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EP181: Hospitality Insights from a Superhost and Co-Founder of GuestBook

Want to get the girl and found a startup? Become a remote host on Airbnb.

Perhaps it’s not quite that easy, but it worked for GuestBook co-founder and Miami Beach Superhost Jeremy Mays. Jeremy lives in Boston, but he met the woman of his dreams in Miami. When he realized that the expense associated with frequent stays in South Beach hotels was not sustainable, Jeremy sought more affordable means to travel back and forth—wooing his future wife.

Initially apprehensive about using Airbnb, Jeremy eventually booked a condo and had a very positive guest experience. This gave him the idea to buy a condo of his own, and let the property pay for itself by listing the space on Airbnb when he wasn’t using it himself. Remote hosting came with its own challenges, and after connecting with a fellow host and technologist, the pair created GuestBook, an all-in-one app for hosts that automates messaging to guests, communicates with cleaning professionals and provides travelers with additional options and information. Today Jeremy shares the factors he considered in choosing a property for Airbnb, his take on hospitality, and how new regulations in Miami affected his business. Listen in to learn more about GuestBook and how its modular service can help you be a better host on Airbnb, even if you don’t live in the same city as your listing!

Topics Covered

Jeremy’s introduction to Airbnb hosting

  • Conducted research re: location, staging
  • Purchased Miami Beach condo for Airbnb
  • Identified staff (cleaning professionals, emergency contact)
  • Smart Lock, Lock Box (remote hosting)

Jeremy’s take on hospitality

  • Overcommunicate with guests
  • Reach out before trip
  • Confirm safe arrival
  • Check-in during stay
  • Offer fond farewell
  • Align expectations with experience via transparency
  • Incur slight expense to provide amenities
  • In-unit laundry
  • Dishwasher
  • Coffee

How changing regulations in Miami affected Jeremy

  • Slight dip in bookings associated with public warnings about Airbnb
  • Hosts in zone still approved by city
  • Chose location regulated privately by condo association
  • Investor-owned building has no rules around short-term rental

Considerations Jeremy made in choosing his Miami Beach condo

  • Location close to beach, tourist attractions
  • Relatively quiet neighborhood
  • Appeal to travelers, tourists (nightlife, shopping)
  • 1-bedroom corner unit with great light set back from street

How Jeremy’s wife facilitated his Airbnb hosting career

  • Met in Miami, traveling from Boston regularly
  • South Beach hotels cost up to $600/night (not sustainable)
  • Friend suggested he use Airbnb
  • Booked entire condo on Airbnb, great host
  • Made decision to buy own place, use Airbnb to finance

How Jeremy conceived GuestBook

  • Born out of necessity
  • Creating own email templates for guests, cleaning staff
  • Explored existing offerings, none offered all features
  • ‘Got to be a better way’
  • Met co-founder Sanjay Patel (fellow Airbnb host, technologist)
  • Shared common challenges
  • Launched GuestBook to provide all-in-one app

How to sign up for a GuestBook account

  • Click ‘Sign Up for Free’ tab
  • Connect with Airbnb account, establish password
  • GuestBook imports reservations, guest info
  • Modular service allows host to choose options
  1. GuestBook Host automates messaging, property info and check-in/-out instructions
  2. GuestBook Pro communicates with cleaning professionals
  3. GuestBook Travlr connects guest to options (property discovery, emergency support, early check-in/late check-out)

How the payment aspect of GuestBook Travlr works

  • Beta testing currently
  • Host activates option in dashboard
  • Enters payout information (third-party provider)
  • Guest pays through app, GuestBook receives small commission

Connect with Jeremy



Airbnb News Facebook Group

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 181

Jasper: Welcome to Get Paid for Your Pad, a definitive show on Air Bnb hosting, featuring the best advice on how to maximize profits from your Air Bnb listing as well as real life experiences from Air Bnb hosts all over the world. Welcome.

AD: this episode is brought to you by Hostfully, a company that helps you make beautiful guide books for your listing. Especially for Get Paid for Your Pad members, get two free months of their premium version. For more details, visit hostfully.com/pad.

Jasper: Welcome everybody to episode 181 of Get Paid for Your Pad, I am with Jeremy Mays, he’s the co-founder of Guest Book and a remote super host in Miami. He resides in Boston. Thanks for being here.

Jeremy Mays: Thanks for having me, I’m excited to be here.

Jasper: Absolutely, Jeremy has been helping me out a lot with the Air Bnb news group, he’s been posting a lot of articles about Air Bnb and giving opinions and asking some questions and he’s having a lot of fun.

Jeremy:  It’s exciting really, getting into the industry and engaging these hosts, and talking to them, asking them questions, sometimes getting them fired up. You know, no better way to get first-hand knowledge of the industry than the people who are at the ground-level operating it.

Jasper: So, for the people who are part of the group, you might already know Jeremy. For those who are not, could you give us a summary of your background?

Jeremy:  Sure. Back in 2015, I decided to buy a condo down in Miami Beach, partially to chase a girl who is now my wife, so I guess it worked. I knew obviously being in Boston I wouldn’t be there more than a handful amount of time in the year. I didn’t want it to be empty, I wanted to pay for itself, so I bought it with intention to put it on Air Bnb. So, I did a little research and figured out the right place to buy. The right combination of décor. As a marketer and a creative, I have a strong attention for detail and visual appearances. Clean lines, bright spaces. I went down there, bought the place, connected with some people who sourced someone to clean it. I figured out the right combination of lock box and smart lock, I wanted to make sure people could get in or out, I wanted to make sure there was someone to handle emergency situations. That was my first jump into Air Bnb, and I think I didn’t realize what I was going to get into, the amount of work or the detail. But as a marketer and someone who believes in treating other people as I’d like to be treated, I wanted to make sure everyone felt welcome and excited about showing up and their stay. Was happy, and well taken care of – they left with a smiling face because I wanted good reviews. That’s not the only motivating factor, but I wanted to make sure that was well executed.

Jasper: You’re a remote super host, and that’s a great achievement, I think it’s more challenging if you’re not interacting with your guest in person, you’re not there to meet your guest. That’s great, we talked a little before that you mentioned you have some views on hospitality, that’s something you focus in your experience. We’re going to talk a little about what you’ve done to create the outstanding experience for your Air Bnb guests.

Jeremy:  So, hosting to me, and hospitality is everything. I’ve been a traveler as well and stayed at places where the communication was less than ideal. Where you walk into the place and question whether the sheets have been washed. Where the host hadn’t been quite as transparent about noise or people who would be around the general area, so, I’ve been on that side of missed expectations. For me, it’s important to be at bare minimum, over communicative to guests coming into your place. When I furnished the place, I wanted a clean, functional, comfortable décor. Something that wasn’t overly themed, it was white, bright colors, made people feel excited about being in Miami. As I got into hosting, I found it simple. Reaching out to guests before their trip, making sure they arrive safely. Checking in with them while they’re on site or staying at the place. Sending them off with a fond farewell. I’m trying to think of what else I do, it seems natural. I have in-unit laundry, dishwasher – I take on an extra expensive by providing coffee pods, laundry pods – if someone wants coffee, no one wants coffee more than someone who arrived in the middle off the night. Those are the kinds of things I’ve thought of so far.

Jasper: you’re hosting in Miami, I know there’s been some new regulations and issues when it comes to hosting in Miami recently – have they affected hosting?

Jeremy:  Maybe I saw a dip in travel, there was one year where Miami beach got really aggressive in PR campaigns warning travelers they’d be kicked out in the middle of the night or the police would harass them – I happen to host in a zone that’s still approved by the city. I know the city has been focusing on single-family home owners, the rest of Miami when it comes to condos and buildings, some of it is regulated privately, so it’s a building by building issue. Initially when searching for a place, because I knew I’d put it on Air Bnb, I specifically looked for a condo association that had no rules on short-term rentals. It’s primarily an investor owned building. So, 70 percent of the units in my building are owned by investors

Jasper: I get a lot of questions from listeners who want to invest in Miami, could you tell us more about what you looked at in making that decisions of which apartment to buy in Miami?

Jeremy:  I had a lot of criteria and variables that I asked my broker to fulfill. I wanted to be close to tourist attractions in a quiet neighborhood, which does exist in Miami. I should also make the distinction that I’m in Miami Beach versus Miami, they are two different cities. Municipality perspective. Thinking about the people who would come in and stay at my place, I wanted to hit on all the different notes that would appeal to tourists. Most of the people who live in Miami aren’t from Miami, or who traveled to Miami, tourists. A lot of international tourists who want to experience the beach, nightlife and shopping. I happen to be dead smack in the middle of Miami beach. You couldn’t get any closer to all the attractions.

Jasper: what about the actual unit?

Jeremy:  The unit itself is a 1-bedroom. It’s slightly set back from the street itself. Obviously clean, it’s a corner unit. I was looking at buying another unit on the same street and last minute, when that deal wasn’t going to go through, my broker turned me on to this unit, the stars aligned in the right place and right time. The right opportunity. I was in there, set it up in ten days, was back in Boston and had it listed on Air Bnb in about two weeks.

Jasper: Awesome, awesome. That’s good work, man. In the process, you managed to meet your wife.

Jeremy:  I’d met my wife a couple months before. This was important – how I decided to buy the place was because I met this beautiful woman. I traveled to Miami, was staying in these hotels, south beat hotels were running $600 a night, that was becoming economically too challenging to sustain. And there was no way I was letting this woman out of my sights, and a good friend of mine said look around for a place on Air Bnb, and I’d had a lot of people with a certain level of expectations, I’d been used to staying in luxury hotels and a certain level of desires when it came to travel accommodations. When the first person, my friend suggested I stay in Air Bnb – my immediate reaction was to push back. I don’t think I want to deal with having some creepy place, I don’t know who the host is going to be. I think a lot of the common apprehensions and fears that peoples till have, though it’s a lot less these days. Finally, I was convinced. I booked a place, it was an entire condo with a pool on the roof of the building, the host was more than friendly. Two years later, almost three years later, we’re still in touch. We’re still friends. When I go to Miami now, we get together. That was my first experience with Air Bnb, chasing after my wife, while I was there, running the numbers, I was saying if I keep this up, it doesn’t make sense, even using Air Bnb. I might as well buy a place and do the exact same thing. That’s only because the host I was staying with was very open and transparent about how much money he’s making, so. That was kind of the motivation.

Jasper: Should we call this podcast How Air Bnb Hosting Can Lead to Getting Married to the Woman of Your Dreams?

Jeremy:  My wife would probably kill me for saying that, but deep down inside she’d like that.

AD: You’ve heard me talk about Hostfully a lot over the past few months. I love sending my beautiful Hostfully guide book to my guests as it makes me look very professional. I also love including screenshots of my guidebook in my Air Bnb listing. This helps me stand out from the crowd. Now, I’m thrilled to announce I’m a sponsor of the Hostfully host program. Twice a month, Hostfully selects a host and features them on their top-ranked blog. This is great promotion for your listing and a cool way to share your favorite local spots with a large audience. What’s even cooler is that each Hostfully hosts gets a free set of sheets from the Clean Bedroom. And now that I’m a sponsor, you’ll also be featured in my newsletter, my social media feeds, and free access to my video on how to be a great host. For more information, visit hostfully.com/hostfullyhost

Jasper: Let’s talk a little about Guest Book and what they do, and how they can help.

Jeremy:  I think like a lot of start-ups and a lot of ideas, really it was born out of necessity. Coming back to Boston and being into technology and being a marketer and stringing together email templates for my incoming travelers and the right blend of technology was for my own needs. I became frustrated to a certain degree and thought to myself, there’s got to be a better way. I looked around and the offerings that were out there and some of them were good, not great. Some accomplished some of my needs, but not at all. I didn’t want to add five or six different apps for my needs. For a while, I was doing it on my own, setting calendar reminders for myself about my cleaning person and keeping them well informed to ensure reliability, that was a big concern of mine. If there was ever an instance where a person couldn’t clean for me, that’d be a problem. Consistently being faced with challenges of being a host, I thought to myself that there’s got to be a better way. I ran into a colleague, he’s the CEO of guest book. He happens to be an Air Bnb host in Boston, he owns five properties. We started getting together and talking about the common challenges and realized they were the same. Remembering to send guests emails and check-in instructions and keeping our professionals informed for when we needed our places turned over, making sure our guests have great experiences we want them to have so they feel like they enjoyed their travel experience and we also get the good reviews. All those things became challenges we were passionate about solving. He’s a technologist, I’m a marketer and a technologist. We came up with ideas, testing them out in our own properties, that’s how Guest Book was originally born if you will.

Jasper: I know Guest Book recently opened, so if I was an Air Bnb host and I wanted to make use of your services, what’s the process?

Jeremy:  Right now, it’s free, that’s the most important point, we’re working on pricing model. There’s no imminent plans to implement it until we’ve sorted out the how’s and the when’s. Signing up is super easy. Log onto our website, useguestbook.com, click sign up, and in about 15 seconds, link your Air Bnb account. We’ll do the rest. We’ll import all of your reservations. You’ll then have options. We made sure our program was modular. Right now, we have two features, soon to be three. Feature one is automation, a bit to help you communicate welcome messages and property information, check-in instructions and check-out instructions. We call that in hospitality, a warm and sincere greeting. Making sure they receive that information days before they travel so there’s no question about where they’re expected and chasing down hosts for information. It’s just enough. We’re not over-relying. There still has to be a personalized touch. The second service that we have, which I think is one that’s absolutely crucial to anybody’s hosting experience is Guest Book pro. That’s a product that enables your cleaning professional to stay on top of the jobs. Every time a guest books on Air Bnb, we import those reservations into Guest Book. There’s a check-out time associated with those reservations. The day and time of check-out equals day and time of cleaning job for your cleaning professional. There’s another product, another service that we’re playing around with right now. There’s been mixed emotions about it, but we want to experiment with it and see how people respond to it. It allows host to activate and earn extra revenue by offering guests early check-ins and late check-outs for small fees. A lot of hosts and myself included have just taken the position that if their place is open and there’s no one else coming in, then why not let the guest utilize the space, that’s good hospitality. At the same time, we need to remember there are resources being allocated to accommodate those guests. We allow for some windows to remain free. It becomes a convenience for the guest as well. If the guest doesn’t want it, they don’t need to purchase it. But if they do, we’d like to eliminate the awkward conversation where if they need it, they can have it for a small fee. Hosts don’t always feel great about it. This kind of eliminates that challenge in the process. How often can you think of in your travels Jasper where you book an Air Bnb at 4pm and it’s an international flight and you get there at 8 am in the morning so you’re left walking around in a foreign city with your backpack and not knowing what to do.

Jasper: I’ve been in that situation a lot of times in the last seven years.

Jeremy:  yeah, we think everyone can win. We want to strike a balance where guests don’t feel nickel and dimed, which leads us into our third product which is Traveler. We look at Traveler as a travel companion for guests. It’s connected to the hosts Air Bnb account. So, when the booking happens on Air Bnb and we import those into Guest Book, five days out, they’ll receive an invitation to download Traveler with matching credentials they used to book their Air Bnb account. They have access to a world of options. Early check-in, late check-out, support during their trip. It will connect them to their host. No more guessing. It’s all right there for the guests. We’ll add later neighborhood discovery that other guests would want to take advantage of or things that have been requested by guests.

Jasper: It’s a combo of a number of different services. Instead of using a lot of separate applications for Air Bnb hosting, it would be cool to have one app that does everything for you. I was just curious. When you offer that, how does the payment work?

Jeremy:  We’re handling that for hosts. If they activate this within our dashboard. I should preface this by saying we’re beta testing this on a few accounts privately, but we want to make sure we’re compliant and secure, guests and hosts alike need to know their payments are protected. The way it works, the host will activate that service inside their account. IN order to activate that, they need to have Guest Book Pro as well. They enter their pay out information, we connect into a third-party solutions provider. A host can choose their credit card or bank account as a payment method. Hosts will sit back, we run algorithm on their schedule because we know who is going. If they download the travel app, they’ll be able to see what’s available for them. IF there’s early check-in available, and if there is late check-out, that will also present itself. We’re charging incrementally now, just testing it. Guests will pay through their end of the app. That payment will be transferred into the pay-out method, minus the small commission we take off the top for doing the entire service. No longer are you sending the request on paper. You know, you’re not using some weird payment. No awkward conversations. It’s totally by choice, if guests want it, they can pay for it. If they don’t want it, they don’t have to pay for it. They can wave it all together or they don’t have to activate it

Jasper: Well, Jeremy. Thanks for coming onto the show. Of course, we’ll see you in the Air Bnb Facebook group. I look forward to checking in with you in the future.

Jeremy:  I appreciate you hosting me, Jasper. Of course, everyone come find me, either in the Air Bnb Facebook news group or useguestbook.com, I look forward to reconnecting and giving you guys updates in the next few weeks. Whenever I reconnect with Jasper here on this podcast for round two.

Jasper: Thanks for listening. We’ll see you on Friday with the next news episode. See you then!