The Beauty of Being Rejected

I thought my idea to shake up the book industry was brilliant. Investors didn’t. That ended up being my greatest asset.

JESSICA EWING

In 2009, after five years as a product manager at Google, I quit my job to become a novelist. I loved my time at Google, but I just felt like I wasn’t on my own path. So I went off in pursuit of finding it.

I spent six years writing fiction. It was hard, vulnerable work—work that I then had to beg publishers to read. I never became a best-selling author, but I gained deep insight into the book industry, and empathy for the writers who are being squeezed between two giant forces: disruptive technology and the traditional publishing industry. I started dreaming up ways to improve the space, including an idea for a startup that would let authors share their works in progress and get early feedback from readers. I started shopping it around to investors.

Because of my history at Google, I was able to get a lot of investor meetings, which gave me a false sense of confidence. My first was with Sequoia Capital, one of Silicon Valley’s most prestigious firms, which was an indicator that I had no idea what I was doing. Sequoia is not anyone’s warmup conversation. The meeting was lovely and encouraging, which only fed my naivete.