7 sad emails

Turned down, and turned down, and turned down, and turned down, and turned down, and turned down, and turned down—and now: IPO. Also, 7 other things worth your time.

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AirBnB is expected to file to go public next week. A dozen years ago, you could have bought 10 percent of it for $150,000—less than the price of a studio apartment in many cities.

At least, you could have done so if you were one of seven investors that co-founder and CEO Brian Chesky was eager to get involved in his company. As Chesky wrote in a widely circulated post on Medium:

On June 26, 2008, our friend Michael Seibel introduced us to seven prominent investors in Silicon Valley. We were attempting to raise $150,000 at a $1.5M valuation. …

Below you will see five rejections. The other two did not reply.

“Next time you have an idea and it gets rejected,” Chesky wrote, “I want you to think of these emails.”

Here are some of the highlights. You can read the whole post on Medium:

Investor No. 1: “Not in our area of focus, do wish you best of luck...

Investor No. 2: “The potential market opportunity did not seem large enough for our required model.”

Investor No. 3: “It’s not in one of our five prime target markets, so it’s a long shot for involvement … If you get to the point of a Series A investment please let us know and we’ll take a look.”

Investor No. 4: “Thanks for the follow up. … I really like the progress you guys have made, but between issues outstanding with ABB and my current time commitments to other projects … I’m not going to be able to proceed with an investment.”

Investor No. 5: “We decided yesterday not to take this to the next level. We’ve always struggled with travel as a category. We recognize it's one of the top e-commerce categories but for some reason, we’ve not been able to get excited about travel-related businesses.”

Investor No. 6 and No. 7: [No reply.]

None of these investors was stupid or blind. In fact, by any logical standard — even now — the early version of Airbnb seems like a pretty crazy idea.

“Who’s going to stay on an air mattress in a stranger’s apartment, honestly?” asked Sam Altman, who was running Y Combinator at the time.

The reasonable thing to do if asked to invest back then was probably to say no. But as George Bernard Shaw wrote:

“The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man.”

Be a little bit unreasonable, today.


Mistake! Yesterday, I meant to write that Canadian Prime Minister Justin Trudeau shared a tweet in the hope of helping to “save a three-month-old baby’s life,” not his “wife.”

Thank you to the roughly 30 readers who emailed me to make sure I knew about the error. I know I make more of these than I wish I did. 😊


7 other things worth your time

Photo: Pixabay. I once wrote about these Airbnb emails before at Inc.com. If you liked this post, and you’re not yet a subscriber, what are you waiting for? Please sign up for the daily Understandably.com email newsletter, with thousands and thousands of 5-star ratings from happy readers. You can also just send an email to signup@understandably.com. 

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