Airbnb: The cardboard box strategy

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Welcome to the Supernatural Stocks podcast on Moneyweb, with your host The Finance Ghost – your weekly fix of local and international insights for investors and traders.

As the jets flew overhead in Cape Town to mark the State of the Nation Address [Sona] event, I couldn’t help but reflect on the city I live in. Goodness knows it’s not perfect, but at least we have water – for now at least, subject to rainfall. South Africa is certainly never boring, that’s for sure.

Cape Town is a special place, but there’s a company that has caused a lot of pressure on property prices in the city bowl and other sought-after areas. And this issue is not unique to Cape Town.

Read:
Inner-city Cape Town: No room for locals
Bo-Kaap residents call for Airbnb to be regulated
Cape Town needs rent control

Barcelona. Lisbon. New York. And yes, Cape Town – these are cities that have blamed Airbnb for turning residential neighbourhoods into tourist districts, with serious questions around zoning for these properties. And more recently in Cape Town, around rates and taxes as well.

Hotel groups have suddenly found themselves competing against everyone with a spare room. Local residents have been priced out of areas that they could traditionally afford to live in.

This doesn’t tend to be a popular outcome. And let’s face it – Airbnb as we know it today has gone way beyond the original DNA of the business, where the name was derived from having an air mattress at home and some space to put it on the floor for someone to sleep on it.

Listen/read:
Locals priced out as Cape Town’s luxury property market soars
Cape Town homeowners urged to challenge new property valuations

It’s no longer about just having a spare room.

These days, Airbnb has created an entire industry of professional hosts who own and manage multiple properties. It looks like a business and smells like a business, yet these super hosts often get away without being treated as a business.

This is where the regulatory minefield becomes relevant.

There have been many steps taken worldwide to address this.

Barcelona is pursuing a full ban on short-term rentals in the next few years, with Spanish courts lending their support to this plan thus far. In New York, hosts are required to be physically present, so that puts the Airbnb business firmly back to its original purpose: a source of side income for hosts, rather than a way for hosts to become hoteliers.

The above-mentioned ‘solutions’ are far from perfect. Proponents of Airbnb would quite rightly argue that it attracts tourists to an area, with many knock-on benefits.

In the absence of Airbnb, hotels would have more pricing power and could price people out of the area anyway due to the reduced supply of beds, in which case tourism becomes difficult.

And when there are major events in cities where there clearly won’t be enough hotels, Airbnb plays a very important role in creating the short-term supply increase for an influx of tourists.

A perfect example is the 40 000 additional listings that were created for the 2024 Summer Olympics in Paris.

Of course, Airbnb loves this because a large percentage of those listings will be sticky – in other words, they will endure beyond the event.

This is where it becomes a difficult conversation with regulators in these cities who need a solution for large events, but who also don’t want to create more problems down the line.

Airbnb cites the 2026 Fifa World Cup in the US as their next big event – I guess we will see whether threats of a travel boycott are serious or not. I genuinely look forward to seeing whether stadiums are filled with domestic fans or international travellers.

Airbnb has become a part of our lives, yet I haven’t owned shares in the company since the IPO. The simple reason is that the valuation has always been much too high.

Patience has paid off, as the share price has returned absolutely nothing if you take a three-year view. The chart is choppy over that period, so traders could’ve made money along the way. But for buy-and-hold investors like me, I haven’t missed out.

Is there anything happening at the company that might change my mind?

Inspired by Amazon

In its latest earnings transcript, Airbnb co-founder and CEO Brian Chesky references Amazon’s business in the 1990s.

Specifically, he reminds everyone that they started as a book retailer and grew into the “everything” store. The common thread on this journey? According to Chesky, it was the humble cardboard box – and anything you can send in it.

Airbnb is figuring out its cardboard box.

The company is adding new offerings to the platform that might come as a surprise, including independent and boutique hotels.

With around nine million active listings on the platform, Airbnb needs to find meaningful additional growth engines to try and get the share price to move higher.

Could hotels, traditionally their biggest rival, be the answer?

I actually like this strategy. There’s a certain percentage of people who will simply never book with a host, as they aren’t prepared to risk their holiday experience on that outcome. Hotels give a sense of trust, even though bad hotel experiences do happen.

By tapping into independent and boutique hotels, Airbnb can still give the impression of a curated and interesting offering. They can take advantage of their excellent distribution and technology to earn fees that used to go to other travel companies. And for those hotels, Airbnb provides a valuable route to market.

Being inspired by Amazon seems like quite a clever strategy.

Higher revenue guidance – but it comes at a cost

The numbers are what really count, of course.

The latest quarter boasts revenue growth of 12% year on year, above the upper end of guidance. Gross booking value [GBV] increased 16%, representing their best growth quarter in more than two years. The take rate dipped from 14.1% to 13.6% though, hence why revenue growth was slower than GBV growth.

These are solid numbers. But what really pleased the market is that they are expected to get better, with Airbnb’s guidance for the first quarter of 2026 reflecting revenue growth of 14% to 16%. This is boosted by a slight increase in the take rate as well. For full-year 2026, they expect revenue growth of at least low double digits. Again, that’s decent.

What about margins?

Well, adjusted earnings before interest, tax, depreciation and amortisation [Ebitda] margin is expected to be flat. This means that adjusted Ebitda would grow in line with revenue growth.

This tells you that there is little operating leverage in the model, with Airbnb having to reinvest heavily in the platform to protect the moat and continue growing.

This brings us neatly to the focus on technology as it builds the moat.

Will AI be booking your next holiday?

Agentic commerce came up in Alphabet’s recent results. Essentially, this speaks to a world in which an AI agent is making your shopping decisions.

It’s therefore not a stretch of the imagination to think that we could end up in a world where your trained model – for example, Gemini within the Alphabet Group – speaks directly to Airbnb’s AI and then books your trip.

You can easily imagine all the ways in which this could be an absolute disaster, but technology always feels silly until suddenly it doesn’t.

Airbnb isn’t making promises that are quite that dramatic.

In fact, many of the improvements to the platform have been rather simple: things like making sure there is proper pricing transparency, where all the charges are shown at the time of making the booking.

They’ve also been making sensible decisions around removing low-quality listings and boosting ‘guest favourites’ that have proven themselves. This is solid execution.

But, unsurprisingly in this environment, there’s also serious focus on AI. And if you’re tired of dealing with AI support agents, then I’m afraid that I don’t have good news.

Airbnb claims that they are now resolving a third of all support issues without needing a live specialist. I often wonder how they define someone giving up in immense frustration – is that also a resolution?

Jokes aside, Airbnb is taking AI very seriously, having hired an executive who led the generative AI team at Meta.

This is part of why the Ebitda margin is expected to be flat, as this stuff comes at a serious cost.

There’s an interesting concern among analysts that AI could be a disruptor to the business, not just an enabler. You could have other platforms that spring up that work purely off AI, potentially disintermediating Airbnb. Management’s response is to point to their rich dataset and the extent of trust baked into the model, with 200 million verified IDs as just one example of how established the business is.

Nobody knows where this will end. But we do know that Airbnb is investing heavily in it.

Finding more growth engines

One of the big wins in this quarter was the introduction of Reserve Now, Pay Later – an obvious play on Buy Now, Pay Later.

That’s not an easy thing to implement correctly, as you can imagine all the issues around cancellations and what this means for hosts. Still, Airbnb is seeing an uptick in bookings, as you might expect when you offer better payment terms.

Read: Balwin faces court challenge as Airbnb-type letting divides residential estates [Oct 2025]

The growth strategy is also regional, rather than just based on products. Currently, 70% of revenue comes from just five countries. They are trying to diversify, identifying high-growth markets where they can execute specific strategies and campaigns to drive increase supply – listings – and user adoption.

In a two-sided marketplace, you have to drive growth on both sides for the thing to work properly. Therein lies the challenge, but also the moat.

A good example is Brazil, which has moved from a Top 10 market to a Top 5 market after a concerted effort to drive growth there. The momentum is impressive: in Q4, it was the second largest contributor to first-time bookers, trailing only the US!

Does it generate cash?

Yes, it does. In fact, Airbnb’s free cash flow margin tends to run at nearly 40% on a full-year basis. Sure, share-based payments are a feature rather than a bug, but there’s no getting away from that in Big Tech land.

Read: Short-term rentals move from seasonal ‘gold rush’ to long-term property play

Another feature is annual share buybacks, something that always makes me think of the choice words that Jamie Dimon of JPMorgan dishes out to the analyst community when they hound him about returning cash to shareholders.

In tech, share buybacks are important to offset share-based payments. According to management, Airbnb has reduced the number of shares in issue by roughly 9% since 2022.

But the challenge, and Jamie Dimon’s point, is that buybacks only make sense when shares are undervalued.

Airbnb’s shares haven’t been undervalued since the IPO, so buybacks aren’t as effective.

To be fair to Airbnb though, they don’t have many other competing uses for the cash. Unlike banks, they operate capital-light models. Dimon is even more scathing of special dividends rather than share buybacks at the wrong price, so perhaps the annual buybacks are the lesser of two evils.

What about the valuation?

The price/sales multiple is now 6x. That’s well off the three-year average of 12x. It’s also lower than the one-year average of 6.9x.

Cheap? No. Cheaper than it used to be? Absolutely. And with more growth engines coming through, the market just might show this name some love now.

The 52-week high is almost $164, the 52-week low is just below $100 and the current price is around $116.

Read:
Airbnb to boost IPO price range [Dec 2020]
Airbnb chooses IPO venue in big win for Nasdaq over NYSE [Oct 2020]

There’s a lot of selling pressure in the tech space at the moment, but this is a worthy addition to the watchlist as a baby potentially being thrown out with the bathwater.

This is the most interested I’ve been in Airbnb since the IPO.

And whilst I’m always nervous to place too much importance on after-hours trading, there was a nice bump up from the levels I’ve quoted in this podcast, so the market is showing signs of bullishness here.

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