128. A Wild Story: An Unorthodox Short-Term Rental Journey in Puerto Vallarta, Mexico

Uncategorized Sep 09, 2021

Everyone has a story for how they got into short-term rentals. Few, however, are anywhere near as wild as Dan’s.

Dan Ferretti has spent most of his life acting, singing, and pursuing a career in theater. He supplements this unstable career choice by managing a rooftop baseball club at Wrigley Field in his hometown of Chicago, as well as working as a standardized patient at Rush University Medical College and Northwestern University Feinberg School of Medicine. Dan is also a Superhost of his vacation condo in Puerto Vallarta, and co-host of two other units his friend owns there. 

He shares the entire story of how he found his first property in Mexico, how he used his personal traveling experience to inform how he ran his rental, and the wild ride that came along with it.



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#STRShareSunday: Wild Pines Cabin

strsharesunday Sep 05, 2021

It’s time for #strsharesunday and today we are sharing Wild Pines Cabin!

This is a renovated 1974 A-frame in Minnesota situated on 40 private acres. Yes. 4-0. This is a four season location and their feed makes you want to experience every single season here.

Their feed really gives you the vibe and what they want you to expect prior to arrival, and they do an amazing job about letting their guests know what to be mindful of before booking. They let their guests know that one of their bedrooms is in an open area without a door, that the steep staircase isn't necessarily great for kids or those with limited mobility, how you need a truck or SUV to access the property, etc.

Letting us know about these things made us want to book here MORE. We love transparency and authenticity!

Todd and Tessa, you're crushing it!

Wild Pines Cabin on Instagram

Wild Pines Cabin on AirBnb

We would love to feature YOU, so don’t forget to use the #STRShareSunday to get your chance!

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127. How to End a Property/Manager Relationship That’s Out of Alignment

Uncategorized Sep 02, 2021

Last week we talked about how to find a property manager that’s a good fit for you. But what if you’re on the management side, you take a job and, down the line, you realize the property doesn’t align well with your brand? 

Whether you're co-hosting, you’re looking to bring a property into your portfolio, or you’re stop-and-go on getting started, we’re going to help you listen to that inner voice.


First, what goes through your mind when you’re looking at a property and you have that conflicted feeling?

  • You’re looking at the property and your gut is sending you all these warning signs, but your brain is trying to dismiss them as illogical.
  • You walk in expecting to say “yes” because this is what you’ve been working towards. This leads to a bias in favor of “yes.”
  • As an entrepreneur, you are looking for the opportunity to grow at any cost and find hidden opportunities possibly seeing...
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126. 11 Things to Look for When Hiring a Co-Host

Uncategorized Aug 30, 2021

Even if you LOVE being a property manager, practically everyone hits a point where they realize “You know what? Maybe I don’t want to be managing all of my own properties forever.”

When you get there, there’s only one thing to do: start hiring. But when it’s time to hire, how do you make sure you find a great property manager, co-host, or hosting company? We’ve narrowed it down to eleven things to look out for when you’re hiring help.


1. Look up their experience online

 Try and find their online presence. If they haven’t been doing property management long, what were they doing before and could it lend itself to that experience?


2. Interview them

You are going to be working closely with the property manager and you need to be able to trust them. Set up an interview where you can start asking about the points that follow.


3. Talk about their fee structure

 Find out what their fee structure is going to be....

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#STRShareSunday: The Hideaway Torquay

strsharesunday Aug 22, 2021

It’s time for #strsharesunday and today we are sharing The Hideaway Torquay! 

You're gonna want to get over to their instagram STAT. We have not, in all of our time doing #strsharesunday, been totally swept away by a porch. This porch is AMAZING. Take notes!

The window to the kitchen that basically functions as an outside bar. They have extended their living area to this porch and you just wanna hang out there. You can drink coffee, read a book, relax, sit at the bar, you name it!

So many times when we highlight a space, we talk about the interior, but they have really revolutionized the exterior and utilized every square inch of the outdoor space! Not only is their porch incredible, but there's an outdoor shower and a fire pit too.

Rather than inviting them in, they have invited their guests outdoors.

Save us a seat at the bar!

The Hideaway Torquay on Instagram

The Hideaway Torquay's Website

We would love to feature YOU, so don’t forget to...

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125. 3 Things a Property Manager Can Focus on Now to Help Them Achieve the Best Exit with Jacobie Olin

Uncategorized Aug 19, 2021

We’ve spent a lot of time focused on two phases of the property-owning process: buying and renting. But there’s another step we have had a chance to dive into yet, and that’s the selling process.

Jacoby Olin has been involved in short-term vacation rentals, litigation consulting, food and beverage, and real estate for over a decade. He’s one of the preeminent M&A consultants in the short-term rental industry. He specifically advised buy-side clients looking to expand into new markets through acquisitions and developer partnerships.

We discuss why you would want to sell your property, define cap rates and capital gains, and the steps you can take right now to set you up for a successful sale down the line.


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#STRShareSunday: The Oliver OKC

strsharesunday Aug 15, 2021

It’s time for #strsharesunday and today we are sharing The Oliver OKC

! Three huge things about this space that we want to highlight:

1. They have really paid attention to every single light fixture in their property, and if you've never paid attention to your light fixtures, we encourage you to look up, because it is an affordable investment you can make to really transform your space.

2. The reason why we really noticed their lighting is because they purchased it all from a local shop in their town and it's all custom made. Be intentional about your lighting AND be intentional about who you purchase it from! Check out the shop too: @livebohookc

3. They have a GUEST CHALKBOARD WALL where people can write little notes, so the guest, turnover team, and all future guests can enjoy the messages! We love this modern and unique take on a guest book.

The Oliver OKC on Instagram

The Oliver OKC on AirBnB

We would love to feature YOU, so don’t forget to use the...

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124. Buying Land & Property Using Creative Financing Options with Mike Hicks

Uncategorized Aug 12, 2021

Does the thought of financing your short-term rental business stop you from turning those dreams into a reality?

Mike Hicks is a real estate maverick. He’s been involved throughout the industry for over 20 years, beginning in new construction and working his way to long-term rentals, flips, and short-term rentals as well. When he converted a duplex to a STR in 2016, he was hooked. Now he’s a veteran, buying up properties and converting them into unique rental opportunities.

We talk about real estate, his journey into short-term renting, the pros and cons of short and long-term renting, and building a rental inside of a shipping container.



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#STRShareSunday: Hiplandia

strsharesunday Aug 08, 2021

It’s time for #strsharesunday and today we are sharing Hiplandia! First of all, we love the name, and second of all, we don't see this very often (so everyone should head over to their account to check it out!): they have a direct booking site and they manage multiple properties.

We've been talking a lot about direct booking lately, and their site has a handful of properties, but what we love is that you also get to see their portfolio. They are located in Long Beach, CA but they also have a few offshoot properties in Colorado.

Take a peek at how you can make it work and display multiple properties if you have them. So whether you add properties that are your own or whether you're adding properties that you co-host or manage, Hiplandia has done it so nicely and we hope it inspires you!

Can't wait to stay the next time we are in Long Beach!

Book Hiplandia Directly

Hiplandia on Instagram

We would love to feature YOU, so don’t forget to use the #STRShareSunday...

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123. Our Mistakes Making Property Offers & How to Avoid Them

Uncategorized Aug 05, 2021

We always try to be transparent about what is going on in our businesses in the hopes that doing so will serve you. We share our hopes, ideas, struggles, and more. And on that note, we’re going to share one of our most recent embarrassments because you can learn from it.

As we’ve worked together, we have evolved from wanting to focus on education (don’t worry, we’ll still be doing that!) and into growing our own short-term rental empire together. In fact, we just took the first step by making an offer on a property! This has been a long time in the making, and – honestly – we made it take a LOT longer than it needed to. That’s what we’re going to discuss.

When you have these big dreams, they often start out as a whisper. You say it almost hypothetically. “What if we did this? Wouldn’t it be crazy?” It feels uncomfortable to admit that it’s something we might actually want to do, or that we might even feel...

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