Airbnb

Instacart

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.

Instacart

Instacart operates as a marketplace connecting consumers with personal shoppers and grocery retailers. Revenue comes from multiple streams: delivery fees and service fees charged to consumers (typically $3.99+ per delivery), tips to shoppers (passed through, not revenue), retailer partnerships (grocers pay Instacart for access to the platform and fulfillment services), and advertising.

Advertising has become the crown jewel. Instacart Ads lets consumer packaged goods (CPG) brands like Coca-Cola, Procter & Gamble, and Nestlé pay for sponsored product placements within the Instacart shopping experience.

When someone searches for "chips," Doritos can pay to appear first. This is incredibly valuable because it's advertising at the exact moment of purchase intent.

Ad revenue was $871 million in 2023 and crossed $950 million in 2024.

The retailer partnership model is key. Unlike DoorDash or Uber Eats (which listed restaurants without permission early on), Instacart works with grocers as partners.

Over 1,500 retail banners including Costco, Kroger, Albertsons, and Publix have formal partnerships. Instacart provides the technology and shoppers.

Grocers provide inventory and stores.

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.

Instacart

Apoorva Mehta was a 26-year-old Amazon engineer in Seattle who quit his job in 2012 to start a company. The only problem: he had no idea what to build.

Over the next year, he started and abandoned roughly 20 different projects. A social network for lawyers.

A way to track restaurant wait times. Nothing stuck.

Then one day he was too lazy to go grocery shopping. He looked for a service that would shop for him and deliver everything to his door.

Nothing good existed. The existing options were grocery store delivery services that only worked during specific windows, had limited selection, and required ordering days in advance.

Mehta wanted to order groceries the way he ordered everything else online — immediately, from whatever store he wanted.

He built a prototype in 2012 and applied to Y Combinator. The demo was rough — he ordered a six-pack of beer through the app and had it delivered to a YC partner's house during the application process.

It worked. He got in.

Instacart launched in the San Francisco Bay Area in 2013 with a simple promise: order from your favorite local grocery store and have someone shop for you and deliver within an hour.

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.

Instacart

Instacart grew by solving a problem one city at a time. They launched in San Francisco, proved the model, then expanded to other major metros.

Each new market required recruiting shoppers, signing up retailers, and building enough consumer density to make the economics work.

The COVID-19 pandemic was the inflection point. Grocery delivery went from luxury to necessity overnight.

In March 2020 Instacart announced it would add 300,000 shoppers, then raised that by another 250,000 weeks later. Order volume increased 500%.

Years of planned growth happened in weeks. The pandemic proved that grocery delivery wasn't a niche — it was the future of how a significant chunk of the population would shop.

The enterprise play is the long-term moat. By providing white-label technology to grocers, Instacart becomes embedded in their operations.

Even if a grocery chain wanted to build its own delivery service, they'd need years and hundreds of millions to replicate what Instacart provides. The more deeply integrated Instacart becomes in grocery operations, the harder it is to rip out.

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.

Instacart

The post-COVID hangover was brutal. After pandemic demand normalized, growth slowed dramatically.

The company's valuation dropped from a peak of $39 billion in early 2021 to about $10 billion at IPO in September 2023. Investors who bought at the peak saw a 75% paper loss.

The narrative shifted from "essential infrastructure" to "nice-to-have luxury."

Unit economics are perpetually tight. Paying a person to walk through a grocery store, pick items, bag them, and drive them to someone's house is expensive.

Unlike meal delivery (one restaurant, one bag), grocery delivery involves dozens of items per order, refrigeration requirements, and substitution decisions. Every order that requires a shopper to call the customer about an out-of-stock item eats into efficiency.

Amazon is the existential threat. Amazon Fresh, Whole Foods delivery, and Amazon's own logistics network represent a competitor with nearly unlimited resources and a Prime membership base of 200+ million.

Amazon has been willing to lose billions on grocery delivery to build market share. Instacart's advantage is retailer partnerships — Kroger and Publix use Instacart specifically because they don't want to help Amazon dominate grocery.

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.

Instacart

Instacart Marketplace — the core platform where consumers order groceries from 80,000+ stores for delivery or pickup, with personal shoppers fulfilling orders. Instacart+ — subscription service ($9.99/month) offering free delivery on orders over $35, reduced service fees, and credit back on pickup orders.

Instacart Ads — a retail media platform letting CPG brands run sponsored product listings, display ads, and coupons within the shopping experience. Instacart Platform (Enterprise) — white-label e-commerce technology that lets grocers build their own online ordering and fulfillment powered by Instacart's infrastructure.

Caper Cart — AI-powered smart shopping carts (from the 2021 Caper AI acquisition) with built-in screens, barcode scanners, and payment that let shoppers skip the checkout line.

Airbnb

Y Combinator, Sequoia Capital, Andreessen Horowitz, Greylock Partners, Founders Fund, General Atlantic, Jeff Bezos (personal investment)

Instacart

Sequoia Capital was an early and consistent backer. Andreessen Horowitz invested in growth rounds.

D1 Capital Partners led the 2021 round that valued Instacart at $39 billion. Existing investors including Valiant Capital, T.

Rowe Price, Fidelity, and Tiger Global participated across rounds. Y Combinator was the starting point (Summer 2012 batch).

The September 2023 IPO on NASDAQ priced at $30 per share, valuing the company at approximately $10 billion.