may be worth pursuing.

Disclaimer

This episode and page are for educational and informational purposes only and do not constitute financial, tax, legal, or real estate advice. Short-term rental investing involves risk, including the potential loss of principal, regulatory changes, vacancies, unexpected expenses, and market downturns. Tax strategies discussed are general in nature and may not be appropriate for your specific situation. Always consult your own financial advisor, tax professional, attorney, and real estate experts before implementing any strategy involving leverage, short-term rentals, or bonus depreciation.

Next Steps

If you’re a high-earning professional or business owner who’s starting to question whether your current path will fund the lifestyle you actually want, this episode is a good nudge to explore alternatives. Short-term rentals aren’t for everyone – but for the right person, with the right blueprint, they can become a powerful pillar in a hybrid retirement plan.

When you’re ready to see how real estate and other strategies could fit into your version of a rich life, dive into more episodes and resources at Making Sense of Your Money, or learn how Tailored Wealth partners with equity-rich professionals and leaders at yourtailoredwealth.com.