My First Airbnb


When I travel I always like to stay in vacation rentals, but until recently I hadn't even so much as created an account on Airbnb, much less actually stayed in an Airbnb home. I needed to end that streak.

And when planning my visit to New York City -- pretty much the bubbling cauldron of the shared economy -- I figured it would be a fitting place to lose my Airbnb virginity and give it a go. Here's everything I learned.

1. Setting The Stage

In technical terms, Airbnb represents one of several large listing sites in the broader short term rental market. Airbnb is kind of a separate ecosystem with it's own culture, momentum, rules, quirks...etc. If the vacation rental industry was a country, Airbnb would be it's own semi-autonomous island off the coast.

On a more qualitative scale, Airbnb seems to be much more polarizing than other vacation rental companies like HomeAway, FlipKey, VRBO...etc. Neighbors, families, city councilmen tend to either really love or really hate Airbnb. In fact, about one week before my trip, I read in the news that NYC passed a law killing Airbnb[1. New York Rejects Free Market Innovation, Passes Law Killing Airbnb, Jason Hopkins,]. Just to be sure, I reached out to Inner Circle member Evelyn Badia who is pretty much the Airbnb whisperer. Based in NYC, Evelyn walked me through the experience and assured me I should be fine.

2. Unpredictability (In Moderation)

It's the quirky travel stories that always seem to become memories. Take my trip to Montreal 25 years ago. I couldn't tell you one single detail from that trip other than that my mother had to hide naked in the hotel closet when the bellboy opened the door unannounced (we still tell the embarrassing story to this day). Quirks make for memories!

We often discuss unpredictability as both an asset and a liability in the vacation rental industry -- about why establishing some standards to close the gap between what a traveler expects and what they actually receive is so important to achieve travel zen (or at least to reduce travel angst).

In NYC, arriving to my Airbnb would serve as a good example of fun unpredictability. Several days before my Airbnb stay, my host sent me GoogleDocs instructions on how to arrive and upon reading through it, I immediately felt like a spy:

Find the secret phone booth and corresponding lock box > scramble once you've got the key > now slip between tavern and Amish Market > unlock bottom lock with red key > make your way to top floor unit > if anyone asks, "you are working in New York City for a few weeks"

I very much enjoyed our secret spy arrival. But because Airbnb is so controversial (and illegal in some cities) I could see sensitive travelers getting flustered with this kind of unpredictable arrival.

3. The Side Hustler

I have noticed that lots of Airbnb hosts are side hustlers. And it's important to remember that the side hustle is about more than just money: it is a hedge against feeling cornered and bored by life. In this sense, Airbnb hosts are passionate people reinventing themselves, creating better communities, and sharing their corner of the world with like-minded peeps.

Not unlike with vacation rentals, however, when a side hustler enters a professional's arena to compete for the same client, things can get tricky. For instance, our Airbnb host charged $450/night, which was the same price of a few other hotels I found on HotelTonight. And when you're competing for with hotels, you are (however fairly or not) setting yourself up to be expected to deliver a comparably professional experience.

I was a little disappointed, for instance, when I emailed my host about the Airbnb ban (to ensure the flat would be available or if we could email outside of Airbnb in the case that his listing was taken down). His response was a polite "you'll need to talk to Airbnb about that." Another example, we asked if we could arrive before 3pm (check in time) in order to drop of our bags for meetings: the request simply went ignored. Goldman Sachs recently came out stating that most people who use Airbnb don't want to go back to hotels[2. More and More People Who Use Airbnb Don't Want To Go Back To Hotels, Julie Verhage, Bloomberg]. So these questions may be getting more pressing by the day.

4. Professionalizing The Host

The beauty of the side hustle is that people are less driven by profit and really truly want to share their lives with you!

Because with Airbnb you are frequently staying in someone's living space (as opposed to a vacation home that has been designed for the purpose of visitors) there are some little nuances that travelers should expect. My host's clothes in the closet would be a minor and unobtrusive example. My host's hairs on the shower would be...umm...another. Now that I've stayed in an Airbnb, I can resonate with the HomeAway commercial (below).

But during my first Airbnb stay, I also realized that "staying in someone's home" sounds way more uncomfortable than it is. While there are bound to be horror stories because Airbnb moves so many travelers, the company really impressed me with their review process, which acts like a self-governing mechanism. In this sense, it's almost like Airbnb is becoming a hospitality school for millions of people world-wide. And that is an incredibly powerful thing.

As we learned in Inside The Mind of VR Guests, short term rental guests want to be treated with white gloves. So professionalizing the hosting role definitely has serious rewards.

5. Rent-A-Local

When I travel to new places, I like to pick destinations where I have friends because they can seriously enhance the local experience. And if I'm lucky, those friends have an extra bedroom or happen to be out of town for the week and will lend me a place to stay. This kind of insider access is what I would call "the new luxury" and replicating it seems to be at the core of what makes Airbnb so successful.

The slight difference however is that my friends don't offer these things in exchange for money. They do it because we have a pre-existing relationship...they do it based on reciprocity. The moment an act of generosity is turned into a business transaction with the exchange of money, it takes on whole new context and responsibilities. (On the flip side, if I'm staying at a friend's home for free, I don't really have the right to complain about anything.)

"When money is exchanged, staying @Airbnb becomes a business transaction w/ responsibilities"

Click to Tweet

I have a feeling that this grey area might be the root of some Airbnb controversy. If I had the chance to meet the CEO, I would ask how the live-like-a-local concept scales and what expectations are appropriate when selling the service of insider experiences?

6. Conclusion

This was my first Airbnb experience and not unlike the people featured in the Bloomberg article, I will stay at one again. I have been critical of Airbnb in this post in an effort to stimulate conversation and open dialogue about where this company and side hustle short term rentals fit in the big picture. I am not suggesting that one Airbnb experience represents them all, but I am curious...

If you are an Airbnb host, do my observations offend or annoy you? Was my experience accurate of what Airbnb is all about?

If you are a traveler, do you think my expectations fair?

If you are a vacation rental professional, what's your experience with Airbnb and how do its clients match up to that of more traditional VR sites?

Really curious and excited for everyone's take on this...




  1. Hi Matt,
    I, too, am very surprised that this is your maiden voyage into ABNB. To answer your questions — yes I’m an ABNB host, starting my 4th year. Yes, some of your comments I took personally, but am not at all surprised, given that I stay in VRs booked through ABNB. I have experienced the same issues — a hair on a used bar of soap? Heebie Jeebie time. Clothes in the closet? Yikes! I almost took home a host’s garment because I had one almost exactly like it.

    I have two condos in a resort town in CA, a gated community with a golf course, etc. The difference between my experience and many others is that I began this venture AS A BUSINESS. Having 25 years owning and operating a computer sales and service business gave me the background to succeed. That said, whenever I stay at another host’s property, I give them pointers (in a very nice way) of how they can improve. They always appreciate it. It’s a small thing, but I think if all of us are willing to make an effort to provide constructive feedback to other hosts that is specific, the entire market will benefit and the quality of VR experiences will improve exponentially.

    I use VRBO, Flipkey and ABNB for my bookings at this point. I think what’s great about the ABNB platform is that they have a vision, execute that vision in a superior way, and know who they are. For better or worse, the company is predictable, or has been so far.

    Many others have said this, but I think it bears repeating — the host and guest review process is one key to ABNB’s success AND to ours. The platform requests the reviews, which is to the host’s advantage for two reasons: number of reviews ( I have 73 reviews on ABNB, 10 on VRBO and 3 on Flipkey), and quality of those reviews (if a host has to solicit a review, it is less likely to be positive).


    It’s the personal, emotional touch that my guests interject that have made my reviews great. Anybody can say very clean, great location, etc. I’ve been astonished at the personal comments I have received — some far better than I could write myself. I never meet my guests, and very rarely speak to them on the phone. I have at least six points of contact, either text or email and I always have a REASON to reach out:

    Personal email address request
    Guest Information request
    Rental Agreement
    Check-in information and documents
    Thank you

    Usually during that process I get to know them in some personal way, and the personal connection that we share is reflected in my reviews: my guests almost always mention me by name.

    This is a point of departure from your usual hotel stay.

    Another key to ABNB’s success is that they realize the importance of differentiating those of us who operate a business versus those who want a little extra income. They have done this through the Superhost designation. The metrics that are used to qualify are not easily attainable, and metrics are reviewed every quarter. It’s not perfect — I truly wish they marketed this fact more to guests, but I suppose they can’t alienate their base.

    As others have mentioned, the demographics of VR site users are different. I have a winter high season, and most of my longer-stay guests who are retired use VRBO. ABNB helps pay the bills through the shoulder seasons and low season with 30 somethings looking for weekend stays AND with international guests. SO I benefit from both sites. Recently I’ve had children booking for their elder parents on ABNB. In choosing sites for your vacation rental, make sure you know your target market and sweet spot, and make sure that your plan holds water, which means lots of research.

    The ABNB booking process is streamlined, and saves time as mentioned below. The initial vetting of users is key to my peace of mind in hosting. It is definitely worth the price of admission.

    Not that they don’t DRIVE ME CRAZY with their accounting practices (rounding — who came up with that one?), tax collection, etc.

    Lastly, I can’t find a way to handle credit card transactions with foreign currency exchange for as cheaply as ABNB does it (3%) inclusive of the listing.

    1. Hey Judy, I am supremely impressed by your comment – it’s like a complete standalone blog post on it’s own! Thank you for taking the time to share your experience — both pros and cons — with the VRMB community 🙂

  2. Hi Matt
    This brings up a point about what really is a vacation rental property. I would argue that you stayed in “not a hotel room” rather than in a vacation rental. Many people on AirBnB call what they have a vacation rental but I think the vast majority are “not a hotel room”. We have hosted on AirBnB for years but don’t get a lot of traffic as compared to VRBO etc. and lately I have been thinking that it is because of this distinction that I don’t think people understand. It really is a different market. I am guessing that most people that consider VRBO go straight there and never consider a hotel. However I bet most people that consider AirBnB go there after thinking of a hotel room, or an an alternative to one.

    1. Hey Duane, I’m with ya. And it’s the answer to this question — “what is a vacation rental?” — that we’re constantly asking in the IC, which is really key to the big picture. I think this is where Airbnb, HomeAway, FlipKey…etc. could all get on the same page and really move this industry forward in a holistic way.

    2. I agree with you. But there is a problem. After Expedia took over HA/VRBO the number of inquiries we get through them dropped very much. Airbnb is taking over so we are almost forced to work with them although the guests we get from them have really to be checked in order to avoid problems. There is definitely room for a new listing that would be selective.

      1. Please don’t get this wrong: you are not forced to work with any major listing site and merely thinking that way can seriously disable your business growth.

  3. Hi Matt, great article. I am a vacation rental owner, with 3 cottages in an Australian wine region, operating for 20 years. I listed our smaller rental with Airbnb 2 years ago. We have only had 4 bookings but our prices as a fully registered 4-star property, are higher than most listings in the area. Stayz (Homeaway) still provides us the most leads. When we’re new with Airbnb we got lots of enquiries but these dropped to almost zero after 3 months. Possibly we didn’t follow up with guests to post Airbnb reviews. In Australia more and more Airbnb listings are vacation rental houses, nor sharing host homes.

  4. Hey Matt, congrats on the first experience! I think when someone says “I’m staying in an Airbnb” many people immediately think of room sharing and all that goes with that. However, I check the “Entire Home” box so that I’m only searching for whole homes.

    I’m still shy about the sharing option! But, more than that, I like my own space (physical and mental!) after a day of conferences or meetings. It’s more personal preference, at least for me, than it is a lack of trust in the host or the standard of accommodation.

    It’s also interesting that I’ve only ever used Airbnb for business travel or a city break. When I’m planning a family holiday I only ever search VRBO, HomeAway, etc. On the flip, I would never search VRBO for a city break. Is that just me, or do you think that many people still see Airbnb as city oriented?

      1. Agreed. I think the growth in use of channel managers will certainly result in a greater % of homes being found on most major listing sites. I’ll check VRBO next time the city calls!

    1. I think we all have our own habits, Andy. I’m shy about the sharing option too, while that’s something I embraced many years ago and that’s because as I grow “older” and despite being a very sociable people person, I tend to prefer my own space over a shared one, when it comes to privacy and a place to stay. I’ve recently stayed in a few Airbnbs and always look for the “Entire Home”.

      With that being said, I tend to search multiple listing sites, then check owner’s direct sites to make the best possible decision; yet sometimes Airbnb comes in quite handy because they make the whole search phase very easy, seamless and fast, if you don’t want to spend ages finding the best place.

        1. If the owner has booking enabled, yes. If not, I have to go back to the listing site of choice.

          In our own case ( direct bookings work really well. I have online bookings enabled and I get lots of direct bookings on my site. I always ask how they find us and often they say they found us on a listing site, then googled the property (because I put the name of it in each description, photo captions, etc.) and decided to book direct.

          1. But are you not screening who is booking in order to avoid bad experiences? Today for example, I received an AIRBNB inquiry for my Brussels apart. But by checking the reviews I clearly understood that these people would not follow the house rules.

      1. Hey Antonio,

        “Airbnb comes in quite handy because they make the whole search phase very easy, seamless and fast”

        Totally agree and that’s why I use that for business or quick weekend breaks. For a larger family holiday investment ($ and family peace!) I spend much more time and will almost always choose to book directly with an owner/manager that I believe in more, i.e. personal and friendly approach on their own website!

  5. Hi Matt. Thanks for sharing your story, and generating this discussion thread. Here is an ‘unexpected’ perk that I provided a week or so ago for a guest. The guest came down from Seattle to stay in my AirBnB farmhouse (you can find it by searching in ‘Hillsboro, OR’ and ‘B & K Farmhouse’, I know, shameless plug. 🙂 ) He was here for an interview at Intel, which was being conducted the following morning. After providing a bit of breakfast and coffee to him in the morning, I asked him what position he was interviewing for, and he explained that it was a Director position. So I ask if he would be open to a practice round of questions (I worked in technology field for over 20 years, so I know the lingo, and style of behavioral questioning he would encounter. He said ‘yes’, and I began the standard list of questioning (‘Describe a time when things went badly on a project you were in charge of, and how did you turn it around’, ‘Tell us about a specific project that you were in charge of where the stakeholders weren’t on the same page, and the project was overdue. ‘What did you do to address the communication challenge, and what steps did you take to make sure that the project would still be completed on time’, etc.
    So of course I was curious as to how things went, and sent a message that evening to inquire. He told me that ‘he had advanced to the second round of interviews’, so very positive outcome.
    Here is what he had to say in his guest review: “What an Amazing host ! I have yet to come across a warmer host than Kim in Oregon. She really took care like an elder sibling would.”
    This is one example of many. I don’t think you would get this kind of fringe benefit in a standard hotel, do you? 🙂

    1. Wow, that is SOOOO cool, Kim! You could start to promote that — “We also help you prepare for tech job interviews.” What a great niche!

      1. LOL, I guess so! I also make homemade jams & jelly with the fruit grown right here. I put it out for breakfast every morning along with homemade sourdough bread. ( I sell that too)
        If you come to Portland, OR anytime, look us up! ‘B & K Farmhouse’ ‘Hillsboro’ (more shameless plugs 🙂

          1. The great thing about AirBnB hosting, is that you have an ability to be as creative as you want to be, and since we all have our respective talents, it makes for a unique experience every time. Instead of all the predictable boring hotel franchise staleness, right?
            We can also provide a lot of insight about the area, including what to avoid (which can be most helpful too), and tailor the experience to be customized to the guest, by taking the time to find out what they expect to get out of their trip.
            For example, if you tell me that you are a wine enthusiast, I’m going to tell you about the 9 wineries that are within 5 miles of our home. Or maybe how GREAT the Tuesday night farmers market is a MUST to go to, and why.
            I could go on, but you get the point, right?

  6. Matt! Such a thoughtful overview of your experience! With so many extreme stances on both sides out there, it’s great to see someone with great perspective like you actually walk through their experience and call out the pluses and minuses. I definitely think that, as guests, there are people who are “better” at finding consistently great listings, which comes from both knowing what to look for (book a Superhost whenever possible!), but also knowing themselves well enough to factor in certain things when searching and ignore others factors.

    Love the great conversation here, and glad you’ve decided to sparingly give Airbnb a shot – I think it’s a great, low-friction way for people to try being a host, and then at some point transition to a more sustainable, controllable, lower-risk model running full time independent VRs.


    1. Thanks Tyler! Totally agree, I think we should call Airbnb “the gateway drug” to the greater VR industry 🙂

  7. In our neck of the woods – coastal SoCal…AirBnB has largely been a curse to established VR owners. Since their SV (grow as fast as you can then sell and cash out) meets WS (keep the VR biz owners money as long as you can and invest it in xyz) driven hyper growth disruption of the home (in AirBnB case the spare bedroom/apartment/converted garage) sharing economy drove the coastal SoCal cities banning stvr’s altogether.

    AirBnB lowered the barrier of entry so that anyone (owner and renter alike) could list their spare bedroom, converted garage, or apartment for a night, a weekend, or longer with NO upfront cost. The backlash up and down the California coastline has been fierce – to the point their own corporate HQ hometown tried to ban them and LA – where they just hosted their annual cheer rah rah meeting with celebrities – put a limit of 90 days per year along with all kind of other bureaucratic requirements.

    We are adjusting and admittedly they are a much more modern (www 3.0+ vs HA/VRBO stuck in AOL 1.0-2.0 tech…) and overall better run business than HomeAway/VRBO or the worst of all Flipkey. The city backlash is forcing them to adjust their business model before and IPO with so many cities now banning or limiting stvr. We shall see how this all pans out…

    Onward & Forward!!

  8. Any tips for using AirBnB overseas for the first time? I have used it locally and had a mixed experience and myself and my partner are debating if its worth the risk when we travel Europe at the end of the year…

    1. Mind if I chime in here? Marcus, my suggestion is to exchange emails with your host until you are very comfortable with the accommodations. Ask all the questions you’s can think of, without being obnoxious and get a feel for your host’s personality. If you don’t feel like you ‘connect’ with him/her, keep looking, until you find the kind of communicator you need.

  9. Great information here, thanks so much for sharing it. I have been searching for more intel about Airbnb and where these places are across the country. Thought others might like to know that shares all kinds of significant info in their blog related to airbnb information. It might be helpful for those just hopping into this market too!

  10. Great stroy Matt! MadeComfy provides an end-to-end property management service, which means property owners don’t need to do a thing when they hand over their keys. MadeComfy makes the process of earning greater returns from short-term renting effortless, consistently achieving occupancy rates of over 70% and delivering returns over 40% higher than long-term rentals and self-managed Airbnb listings. Get in touch with us today to see how we can help!

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