Office Hours: I’m the Co-founder and GP at Coalition Operators. I previously led Communications at Glossier and Box. I’m Ashley Mayer. AMA!Featured

ashleymayer·Jan 01, 2024

Posted in:Venture Capital Office Hours Startups

Hi all! I’m Ashley Mayer, the co-founder and GP of Coalition Operators, an early stage venture fund and operator network that I started with three friends.

We’re massive believers in the value operators can bring to early stage startups as investors and advisors, and equally passionate about the benefits of that learning and cap table exposure when it comes to growing your career beyond your core job. That was the inspiration behind Coalition Fund I, where we back early stage startups with capital and expertise from active founders and operators (my co-founders are part time on Coalition, full-time as the founders and CEOs of Cityblock Health, Tribe AI, and Umbrella, which was acquired by IAC). And with the Coalition Network, we’re building the on-ramp and routing system to connect world class women operators with early stage cap tables at scale through a novel economic model (no personal capital required) and our partnerships with top VC firms. Operators in the Coalition Network are senior leaders and founders at companies like Airtable, Brex, Chief, Figma, Notion, OpenAI, Ro, Shopify, Solv, Stripe, Vanta and many more.

The first era of my career was in communications. I joined Box early on, when it was just 50 employees, and led global communications there for six years, through an IPO. My whole world was Box and enterprise software, so for my next role, I wanted to zoom out and get an ecosystem view. I joined Social Capital as its first marketing partner, where I helped launch new capital products (including capital-as-a-service and the SPAC that kicked off the SPAC craze…oops?) and worked with founders spanning healthcare, aerospace, climate, fintech, enterprise and education.

I then joined Glossier to lead communications over three years, two unicorn rounds of funding, and one pandemic. I learned a ton about consumer audiences and how people respond to women in positions of power (I recently wrote a response to the book about Emily Weiss, Glossier’s CEO). It was while I was at Glossier that I caught the angel investing bug, which was the gateway to my accidental pivot to investing full-time.

I started my career in San Francisco, and moved to New York City in 2018 for Glossier. I love both startup ecosystems—they’re so different! During my downtime, I’m a voracious reader (90% fiction), enjoy drawing for relaxation, and love hanging out with my dog.

Ask me anything about venture capital, angel investing, taking a “portfolio approach” to your career, startup communications, building a profile as a female leader, Twitter (RIP), making a career pivot, IPOs, book recommendations, or anything else!

ElphaStaff·Jan 01, 2024

Thanks so much for joining us @ashleymayer!Elphas – please ask @ashleymayer your questions before Friday, January 5th. @ashleymayer may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕

emilydrewry·Jan 02, 2024

Thanks for doing this - big fan via your twitter! Wondering if you have any advice on pivoting from marketing / media into VC and how you can best get experience to prepare you. I’ve read the books but want to get a little more hands on prep.

ashleymayer·Jan 05

Assuming you’re talking about the investing side of venture, @emilydrewry? It’s a tough field to move into! I think there are generally three paths:1) Be a “celebrity” founder/operator and leverage your professional brand to make the transition. This option is open to very few. 2) Enter venture either in a non-investor role through your area of strength (content, marketing, etc) and then try to move within a firm, or come up through an associate program. Both of these are tough, but not impossible. It’s worth noting that most associate programs don’t have a clear path to a partner role. 3) Start investing, either with your own money or someone else’s (as a scout for a venture fund), and build a track record. This takes time, of course. And definitely a good dose of luck. But if you can show that great founders want to work with you, and you have a talent for picking companies, you’ll either be able to land a job at a firm or raise your own fund. The last was my path…first as a solo angel, and then investing with pooled scout capital with the three friends/founders who are now my partners at Coalition. It’s also a great way to figure out whether you love investing, which is important, because it’s a weird job! In marketing or media, you have really tight feedback loops. You’re able to understand if you’re doing a good job, and adjust accordingly. In venture, you’ll take a ton of meetings, but make relatively few investments…and then wait years and years to see if they were good ones. It’s an enormous privilege to work with founders and invest with other people’s money, but it requires a lot of patience, conviction and tolerance for uncertainty. It’s not for everyone, and it’s why you see a lot of former operators move into investing, and then back into operating—they miss the pace and proximity to the actual work.

emilydrewry·Jan 06

Thank you so much, I appreciate your clarity and thoughtfulness!

noopursingh·Jan 02, 2024

@ashleymayer Thank for being part of Epha office hours, you couldn't have come at a better time :)Enjoyed reading your bio, how exciting and inspiring.I have a tech background and launching a venture has been on my mind for a long time now.What would you say is the first crucial step for me to get started- given I already have a product idea?Thank you!

ashleymayer·Jan 05

That’s so exciting, congrats @noopursingh! I would say don’t wait to get started to get started :) If you’re not ready to make the leap full-time just yet, start talking to prospective customers to get their feedback, make friends with other founders so you’ll have that network, reach out to early stage investors to get their perspectives. It’s silly, but people are often more willing to help before you’re asking for anything specific (a pilot, funding, etc). Start building a network and get people invested in your success early on.

noopursingh·Jan 08

@ashleymayer thank you for the encouragement, and great advise- something I can see myself actually doing and achieving as the first step forward.

lauraglu·Jan 03, 2024

Best books you read last year that nobody's heard of?

ashleymayer·Jan 05

Oh hi, @lauraglu! Such an on brand question :) I have no idea what people have or haven't heard of, since I tend to stumble onto books. So here are a few of my favorites for this past year, and apologies if you’ve all heard of them:Novels:Tomorrow and Tomorrow and Tomorrow (a story of friendship and creative partnership) The Song of Achilles (a re-imagining of a Greek myth through the eyes of a minor character. I loved the preceding book, Circe)The Dog Stars (not your typical post apocalyptic novel…slow moving and poetic) Tom Lake (the audiobook is read beautifully by the one and only Meryl Streep, so no way is this in the “nobody’s heard of it” bucket) Carrie Soto is Back (fun behind-the-scenes of a tennis pro’s comeback, physically and mentally) Bewilderment (this is a lesser known book from the author of the Overstory, which was shortlisted for the Pulitzer Prize…it’s a heartbreakingly beautiful story of a neurodivergent boy through the eyes of his father)Non-fiction:Outlive (a far more pragmatic and human approach to longevity than I was expecting) Dopamine Nation (a look at addition and the pain-pleasure balance through the author’s patients’ stories) Power Law (a book about the history of venture capital…fun to zoom out and see the different eras, infuriating how few women characters there are!!)

Iynna·Jan 05

power law's sooooo good!

KT·Jan 03, 2024

I'd love to learn more about your thoughts on what it means to take a “portfolio approach” to your career. What can that mean for someone who has a pivot (or two!) in their career history?

ashleymayer·Jan 05

Hi @kristatdeau, I’m so glad you asked this question! I’m seeing it pop up in a few questions, so I’ll spend some extra time answering. There are several ways to define “portfolio approach,” and they all describe expanding beyond a core function or career track to grow your track record, impact and wealth. The way we think about building a portfolio at Coalition is very much rooted in the realities of the startup world. Startups are high risk, high reward. Most of them won’t have a meaningful exit (acquisition or IPO), but those that do can change the trajectory of their employees’ careers, in terms of access to future opportunities and wealth creation. Because there’s such an uneven distribution of outcomes, the best way to participate in the upside of the startup ecosystem is to have equity in multiple companies. This is what investors do when they build a portfolio of startup investments across a fund, knowing that most won’t make it, a handful will have modest exits, and one or two could become generation-defining companies and drive massive returns. As an employee, you tend to put all your eggs in one basket, equity wise, and sometimes that works out! I was exceedingly lucky that the first startup I joined, Box, ultimately went public. That’s pretty rare, and certainly wasn’t something I was counting on when I joined (I was just excited to have a job I loved). As an startup employee, you can build a small portfolio over time through a series of startup jobs. But there’s a more scalable approach that’s available to you once you reach a point in your career where you’ve accumulated meaningful expertise (for you, it looks like that’s in customer success). Senior leaders can leverage their hard-won experience to access more cap tables as an advisor (compensated in equity) or value-add angel investor (if you have personal capital) alongside their core jobs. And eventually, even board seats, or investments in venture funds as a limited partner. In the near-term, the benefits to doing this include learning (I deeply believe that exposure to the challenges and opportunities of other companies makes you better at your core job), building a professional reputation and track record beyond your core role, and expanding your network to include early stage founders and other advisors and investors. In the long-term, you have a much better chance of building your wealth with exposure to multiple cap tables. This matters on an individual level, but even more so for the broader tech industry. One of the beautiful things about the startup world is that people who benefit from acquisitions and IPOs tend to put that capital back into the startup ecosystem—as angel investors, as LPs, or maybe they even start their own companies or funds. Historically, the beneficiaries of the biggest exits have been a pretty homogenous group, and they tend to invest in and hire people in their networks, people who look like them. And the flywheel of the startup world perpetuates. This is why our mission at Coalition is to get more women and women of color on cap tables, and ultimately, to help a more diverse set of operators build wealth. With the Coalition network, we’re building the on-ramp and routing system to connect top women operators with early stage cap tables, and we’ve partnered with larger VC firms on a new economic model that doesn’t require personal capital (it’s a twist on traditional advisory roles, where the VC firm, rather than the startup, shares their upside). We’re still very early in this journey, but we’ve connected 100 wildly talented operators from companies like Airtable, Brex, OpenAI, Notion, Ro, Stripe, Vanta, etc. with cap tables as angels and advisors, along with a few full-time executive roles. If you’re a senior tech leader and you’d like to be considered for future opportunities, you can tell us about yourself here: https://bit.ly/coalition-survey.

Natalya·Jan 03, 2024

Hi Ashley, your story is truly impressive and inspiring. I am producing Women’s Comedy festival and we doing sponsor outreach. I am curious if you have any advice on reaching out to Glossier and women lead/focused companies like Glossier if I don’t have a contact that I specifically know. We’ve had success with sponsorships in the past that we have a first connection with and we have a deck.

ashleymayer·Jan 05

That sounds so fun @Natalya!Pitching sponsorships without a warm contact can definitely be tough. Most of these brand-forward companies are bombarded by such requests, and they can feel quite transactional and impersonal. Beyond searching for a mutual contact, maybe try showing your prospective sponsor how their product is already showing up in your world. Is there a comedian who is a mega [Glossier, etc] fan? Are you using a company’s product during rehearsals? Creating original content and tagging brands on social media to start a dialogue is much more likely to get their attention. Good luck!

Natalya·Jan 06

Thank you so much Ashley! That’s a great idea to show how we already use their product—will put something together. Much appreciated

ChristinaKFedor·Jan 04, 2024

In your Medium article, you wrote, "awareness is not a meaningful growth lever for every business, and not every founder needs to be a public figure. But for startups where it’s an advantage, and for leaders who have the aptitude, the opportunity cost of keeping your head down can be the difference between failure and survival." Could you offer some insights and examples from your experiences that would help women recognize these pivotal decision moments and better understand how to address opportunity costs associated with not pursuing an offensive leadership strategy?

ashleymayer·Jan 05

I love this tweet from Celine Halioua, the founder of Loyal (I’m an angel investor). “Early in building Loyal I made the decision to be a public facing CEO because 1- Loyal will ultimately be a consumer brand, & 2- it was one of the few “unfair advantages” we had available to us.This was a hard decision b/c i knew it put a big fat red target on my back, because I'm a female founder of an ambitious company.”https://twitter.com/celinehalioua/status/1719896828337152489The lens of “unfair advantages” is a good one. Building a company from scratch is so incredibly hard, and the odds are so stacked against you, which means being hyper aware of any forces in your favor is essential. In Loyal’s case, Celine’s visibility as a CEO has been essential. Loyal is developing a longevity drug for dogs. This means building for years and years before having any commercial product available. FDA approval to develop a longevity drug (which, until Loyal, had never been granted) was a huge existential risk. Celine’s ability to generate momentum for her company through storytelling and get people excited about their mission and product years before it’s available to consumers has made it possible for her to hire a world class team, raise venture capital from top tier funds, and lay the groundwork for a resonant consumer brand. She’s acutely aware of the downside, but she also knows that this is her best path to success, so she’s willing to accept the additional scrutiny that comes with her visibility.

chieremefortune·Jan 04, 2024

Hi Ashley! Thanks so much for being willing to share your wisdom and insight with us!I'm currently a Communications Director of a non-profit (recently switched from a SAAS HR tech company account manager role), and find myself in a similar situation to that of the startup I previously worked for: we do great things, but not that many people know about us. My first priority is extending our brand recognition, helping the community connect with our story, and getting more face time for our leadership team in thought leadership spaces. I'd love to know your thoughts on how to grow a non-profit (which acts more like a cause-based startup) from a 50-mile radius to a state, regional, and eventually national level of recognition. We advocate for all youth (0-25) in the state of Virginia in the areas of health equity, family economic security, mental health, early care & education, and child welfare (foster care). Thank you!

ashleymayer·Jan 05

Hi @chieremefortune! I know very little about the non-profit world, but maybe my answer to @Limilima can be helpful. To restate: Figure out the macro trends you fit into, at a state, regional and national level. From a narrative perspective, use your work as a microcosm of those trends (or, if what you're seeing contradicts those themes, that's even more interesting!). But basically, don't expect media or broader audiences to do the work to understand why they should pay attention to your non-profit. Shape your story around the things they already care about. Be a resource, weigh in on big moments or reports, offer useful examples and data. Good luck!!

Limilima·Jan 04, 2024

Hi Ashley. Wonderful career trajectory.I am in my early career as a communication assistant and look forward to blazing my path on the communication ladder. I like to ask what you would say are some essential "needs and musts" for someone in that career path beyond the conventional skills and technicalities we all know. Also, looking to build thought leadership in the field from an early stage, are there some life hacks and lessons you could share?Thank you.

ashleymayer·Jan 05

Hi @Limilima, I love this question! Two answers come to mind. First, to be successful as a communications leader, it’s essential that you understand the goals of the business. Too often, communications functions operate in a silo of sorts, with a mandate to “get press” around pre-determined milestones. The more you as a communications professional can be embedded in strategic conversations, the more successful you’ll be. This was a lesson I learned at Box, where comms was seen as a strategic function, and my teammates and I got to help shape big moments and proactively mine our roadmap for potential stories. The biggest unlock is a relationship with the CEO: they should be the #1 partner to a communications team, since they’re responsible for the company’s vision. If that’s too much of a leap, start with other functional business leaders…be deeply curious about the goals for their function and how communications can play a role in that success. The second thing is almost the opposite of the first: you need to understand the outside world. Operating in a company can be a bit of a bubble, where your internal realities dominate. It’s the role of the communications team to 1) understand what’s happening beyond the business, and then 2) figure out how what your business is doing maps to that external reality. In most cases, it’s very hard to get people, including reporters, to care about what’s happening with your product or business. Understanding the bigger themes that people already care about and how your company can provide a unique perspective on those topics is a huge unlock. You’ve probably heard the term, “meet your audience where they are,” and that applies to narratives as well. This is the job of a reporter: to explain to broader audiences why they should care about any company’s news. You will be 10X more effective as a comms pro if you can figure out what they and their audiences already care about, and then offer a perspective or announcement that addresses that topic. This is also a superpower when it comes to helping internal stakeholders understand how an announcement will be perceived externally. Some of the biggest unforced errors happen when a business underestimates how its news will be received in light of conversations that are already happening externally. It’s the job of the comms team to help them understand how something might land, and to time or shape that story accordingly. Re: thought leadership, I think it’s all about figuring out what’s authentic to you. For me, it was taking a more informal and humorous approach to my profession on twitter, which also had the benefit of helping me build relationships with reporters. Don’t force it! Experiment and figure out what’s right for you. If you’re early in your career, your #1 job is to learn. You’ll have lots of material to work with as you progress. I worry that sites like Twitter (now X) and LinkedIn create the impression that we all need to be thought leaders, all the time. I’m a big believer in publishing an essay because you have something to say, versus trying to find something to say because you feel like you have to publish something (although sometimes that means I go years in between posts!).

kimberlyjanelafleur·Jan 04, 2024

Hi Ashley, I am really excited about what you're doing at Coalition. I'm a founder in the women's health space and I was curious about how to work with Coalition? I specifically would like to know how to work with the network you've built. Currently a solo founder but looking for a co-founder, curious if Coalition is able to help in that search or be a partner through the network?

mroussi·Jan 04, 2024

Hi @kimberlyjanelafleur I'm also a solo founder looking for a cofounder, maybe we can connect networks? I'm in space tech but potentially know a few people who are also in the health space you can connect with. If anything, would be good to connect with another female founder. If you're interested feel free to shoot me a DM:)

ashleymayer·Jan 05

Hi @kimberlyjanelafleur, thanks for this question! There are two ways we work with founders at Coalition: through our early stage fund, where we’ve backed a number of healthcare startups, like Summer Health, Vitable Health, Journey Clinical, Little Otter, Medivis, Cofertility, Equip, and more (mostly at Seed and Series A). My partner, Toyin Ajayi, is the co-founder and CEO of Cityblock Health, so healthcare is a big focus for us. We also have a number of founders in our operator network (including the founders of healthcare startups like Eleanor Health, Solv, and Boulder Health). There, our goal is to connect women leaders with opportunities outside their day jobs, like angel investing, advisory roles, board seats, etc. We don’t have any explicit programs around co-founder matching, although there’s a lot of magic that happens organically across the network. If you think I can be helpful, feel free to shoot me an email: [email protected].

lauraglu·Jan 11

@ashleymayer BTW if you want any of your founders to engage with Him For Her on board seats (as candidates or holders), let's chat!

Tetiana·Jan 04, 2024

Hi Ashley, I actually would like to ask for books recommendations. What are your recent favorite ones? What would you suggest someone who likes "real-life" detective stories and not much into fantasy? I find it hard to switch from non-fiction reading and so far stuck with occasional classics.Thank you!

ashleymayer·Jan 05

Hi @Tetiana, I love this question! See my answer to Laura below for a more holistic list of books I read this year. I don’t read a ton of detective stories, but one I read this year that definitely had an element of mystery was “Happiness Falls.” It starts with the disappearance of the protagonist’s father (I promise I’m not giving anything away), and there’s a poignant exploration of the factors that determine happiness alongside the unfolding mystery. I can’t recommend it enough. I also loved the Magpie Murders, which is a more classic detective story, although probably not “real life.” It’s a story within a story, and very cleverly done.

NihaReddy·Jan 04, 2024

So impressed with your career trajectory! I'm navigating my own and would love to hear more about taking a "portfolio approach" to your career. I'm a copy director in branding and looking to make a pivot (maybe back to tech and pivot to UX copywriting? though maybe not the best time). Generally, any advice you have for thinking about next steps in your career (where to get inspiration, how to think about what's a good next step, networking etc.) would be great.

ashleymayer·Jan 05

Hi @NihaReddy, please see my response to Krista’s question for a more in-depth description of what I mean by “portfolio approach.” On a related note, I think advising startups can be a great way to get a feel for what you’re drawn to—which markets, which problems, which teams. I’m as biased as they come, but I think it’s a great time to re-enter the tech industry. Many of the most iconic tech companies were built during these tougher periods. And given contraction in the startup ecosystem, more capital and talent are going to accrue to fewer companies, which will also face less competition than in buzzier times. Definitely do your homework, though, and make sure you’re joining a company that’s well capitalized and has strong business fundamentals. One of the things that most blew my mind when I started angel investing was how much more access I had to information about the health of a business as an investor than I ever did as an employee. As for how to approach thinking about next steps—it’s sounds like you might be like me, and don’t have a defined career north star (i.e. “I want to be the CMO of a Fortune 500 company”). I used to be really jealous of people who had that level of clarity, and could work backward from that ultimate destination in terms of what their next steps should be. However, I’ve since embraced thinking about careers as a process of discovery versus strategy. You’re accumulating skills and experiences that will become your building blocks, and you can later put those building blocks together in whatever way you want. In the near-term, that means optimizing for learning—letting yourself feel the pull of curiosity, and not worrying yet about what that next step will be. Talking to people in roles and companies you admire is a great way to start this exploration. If you don’t have those contacts, look for mutual connections or try reaching out cold. And if you’re able to, I’ve always found it’s helpful to put it out there that I’m figuring out my next move—stuff will come your way that never would have been on your radar (for instance, I never would have imagined going to Glossier, given my lack of consumer experience, let along beauty). Best of luck and don’t overthink it! Many of the most interesting careers look strategic, but that’s a story told in hindsight. The paths are often quite random.

Josefina·Jan 05

"I’ve since embraced thinking about careers as a process of discovery versus strategy." love this!

Lynda122·Jan 05

Hi Ashley! Love following you and your career! Would love to learn how you marketed yourself as you transitioned to being an operator. I am also a startup comms leader (internal and employee comms) with the goal of being in a CoS-type role someday. I can see the connections between the two but struggle selling myself and I lay the groundwork for a transition. Thanks so much for your insight!

ashleymayer·Jan 05

Hi @Lynda122! The good news is that I’ve seen lots of communications leaders successfully make this transition. The skills you build supporting a leader on all things internal and external comms are so relevant to a chief of staff role. It’s really a superpower. My hunch is that the easiest way to make this transition is less about marketing, and more about taking on more CoS-type responsibilities beyond your current role. Do you think you could make this transition at your current company? If so, try raising your hand for projects that leverage your comms skills and get you closer to that leader…helping with a board deck or gathering materials for an exec meeting, for instance. Beyond that, from a positioning standpoint, my advice would be to pick a theme that best bridges your comms career with your chief of staff aspirations, like leadership, or cross-functional alignment.

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