Compare / Airbnb vs Pinterest
AIRBNB
Three guys who couldn't pay rent decided to rent out air mattresses in their San Francisco apartment, sold cer…
Ben Silbermann built a virtual pinboard for collecting pretty pictures and accidentally created one of the mos…
AT A GLANCE
FUNDING HISTORY
Airbnb
BUSINESS MODEL
Airbnb
Airbnb is a two-sided marketplace. Hosts list their homes, apartments, treehouses, or whatever else they've got.
Guests book and pay through the platform. Airbnb takes a cut from both sides — roughly 3% from hosts and up to 14% from guests as a service fee.
That's it. They don't own a single property.
They just built the world's largest hotel chain without owning a single bed.
Pinterest makes money through advertising — specifically through "Promoted Pins" that look nearly identical to organic content. This is the magic of Pinterest's business model: ads don't interrupt the experience because the experience IS discovering products and ideas.
A promoted pin for a kitchen knife set appears right alongside organic pins of kitchen designs. The user doesn't distinguish between "ad" and "content" because both serve the same purpose.
Shopping ads are the fastest-growing segment. Brands upload their product catalogs, Pinterest matches products to user searches and boards, and users can buy directly through the platform or click through to the retailer's site.
Pinterest gets paid per click or per thousand impressions.
Revenue reached $3.65 billion in 2024, up from $3.05 billion the year before, and 2024 was its first genuinely profitable year. Average revenue per user is growing but still well below Meta's — the upside is enormous if Pinterest can close that gap.
HOW THEY STARTED
Airbnb
In 2007, Brian Chesky and Joe Gebbia were two Rhode Island School of Design grads living in San Francisco and struggling to make rent. A big design conference was coming to town and every hotel was booked solid.
They bought three air mattresses, put up a simple website called AirBed & Breakfast, and charged $80 a night including a homemade breakfast. Three strangers actually showed up.
That was it — the entire origin story of a $75 billion company is three air mattresses and desperation.
They recruited Nathan Blecharczyk, a Harvard-trained engineer Joe knew, to build the real website. But nobody wanted to fund them.
They applied to 15 investors and got rejected by every single one. To keep the company alive during the 2008 election, they designed limited-edition cereal boxes — Obama O's and Cap'n McCain's — and hand-assembled 500 of each.
They sold the Obama O's for $40 a box and made $30,000. That cereal money literally kept Airbnb from dying.
Paul Graham at Y Combinator finally let them into the Winter 2009 batch — reportedly because the cereal stunt proved they were "cockroaches" who would never die. YC invested $20,000.
Within a few months, Sequoia Capital led a $600,000 seed round. The rest is history.
Ben Silbermann was a former Google ad operations employee who quit in 2008 to build apps. His first attempt was an iPhone app called Tote — essentially a mobile catalog that let women browse and bookmark products from fashion retailers.
Nobody downloaded it. But Silbermann noticed something in the data: users were saving products obsessively.
The collecting behavior was more interesting than the shopping behavior.
He teamed up with Paul Sciarra, a classmate from Yale, and Evan Sharp, a designer who was studying architecture at Columbia. Together they built Pinterest — a visual bookmarking tool that let people "pin" images from around the internet to organized boards.
Think of it as a digital mood board that anyone could make.
Pinterest launched as an invite-only beta in March 2010. Growth was painfully slow at first.
Silbermann personally wrote to the first 5,000 users, giving them his phone number and asking what they wanted. The early community was overwhelmingly women interested in home decor, fashion, recipes, and DIY projects.
By 2011, Time magazine named Pinterest one of the 50 best websites. By 2012, it was the fastest site in history to reach 10 million unique monthly visitors.
HOW THEY GREW
Airbnb
The early growth was pure hustle. Chesky and Gebbia flew to New York — their biggest market — and went door to door visiting hosts.
They noticed the listings with bad photos got no bookings. So they offered free professional photography to every host.
Bookings exploded. That single move — better photos — was probably worth more than any ad campaign they ever ran.
They also pulled one of the most legendary growth hacks in startup history. They reverse-engineered Craigslist's posting system so that Airbnb hosts could cross-post their listings to Craigslist with one click.
Craigslist had millions of people looking for rentals. Airbnb had none.
The hack funneled Craigslist's traffic straight into Airbnb. It was borderline shady and absolutely brilliant.
Word of mouth did the rest. Every guest who had a great stay told their friends.
Every host who made easy money told their neighbors. The product sold itself because both sides benefited immediately.
By 2015, Airbnb had more listings than the top five hotel chains combined.
Pinterest grew organically through women sharing boards with each other. The weddings use case was the killer app — brides-to-be would create boards for dresses, venues, flowers, and invitations, then share them with their wedding parties.
That viral loop drove millions of signups.
SEO is the secret weapon. Pinterest pages rank extremely well in Google Image Search.
Someone searching "modern living room ideas" often sees Pinterest results on page one. That drives a large stream of organic traffic from people who were not looking for Pinterest at all.
Unlike other social platforms, which compete with Google for attention, Pinterest quietly benefits from it.
The shopping pivot has been the growth unlock. Under CEO Bill Ready (former Google and PayPal executive who took over in 2022), Pinterest aggressively invested in shopping features — catalog integrations, buyable pins, merchant verification, and visual search for products.
The thesis: Pinterest users are already in a shopping mindset, so removing friction between "I like this" and "I bought this" is the straightforward path to revenue growth.
THE HARD PART
Airbnb
Regulation. Full stop.
Cities around the world have gone to war with Airbnb. New York, Barcelona, Amsterdam, Paris, Berlin — all have passed laws restricting or outright banning short-term rentals.
The hotel lobby has spent hundreds of millions fighting Airbnb at every level of government. In New York City, a 2023 law essentially banned most Airbnb listings overnight.
Then COVID hit. In March 2020, Airbnb's business dropped 80% in eight weeks.
Chesky had to lay off 1,900 employees — 25% of the company — in a single memo that became famous for how honest it was. He gave everyone 14 weeks of severance and a year of health insurance.
The company burned through its IPO plans and took on $2 billion in emergency debt at brutal interest rates.
But here's the thing — COVID also saved them. People stopped wanting hotel lobbies and started wanting isolated cabins and rural homes.
Airbnb's bookings came roaring back by summer 2020, and the rural/unique stays trend became permanent. They IPO'd in December 2020 at a valuation that stunned everyone.
Pinterest's demographics are both an advantage and a limitation. The platform skews heavily female (over 60% women) and is strongest in home, fashion, food, and weddings.
Expanding beyond these categories to attract male users, younger demographics, and different use cases has been slow.
Competition for ad dollars is fierce. Pinterest competes with Meta, Google, TikTok, and Amazon for advertising budgets.
Most advertisers allocate the bulk of their spend to Meta and Google first, then consider others. Pinterest needs to prove its return on ad spend is competitive to win larger budget allocations.
Creator economy is underdeveloped. While Instagram, TikTok, and YouTube have massive creator ecosystems with monetization tools, Pinterest has historically been about content discovery, not content creation.
Users pin other people's content — the original creators often don't even know their work is on Pinterest. Building a creator program and driving original content creation on the platform has been a recent focus but lags far behind competitors.
THE PRODUCTS
Airbnb
Airbnb Stays is the core product — book someone's home instead of a hotel. Airbnb Experiences lets you book local activities run by hosts, like cooking classes in Rome or surf lessons in Bali.
Airbnb Luxe is the ultra-premium tier — think private islands, castles, and villas with dedicated concierge service. Airbnb Plus, an inspected-homes tier, was wound down in 2023 after proving too costly to verify at scale.
Categories (launched 2022) lets you browse by vibe — treehouses, lakefront, tiny homes, mansions — instead of just searching by location.
Pinterest Home Feed — the core discovery surface showing personalized pins based on user interests, boards, and search history. Pinterest Lens — visual search technology that lets users take a photo of any object and find similar items to buy on Pinterest.
Pinterest Shopping — integrated e-commerce allowing users to browse and purchase products directly from pins linked to retailer catalogs. Pinterest Boards — the organizing system where users save and categorize pins into collections, used for wedding planning, home renovation, recipes, fashion, and more.
Pinterest Shuffles — a collage-making app for Gen Z users to create aesthetic mood boards, driving younger user adoption.
WHO BACKED THEM
Airbnb
Y Combinator, Sequoia Capital, Andreessen Horowitz, Greylock Partners, Founders Fund, General Atlantic, Jeff Bezos (personal investment)
Bessemer Venture Partners, FirstMark Capital, and Andreessen Horowitz were early investors. Fidelity and Valiant Capital participated in later rounds.
Rakuten invested strategically. The April 2019 IPO raised $1.4 billion at a $12.7 billion valuation.
Elliott Management, the activist investor, took a large stake in 2022 and pushed for operational improvements that contributed to the company's path to profitability.