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

Working at Box was a revelation. I had come out of an environment with a lot of hierarchy, where everyone was doing variations of the same job. Box had just 50 employees and was hitting an inflection point when I joined in 2009, so there was far more work to do than people to do it. My boss, Jen Grant, was an incredible manager, and Aaron Levie, the co-founder and CEO, was a fantastic partner on all things communications. Every milestone was an opportunity to tell the biggest possible story.

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.

Until then, Box’s narrative had been consistently up and to the right. We were interesting enough to be newsworthy, especially since Aaron was such a compelling spokesperson for the evolving enterprise software category, but we hadn’t attracted the same level of skepticism as our buzzier, more highly valued consumer contemporaries. So when public perception of Box changed overnight, I wasn’t prepared, emotionally or strategically. Years later, I wrote about several of my hard-won lessons from Box’s IPO process.

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?

AM: Angel investing was our collective gateway to building Coalition. We were all at different points in that journey, and in early 2020, we started investing together with pooled scout capital from Thrive Capital. We each have different functional and sector expertise, so this was an opportunity to learn with and from one another while supporting early stage companies, alongside our core jobs as founders (Toyin Ajayi at Cityblock, Jackie Nelson at Tribe AI, Lindsay Ullman at Umbrella) and operators (I was running comms at Glossier).

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.

Now in 2022, we’ve taken both of these efforts to the next level. We recently announced Coalition Fund I, a $12.5M early stage fund (our sweet spot is Seed and $200–300K investments), and the Coalition Network, a place where top operators can take a “portfolio approach” to their careers and build their wealth and impact beyond their day jobs. We’re unsurprisingly very founder driven in our investing, and while we’re category agnostic, focus a lot of our time in areas where we have experience building, including healthcare, future of work, e-commerce, marketplaces, and climate. We’re also constantly meeting with incredible operators, and in addition to the model we’ve created with Thrive and GC, love pulling them into deals alongside us as angel investors. We’ve basically built the products we’ve always wanted for ourselves as founders and operators.

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!

You Might Learn About Entrepreneurship Reading Andy Dunn’s Burn Rate But You’ll Learn Much More About Being Human

The realization of how mistaken I’d been hit somewhere around page 24 when the author details slipping into a psychotic state where he believed he was the returning Messiah. You see, my purchase of Andy Dunn’s Burn Rate was primarily to be supportive (I like him), and this past spring, it went from its Amazon package to a ‘Later’ pile in my office. Last weekend, the yellow-covered memoir moved from that stack to my hand. And then I proceeded to binge-read Andy’s memoir.

Burn Rate punched way above its weight, but before I celebrate it, I want to be honest about what caused my initial hesitancy: Skepticism around whether the author was the right avatar to become celebrated for talking openly about mental illness. Andy and I are friendly and have that shared “lots of mutuals” Venn diagram which makes people feel connected. In short, I knew the public-facing version of Andy but actually not much of the human behind. And so my not-overly-generous assumption was this book was going to be more like a press release than a personal journey.

Wow, I sound like a cynical asshole for sure, but societal issues are frequently represented and explained not by the individuals who are most qualified to speak, but instead the people who have the means, access and ‘camera ready’ soundbites. And in doing so they distort the discussion, push aside others, and are ultimately extractive before moving on. The best version of these folks actually do want to help (and yes, I assumed Andy was in this group), but they’re still misunderstanding the impact of grabbing the mic versus using their status to elevate others.

However as the title of this post suggests, I was wrong. Burn Rate is an honest, vulnerable account of a life. A journey that Andy is still on, but at a point where he’s ready to talk about it. For himself. For those who experienced him along the way, knowing or not knowing the full story. And for those who don’t know Andy but might be on a similar ride (we all are to different extremes). And I am very very glad it got out of the ‘Later’ purgatory. I’d urge everyone to read it for themselves.

Before I hit publish on this, there were two things that especially stood out for me:

A) Family is everything. The family Andy was born into, the one he extended into via marriage, the one he’s creating with his amazing wife and child.

B) The parts of us that we know aren’t our best selves but we also fetishize their ability to drive us to success, and worry that without them we’ll somehow be less. Andy has lived this. I’ve lived this.

Thank you Andy for Burn Rate. I learned about you but I also learned about myself.

Why Bringing These Two Skillsets Onto Your Cap Table Early Is Worth It

In 10 years of venture investing I don’t think I’ve ever participated in a seed round which had less demand than supply. From a macro sense, you can thank the bull run our industry was in for the last decade. And then specifically there’s surely some social proof dynamics as well — I’ve always believed that if Homebrew commits to your seed round the risk of not raising the amount you want basically goes to zero (equally so, since we see many opportunities from coinvestors, there’s often already capital coalescing around the startup).

In addition to our dollars, we are eager to help founders with the construction of their cap table, not just generically with the highest profile folks available, but more specifically where they might get some help along the way. Some angels are what I’d call Type O Negative in that they are so universally beloved and dynamically useful that we’d welcome them into *any* investment. More often though it comes down to a combination of circumstances: in what industry is this startup building? What expertise do the founders personally have? Who else is already committed to the round and what do they bring to the table? And of course the angel needs to be interested themselves. Plus all the puzzle pieces in terms of allocations need to fit. It’s not as easy as it used to be!

So while every seed round, and every startup, is its own special unique situation, I will say that there’s a set of skills that I often see underrepresented and which we advocate for including: marketing and communications. I could speculate *why* this gap exists (there are a number of reasons), but rather use the following paragraphs to make the case for including these folks (people like Jen Grant and Ashley Mayer, who we’ve had as advisors for Homebrew companies, and routinely seek to bring into funding rounds whenever they’d like).

1. Founders Often Don’t Come From These Backgrounds…

Founders seem to disproportionately come from engineering, product and sales/business unit career paths. Seed cap tables are about adding new perspectives and abilities, not just another 10 angels who share the exact same background as the founding team.

2. ..Nor Do VCs

While there are excellent counter-examples, your VC also likely didn’t spend their career as a marketing or communications leader! While I believe I personally was one of the best product leaders of my timeframe when it came to understanding the nuance and strategies of comms [yes, I just broke my arm patting myself on the back], I’d still defer to people like Ashley or Aaron Zamost if they disagreed.

3. Seed Stage Startups Don’t Hire Fulltime For These Roles, And Certainly Not Senior Hires

These roles typically become FTE in your growth from 10 to 50 employees, not 1–10. So get them on your cap table instead of your org chart, versus just lacking access to this DNA until post-Series A.

4. Best Practices In Marking & Comms Are Highly Extensible

There are certain types of help that’s difficult to get if the person providing the input isn’t deeply involved in your day-to-day. And definitely once they’re on board fulltime, marketing and comms will be even more valuable. But at the same time, for seed stage needs, I’ve generally found they can provide much value ‘on demand’ without having to be caught up on the intricacies of your business.

5. Seed Stage Needs Here Are Usually About Preventing Things From Going Wrong

There are startups who are just amazing at marketing and comms from Day One, but for many it’s not an immediate critical workpath. You’re trying to build a software product, do customer development and find PMF. *But* doing marketing or comms poorly can create huge wastes of dollars or in the worst cases, get you in trouble. So think of these angels as risk management that can eyeball your general plans, and called upon strategically if there’s an unexpected issue to navigate.

6. Hiring Marketing or Comms Consultants/Agencies At Seed Is Often a Terrible Idea

What a waste of money (and time) to engage with mediocre or junior talent. The reality is that the best ‘for hire’ practitioners here are not doing seed-level consulting. It’s just not worth their time. And so instead you get what you pay for. This wasn’t always the case — there used to be, for example, a roster of excellent comms folks and even boutique agencies who enjoyed consulting for very early stage startups, but they’ve all gotten hired by VCs or growth stage companies, or themselves moved into more strategic upmarket roles, charging as much as the best lawyers, exec recruiters and other top tier service providers.

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So there you go. Please make an effort to bring marketing and comms angels into your seed round. And when I specifically recommend this, and you ask ‘why,’ expect this URL in your inbox. Cheers!

Fortunately They’re Really Simple To Fix!

You might think my job is about saying “yes” to founders, but statistically it’s *actually* about saying “no,” given we typically see 3,000+ companies annually in order to make 10–12 investments. Despite the volume, each opportunity to hear or read more about someone’s idea is a privilege and I try to treat it respectfully, despite not being able to spend meaningful time on the majority of inbound we receive. Hopefully every startup finds the right investors!

Some entrepreneurs are born salespeople, others find it more awkward but ultimately realize getting comfortable pitching — to investors, to the team, to potential employees, and so on — is part of the job. And without this talent, the risk unintentionally lowering the probability of building the success they desire.

The deck you send to an investor is often the first opportunity you have to tell your startup’s story, and there’s lots of great material out there on what a deck should do. But there’s fewer posts on the classic, and repeated, mistakes people make in these summaries. Here are three of them, which I believe will make most VCs lean towards the “PASS” button…

1.           Don’t Put an Exit Slide in a Seed Deck (or any deck before growth round IMO)

I see these most often when entrepreneurs come from regions/cultures where tech startups are still new, or the investors they’ve been pitching are more traditional non-venture groups. But as a venture investor, I hate it. So much so that I wrote an entire post earlier on this topic alone. Here’s the most salient portion from that essay:

Why don’t I like to see “exit” slides in seed decks:

Narrows Thinking: Usually conceived based on what company is today, not what it can be

Speak of the Devil & He Will Won’t Appear: Often talks of different acquirers and market comps. Companies don’t get sold, they get bought so just go and build a big business. By ID’ing potential acquirers too early one may obsess over their market moves, etc.

Tell Me How You’ll Create Value, Not Just Realize It: Build a big profitable business. If you can do that (which is hard enough), I guarantee you there will be exit opportunities. Don’t try to reverse engineer.

Suggests Risk Aversion: Makes me wonder whether entrepreneur is looking for quick cash out rather than wanting a venture partner for a longterm company.

2. Focus on Milestones You’ll Use This Funding Round to Achieve, Not Just Time It Buys You

18–24 months. 18–24 months. 18–24 months. That’s what I see most often on fundraise slides. But companies don’t earn rounds based on how long they’ve been working since the last fundraise! They get more capital because they’re learning, growing, achieving. Tell me what you’re going to accomplish with my dollars as the headline. Then support this with how long you think it’ll take and why this capital is 100–125% of what you’ll need to get there.

3. Founder/Team Bios Which Feel Deceptive

Nice pictures of happy looking cofounders. With a bunch of education and corporate logos underneath. First and biggest are GOOGLE! HARVARD! Then I go to LinkedIn and see you have eight years of work experience, of which Google was a summer internship in operations team while you were in grad school. And Harvard was a two week executive ed course. And I wonder why you are playing these games with me, when I rather hear about where you actually worked or why you decided to study philosophy at a perfectly fine state university (or skipped college all-together).

Look, I get it, you’re trying to draft off the social proof of some credentialing, hoping that it at least gets you in the door, and fearing that without these logos, you won’t be able to permeate the notoriously homogenous (but changing!) faces of venture capital. But I truly believe you’re doing more harm than good when you push away your real lived experiences for what you think I want to see. At best, you’re going to get the investors you deserve (bad ones who care mostly about status), and at worst, you’re going signal lack of self-confidence, when we should be building mutual understanding and trust.

As with all advice, Your Mileage Might Vary. There are lots of different investor mindsets and preferences in what they fund. Don’t listen to me if this doesn’t ring true to you. But after thousands, and thousands, of decks, these are three slides that distract me and if I’m making quick judgment calls whether to lean in or not, cause me to pause.

Best of luck!