When not to take no for an answer

Airbnb’s co-founder and CEO Brian Chesky shared 7 rejection emails from investors while the company was trying to raise a seed round in 2008. I wrote about the key learnings from these rejection emails in an earlier blog post.

It turns out that while many investors rejected Airbnb, there was an investor who agreed to invest before the company entered Y Combinator in 2008. This was Paige Craig, currently of Arena Ventures. I covered Paige’s innovative approach to using online fundraising to complement the investments that he makes through Arena Ventures in an earlier post. I think that this is a win-win for Arena and the startups that it backs because it provides Arena with more financial firepower while giving the startups it backs a wider network of people who can support the company.

Paige recently shared the details of how he discovered, thought about, decided to invest in, but unfortunately was passed over by Airbnb which decided to take money from Y Combinator. You can check out the full post here.

I appreciated Paige’s transparency in sharing the email exchanges he had with Airbnb’s founders, the company’s original pitch deck, and metrics. It’s a great story about hustle, making investment decisions based on the positive case (Chris Sacca passed on Airbnb due to thinking about the negative case), and independent thinking.

But most importantly, it teaches that founders aren’t the only ones who shouldn’t take no for an answer. The best deals can be very competitive. When this is the case, the most successful investors know not to take no for an answer.