From near-failure to global giant: Airbnb's co-founder on how it all almost never happened

June 18, 2026

AI Summary

5 min read

From near-failure to global giant: Airbnb's co-founder on how it all almost never happened

In late 2008, Airbnb was generating roughly $200 a week in revenue, its founders were deep in credit card debt, and no investor would give them money. The company had been flat for a year. Nathan Blecharczyk, co-founder and chief strategy officer, had already written off the idea in an annual update to friends, calling it something that "probably won't go anywhere." What turned things around was not a better pitch deck or a clearer business model — it was a box of cereal.

The cereal that saved the company

The origin story is now well-known but worth retelling for what it reveals about the founders' operating style. In August 2008, the team launched a dedicated site for the Democratic National Convention in Denver, where hotels were sold out. They got 800 homes listed and significant press coverage — but after the convention ended, bookings collapsed to zero. Desperate to stay relevant to the political reporters who had covered them, Joe Gebbia and Brian Chesky created presidentially themed breakfast cereal: "Obama O's" (tagline: "Hope in Every Bowl") and "Captain McCain's" ("A Maverick in Every Bite"). They mailed 100 boxes to reporters, got calls back from Good Morning America and CNN, and sold the remaining 400 numbered collector's boxes at $40 each — generating $30,000 in a wee

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What you'll learn

1 (01:00) **Existential Threat & The War Room** - Nathan recounts the moment Airbnb faced a near-death crisis and the company's response.
2 (01:09) **Introduction: From Air Mattresses to a Global Giant** - Host Michelle Toh sets up the improbable journey of Airbnb.
3 (03:40) **The Making of an Entrepreneur: Tinkering, Coding, and the First Business** - Nathan traces his early ambition from a childhood of taking things apart to running a profitable business at 14.
4 (06:59) **Learning "Everything Not to Do" at a Failing Startup** - Nathan explains why he quit a comfortable engineering job and what he learned from a disastrous first startup experience.
5 (08:51) **The Accidental Birth of Airbnb** - Nathan details how a rent hike and a design conference led to the creation of "Airbed and Breakfast."
6 (11:57) **Handling Skepticism and the "Breadcrumbs" of Hope** - Nathan describes the visceral negative reactions to the idea and what kept the founders going.
7 (14:57) **The Pitch Deck Disaster: "Investors Want B's, Baby"** - A hilarious and insightful story about Brian Chesky changing the pitch deck numbers based on advice from Sam Altman.

+ Full timestamped outline available in the app

Show Notes

We are back! Our first guest of the new season is Airbnb co-founder & Chief Strategy Officer Nathan Blecharczyk.

Airbnb now spans almost every country in the world. But there was a point early on where the team agreed: if things didn’t improve in 13 weeks, they’d quit. In our first episode of Season 2, co-founder Nathan Blecharczyk takes us inside the making of Airbnb — from “ramen profitability” and investor rejection to global expansion, crisis management and what comes next.

In this conversation, we dive into:

00:00: Introduction

03:51: Teaching himself to code at age 12 and becoming an entrepreneur at age 14

05:52: First job and learning 'what not to do' at a startup

07:35: Meeting fellow Airbnb co-founder Joe Gebbia as his roommate through Craigslist

08:01: The birth of Airbnb

11:02: Handling skepticism, rejection from friends and investors

13:36: Pitch deck advice from OpenAI co-founder Sam Altman

16:01: PR stunt at the DNC — selling $30K of "Obama O's" and "Cap'n McCain's" cereal in one week

20:27: Teetering on the verge of quitting

20:53: Applying and getting into Y Combinator

24:10: "Ramen profitability" and the company's turnaround

25:35: Advice from YC founder Paul Graham on doing things that don't scale

30:33: 'War time mode': Fending off a European clone 35:07: The company's 'first real trust and safety incident'

37:56: Delayed IPO - eventually going public in one of the most successful debuts in tech history

38:39: 80% revenue drop during Covid

41:06: Fear of survival and navigating painful layoffs

46:41: Airbnb's reinvention and quest to become a 'super app'

50:15: Outlook on AI

52:38: What happened with Airbnb in China

55:42: Global outlook and key markets

1:00:08: Rapid-fire round

Season 2 is here, featuring the leaders of brands including Airbnb, Rivian, NYSE, Canva, Samsung, Poppi, Peloton, Revolve, Lucid Motors, PHLUR, The Points Guy and Away. Catch new episodes every Thursday.

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About Behind the Business
Behind the Business is a Webby Award-winning, thoughtfully produced video podcast grounded in the belief that business is in fact personal. This is not a fawning interview show. We pair deep research with thorough interviews — asking the real questions and avoiding fluff, while keeping it fun! What’s the toughest day you’ve ever had at work? How do you mentally prep for a big event? Or what’s a pinch-me moment you’ll never forget? In each episode, guests get into it all. Each episode also connects