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.

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 I learned they were hiring a community manager, I threw everything I had at the interview process. They gave me a shot.

With the benefit of hindsight, I’m glad I spent those first two years feeling somewhat lost, career-wise. There’s a lot of pressure to build the perfect resume right from the start, but once I’d failed that assignment, I was free to optimize for different things, like learning and having fun.

My advice to people early in their career is pretty simple: your mission isn’t to pursue a career, it’s to discover it. Put yourself in interesting situations. Each experience is a building block and, in the future, you’ll figure out how to arrange (and rearrange) all those blocks in ways that make sense for you. People with impressive careers may sound like they were strategic all along, but I’m convinced that in most cases, that’s only because they’re looking backwards. Especially in the unpredictable and fast-moving world of startups, careers are stories that only make sense in hindsight.

HW: Anyone who’s been through an IPO, I always like to ask about the experience because it’s such a classic, if statistically rare, startup milestone. I assume leading Comms you really had to be careful during the quiet period and so on, all while letting Aaron still be Aaron. Any good stories or memories about the process or listing day itself?

AM: Getting to work on the Box IPO was one of the coolest things I’ve ever done. It was also one of the hardest. We originally filed to go public in March of 2014, and didn’t actually become a public company until January of 2015. A process that normally takes five weeks, give or take, took us ten months! Our timing was brutal: the Box S-1 coincided with the start of a major market correction for SaaS stocks, and our newly revealed financials made us a natural poster company for that change in sentiment.

Two additional moments stand out to me. The first was in July of 2014, when we made the unusual move of raising and announcing another round of private financing while on file to go public. We could have just left the news cycle at that, but decided to proactively release our Q1 numbers in tandem to show our progress, like a mini earnings. I remember at the last minute we had a crisis of confidence…was this really the right move? Could we still trust our instincts? We forged ahead, and reception was positive. Putting out those numbers didn’t magically fix our story, of course. Box’s ten-month quiet period taught me that rebuilding trust and confidence is something that happens incrementally. We continued to report our financials every quarter leading up to the IPO, and by the time we were finally ready to go public, people had a much better understanding of our business fundamentals and trajectory.

The second moment was the IPO itself. I remember feeling oddly calm amidst the clamor of the NYSE trading room floor. I was on the balcony with my colleagues for the bell ringing, and during all that clapping and cheering, I felt a wave of gratitude for all we had experienced to get to that milestone. It was clear to me that this team and company were so much better prepared for whatever was ahead because we’d been through something hard, and had made it to the other side with a deeper resolve and thicker skin. Whenever I’m at a career low point, I go back to that moment.

HW: Then you did a bit of a Venture (Social Capital, someone else’s firm) -> Glossier -> Venture (Coalition Operators your own firm) loop. Social Capital has obviously evolved from its original form and that was the period where you moved on, so I want to focus on the decision to return to operating. Box and Glossier feel like two very different industries! Are they kind of like the ‘two sides of Ashley’ or are they actually more similar (from the perspective of your role: work with a compelling founder/CEO, help other people understand what is special about the company, and so on)?

AM: I love switching between an operating view (depth) and an ecosystem view (breadth): it’s the only consistent pattern in my career! Operating keeps you honest, while getting to work across multiple companies and categories gives you perspective. It’s a powerful combination, and I later learned I could have my cake and eat it too when I started investing and serving as a Homebrew Advisor while leading Comms at Glossier.

I was originally going to take time off after leaving Social Capital, and even try to write a book (something that is still on my bucket list). But a casual coffee with Emily Weiss on the eve of my last day at Social Capital ultimately changed those plans. I joined Glossier because of all the things I hoped I would learn: about consumer businesses, the beauty industry, brand and community building, and beyond. After working for two male CEOs, I was ready to support a visionary female leader, and hoped I would be able to challenge and expand traditional founder archetypes through my work at Glossier.

Additionally, my Box experience taught me that I loved telling stories of category transformation, and that becoming a poster company for an evolving category can create major narrative tailwinds for a business. I thought maybe Glossier would be another opportunity for that type of story — either in beauty specifically, or e-commerce more broadly.

HW: You consistently speak out when you see female CEOs get treated differently by the press. Not that CEOs are above criticism or analysis, but that there are profile tropes which seem pretty gendered and don’t get applied to male leaders in the same way. How do you help female leaders navigate this potential bias? I’m particularly interested in how language once used supportively for empowerment by some female CEOs (#girlboss) can then be used negatively by media and detractors later on. The answer can’t just be “stay very boring” right?!?

AM: The thing that worries me the most is the hidden industry-wide toll these stories take. I’ve heard from too many founders, including those at the very earliest stages of company building, who’ve read these articles about some of the most visible women in our industry and feel like they already have a target on their backs. That’s a heavy burden to carry when your job is to push boundaries and break with the status quo.

Fortunately, I don’t think the path forward is to “stay very boring.” Maybe this is my inherent bias as a comms pro, but in aggregate, I believe the uncaptured upside when women founders stay under the radar is far more detrimental than the risks that come with visibility.

For any individual founder, all comms decisions should start with the desired business impact. Which audience do we need to reach, and what do we want them to do? For some early stage startups, investing in comms won’t meaningfully move the needle; for others, it can be transformative. Framing profile building decisions in terms of business goals not only makes this aspect of the job more palatable for founders who aren’t publicity inclined, it also makes it easier to weigh potential risks against potential rewards.

These decisions become more nuanced with visibility and success, when women and other underrepresented founders are invariably held up as symbols of their respective identities. Deciding whether to embrace this aspect of profile building, and any of the “girlboss” type lingo that comes with it, is both a professional and deeply personal calculation. What’s essential is that founders are prepared for the additional scrutiny this attention will bring, whether or not they seek it out. Investing in internal communications, building out owned channels, and identifying advocates who will call out unfair treatment when they see it (a role we should all play if we can afford to) give founders a stronger foundation as spokespeople for companies, categories and movements.

Of course, media scrutiny doesn’t exist in a vacuum. Many of these stories, and the anecdotes that shape them, are a reflection of the way society as a whole views women in positions of power. Today, my best advice is to be prepared, and when things get tough, for founders, boards and comms teams to take a deep breath and not overreact (I could write a whole blog post on this). But what I really want for this next generation of founders isn’t just a good defense. I want to see women on offense: taking risks with bold ideas, and experimenting with new ways to get them in front of people. I guess we’ll know we’ve made it when a woman can get away with behaving like Elon Musk.

HW: You recently launched Coalition Operators, a venture firm + operator/advisor network to really help startups with more than just capital. I’ve seen your work firsthand since we’ve been lucky enough to have you as an Advisor to Homebrew’s portfolio. What convinced you — and your other partners — that this was the next phase of your career? What type of opportunities are you most interested in?

In the process of investing, we became rather obsessed with helping founders build more diverse and impactful cap tables. We’d all benefited tremendously from having access to scout capital…could we create a new model to bring more women into this part of the startup ecosystem at scale? So in 2021, we partnered with Thrive and General Catalyst to connect wildly talented operators and startups in their portfolios, with the VC firms sharing a portion of their potential upside in exchange for advisory support.

This is now my full-time job (my partners are part-time as they run their companies), and I’m still in awe of how I get to spend my days. For me, this was the most organic and obvious career move I’ve made to date, even though it’s also my biggest pivot and I have so much to learn. When you spend your nights and weekends building something you care a lot about, getting to give it your full energy and attention is an incredible privilege.

Thanks Ashley, looking forward to working with you and Coalition!