Airbnb Broke My Heart
I knew this day would come. I’ve been dreading it for the past decade. Almost everyone in Silicon Valley can tell you a story about their near misses. But Airbnb was different. Airbnb broke my heart.
In April 2010, Elad Gil, a colleague from Google, introduced me to one of his angel investments. In the introduction email he wrote: “Brian and Joe are two of the founders of AirBnB, one of the most exciting startups out there today. They are kicking lots of butt.” I think we can all agree that they did a lot more than “kick butt” today as they took the company public topping a $100 billion dollar valuation.
A decade ago, I met Joe, Nathan, and Brian at the AirBnb “office”, a loft at 19 Rausch Street in San Francisco. The team was about 10 people crammed onto Ikea desks. Product and engineering were in the living room and customer support was in the dining room. The bedrooms were reserved for conference calls. I spent a full day with the team getting to know them and I fell in love with their company, team, and vision. Brian and I grabbed dinner at a Thai restaurant across the street from the loft and I listened with great enthusiasm as he shared his vision for the company. I love travel and I value companies with high affiliation cultures. (Years later, their tagline would become “Belong Anywhere.”) I’ve never had such immediate good vibes from meeting a founding team. I knew they were on a rocket ship and I desperately wanted to be a part of it. After spending the day with the team, I wrote to Elad “ I have a total start-up crush on AirBnB.”
My follow up email to Brian included a presentation I had done for the team, a link to an unusual rental in Paris called Chez Bernard, and a Burning Man First Timer’s Guide (how very San Francisco). I also wrote “I enjoyed our conversations … and the pull-up challenge.” I have no recollection of doing pull-ups as part of my interview, but it was a long day so anything is possible. Brian wrote back “I was very impressed by the insights you had in your presentation. Many of these ideas took us quite a while to grasp, and you recognized them in 24 hours!…We are very interested in you…We are in the middle of filling a number of engineering positions, as well as negotiating a lease in South Park, but I have you on my list of candidates to strongly consider next.”
Things were going great! We kept in touch over the next few weeks.
In the meantime, I stayed at an Airbnb listing and shared my feedback on the experience. Brian wrote “Thanks for the feedback. This is a very insightful chronicle of your experiences using Airbnb. Clearly, you have a great product understanding…We are very interested in you. The question we have is exactly what you would do for us, and when we need to fill this position.”
This is where it all went wrong.
What I should have said is I’ll do whatever is needed and I just want to be part of your team. What I did instead was I got anxious and shared that I had an offer in hand from Polyvore hoping to push Airbnb to make an offer. Instead, Brian wrote back “Congrats on your offer. We will not be able to make an offer in time, though I do want to keep in touch.”
And we did keep in touch for months and years afterwards. But over time, Airbnb took off and Brian and the team had a thousand other priorities and interested candidates.
I don’t have a lot of regrets in life, but this is my single greatest professional regret. Not because of the payday, although it would have been life-changing and substantial, but because I wanted to be part of the Airbnb story. I wanted to live my values and felt like I failed to live up to my professional potential.
The advice that I give to students today and the advice I would give to myself 10 years ago is the same. Forget about the title, compensation, and role. When you stumble upon something that you believe in, do whatever you can be to be part of it. These opportunities are so rare. I should have quit my job at Google that day and told Brian that I’d be at the loft on Monday. I’d help recruit engineers or talk to angry customers or finish the investor deck no one wanted to work on.
It’s been fun to cheer on Airbnb from the sidelines as an avid customer and to see Brian grow into the leader he’s become today. I’m still heartbroken and mourning what could have been. I hope that the silver-lining is that by sharing my story it inspires you to fight harder when life gives you a shot.
