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EP149: Airbnb Hosting Tips From The Laptop Landlord

Whether you’re just getting started as an Airbnb host, or you’re looking to upgrade your status and pick up a few more five-star reviews, the Laptop Landlord is here to share some killer advice that will help you find the right guests for your property and provide high quality customer service during their stay.

Tyler Knudtson is an Airbnb host in Chicago who runs the Laptop Landlord website. He utilized Airbnb for the first time in 2012 as a grad student in Eugene, Oregon, during the US Olympic Trials. He realized that local hotels were overloaded, and living only seven minutes from campus made his place prime real estate. Looking to make extra money, he and his fiancé listed their home on Airbnb and hosted two sets of guests during the course of the event.

After a move to Chicago, Tyler forgot about Airbnb until he started looking for a side hustle to help pay off his student loans. He tried several other things before remembering just how easy it had been to set up a listing on Airbnb. Now he sets availability whenever he is going out of town, and his guests receive the benefit of his customer service background via clear communication. Today Tyler shares his best advice for Airbnb hosts, explaining how to identify your niche and why overcommunication is key in receiving five-star reviews.

Topics Covered

How a background in customer service helped Tyler as an Airbnb host

  • Quality communication with guests led to positive reviews early on

Tyler’s ‘opportunistic’ approach to Airbnb availability

  • Set availability when you already plan on being gone
  • Could also set availability for weekends, and do a free ‘staycation’ if listing is booked

Why Tyler created the Laptop Landlord website

  • Compiled Airbnb hosting resources
  • Wanted to share info, help other hosts plug into Airbnb ecosystem

Tyler’s 4 best tips for Airbnb hosts

  • Figure out who you are as a host, and create a listing that attracts the right guests
  • Take time to set up your listing correctly with a specific headline and photo captions
  • Be proactive with customer service and overcommunicate before, during and after the stay
  • Perform hosting duties yourself before you delegate, outsource or automate

Connect with Tyler


Take the “What Kind of Airbnb Host Are You?” quiz!


Connect with Jasper

Email: jasper@getpaidforyourpad.com

Twitter: @GetPaidForUrPad

Instagram: @GetPaidForYourPad 

Facebook: www.facebook.com/getpaidforyourpad

This episode is sponsored by Hostfully.com where you can create a custom digital guidebook for your guests!

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Complete Transcript for Get Paid for Your Pad Episode 149

Welcome to Get Paid For Your Pad, the definitive show on Airbnb hosting, featuring the best advice on how to maximize profits from your Airbnb listing, as well as real-life experiences from Airbnb hosts all over the world. Welcome.

Jasper: This episode is brought to you by Hostfully, a company that helps you make beautiful guidebooks for your listing. Make your own at hostfully.com/pad, and a special for Get Paid For Your Pad listeners, you’ll get a free guidebook consultation after you make your guidebook.

Welcome back to another episode of Get Paid For Your Pad, episode number 149. The big 150 is coming up, this Thursday actually. But today, I’m talking to Tyler Knudtson. He’s an Airbnb host in Chicago, and he also runs a website, the Laptop Landlord, where you can find information about Airbnb hosting. Am I correct, Tyler?

Tyler: Yup, you got it. Perfect. Thanks, Jasper.

Jasper: Awesome. How’s life in Chicago?

Tyler: Life is good. We’re finally getting some spring weather here, so you know, I think we’re going to talk for a little bit today, and then I’m going to spend the rest of the day outside.

Jasper: Nice. Well, I have lived in Chicago, for about one and a half years. This is a long time ago, though. I moved in 2009. And I remember two things. It was extremely cold in the winter, but on the positive side, I remember that once the sun started shining and the temperature kind of got above 70 degrees or so, the town completely shifted into spring mode and everybody would throw parties, barbecues, beach volleyball. People really make the most out of the late spring and summer. That’s a great time to be in Chicago, I found.

Tyler: Yeah, no doubt. Yeah, we definitely know that we have a limited time until that cold winter you mentioned comes back, so we like to get out there and have some fun while the sun shines, for spring and summer, at least.

Jasper: Right. Yeah, it’s a great city. It’s a great city. I love going back there. Are you originally from Chicago?

Tyler: So, I’m from just north, in Wisconsin, so I grew up about three hours away from here, and so kind of through some different things, I’ve landed here in Chicago. We’ve been here about five years now, so just a little bit longer than you, but we’ve had plenty of those cold winters and beautiful summers.

Jasper: Awesome. Well, Wisconsin is a great state, as well. I did a road trip along the Mississippi River, all the way up to Lake Superior, I think, spent a week there. It was great fun. Ate a lot of cheese, which we do in Holland, as well, so we have that in common.

Tyler: Yes.

Jasper: But, let’s get into Airbnb because your story’s quite interesting. So, let me give you the chance to sort of introduce yourself and tell us how you got involved with Airbnb in the first place.

Tyler: Yeah. So, I think like a lot of people, I kind of accidentally became an Airbnb host, and then kind of forgot about it, and came back to it later out of necessity. So, kind of my origin story as an Airbnb host was, my (not wife then) fiancée and I lived out in Eugene, Oregon, on the West Coast here in the U.S., and I was at graduate school out there and was just kind of wrapping that up, and was starting to think about student loans, you know, in the near future, as well as kind of looking for work and things like that. And it was summer of 2012, and if anybody remembers, in late summer of 2012, it was the London Summer Olympics, but the U.S. trials for those Olympics were in Eugene, Oregon, which is kind of the track-and-field capital of, at least, the U.S.

So, there were thousands and thousands of spectators, and athletes, and coaches, and people doing promotions and things coming to Eugene, Oregon, meaning that, I think much like the origin of Airbnb itself, meant that the hotels in town were overloaded. It’s a college town, there’s some hotels and things, but they quickly filled up with some of the early birds and a lot of the spectators that were going to come and watch the Olympic trials, family members or just people from kind of near and far were coming, and they needed a place to stay.

And so, back to me kind of thinking about wrapping up school and having to start paying back the student loans, I thought, “Well, you know, I wonder if we could put our place up for rent on Airbnb?” It was fairly new to me at the time. This is 2012. And so, listed our place, and I was surprised at how easy it was to find people, and I think some of that had to do with, like I mentioned, people not having anywhere to stay. They were probably looking at hotels either being booked, or kind of ridiculously expensive in town, or staying a long way away. So, we were a seven-minute drive from where everything was happening with the Olympic trials right near the campus.

So, ended up hosting two different set of guests throughout that two-week period or week-long period that was the Olympic trials, and kind of forgot about it for a while, you know. And through looking for work and kind of trying to move back closer to family where we were from, we ended up back here in Chicago, and still kind of while looking for work and things throughout the year or two that followed that. You know, I still hadn’t fully paid off those student loans, or even close, and at one point, we were looking for ways to make some extra money, and tried everything, it felt like, so delivering different things, selling off what you have, which you can only do so much of before you run out of things to sell, and finally ended up remembering, a kind of head-slap moment, “Why don’t I try Airbnb? We live in one of the largest cities in the U.S. and in the world. There’s got to be some demand for it.”

And kind of the same story, put our place up on Airbnb, and it didn’t take very long before people were really interested in our place. And then, I got really interested in becoming a host again and again. I had some background in kind of customer service, and really, accidentally, was pretty great at making people’s stay great, and got some great reviews early on, which I later found out is very important but really wasn’t trying to do that at the time, and it ended up being pretty successful for us. That’s kind of how I became an Airbnb host originally, and then stepped away from it for a little while, and then kind of became a fairly consistent part-time host again a few years later.

Jasper: Where do you stay when you rent out your place?

Tyler: Yeah, so that’s kind of something else I stumbled across accidentally, is that there’s different types of Airbnb hosts, and we were kind of opportunists, if you will. So, we really just, for the most part, when we were already going to be gone, I would know that far enough ahead of time that I would put our place available, I would set our calendar to available. So, you know, a lot of times, we would be back up in Wisconsin visiting family, or going to someone’s birthday party, or just going up to visit family, or go on vacation or something up there, and we would put our place up if we knew were were going to leave.

So, a lot of times, we knew that well ahead of time, which I think helped, you know, if I could put it up a month or six weeks ahead, but even, sometimes, we would decide on a Wednesday that we were going to be gone for the weekend, and even on some of those occasions we were able to, still. At least during the right season here in Chicago, the season that is starting right about now, it becomes even easier to get some folks last-minute to rent our place. So, usually, we were only renting when we were already gone, which I think is a very specific type of Airbnb host. There’s kind of a whole range of them.

Jasper: Yeah, absolutely, and that’s one of the cool things about Airbnb, is that you can use it in so many different ways. There’s also people who put their place up every weekend, and then if somebody books it, then they just go on a last-minute city trip.

Tyler: Yeah, I know. I’ve seen that before, too, where people will, you could call it like a break-even weekend, where you kind of do a stay-cation, and you put your place up and you just need to know that you’re going to be able to. And it probably helps to be in a larger city. It would be hard to do, maybe, in a rural area. But, you know, you can be confident that you’re going to be able to find somewhere that’s roughly the same as what you’re collecting as a host, so essentially, you can kind of do a stay-cation and explore different areas of your own city for free, after it’s all said and done.

Jasper: Yeah, absolutely. It’s pretty cool.

Tyler: Have you done that before?

Jasper: Well, I mean, I’ve always rented out full-time, my place. So, you know, my place has always been available except for maybe about four weeks a year where I would stay at my own place, but my good friend and co-author of the book “Get Paid For Your Pad”, Huzefa, he used to do that. He used to rent out his place in Los Angeles. He’d put it up on the weekends, and then if somebody would book it, he and his buddy, they were living together, would just grab the car and drive to Vegas for the weekend. And that would be exactly like you said. The amount of money that they would make on Airbnb would be their budget. So, that’s a cool way to use Airbnb.

You’ve also started a website, laptoplandlord.com, and your goal is to educate other Airbnb hosts. Is that correct?

Tyler: Yeah. So, I didn’t want to keep all this information to myself. There was, even back in 2012, 2013 when I started, I started noticing that there were websites starting up, like yours and others, that I started bookmarking. You know, I just had all these different resources, that I built this little system for myself so I could reference different things, on everything from photography to writing reviews, to kind of some of the tips and tricks that some of the more advanced hosts were using.

And I also realized that I was starting to get a lot of question from friends and family about being a host. They knew that I had hosted people on Airbnb, and so whenever we were on one of those weekend trips or whatnot that took us out of town, people would ask me, you know, “Are you hosting guests this weekend? What’s that like?” And kind of everything from, “Oh, I could never do that,” to “Oh, I think that’s awesome,” and they liked hearing the stories of different interactions with guests.

So, I thought, “Well, I’ve got all these resources, I really enjoy hosting and talking to other people about it, people are curious about it, it would be kind of selfish of me to keep all these resources that I had kind of so meticulously organized to myself.” So, that’s what kind of led to me thinking about, “Well, why don’t I put it out there on a website where I can share with other people and, hopefully, help whoever’s just getting started with it or even people that have already become hosts and maybe took a different path, just to help people kind of plug into this exploding ecosystem of all these different resources now that weren’t necessarily available back when Airbnb started.

Jasper: Yeah, absolutely. I mean, I remember when I started in 2012, I was kind of doing the same thing. I was searching all over the Internet to find information, and then I wrote a lot of stuff down, and that was kind of the basis for the book.

Hosts, I can’t emphasize how important it is to share recommendations of things to do or eat near your listing beforehand. Your guests won’t have to go through TripAdvisor, Foursquare, or Yelp. They won’t have to scratch their head and think about possible places right in the moment. I’ve been using Hostfully to create an online and printable guidebook to show my guests my favorite coffee places in Amsterdam. They use my recommendations, and I’m getting fewer questions from my guests as a result. I’ve also included screenshots of my guidebook on my Airbnb listing as a way to differentiate my listing from others. So, make your own guidebook at hostfully.com/pad.

You’ve created a really good resource, I have to say, with lots of useful links and lots of useful tips, so I definitely recommend people can check it out at laptoplandlord.com. But, you’ve also composed a number of tips you want to share with the listeners today, right?

Tyler: Yeah, yeah. So, I think it’s helpful sometimes, you mentioned and I appreciate you mentioning, kind of the resource that’s featured on the site now, and one of the downsides of that… It sounds great, you know, I’ve got, I think there’s over 65 different resources there of some of my favorite things or places to go when I need inspiration or some reference points, but at the same time, when you get in there, it’s like, “Wow, 65-plus resources!” is also a lot to go through and look at.

So, you know, I thought it would be helpful to kind of go over, I’ve got four different tips that I think are most helpful. And I tried to also think about things that wouldn’t just be helpful for people that haven’t hosted before, but also that wouldn’t just be helpful for those that are kind of seasoned hosts. Hopefully it’s, I think, things that I see missed a lot when I’m reading different resources and reading about hosts, or looking through and looking for Airbnbs myself.

We’re traveling, upcoming, this June and July, and we’ve been looking for listings, and I see a lot of these things missed. That’s kind of the four different tips I have, all relate to that, and hopefully, can be helpful for people who haven’t hosted or are thinking about it, but also people who are hosting and maybe want to take things to the next level or make sure that they’re doing it correctly. So, do you want me to share those?

Jasper: Yeah, let’s hear them.

Tyler: Cool. So, I think one of the things, and I almost call it Step Zero because I think it’s one of those things that’s important to almost call out before you even start to be a host, I think it’s important to figure out who you are as a host and what type of place you are or what type of place you want to have.

So, a few things under that, I think it’s important to pick a niche and try to be a lot to a small group of people, rather than try to be something to everyone and try to appeal to everyone. I think, for anyone that hasn’t done hospitality type background, they might try to just please everyone because they’re coming from different walks of life, and I think it’s a lot easier to create a listing that attracts the exact right person based on what your area is best suited for, versus trying to please everyone. And I think a great example of this is what you did. And I know you’ve now sold your place in Amsterdam, but, Jasper, you had your listing in Amsterdam, I know you talked about before, was suited for couples. Is that right?

Jasper: Yeah, that’s correct.

Tyler: Yeah, so I think you had, because of the layout of the place and what you had, you kind of figured out over time that you were going to market directly to couples and write your description that way, and maybe have your photos in a certain way or your captions in a certain way. So, I think that did a great job of attracting couples, while, I think, on the other side of that, is it may have repelled non-couples because it was, “Oh, that’s not really for me if it’s talking about that as perfect for couples,” which, people might think, “Well, I don’t want anybody to not want my listing,” but I think you do. And it’s a little counterintuitive, but I think if you can kind of specialize in something while everyone around you in your neighborhood might be trying to be everything to everyone, you can really kind of customize your experience.

So, I don’t know if you did this, Jasper, but if it’s somebody looking to have couples, you know, a lot of people will have like a welcome package or whatnot, you might have something different in that welcome package. Whether it’s snacks or a bottle or wine, or whatever it might be, that might be different if your place is suited for couples, versus if you found out, you know, there’s a lot of bachelor parties in your area and you want to cater to that. The experience that you’re going to want to create is going to be very, very different, and I can’t imagine a listing that serves both of those kind of two different extremes.

Jasper: Yeah, absolutely, and the bachelor parties are the type of crowd that I try to avoid.

Tyler: Yeah, exactly. So, leave that for somebody else who’s maybe ready for that. They maybe wrote some really specific guest guidelines in their house rules area specifically suited for that, where, you know, if you wrote those same rules in your couples listing, they might kind of look at the listing like, “Well, we would never do half of these things. Why are they even saying this?”

So, I think that’s the first one, is kind of figure out who you are as a host, and it kind of depends on what type of property you have. I know your place in Amsterdam, Jasper, was laid out in a certain way that was great for couples, which is perfect. Your own personality, what are you best suited for? Do you want to be kind of that hands-on host that’s maybe there if you’re just renting out a room or you’re nearby, or are you somebody who’s going to be a little bit more remote? I know there’s both types there.

And the time commitment, so what type of time commitment do you want to make? Are you going to want to be pretty heavy and hands-on with people and commit a lot of time yourself, or is it something where you have a pretty busy lifestyle and you just want to give, maybe, a few hours a month or even a few hours a year? You can do that.

So, that’s the top one, is kind of figure out who you are.

Jasper: It makes a lot of sense, like pick your niche. I think that’s great advice.

Tyler: Yeah. So, I think the second one is just to take some time to set up your listing correctly. A lot of people, I see a lot of partial listings out there. So, that can come in the form of a headline, which is so important, the headline of your listing, a headline being just pretty vanilla or not thought out, or even relating back to the last point, being general versus making it very specific about your area. And there’s a lot of great resources out there about writing headlines, so I won’t dive too much into that.

But, things like photos that don’t have captions, that’s one that I see quite a bit, where the photos, obviously, are great, but I think there’s a lot of opportunity to kind of frame those photos with words to make sure that people are kind of seeing things the way that you want to see them. So, I think there’s ways to do that, as well.

So, I think, in a nutshell, that’s the second one, is just take some time to set up your listing correctly. There’s lots of resources out there to help you do that, so you don’t have to do that from scratch or kind of figure out what that means, but I know you’ve got several different pieces on your website, Jasper, where people can learn about that, as well. So, that’s the second one, is take some time to set up your listing correctly.

And then, I think the third one is just to be proactive with customer service, and this is something, I think that I mentioned a little bit before, is part of why, almost accidentally, I was able to be fairly successful early on as a host. I had a customer service background, worked in retail management in the past, so just kind of have that natural ability to communicate with guests.

So, I think, to be specific around that, a few things that people can do is, I think it helps to overcommunicate with guests, or at least what most people would feel like they’re overcommunicating. And, you know, you can definitely go overboard with that, but I think the line to cross to where you’re overboard is a lot further away than most people think it is. So, some specific examples to communicate with guests, before, during and after their stay. That doesn’t mean being in constant communication unless you kind of get a sense that the guest wants that from you.

Beforehand, I think it helps to send the guests a guidebook if you have one, or at least kind of encourage them to look over the guide materials that you probably put into your listing on the Airbnb site, and instructions is helpful, as well. So, I think right after someone books is a great time to send that guide and instructions, or a reminder that they’re listed on the Airbnb listing that you have. And then, I think a few days before their stay is helpful, as well. A lot of times, people book two or three or four months ahead of time, and while it’s great that you sent them that guide three months ago, they may not remember that it’s buried deep in their inbox, and now they’re wanting to take their vacation and they may not remember all those important things that will help to make their stay smooth.

So, that’s kind of the before, and then during, I don’t love to be all up in people’s business while they’re staying. They didn’t come on vacation, most likely, to hang out and interact with me. They came to be in Chicago, or wherever they’re staying, and they want to kind of enjoy the company of whoever they came with.

So, reaching out during their stay, I’ll just usually send a text or a message through the Airbnb app at the end of their first day, just as a “Hey, just checking in, I hope you’re enjoying Chicago,” and just invite them, again, to reach out for anything via text or email. You kind of have to feel that out, whatever they’ve been doing along the way. If they’ve been emailing you the whole time, then make sure you use email for that. Even little things like that, I think, help. Whereas, if you’re texting someone and they’re not somebody who uses text messages, you’re not going to necessarily get credit from them for being that host who’s reaching out and making sure that they have whatever they need from you.

And I think the last piece is after. So, you know, review them before they review you. So, Airbnb, for those that don’t know, has a two-way review system, which is awesome. You can kind of review both. Hosts review guests, and guests review hosts, and one of the things you can do proactively is, even though you can’t see each others’ reviews until you’ve both filled out a review or, I think, until the review period has expired, you can show them. It does alert the guest that you have reviewed them when you do that.

So, I think reviewing them as soon as you can after their stay is over, does two different things. It encourages them to respond back, because Airbnb has that built in. They know how important reviews are to their system, so when you review them, Airbnb sends them an email and says, you know, “Tyler has filled out a review about you as a guest. Make sure that you review them by this deadline.”

So, it encourages that, and I think, even though they can’t see your review, they probably assume that it’s positive. I mean, unless you had a really negative experience and they might know that it’s negative. In that case, there’s kind of a whole different approach, but in most cases, they probably assume that it’s positive, so they just see that coming through and they go, you know, on top of you being someone who overcommunicates beforehand, and then during the stay to make sure that things are going well, just one more touchpoint where they’re seeing, “Oh, Tyler reached out and reviewed again, so this guy’s really on top of things. I want to make sure that I review him.” And they may review right away after they see that alert from Airbnb, so they’ve got a positive thought about you in their mind right as they’re going to review you.

So, I think that’s kind of the third piece, is just to be proactive and overcommunicate with customer service.

And then, the last piece, I think, is I’ve seen a lot of people try to kind of, now that there are so many tips and tricks out there, people try to automate things as a host too quickly. So, tip number four is to do it all yourself right away before delegating to someone else, or outsourcing, or trying to automate things. I think you need to have at least five to ten guests, I think is a good guideline, where you’ve kind of been a full-service host as much as you’re able to so that you understand the guests’ pain points and what your pain points are as a host before you move into, say, having somebody help you host.

I know Airbnb started a co-hosting program not too long ago, so you can have hosts in your area help you out. You can also, there are people who have purchased… I was listening to one of your episodes recently, Jasper, there was somebody who had purchased properties they’d never been at and started hosting them, and obviously, they have somebody helping to host them because they not only don’t go visit those properties, but they had never visited those properties, which I think is totally great if you’ve been a host before. And I think, listening to this particular case, they had kind of been in the trenches before, so that’s great, but I think a lot of people try to skip right to that before they’ve been a host and understand both what it takes to be a great host and what guests expect in your specific place.

So, I think that can actually be more work right away, to set up some of that delegating and outsourcing and automating if you don’t know what guests need and expect from you. And, those early reviews are so important, so you don’t want to start yourself in a hole by getting a few poor reviews because you tried to be a remote automated host right out of the gate. You can do it and you can get there, but I think you kind of need to pay your dues first so that you truly understand what it takes to be a host before explaining it someone else or trying to do it from afar.

So, those are kind of the four tips. Figure out who you are so that you’re attracting the right people and repelling the wrong people. Take some time to set up your listing correctly. Be proactive with customer service and overcommunicate before, during and after the guests’ stay. And then, to do it all yourself right away, if you’re just starting hosting, before you delegate, outsource, or automate your listing.

Jasper: Awesome, dude. Lovely advice. I think it’s all really good points. To finish up this episode, can you tell the listeners where they can go to find out more about your advice and your website?

Tyler: Yes. So, the website is laptoplandlord.com, and I’ve got something specifically that I thought would be helpful for Get Paid For Your Pad listeners. So, there’s a quiz on there that will basically help you figure out what kind of Airbnb host you are. So, going back to tip number one that I just talked through, you know, you kind of need to figure out who you are as a host. So, whether you’re just starting out, or even if you’ve been a host for a while, there might be some things that aren’t quite going right or just some friction points that are always kind of difficult and you don’t know why. It might be because you’re trying to be a type of host that’s different from what you’re best suited for.

So, I put together a 30-second quiz that kind of helps you figure out what type of host you are, I think, like I said, good for both people who are thinking about hosting and are listening to the show but haven’t really figured out how to get started, but also people that are already hosts. So, they can find that at laptoplandlord.com/getpaidforyourpad.

Jasper: Awesome, dude. Love it.

Well, thank you so much for your time and sharing all your advice with the listeners. I think it was very insightful. And good luck with your Airbnb hosting business.

Tyler: Thanks a lot. Same to you, Jasper.

Jasper: All right. And for the listeners, of course, thanks for listening, and we’ll be back in a few days with another episode.