HE SHOULD HAVE FINISHED HIS SMOOTHIE: How One VC Passed On A 2,500X Return; At SXSW, Brian Chesky, co-founder and CEO of Airbnb, reminisced about the difficulties of building a business.


Megan Rose Dickey | Mar. 15, 2013, 8:51 AM | 1,908 | 1

Airbnb CEO Brian Chesky InterviewAt SXSW, Brian Chesky, co-founder and CEO of Airbnb, reminisced about the difficulties of building a business.

Airbnb, an online marketplace for renting out rooms and homes, is a $2.5 billion company, according to Bloomberg.

But in the company’s early days, Airbnb founder and CEO Brian Chesky had a hard time convincing investors to back his company.

At one point, Chesky was asking for $100,000 in exchange for a 10 percent stake in the company, Bloomberg’s Adam Satariano reports. But Chesky couldn’t seem to get anyone to bite. In fact, one investor even walked out mid-pitch, leaving his half-finished smoothie behind.

Today, that investment would be worth roughly $250 million — a 2,500x return.

Earlier this year, Wedbush Securities analyst Michael Pachter estimated that Airbnb booked 12 million to 15 million nights in 2012. He thinks that could increase to 100 million nights, whereby Airbnb could generate $1 billion a year in revenues.

The Missed Airbnb Investment, Now Worth $250 Million


Airbnb Chief Executive Officer Brian Chesky still crashes on couches. The difference is that now, Chesky, the co-founder of the service that lets people rent out rooms and homes online, doesn’t have to.

Before the 6-year-old company took off, Chesky was so desperate for money that he was offering a 10 percent stake in Airbnb for $100,000. Everybody passed. One investor walked out of a pitch meeting at a restaurant, leaving behind a half-finished smoothie on the table, Chesky recalled on stage at the South by Southwest Interactive conference today in Austin, Texas.

Today, that investment would be worth about $250 million.

During those dark days, Chesky kept a binder full of credit cards to manage the growing debt he had accumulated to build the company. But eventually, investors came calling. Peter Thiel, one of Facebook’s earliest backers, led a round of financing of about $150 million in Airbnb, valuing the San Francisco-based company at about $2.5 billion, Bloomberg News reported in October.

The site is now being used by about 50,000 to 60,000 people a night, Chesky said. Last June, Airbnb was booking 38,000 a night. For the SXSW festival, which began on March 8, about 8,000 people booked accommodations in Austin through the site, out of 28,000 people expected to attend the tech convention, according to Adweek.

Airbnb also has helped spawn the so-called sharing economy, where people offer services directly to one another through online hubs. With TaskRabbit, for instance, people will perform chores for a fee. Other services, like Getaround, allow people to rent out their cars by the hour. “The sharing economy could replace a huge part of the existing economy,” Chesky said.

One challenge that Airbnb and its sharing buddies face is from local regulators. Tax and safety rules are less clear when it comes to the new breed of Internet startups. While Airbnb facilitates room rental transactions through its website and takes a commission, the company says it should not be responsible for collecting hotel tax.

Even though his fortunes have changed, Chesky said he doesn’t have a home and instead stays in apartments booked through Airbnb. He said he doesn’t want the company to become like a musician who grows popular and can no longer relate to the audience.

“That is the point that they become irrelevant,” he said. “I still live on the site. It’s a big statement to say the CEO doesn’t have a home and lives off the website.”

About bambooinnovator
Kee Koon Boon (“KB”) is the co-founder and director of HERO Investment Management which provides specialized fund management and investment advisory services to the ARCHEA Asia HERO Innovators Fund (www.heroinnovator.com), the only Asian SMID-cap tech-focused fund in the industry. KB is an internationally featured investor rooted in the principles of value investing for over a decade as a fund manager and analyst in the Asian capital markets who started his career at a boutique hedge fund in Singapore where he was with the firm since 2002 and was also part of the core investment committee in significantly outperforming the index in the 10-year-plus-old flagship Asian fund. He was also the portfolio manager for Asia-Pacific equities at Korea’s largest mutual fund company. Prior to setting up the H.E.R.O. Innovators Fund, KB was the Chief Investment Officer & CEO of a Singapore Registered Fund Management Company (RFMC) where he is responsible for listed Asian equity investments. KB had taught accounting at the Singapore Management University (SMU) as a faculty member and also pioneered the 15-week course on Accounting Fraud in Asia as an official module at SMU. KB remains grateful and honored to be invited by Singapore’s financial regulator Monetary Authority of Singapore (MAS) to present to their top management team about implementing a world’s first fact-based forward-looking fraud detection framework to bring about benefits for the capital markets in Singapore and for the public and investment community. KB also served the community in sharing his insights in writing articles about value investing and corporate governance in the media that include Business Times, Straits Times, Jakarta Post, Manual of Ideas, Investopedia, TedXWallStreet. He had also presented in top investment, banking and finance conferences in America, Italy, Sydney, Cape Town, HK, China. He has trained CEOs, entrepreneurs, CFOs, management executives in business strategy & business model innovation in Singapore, HK and China.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: