The Story Behind My Investment In Pillow

As I began to raise my first fund back in early 2013, I reached out to my friend Satya to see if he’d like to make a small LP investment. We met up in The Mission and I walked him through what I was trying, and he said he unfortunately couldn’t and it was related to something new he was doing with his old friend. He couldn’t participate and share more details about his new thing. It was too bad, but I understood, and was now curious what new company he’d start so I could invest! Fast-forward a few weeks, and he sent me a note right before the news about Homebrew hit. “Ah….so that’s why!”

Always looking out for those around him, I began investing and Satya was kind enough to share a new deal he was working on with Homebrew. It was there that I mean Sean Conway and his company, at the time called “Airenvy.” Back then, Sean’s vision was a bit different, but he was operating in the same market he’s in today, and it’s a big and rapidly-changing market. From the first minute of meeting Sean, it was crystal clear he was a sharp communicator and extremely self-driven. He also had a chip on his shoulder about his previous company. I was invited to the round led by Homebrew with a small check and was happy to sign along.

When I started investing, it seemed like Series As just happened right after seed. That’s not the case anymore. Sean and “Airenvy” (now the company is called Pillow) kept chipping away at their market and embarked on a journey to find the right fit within that market. If you read this piece about what is motivating Sean and his team with Pillow, you will see the deeper motivations that drive the company. It was that motivation and perseverance which propelled Pillow and Sean to raise a hard-earned Series A round from Mayfield last year (with friend Tim Chang joining the Board), which was only just recently announced here.

A theme which has been reinforced for me in the last four years of investing is that the people don’t change much — the products and services in the market, however, will certainly. When I first met Sean, the company then “Airenvy” had a different approach. In building his team and the company into Pillow, they all went on a journey into the market to see how the next generation wants to live. And, that’s where things get interesting — with Airbnb growing, with urbanization growing, and with housing prices in those urban centers growing, the next generation coming up may choose to live differently. That’s where we see the next innovation, with home-share networks like Common and Homeshare, among others. It’s in that world that Pillow found opportunity and launched “Pillow Residential” to build software, workflows, and tools to connect apartment owners with renters. It was a journey itself to discover the opportunity in the market. And, as I alluded to, the market changed and Airenvy changed (into Pillow), but Sean as a leader didn’t change. Satya as a friend didn’t change. They’re still the same people searching for and sharing opportunities with folks like me when I was starting out.

Haystack is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2017 Semil Shah.

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