7 prominent investors rejected Airbnb in its early days

Many startup founders pull out-of-the-box stunts to get their businesses off the ground

Do you know Airbnb’s founders used cereal (yes, as in the breakfast food) to secure their initial round of funding? Or that PayPal’s founders once gave out free money to get people to sign up for the platform? These stories might be crazy, but they’re not uncommon.

Early-stage investors say ‘no’ to the vast majority of funding pitches

Angel investor Alicia Syrett details the top reasons investors turn down entrepreneurs. For example, the entrepreneur didn’t do their homework by, for instance, not researching the investor.

7 angel investors funded Google in its early days

Entrepreneur Shaan Puri shares how seven strangers acted as Google’s earliest angel investors. The first gave Google $100K without even putting his equity agreement in writing. The investors on “Shark Tank” use their personal funds to support startups, but they’re often more predatory about terms than typical angels.

Uber's first investors included StumbleUpon founder Garrett Camp

In 2010 when Uber went out to raise money, prominent investors including Mark Cuban and Gary Vaynerchuk passed. Vaynerchuk actually said no twice.

More than 400 investors turned Peloton down in its initial funding rounds

Peloton founder John Foley said investors rejected the company's initial funding requests because there was no clear indication of what the market for at-home fitness classes looked like. Ultimately, more than 200 angel investors gave the company its first round of cash. (Some users may experience a paywall.)

Airbnb's Brian Chesky explains 'Founder Mode' and how he took back control

The short-term rental CEO learned hard lessons through the pandemic, specifically around a culture focused on management and not building products. In the fall of 2024, Chesky gave a well-received speech at a startup conference that prompted debate in the startup world. He summarizes the talk here.

Airbnb started as a vacation rental startup and soon disrupted the hospitality industry

In this podcast episode, Airbnb gets the "How I Built This" treatment. The "How I Built This" host speaks with the entrepreneurs behind today's largest businesses about how they got started. In this episode, Airbnb's cofounder Joe Gebbia talks about how he built Airbnb.

Andreessen Horowitz is among the most well-known venture capital firms

Also known as a16z, the firm has invested in companies such as Airbnb, Facebook, and Lyft since its founding in 2009. A podcast episode offers a deep dive into how the firm got started and became the industry disruptor it is today.

Airbnb’s S-1 in 2020 revealed how it weathered the pandemic and its financials

An S-1 or prospectus is a registration form filed with the US Securities and Exchange Commission when a company wants to go public. They can be pretty juicy documents, as S-1s can reveal previously private details about companies to the public, often for the first time.

More than $3.5B has been invested through AngelList

AngelList was created to connect startups and angel investors. It’s evolved since its 2010 founding and has been used by companies like Uber and OpenSea.

Many of the 2010s girlboss-era founders experienced a public fall from grace in 2020

In the 2010s, dozens of female founders were celebrated on the covers of business magazines like Inc. for their recent startup success, from Emily Weiss’s Glossier makeup brand to Steph Korey’s Away luggage company. But many of these companies were also the subject of large takedown articles around the year 2020.

Explore Bessemer's anti-portfolio of missed opportunities

From Pinterest to Yelp, Bessemer Venture Partners—one of the most well-known VC firms—has invested in many successful companies over the years. But the firm has also kicked itself for passing on a few great opportunities, like Apple and Google. Check out the other companies in Bessemer's "anti-portfolio" here.

IPOs that failed

Plenty of private companies fail once they try to go public. Failing can mean shares sell for less than their initial asking price on its IPO date, or it can look like a company pulling out of the IPO process at the last minute. Some companies with failed IPOs include Pets.com, Etsy, and Robinhood. Learn more about these companies and others here.

Facebook was almost sold to Yahoo! for $1B, but its CEO refused

The board tried to fire Mark Zuckerberg for his resistance, which he blames for failing to communicate the long-term vision of the company. He claims the company has succeeded by launching products quickly to learn faster than its competitors.

Read JK Rowling's original 'Harry Potter' pitch that a dozen publishers rejected

Rowling claims 12 publishing houses rejected the pitch first written in 1995—which contained this letter and the story's first few chapters—before Bloomsbury accepted it.

A 2002 profile of unprofitable Netflix as it bet on a subscription model

The streaming behemoth saw the potential in subscriptions early, and in this 2002 profile CEO Reed Hastings was already talking about plans to offer "downloadable" movies. The profile serves as a historical artifact confirming the startup's risky bets and showcases the contingent factors that led to its success. (Some users may experience a paywall.)

Y Combinator has a roughly 1% acceptance rate

That’s lower than the most elite universities and colleges in the world—but insiders have some tips about how applicants can have the best shot of being accepted to the selective startup accelerator.

Elon Musk's $100M investment in SpaceX was lost to three failed rocket launches

The attempts with Falcon 1 endangered the company's future but provided valuable information from which to iterate and follow up with the successful first privately funded orbital launch in history and multiple ISS resupply missions.

Bezos has frequently cited a 1999 article titled Amazon.bomb to illustrate how dire the early predictions about Amazon got

Over the years, Amazon founder Jeff Bezos often recalls how wrong the predictions in the 1999 Barron’s cover story were. Among other things, that article declared Amazon’s entire business model to be unsustainable and destined to fail, noting its lack of profit and dependence on a massive amount of capital to fund its growth.

A star investment banker was fired, launching a decade-long court fight

Star bankers are the core of an investment banking firm's business, so when Perella Weinberg let their restructuring guru Mike Kramer go in 2015, he sued, launching a ten-year legal fight.

Eleven of modern history's greatest investors

The greatest investors have all made a fortune off of their success and, in many cases, have helped millions of others achieve similar returns. Read about the lives and approaches of Carl Icahn, Warren Buffett, George Soros, and more.

Adam Neumann started another real estate company after WeWork

Former WeWork CEO Adam Neumann has attempted to purchase WeWork before, although, thus far, he hasn’t been successful. Since leaving the company, he has founded a residential real estate firm, among other projects.

Venture capital is a form of funding provided to early-stage companies with high growth potential, typically in exchange for an equity (or ownership) stake

Key moments in fintech history include the transatlantic cable’s invention and E-Trade’s founding

Founded in 1982, E-Trade was the first-ever online brokerage, pioneering a method of investing that is common today. Its story is part of a timeline that the New York Times put together of key moments in early fintech history.

Steve Jobs saved a nearly bankrupt Apple

Apple nearly went bankrupt in 1997, when the tech company had only three months of operational cash left. Apple's board ousted cofounder Steve Jobs in 1985, but he was brought back as interim CEO to revive the company when Apple purchased Jobs' company, NeXT.

Prediction market Polymarket's CEO dropped out of New York University

Polymarket CEO Shayne Coplan started building Polymarket when he was 21. Polymarket has been backed by billionaire investors such as Peter Thiel and Vitalik Buterin.

SpaceX's S-1 or 'prospectus' revealed many previously unknown details about the company, including its unprofitability despite doing $18.7B in revenue in 2025, exactly how many voting shares Elon Musk will have in the company (roughly 85%), and more.

The Nasdaq's 'Magnificent 7' companies are responsible for roughly 40% of the Nasdaq 100 index's gains, while the remaining 93 companies account for the other 60%.

The name 'Silicon Valley' arose from the founding of Shockley Semiconductor Laboratory in Fairchild Semiconductor in 1956-57, founded near Stanford University in Palo Alto

Netflix profits when you're not watching, and its movies are designed that way—read a detail-rich critical essay exposing lesser-known Netflix takes

The Beatles' US label rejected the band's first two singles, 'Please Please Me' and 'From Me to You,' with one executive calling the band 'dead in the water.'

Frank Lloyd Wright's houses are historically hard to sell because they're old, subject to local landmark commissions, and often unfashionable

See 33 images that became central to huge scandals, including a young Charles and Camilla, Michael Jackson's baby on a hotel balcony, and Hugh Grant's mugshot.

Up to a million Girl Scouts sell about 200 million cookie boxes every spring, generating $800 million, largely because refusing a child is frowned upon

The idea for the Federal Reserve was conceived in secret in 1910—with bankers donning duck hunt gear for disguise while traveling to a remote country club on Georgia's Jekyll Island

Budweiser stores yeast derived from the original 1800s strain in a secret bunker, which only the Head of Yeast Management can access—not even the CEO

US housing costs have risen by roughly 175% between 1991 and 2026—but a growing number of Gen Zers are becoming homeowners anyway. In 2025, 4% of homebuyers were Gen Z, up from 3% the year before.

In 2009, the nation was gripped by the story of a missing young boy who was believed to be floating over Colorado in a homemade balloon, until it was revealed that he was at home the whole time.

Hotels in Cannes, the glamorous city on the French Riviera, hire hawks to ward off seagulls during the city's famous film festival.

A 2019 Facebook event called on attendees to "Storm Area 51, They Can't Stop All of Us," resulting in countless memes, the creation of a music festival, and eventually the arrests of those who did try to approach the area.

A Yale student wrote a profound essay about the consulting industry's influence on elite college students that was published in a book of her writing after she died in a post-graduation car accident.

In 2019, a laptop loaded with six of the worst malware in history and described as 'an exhibit of historical weaponry' sold for $1.3M.

A researcher recently discovered an interview from 1967 between groundbreaking journalist Joan Didion and the Grateful Dead, years before the band became an institution.

Apollo astronauts left items in the moon's 'toss zone,' including golf balls, family photos, and bags of human waste, to make room for lunar rocks.

The first horror movie is believed to be George Méliès' 1986 short 'The Haunted Castle,' which pioneered the use of special effects

Famed poet TS Eliot rejected the manuscript for George Orwell's political fable 'Animal Farm,' writing that its criticism of authoritarianism was not 'the right point of view.'

Comedy legend Catherine O'Hara, star of 'Schitt's Creek' and 'Home Alone,' quit 'Saturday Night Live' after just one week to return to her old job.

Brandi Chastain, the star of the 1999 US victory over China in the 1999 Women's World Cup, was a last-second choice to take the penalty kick that sealed the victory.

The most expensive ad of all time was for Chanel No. 5 perfume and cost roughly $33M to produce in 2004—about $57M in today's dollars.

Long before Major League Baseball began allowing instant replay for balls and strikes, an umpire reluctantly used the technology to determine whether a hit was a home run, a move that inadvertently ushered in a new era for the sport.