Why I’m Still Rooting for Airbnb


Airbnb’s CEO Brian Chesky has gone full Willy Wonka.

I was watching him at a live press event, describing the company’s over-the-top new “Icon” experiences. This program includes a full-scale replica of the colorful house from the Pixar film “Up,” which his team lifted over the New Mexico desert with an enormous crane.

Chesky explained that regular houses can’t be lifted like that, so a special team of structural engineers had been hired to make sure the replica wouldn’t break apart on liftoff.

The flying “Up” house won’t make money for Airbnb or its shareholders anytime soon. It can be booked for $0 by fans who write the most compelling notes for why they want to stay there. All eligible entrants will be placed into a drawing, with up to 20% chosen at random as finalists.

From there, Airbnb has partnered with a third-party company to review answers. The “winners” will be notified of their successful booking with — you guessed it — a golden ticket.

I was ready to dismiss Chesky’s Wonka-ish stunts as the fever dream of a billionaire who had grown profoundly tired of dealing with his platform’s real-world problems, including restrictive local regulations, guest horror stories and the proliferation of corporate megahosts.

But then he said something that struck a nerve in my cold, cynical heart.

“As life becomes increasingly digital, what we’re focused on is creating more magic in the real world,” Chesky said. “The best way to experience Icons is not on a screen, it’s not even in a presentation — it’s in real life.”

It’s true. The best thing about Airbnbs is that they are real things in the real world — not images or reels shared by strangers in the digital swamp. At its best, Airbnb offers an antidote to social media: meaningful in-person connections with family and friends.

And that’s why we get so annoyed when it falls short of its potential.

My rom-com relationship with Airbnb

Yet, like the protagonist in a romantic comedy, all my complaining about Chesky’s short-term rental platform veils an obvious truth: I actually love it.

I’m not alone. The short-term rental industry, which Airbnb dominates, nearly doubled its share of the lodging market between 2018 and 2023, according to a 2023 report from AirDNA, a short-term rental analytics company, and STR, a hospitality industry analytics service.

Far from the “Airbnbust” some predicted, vacation rentals are more popular than ever.

As Chesky explained his reasons for meticulously re-creating a computer-generated movie in the real world, it became clear why we’re all so invested in the platform and harbor such strong feelings about it.

We yearn to connect with real people in real houses.

Reflecting on my favorite memories with family and friends over the last decade, so many stories begin with, “Remember that time at the Airbnb when …” Even my not-so-great Airbnb rental experiences — like when my friends and I cowered in the basement all night to avoid a loose bat — become treasured tales of mutual hardship.

Lost in the media hoopla around Chesky’s flying house was a quieter product launch: new tools to help groups find and book properties together, including shared wishlists and trip invitations. It’s clear that Chesky’s heart is in the right place, and he knows what Airbnb can be at its best. But the pressure of earning profits has clouded that vision.

The profit pickle

Less than two decades ago, Chesky and his co-founders created Airbnb as a way to solve two parallel problems:

  • Many people had guest bedrooms and vacation homes that, much of the time, went unused. 

  • Many travelers were looking for affordable lodging options beyond hotels. 

By setting adventurous travelers up with otherwise unused spaces, the platform was creating a win-win situation. Guests got what they wanted and hosts earned some extra money to pay their mortgages.

Then, an unfortunate thing happened: Airbnb became extraordinarily popular.

More than 1.5 billion guests have now checked into Airbnb properties, according to the company — more than 18% of the entire world population. This success has bred a new kind of Airbnb host, one who wasn’t interested in sharing a basement room for a few bucks: institutional investors.

More than 30% of short-term rental listings in the U.S. are now listed by hosts with 21 or more properties, according to May 2023 data provided by AirDNA. That’s compared with 26% of listings from single-property hosts.

From a business standpoint, this all makes sense. There’s money to be made in buying single-family homes and converting them into short-term rentals, so that’s what has (and will continue) to happen. But for those of us who see Airbnb as a way to connect with friends and family, it’s a catastrophe.

Saturday Night Live” recently skewered the “bland, generic, downright uninviting” interior design of these megahost properties, but it’s about more than uninspired wall art. It’s hard to make meaningful memories in a home that doesn’t feel like a home.

Holding out hope

At some level, I think Chesky wishes he could put the Airbnb genie back in the bottle (though probably not his fortune) and go back to the days when it was making life more enjoyable for backpacking cheapskates.

That won’t happen anytime soon, so he has turned his attention to more interesting projects, like making houses fly.

I still think Airbnb can be better.

By regulating itself (rather than putting the onus on local governments), the platform could limit how many properties a host can run and give preferential treatment to real hosts listing real homes. It could also do more to build and support local communities rather than extract maximum profit from them.

Chesky may have moved on to shinier toys, but I’m still rooting for Airbnb.

(Top photo courtesy of Airbnb)

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