The beauty of Airbnb is the trust people place in each other, allowing strangers to stay in their homes and sharing their space – and often their lives. Comedians are in the business of studying people and learning their stories, and today’s guest was fascinated by the concept of home sharing and curious to understand why people choose to host.

Jasper is chatting with Greg Schwem, a business humorist, corporate comedian, and syndicated columnist. He often travels for work, so Greg started adding an extra day to his trips and booking an Airbnb with an interesting profile. With their permission, he films a segment with each host and posts to his YouTube channel, A Comedian Walks into an Airbnb.

Listen in as Greg shares his unique Airbnb experiences, including a stay on an air mattress in a Volkswagen van and a trip to Miami Beach hosted by a ‘stripper turned house flipper.’

Topics Covered

How Greg chooses an Airbnb

  • Interesting profile
  • Extraordinary location/circumstances

Greg’s unique experiences

  • Row house in DC
  • Volkswagen van in Vail
  • Carriage house in Tulsa
  • Trendy loft in Chicago

Greg’s extraordinary host in Miami Beach

  • Former exotic dancer
  • Hosts property in Miami Beach
  • Career in real estate led to Airbnb
  • Owned rock and roll paraphernalia store
  • Very open about her past

How Greg approaches video production

  • Airbnb host is the star
  • His job is to get them talking

Why Greg is particularly suited to host an Airbnb-themed channel

  • Background in television news
  • Open to staying anywhere
  • Age adds a degree of humor (at 54, he’s often out of his element)
  • Interest in people and their stories

Greg’s plans for his channel moving forward

  • Continue to seek out interesting Airbnb hosts/experiences (i.e.: flea market shopping in Texas)
  • Pursue slot on a streaming video or network channel


 “My Daughter’s Room Would Look Great on Airbnb” by Greg Schwem

Connect with Greg

A Comedian Walks Into an Airbnb YouTube Channel

Connect with Jasper


Twitter: @GetPaidForUrPad

Instagram: @GetPaidForYourPad 


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Complete Transcript for Get Paid for Your Pad Episode 143

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, and a special for Get Paid For Your Pad listeners, you’ll get a free guidebook consultation after you make your guidebook.

Hey, what’s up everybody? Welcome back to Get Paid For Your Pad. Today, we have a very special guest. He is a business humorist, corporate comedian, and syndicated columnist. His name is Greg Schwem. Greg, welcome to the show.

Greg: Thank you, Jasper. I’m glad you could have me. Appreciate it.

Jasper: Yeah. I’m looking forward to this episode. It should be a lot of fun, as you’re a comedian. So, you know, I’m expecting some funny jokes.

Greg: I’ll do my best.

Jasper: You’re based in Chicago, right?

Greg: Correct.

Jasper: And, tell us the story. You created a YouTube channel, and you reached out to me to check it out, and I did. You have some pretty funny videos on there, where you check out different Airbnb listings and you stay with an Airbnb host for one night. So, let’s talk about, how did you get into this?

Greg: Well, as a corporate stand-up comedian, I travel all over the country, and really, all over the world, doing shows for big business groups, and I always stay at very nice places, very nice hotels paid for by the company I’m working for. And that’s great, but I like a little variety in life, and about, I don’t know, I’d say about six to eight months ago, I became fascinated with the concept of Airbnb and the fact that people open up their homes to strangers, and in many cases, live side by side with them, and I thought it must take a very unique person to do that. And, really, as a comedian, any comedian will tell you that, really, our business is people. I am fascinated with meeting different kinds of people and talking to them. It’s really where I get a lot of my material.

So, what I did, I decided, since I was going to all these really nice cities, I would, when I could, when schedule permitted, I would add a day and I would find a unique Airbnb host. And when I say ‘unique’, I want somebody with an interesting profile or an interesting property. I don’t always have to go to the biggest one, or the most expensive one, or the most lavish one. I want to go to one that sounds interesting.

And then, I reach out to them and say, “I have a Web series. It’s called ‘A Comedian Walks into an Airbnb’. It’s kind of a play on that joke about, you know, ‘two guys walk into a bar’.” And I said, “I would like to stay with you. All that I ask is that you sit down to an on-camera interview with me and you let me film your place.”

And it’s amazing how many people have just readily agreed to that. I’ve had very few that I’ve reached out to who said, “It’s not for me.” I had a couple, but just about everybody is very excited about this, and I think that kind of goes along with their personalities. Again, if you’re going to open your home up to somebody, then I think you’re more willing to open your life up to them, too.

So, that’s what I’ve been doing.

Jasper: Awesome. And how many Airbnbs have you stayed at, so far?

Greg: I’ve stayed at six in the past month and a half, and I have three more coming up in the next three weeks. I’m having a good year this year. You know, corporate comedy, actually, it’s always been very popular. A lot of businesses just like to laugh at their events, at least at some point, so I stay very busy.

So, I’ve been to Vail, Colorado, I’ve been to Miami Beach, I’ve been to Tulsa, Oklahoma, to Chicago, my home town. I have been to Washington, D.C. In the next three weeks, I’m going to Nashville, I’m going to San Diego, and I’m going to Denton, Texas, which is about an hour away from Dallas. I’m doing that in the next day or so. And I’ve got a lot more irons in the fire, as the summer heats up.

Jasper: Awesome. So, what have been some of your experiences? What kind of places have you stayed at, so far?

Greg: Well, one thing I like to do, as I said, I just look for people with interesting profiles, so I don’t really say, it’s not like I only stay with people in their 60s or millennials. I find somebody who I think just sounds fun and would be good to chat with on camera.

In Washington, D.C., I stayed in a rowhouse, a seven-bedroom rowhouse. There were three other bedrooms that were occupied at the time. The host was a young couple. He was 28, she was 26, and both with government jobs, and had some very funny stories about the kind of people that they hosted.

One of the funniest stories they had was, the day after President Trump was inaugurated, they had Trump supporters who were here for the inauguration, and they also had women’s marchers who were there simply to protest President Trump, and they were staying in the same house, which I thought made for a very funny story.

Probably the most unique property I stayed in was, I stayed in Vail, Colorado. I found somebody who rented out his Volkswagen van, basically on a bluff overlooking the Rocky Mountains. He found a friend who had some property and let him park the van there, and that was what he rented. It was just the van. So, it had an air mattress in it, and I stayed there. So, that was probably the most unique property that I’ve stayed in.

I’ve stayed in a carriage house owned by a nice retired couple, well, semi-retired couple, in Tulsa, which was on the back of their house that he had grown up in. It’s the only house he’d ever lived in, and he actually fixed up this carriage house for his elderly mother, and it turned out she was sick, and then all of a sudden, she got better and she didn’t need a place. So then, they thought, “Well, we’ve got this great property that we’ve sunk all this money into. What are we going to do with it?” So, that’s how they became Airbnb hosts.

Those are the kind of stories that I love. I just love hearing from people about why they choose to host. And I think, sometimes, I mean, obviously, they want to do it for monetary purposes, but I think a lot of people who host have another reason that they want to offer up their properties. I think, again, I think it’s they enjoy meeting people. I had a woman in Miami Beach who I stayed with. She said, “I like to host people from parts of the world that I will never go to.” I thought that was a really interesting comment.

Jasper: So, let’s go back to the stay that you had in Vail, because I’ve actually watched that video. So, you know, every stay, you make a video of about five minutes, where you talk about the place and interview the host, so it’s pretty funny to watch, but I was thinking, a Volkswagen van… It’s pretty cold in Vail in the winter, isn’t it?

Greg: In February? Yeah. Yes, it is. And, you know, it’s not like he gave me the keys to the van so I could crank up the heat. In fact, he did tell me that the van worked, but I certainly was not allowed to drive it. So, yeah, and I think I know where you’re going with this question, meaning, did I stay there all night? And I will say, no. I couldn’t make it. I stayed there about four hours and, man, I was cold. And he told me that. He said, “You know, you really have to dress for the elements.” And I was only there to do a show for a client, and I just had to pack really light, so I didn’t have my snowmobile suit. It wouldn’t fit into my carry-on bag.

So, yeah, I thought I was going to be able to do it. I stayed there for about four hours, but about, I don’t know, 10:00, 11:00 at night, I said, “No, I can’t do this,” so I went and stayed somewhere else, but then I went back. If you watch the video, yeah, okay, I took little liberties because I did go back there at about 6:00 in the morning to film some stuff. So, I want to say I stayed there about half the night.

Jasper: Yeah, well, that’s already quite a long time. I mean, it must have been freezing.

Greg: Yeah, but, you know, I think it’s just funny that this guy, this is a guy, this is one of the ways he makes money. I was very intrigued by him. He had a lot of different jobs, a lot of different ways to make money, and I thought, you know, you can sit there and, on the surface, say, “Oh, this is silly,” and make fun of the guy, which was certainly not my intent. I thought, if anything, it was very entrepreneurial of him to say, “Hey, I’ve got this van,” and he sees this as a source of income. I think that’s wonderful.

Jasper: Yeah, we were talking about it a little bit before we started recording, because he’s charging $67, which, I think, is quite steep for an old Volkswagen van with a mattress, and I was thinking, I mean, how much does this van cost, a couple thousand dollars? Maybe less? Maybe even less? If he rents it out, let’s say, once a week at $67, times four, that’s around $250 or so, right, per month. Times 12… Well, I guess it’s probably… I don’t know if people go to Vail in the summer.

Greg: They do.

Jasper: Oh, they do, okay.

Greg: It’s actually very busy in the summer, too, because then, then you can stay in there all night and not worry about freezing.

Jasper: Right, exactly. That makes sense.

So, that would be around like $3,000 just by renting out once a week, which is a lot more value than the van, I imagine.

Greg: Right. But, he brought up a good point, too, and again, it shows how his mind works. I mean, Vail, if anybody’s ever been to Vail during ski season, I mean, the average hotel room is probably $350, $400, and that’s before you buy your lift tickets. And, you know, people go to Vail to ski, and it is a very pricey town. I mentioned that in my piece. He did say, in the video, he said, “This is cheapest place. If what you want to do is ski, if you want to come out here,” he goes, “this is the cheapest place you’re going to find.” And I think he’s right about that.

So, yeah, you’re braving the elements, and it’s certainly not glamorous, but think about, you just saved $250 and that’s money that you can now spend on your lift ticket.

Jasper: And those are not cheap.

Greg: No.

Jasper: I think you showed the prices in the video, actually, right?

Greg: Yeah, yeah. I expected those numbers to change as I had the camera on them. That’s kind of how expensive Vail is. “Oh, it’s $179… No, wait a minute… Wait, wait, no, no, it’s $190… Wait! I’d better go get a ticket before they raise.” It’s like Disneyland prices. They just keep raising them.

Jasper: Yeah, I’ve never skied in Vail. I passed through the town one time. I did a road trip from Chicago, where I used to live, to San Francisco, but this was in the summer or the fall, so there was no snow yet. But, if I hear those prices, then I’ll probably pick a different place to go skiing.

Greg: Yes. Yup, not a bad idea.

Jasper: Unless I know somebody who’s hosting there and I can stay for free.

Greg: There you go.

Jasper: Anyway, let’s talk about some of your other experiences. So, you mentioned Washington, you mentioned Vail. Where else have you been?

Greg: Well, I stayed in Miami Beach with, she was probably my most interesting host, definitely the funniest that I’ve ever encountered. She was a retired dancer, but when we say ‘dancer’, that’s another way of saying she was an exotic dancer, or a stripper. So, that’s what she used to do, and I knew that, and I was interviewing her, and she was very open about her past. And so, I’m interviewing her at her property, which is a gorgeous place, right on a little piece of water in Miami Beach, Florida, so I had this beautiful water setting behind me.

So, she said… I asked her about what she used to do, and she said, “Well,” she goes, “I’m a former stripper turned house flipper.”

When that came out of her mouth, I was just like, “Wow, we can end the interview right there! I don’t think I’m going to get anything better.”

And she said that she, you know, once she stopped in the stripping game… I don’t know what prompts you to stop stripping. I didn’t want to get into that too much. But, she got into real estate, and she owned and rented out several properties. And then, when Airbnb came along, again, she just saw it as another stream of income.

So, she was very, very interesting to talk to. She showed me her whole place. She used to own a Rock ‘n Roll paraphernalia store in Miami Beach back in the like late ‘70s, so she had a lot of pictures of her with very well-known Rock stars – Robert Plant, and Eric Clapton, and Steven Tyler from Aerosmith. All of these who had either come into her store, or because of what she did, she was able to get tickets for their concerts. So, she showed me all around, and, you know, we just had a great little tour of her property.

And that’s, again, that’s what I like. When I do these videos, I want those people to be the star. I mean, I really do. I’m kind of, even though I’m a comedian and I like to, obviously, insert humor into the videos whenever I can, I kind of think of myself as more the straight man in these. I want their personalities to come out, and I just kind of roll the camera, and ask them questions, and kind of wait for the magic to happen, I guess. And I always get one or two or three good stories, and that’s what I’m looking for.

Jasper: 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

You mentioned earlier that, being a comedian, it’s a lot of people, right?

Greg: Yes, absolutely. I mean, that’s what comedians do. People think, comedians, we sit and we write jokes, that we just sit down at a desk and we write jokes. And, I mean, that’s some of it, but where do we get the ideas for those jokes? We get them by paying attention to people, and studying them, and watching them, and listening to them. I am a huge cellphone eavesdropper. It sounds… And, I don’t mean that in a bad way, but I just like to listen to people’s cellphone conversations because, every now and then, people will say something funny. They don’t realize it, but it’s something I’ll file away, and that’ll come back, maybe, in my show at some point.

And, also, my background is in television news reporting. And when I did that before I got into stand-up comedy full-time, I was a TV news reporter down in West Palm Beach, Florida. And when you do that, it’s kind of the same thing as what I’m doing now, is you take a camera, and you aim it at somebody, and you have to get them talking, and you have to keep them talking. So, the skills that I learned doing TV journalism have really served me well in this project.

Jasper: I can imagine. And, you know, I was just thinking, from stripper to house flipper, that kind of makes sense, too, because, being a stripper is also about people, and being a house flipper is probably also about people, right?

Greg: Yes.

Jasper: So, I was thinking, maybe this could be a career opportunity for you, as well.

Greg: Stripping or house flipping?

Jasper: I don’t know. That’s up to you.

Greg: Yeah, okay. Put that image out of your mind, please, Jasper.

Jasper: I don’t know.

Greg: House flipper, maybe, not the other one!

Jasper: I don’t know what your skillsets are, other than making jokes.

Greg: You know, I’ll tell you, I’m… Well, I was going to say, how do I segue off of that, but I’m 54 years old, and in a way, I think that my age really benefits this type of show because I think I’m willing to stay anywhere, and I think that as you get a little older, you get a little more set in your ways. I mean, obviously, a 25-year-old or 22-year-old would probably look at a van in Vail in the middle of winter and go, “Hey! No problem! $67? Great!” Somebody my age might say, “I don’t think so!”

But, I’m very open and I think that that’s one of the things that, hopefully, comes through, is that I, you know, I live in a nice house here in Chicago, and as I say, I stay in a lot of nice hotels, and I think the fact that I’m willing to go out there and just kind of put my head on a pillow, wherever that pillow happens to be, really adds an element of humor to this presentation because I’m really out of my element an awful lot.

Jasper: Are you planning to be an Airbnb host, yourself, at some point?

Greg: I don’t know. I’d have to ask my wife. I’m not sure she’d be real keen on the idea. It’s not something… Right now, my house doesn’t… Well, actually, that’s not true. I do have a daughter who’s in college. And, it’s funny, I also write a syndicated humor column for the Chicago Tribune, and I did, a few months ago, write a column that was entitled “My Daughter’s Bedroom Would Look Great on Airbnb”, and the whole gist of the column was that I was going to rent, now that she’s off at college, I was going to rent her bedroom out without telling her.

So, and that’s another thing that kind of got me interested in the Airbnb concept, was writing this column. And then, I thought, “Well, here I’m sort of poking…not poking fun at, but I’m sort of showing, I’m sort of describing how people get into Airbnb, and why don’t I go out there and do it?”

So, I don’t know if I’ll ever become a host. I kind of like it the other way. I like being hosted. Yeah, I like being that person.

Jasper: Right. Yeah, and now, your YouTube channel’s called “A Comedian Walks into an Airbnb”, and it could also be “A Comedian Hosts on Airbnb”.

Greg: It could. I have heard of… Yeah, I did some Googling when I came up with this Web series, just to make sure that nobody else was doing something like what I’m doing, and they’re not, but I did come across a listing, an Airbnb listing. It was in California, and the property was hosted, or owned by, or rented out by four comedians. That’s the way they portrayed it on the Airbnb site. They did say that, a lot of times, they weren’t there. I mean, if you’re a comedian, if you’re not traveling a lot, you’re not making money as a comedian. That was like the closest thing I came to where comedy interlaced with the Airbnb concept.

Jasper: And what are your plans with this series?

Greg: Well, what I want to do, I mean, obviously, “Airbnb, if you’re listening, it’s a lot of free publicity for you.” I really want to take this to one of the streaming video channels, or I can even see it on something like the Travel Channel, a cable network. I think the idea of me entertaining people while I’m being entertained, myself, and doing it every week in a different location, is very appealing to a lot of people. I mean, I’ve been told, “What’s your target audience?” and I don’t think I have one. I think everybody. I mean, everybody travels, and I think everybody likes to see different locations and different ways of traveling.

So, my goal is, I’ve got six done, I’ve got three more coming up in the next three weeks, and once I get about 10 or 11, I think I’m going to take it to streaming media, and so forth, and just kind of see where it goes. I mean, every one that I do, I’m refining my interviewing technique and I’m trying to do more than just shoot the property.

I’m doing one in Texas in a couple of days, and the woman that I found is very big into flea markets. That’s what’s all over her profile. So, I asked her, “If I stayed at your place,” which is an Airstream trailer, by the way, I said, “Do you want to go flea market shopping?” And she goes, “Absolutely!” So, that’s what we’re going to do, and I’m really looking forward to that one.

Jasper: Yeah, you have some pretty interesting listings these days. Like, you have treehouses, and igloos, and God knows what.

Greg: Yeah. Yeah, exactly, and I think that’s what’s so cool about it, is you really get a sense into how other people live. I mean, I was off last week, I didn’t have any gigs, and as I said, I live in Chicago, so I thought, “Well, I’ll do an Airbnb in Chicago.” And I picked a host who lives in the West Loop. And you’ve spent some time in Chicago, so I think you know that that is a really, really happening neighborhood. And this is a guy that owned a three-bedroom loft, and it’s the kind of place that I probably would never stay in.

It’s kind of like the Miami Beach lady. I would never, probably, buy a three-bedroom loft and stay there, and this gave me the opportunity to feel, for a night, like I actually was living there. And it was incredibly, you know, it was walking distance to a lot of the really cool new places that Chicago has to offer in an up-and-coming neighborhood. It was almost like, you know, it was like going on vacation in my own city. That was kind of cool.

Jasper: Yeah, absolutely. You know, it’s interesting because, as a host, I also learned a lot about my own city, because there’s all these tourist places that you, for some reason, living in a city, you just don’t go there, you know?

Greg: Yeah.

Jasper: And, at some point, I asked myself the question, like, “Why not?”

Greg: Right, right. Now, let me ask you a question. When you host people, I mean, do you hang out with them or do you offer to go around the city with them, be sort of a tour guide?

Jasper: If I’m there, yes, but I’m not there very often because I’m pretty much traveling full-time. But, if I am in Amsterdam, then I definitely always ask the guests if they want to have a cup of coffee together, and get to know them a little bit, and kind of get a feel for how much interaction they’re looking for.

Greg: Yeah, and I’m sure that they’re all different. I’m sure that there are some that want to hang out, and there are probably people that don’t want to hang out. I would imagine that you could probably figure that out very quickly, couldn’t you?

Jasper: Yeah, you definitely develop a skill for that. You know, I’ve hosted over 350 groups. But, like I said, most of the time I’m not there, but even through communication, you get a feel for how much contact they want to have, over the phone or over WhatsApp or Skype, or whatever it may be. Some people, they write very short answers, and so, that’s an indication that, probably, I shouldn’t bother them too much, right?

Greg: Yeah, yeah.

Jasper: Whereas, other people, they share a lot about themselves and they ask questions, and then I get very personal. I send them pictures of where I am, and talk to them about travel and all sorts of stuff.

Greg: I think, you know, I think one of the reasons why Airbnb is successful is that… On the surface, what I’m going to say sounds kind of strange, like you would immediately dispute me, but I think it’s true, I think we are a very trusting society now. And part of you thinks, “Oh no, we’re not. We live behind fences and we all carry weapons now because we never know who’s going to, you know, who we’re going to run into.” But, yet, think about it. You think of how successful Airbnb is, you think of how successful Uber is, where we just let people pick us up in their own cars and we trust that they’re going to get us where we’re going, and Airbnb is the same thing. I think it’s a concept that is based on trust.

And, you know, these folks in Washington, D.C., this couple said, “Hey, do you want to go out for a drink, and we know this great chicken place.” And I go, “Absolutely.” And I think that’s very refreshing, that people are willing to do that. They’re just basing it on your reviews and, also, that initial meeting with you.

Jasper: Yeah, I think it’s definitely something that is a trend, people getting more used to sharing things, and meeting strangers.

Greg: Yes. I mean, when you think of how openly we give our credit card to people, that right away says that, “We trust you. I’m going to give you my credit card number over the phone, and I’m going to trust that you’re not going to run wild with this information that I just gave you.” I put a lot of that kind of material into my stand-up act, about how we’re a very trusting society now, and I’ve encountered several situations where it’s just like, “Really? You’re asking me to do that?” But, that’s just the society that we live in now, and I think that’s a good thing.

Jasper: Awesome. So, let’s let the listeners know how they can find your YouTube channel before I let you go.

Greg: All right. Well, my website, first of all, if you want to laugh, you go to The best way to find my YouTube channel is just to search on Google, ‘A Comedian Walks into an Airbnb’. You search that and all my videos will come up there. All right?

Jasper: Awesome.

Greg: And I hope everybody subscribes. I love when people write comments, too. I usually respond to all of them just because that’s something that I enjoy doing. And you know what? It’s funny because when I first launched the channel and I started putting some of these videos up, like on my Facebook page and things like that, I had three of my Facebook friends say, “Hey, I’d love to host you.” So, I thought that was kind of interesting.

Jasper: Very cool. Well, I’ll definitely look forward to checking out some of your videos in the future, and good luck with the show. And thanks for coming on to the podcast.

Greg: Thanks so much for having me, Jasper. Best of luck to you.

Jasper: All right. Bye-bye. And to the listeners, thanks for listening, and until next time.

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March 6, 2017

EP133: When Your Guests Hold a Wedding at Your Airbnb

This week on the podcast, Jasper has a conversation with Brian Chen, lead consumer technology writer for the New York Times and Airbnb Superhost. Brian’s cabin […]
March 2, 2017

EP132: This Week in the World of Airbnb

It was a quiet news week for Airbnb, though the themes of acquisitions, group travel and regulations remain top of mind. This week, Jasper chats with […]