“I guess we’ll know we’ve made it when a woman can get away with behaving like Elon Musk.” Talking With VC Ashley Mayer About Finding Your Career, Taking Box Public, And Why She’s Not Interested In Reading Yet Another Female CEO Takedown

From Box to Glossier, and Comms to Venture Capital, Ashley Mayer Is Carving a Pretty Unique Path. What She’s Learned, And What You Can Learn From Her.

We had overlapping circles and then became friends. I’m an Ashley Mayer superfan so beyond the affinity, have been fortunate enough to also bring her into Homebrew as an advisor to our portfolio companies, and invest in Coalition, a venture firm she founded along with three other amazing female operators. Her personal story and insights into tech are valuable and novel, hence why I asked her to share them with you, in Five Questions.

Hunter Walk: Ok, so we first met when you were leading comms at enterprise software company Box, a startup you joined when they were still pretty early and stayed at until post-IPO. First, congrats! But second, I realized I actually don’t know the story of how you first came across Box and why you decided to join. And then take your experience and turn it into a piece of thought leadership career advice to share with people reading this :)

Ashley Mayer: I was two years post-college and working at a public relations agency in San Francisco, a job and career path I stumbled onto when I was rejected by my top law school picks. I wasn’t particularly brilliant at or inspired by the role, but then I worked with my first startup client and was instantly seduced by the energy and audacity of that project. Better Place was building the charging infrastructure to enable mass adoption of electric vehicles; it was led by a charismatic CEO, raised gobs of capital before that was the norm, and later imploded spectacularly. I tried to get hired at Better Place and failed. But for the first time since abandoning my law school plan A, my mandate was clear: I needed to work at a startup.

Enter Box. I had gone to high school with the founders in the Seattle area, and we had recently reconnected. When…