2302 6:51 Failure Friday

Failure Friday: Airbnb Is Harder Than It Looks

In this week’s Failure Friday segment, we hear from a New York City resident who tries—and fails—to navigate the city’s tough rules on rentals.

6:51

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Episode 2302

I believe we can learn as much from failure as we can from success, if not more. It’s with this principle in mind that I offer you a weekly segment called Failure Friday: a collection of short stories all about mistakes, missteps, disasters, and of course, failure.

Just like our Throwback Thursday segment, you’ll hear directly from side hustlers who have struggled to get something off the ground. They’ll tell you a short story of something that went very wrong.

Today’s short story features Danny from New York. He has an idea to start an Airbnb rental business—and why not? It seems so easy.

Well... this is Failure Friday, right? So without knowing the details, it’s safe to say it wasn’t so easy. But of course, the details are the fun part! So let’s hear the story from him.

Yours in the revolution,

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Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

[Music]

If you live in a big city, why not get an extra apartment and rent it out on Airbnb? Hey, how hard could it be? It works for everybody, right? Everybody makes a lot of money doing Airbnb. Well, that's actually not how it works.

In fact, a lot of people end up losing money on Airbnb. A lot of people find that it's harder than it looks. And in cities like New York, and it's not just New York, we're gonna hear from somebody calling in from New York today, but lots of other cities as well, there is a lot of regulation around Airbnb rentals or other vacation rentals that makes it quite difficult to be profitable, or even just to operate in general. So with that in mind, welcome to Seto Soul School. My name's Chris Guillebeau.

Today, we're gonna have a story in the segment known as Failure Friday. Failure Friday, a collection of short stories about mistakes, missteps, disasters, and of course, failure, all of these things that go wrong. So somebody's got what they think is a great idea, and once they put it into action, reality hits, and they realize maybe it's not as easy as they thought, or maybe something comes along that proves to be difficult or challenging. And we like to see how do people navigate that situation, and what do they learn from it? So today's short story features Danny from New York, as mentioned.

He's got an idea, or he had an idea to start an Airbnb rental business. And as I said, why not, it seemed so easy. But of course, this is Failure Friday, so even without knowing the details, it's safe to say it wasn't so easy. But of course, the details are the fun part, so let's hear the story from Danny. [Music]

So once upon a time, actually more like a few years ago, in the bustling city of New York, there I was, an ambitious salesperson who dreamed of making a bit more money.

A common story, right? I'd used Airbnb a few times on vacation and was starting to think this is my chance to make a fortune in the home-sharing business. Little did I know, the dreams of becoming an Airbnb mogul were about to take a detour. I spent weeks digging around, researching the perfect property to host my guests. I found a cozy apartment in Staten Island with a stunning view, the city skyline right there, and I was sure that people would be booking their tickets to stay at my place in no time.

I was ready to give my guests a key to a memorable experience in the Big Apple, right? However, my enthusiasm quickly hit a roadblock. It turned out that I had severely underestimated the competition in my area. The market was flooded. There's countless other Airbnbs listed everywhere.

My humble abode was lost in the sea of five-star reviews and professionally photographed penthouses. And of course, I was on Staten Island, which I thought was cool, but many tourists preferred Brooklyn or Manhattan. You know what I mean? Undeterred, yeah, I decided to up my game and make some improvements to my listing. I invested in new furniture, bought some fancy bed linings, and even a state-of-the-art espresso machine.

I was so fancy. I was sure that these upgrades would help my property stand out from the crowd. Yet as the days turned into weeks and the weeks turned into months, the bookings remained scarce. In the midst of my Airbnb struggles, I received an unexpected wake-up call. I discovered that there were strict regulations in place for short-term rentals in New York City.

The rules dictated that I could only rent out my property for a minimum of 30 days at a time. My dream of hosting weekend getaways for tourists had come to a screeching halt. So I was feeling defeated. I had no choice but to shut down my fledgling business. I still had a lease for the unit, so I had to keep paying for the rest of the 12 months.

So rather than sit around and wallow in my failure, however, I decided to search for the silver lining. I took time to reflect on these lessons I had learned from this experience. So diving into the world of Airbnb taught me the importance of thorough research and planning. I realized that I'd been so focused on the potential profits, I neglected to examine the market and understand all the regulations that governed short-term rentals. Well, despite the setbacks, my Airbnb adventure wasn't a total loss.

I'd gained valuable insights into the world of real estate and hospitality. And this experience gave me a new appreciation for the importance of perseverance and adaptability in business. So now as I move forward with a renewed sense of determination, I'm exploring new side hustle opportunities with a more cautious and informed approach. My Airbnb dreams may have checked out for now, but I'm confident that my future ideas will benefit from the lessons I learned. So hopefully next time my story is featured and you hear from me, it'll have a better ending.

[Music]

Never confuse a single defeat with a final defeat. That's the theme of Failure Friday. And yes, as Denny said, his Airbnb dreams may have been checked out for the moment, but I'm sure there's something else waiting around the corner for him. And for you as well. If you have tried to do something, if you've tried a side hustle or a small business and it hasn't worked out, or maybe you thought you're just not cut out for it, or there's something wrong with you, I assure you, there's not anything wrong with you.

This is normal. Like we kind of go through the path of trying different stuff and we see what works and we learn from it and hopefully the next one's gonna be better. That is the way, not necessarily having overnight success right away. You often have to try different stuff. So I encourage you to keep trying.

Thanks to Denny for sharing this story. Thanks listeners for being out there. If you have a question or an update for us about your hustle, sidehustleschool.com/questions. Today's notes, sidehustleschool.com/2302. We've been going for more than 2,300 episodes.

All thanks to you and our remarkable community. That's all for today, but I got a new episode coming out tomorrow. My name's Chris Guillebeau. This is "Side Hustle School." [Music]

From the "Onward Project."

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