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Airbnb asked $150,000 for a 10 percent stake in 2008. 7 investors turned it down.

Airbnb co-founder and CEO Brian Chesky in 2014.
Airbnb co-founder and CEO Brian Chesky in 2014.

Success is often more painful and hard-won than the effortless veneer it projects when we look back on it in hindsight. Consider, for example, that Airbnb received seven rejections from potential investors in its early days, as co-founder and CEO Brian Chesky revealed in a Medium post.

For $150,000, Chesky described, an investor in June 2008 could have secured about 10 percent of the company's stake.

(Brian Chesky)

Airbnb, for the record, is currently valued at more than $20 billion. Five investors rejected the opportunity directly; two didn't even respond to the pitch (I'm thinking of texts I've sent that have never received a reply, and that nonsense always stings).

(Brian Chesky)

Airbnb isn't unique in its strikeout record in Silicon Valley, but these rejections are the things that can make or break a fledgling company.

Even high-risk investors will reject big opportunities if they don't fit into a predetermined set of criteria. Reading the emails, this seems to have been in the case with Airbnb's early days; the company's ideas didn't fit into guidelines on what would make a successful investment for the potential investors' personal investment goals.

(Brian Chesky)

Chesky shared a bit of advice based on his personal history: "Next time you have an idea and it gets rejected, I want you to think of these emails."

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