Ellen Wilcox: Listening as Power — Turning Women’s Stories Into VC Conviction

What happens when listening becomes a source of power? In this episode of Speaking of Phenomenal, Amy Boyle sits down with Ellen Wilcox, head of listening at the venture firm Listen, to unpack how real women’s stories influence where money flows. From midlife health gaps to breaking stigma and owning nonlinear careers, this conversation shows why being heard can change outcomes—for individuals and entire industries.

Every moment in life has the potential to be phenomenal. At Amy Boyle Photography, we specialize in capturing those moments, whether it's for your business, a milestone event, or a personal portrait. As the host of the Speaking of Phenomenal Podcast, I know the power of storytelling—and I bring that same passion to my photography. Let’s create images that celebrate who you are and wh

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Chapters

• 0:00 Introduction to Ellen Wilcox and Her Role
• 3:46 Exploring the Day-to-Day of a Venture Capitalist
• 6:40 Researching Midlife Womanhood and Health
• 9:07 Insights from Women's Health Research
• 12:12 The Need vs. Demand in Women's Health
• 14:42 The Importance of Education and Storytelling
• 17:48 Defining Phenomenal and Personal Growth

Transcript

Amy Boyle (amyboylephoto) (00:00)

Welcome to the Speaking of Phenomenal podcast. Ellen, I'm so glad you're here.

Ellen Wilcox (00:04)

Thanks, Amy. So glad to be here. Thanks for building a platform for conversations like these.

Amy Boyle (amyboylephoto) (00:09)

So excited to get started in what we're going to talk about today. Before we get into all that, how are you describing your phenomenal self these days? Who is the head of listening?

Ellen Wilcox (00:18)

What a great question. I'm Ellen Wilcox. Personally, I live in Cambridge, Massachusetts, just on the other side of the river from Boston with my husband and my rescue pup, Tallulah. Professionally, I am the head of listening at Listen, which is an early stage consumer venture capital firm based out of Chicago, actually. We like to think at Listen that we invest in early stage entrepreneurs that are

building at tipping points in culture and society. Part of what I do as head of listening is go figure out where are those behavior shifts? Where are these paradigmatic changes in how consumers like all of us are thinking or feeling or believing or behaving? And how can we use human insight to help us make great investments on the front end

that are in alignment with some of those tipping points. And then I spend about half my time helping our companies that are in our portfolio continue to build their organizations to be able to listen and to gather consumer insight. What it really means in practice is I spend quite a bit of time in conversation, usually kind of conversations like these, where they're open-ended. kind of a story gatherer. I like to think I make observations for a living and...

find ways to connect dots across different humans and different stories and find patterns that can help us, as I think about it, of reconcile the rational economic model, which is I think of as how consumers are supposed to behave and the systems that are and structures that are around us with what we know to be true about human behavior, which is that it's quite irrational. I love living in that space and that tension between those two things. And I think that's really what I, what I strive to bring to listen as a company as well.

Amy Boyle (amyboylephoto) (01:55)

You described the what you do now, how does that play out in your typical day to day? Is there a nine to five anymore? What does that look like for you?

Ellen Wilcox (02:03)

Part of what I love about my job is there is no typical day-to-day necessarily, but I do think that's often a cop-out answer, so I'll give you a better sense of it. I divide the listening department, which is the department that I came to listen to build out, into three different components. One is that kind of broader exploratory work around these behavior shifts we think are at tipping points. I know I've shared with you, I did a...

decently sized body of work on midlife womanhood and midlife women's health. That's an example of us kind of going out and saying, we're very intellectually curious about a subject, but how do we convert that intellectual curiosity into investment conviction? I think that's really where I come in, run a human study, gather stories, analyze and synthesize the results to get to a framework that we can use for investment. The second kind of core pillar is in the due diligence process as an investor. So wearing more of an investor hat.

How might I bring these human insights into our diligence process and evaluate desirability and use consumer research to help us build conviction in any specific deal? So I spend quite a bit of my time getting to meet wonderful seed and series A stage founders who are actually actively brand building and thinking about navigating the natural challenges that come with entrepreneurship and get to to spend a lot of time in that diligence component. And then the third bucket is

our kind of support to our portfolio companies. So getting to really partner with our entrepreneurs to help them think about how they might both gather and synthesize the consumer voice and consumer story to help them launch new products or enter new markets or think about their brand strategy or think about their pricing strategy. Really there are very few business decisions I think an early stage entrepreneur can make that wouldn't benefit from some either context or influence of a consumer voice.

Those are kind of the three different big buckets of work that come with my job and my role in the department that we've built out. So in any given day, that means I'm getting to meet founders that are new to me. I'm getting to collaborate with the founders that I love. They're already in our portfolio. And I'm getting to meet consumers who are just experiencing life and start to pull back some of the complexity that makes decision-making as a consumer really hard and really fun in the modern world.

Amy Boyle (amyboylephoto) (04:19)

I love that. to your point about like no typical day to day, that's a space that I've lived in for 25 years with my work. And some people that's absolutely terrifying and you need the guardrails and other people that is just the most freeing, fabulous way for creativity. And once you find your jam in that space, it's always fun to meet other people who like, yes, I thrive like that. It's a good thing.

Ellen Wilcox (04:40)

Totally,

totally. I like to think of myself as I'm a really good uber rider because I know a little bit about a ton of different things that I can usually find some point of commonality or curiosity or interest where I can ask that second or that third question that maybe an average rider wouldn't ask because I have some level of knowledge beyond the surface. it means that I don't go incredibly deep in any one area. I kind of am a generalist at heart, but

I love to get to that kind of, below the surface, at least I can ask an informed question a little bit more in an interesting way. So that's really how I kind of think about my superpowers. I'm really good at riding in Ubers.

Amy Boyle (amyboylephoto) (05:21)

One of the things that we connected over was your research on midlife. Mindsets from the middle, what kind of...

things were you learning, what were you looking for, what surprised you the most in kind of gathering data and talking to women in this space.

Ellen Wilcox (05:36)

Great question. I've always been interested in women's health. Obviously I'm a woman. I've been kind of worked in health and in healthcare. I've been excited by understanding my own body. And I think there was a desire in my mind to, seeing a lot of women's health deals surfacing. We were seeing a lot of amazing women entrepreneurs leading those deals, which is really exciting.

but we didn't really have necessarily a great view on what is women's health as a category. And when I looked around, you it's not uncommon for venture capitalists to put out, market maps on areas that they're excited about. And the typical kind of VC market map, as I observed it for women's health was breaking a woman down into her component parts. It's like, you've got contraception, you've got perimenopause, you've got mental health, you have sexual health. And it was kind of just like piecing her body apart and then

putting market value sizes to each of those component parts. And I couldn't help but wonder as someone kind of coming into this with more of a human-centered design and design thinking background, and so much more of my approach is qualitative, what might a consumer obsessed view into women's health really look like? And so I wanted to get past this kind of piecemeal conversation about women's health. And I want to understand what it felt like and looked like to be healthy for the women themselves.

Another observation I made early on was that when we say women's health, we oftentimes automatically default to the biological parts of womanhood that make women different from men. When in reality, if you talk to women about their health, it's also heart health, it's also skin health, it's also hair health, it's also bone density and things that aren't inherently different from men, we're just not talking about them with a lens of women's health.

I wanted to step back and actually just go talk to women who were experiencing a period of life that we kind of roughly call midlife, which is in and of itself a whole conversation we could have about how we partition women's lives into its component parts. But we roughly said, let's talk to women 37 to 63. There are a lot of stages of life that happen within that phase.

For many women, have, fertility, may have pregnancy postpartum, you may have pregnancy loss, you may have job promotions, you may have, parents that you're starting to see are aging or that you're caring for. You may have neighbors and community members who are relying on you. You may have leadership roles at work where you've got teams and people you're managing. And so all of these things we heard from these women are contributing to making them feel either healthy or not healthy.

in that life stage. So we created a study, more of an ethnographic exploration of modern midlife womanhood, where we invited women in that age group, so 37 to 63, to tell the story of midlife. And it was interesting the way, as someone in a kind of a research role, you always have the choice as a researcher to pick the methods that you're using. And I love live interviews similar to you, Amy. These conversations fuel me. They make me feel very inspired.

But I wanted to find a way to surface a woman's point of view in this life stage and give her the chance to tell her story in her own words and in her own way and to do it without interruption. So no follow-up questions, no interruption, no prompting. I just wanted it to be unmoderated and give her the chance to share her story. So we worked with a wonderful company out of Richmond, Virginia called Share More Stories.

And we invited them, we created these prompts for women to respond to and to truly kind of write the story of midlife. And the stories we gathered were incredible, quite heart wrenching, quite empowering, but also defeating like, as a woman who's kind of to the left of this life stage, being in my earlier 30s, I think it was a bit harrowing at times. And I actually had to step away from the body of work because

The stories that surfaced were things that I was like, oh my gosh, if that's what's coming, I don't know if I want it. And you're having to always as a researcher kind of remove yourself from the research. But when studying something that's so inherent to who we are and who I am as a woman, it was very interesting to constantly have that dialogue with myself. But really at the end of the day, the insights that surfaced, I think, felt very universal to the woman's experience. They just came, I think, in these high acuity moments that come age 37 to 63.

they come out in their most kind of poignant version of themselves. And so it was really, really meaningful to do that. The goal of the work really for us was to say, how might we invest in wonderful women's health brands, consumer brands, and how do we understand women's behavior as it relates to their health so that we can make sure that we're picking winners when it comes to who we, who and how we back these companies.

I think getting from story to actionable insight as an investor is a really hard part of the process, but it's a really beautiful part of synthesis. And where the body of work ended up was published a report to the world, which was a bit of an interesting decision. Not all VC firms choose to publish their secret sauce, but for us, it felt like one, this is a conversation we should be having. Two, it's a maybe a bit of a different lens into the conversation thinking about

you know, asking women to share stories and using that to drive our investment thesis. And three, it was a little bit of a bat signal for us to say, hey, we're we're passionate about investing in the new the next generation of women's health. We're raising our hand to say, come find us. We want to meet you if you're building in this space and you're building a great consumer brand that's targeting women in this life stage. So the most important outcome, I'll say, is I think we really allowed ourselves to

get smart on women's health, such that when we found entrepreneurs that are building in this space, they weren't having to educate us on what women's health is or why it's important. We had a well-researched and insightful point of view that wasn't just rooted in personal experience, but was actually rooted in this kind of deep body of work we'd been doing and evolving over the course of a year.

Amy Boyle (amyboylephoto) (11:39)

Just incredible. And I love how you went about gathering the stories, the unfiltered, Let the woman share her story. feel like so often even just prompting folks, it limits or we want to be correct or all the different things that fall into this equation of where we're at to even present our ideas, to share them, even though it should be.

as easy as for us as it is for anybody else, but there's all these other parameters on answering a question or good girl syndrome or all these things. ⁓ So many things to talk about. But one of the things I love most out of all this is, and this is something I think I'm going to write on my mirror, know, midlife is not a crisis, it's a reckoning. And with the data and the information you were getting from your people.

What was the loudest bell consistently across the board?

Ellen Wilcox (12:34)

there were a lot of, certainly a lot of bells and certainly a lot of divergent bells, which I think is what makes this life stage really interesting is it's, know, the highest of highs and the lowest of lows in a woman's life tend to happen during this life stage, which I think is fascinating. For me as an investor, one of the things I've had to sit with and think through, and this gets back to one of the bigger insights and bigger bells that came out of this, which is there's one of the kind of maybe

five big insights that came out of this work was around self-treatment and tends to be a woman's desire and inclination to self-treat before seeking out medical help or seeking out the help of others. It's this kind of learned trait of if we can do it ourselves and I should do that and I'm going to focus on that. And I think there are what it led to for me as an investor is one of the things that made me perhaps

the saddest in this work, but also maybe the most optimistic is there's a difference in women's health between need and demand. And again, going back to my human centered design and design thinking roots, so much of what we're doing with design is trying to surface need, trying to understand, you know, where might there be latent needs that even women themselves don't talk about or think about or articulate or know how to seek out.

But putting on my business and investor hat, you realize that just because somebody has a profound and important need does not necessarily mean they're going to change their behavior around it. And there are a lot of factors that lead women to have this kind of need demand gap. And we talk about it in the report as the kind of the, the time in your life where there's like a stigma associated with, with what you're doing and

the normal common trap is how we talk about it where just because something is common, that doesn't mean it's normal. But sometimes the more you normalize something, the less motivated people feel to actually do something about it. Incontinence is a really interesting subject on this where women would tell me, you know, I'd rather work out in the basement, in my basement with the lights off in dark bottoms because I know I'm going to pee all over myself versus, you know,

getting surgery or dealing with other potential pathways for incontinence or talking to my doctor about it. And so it goes back to this notion of self-treatment, but I'm just very curious about when in women's lives they feel motivated to actually change behavior. And in this life stage, there are these kind of high acuity moments where the demand is similar to the need. So postpartum is a great example where women postpartum may be more likely to tell their doctors, hey, I'm, I'm

I'm having leaking, like I'm leaking urine and I've never done that before. I'm way too young to be doing that. That's a moment of acute higher acuity where people may be open to behavior change. But there are a lot of times where you could be pounding the table saying this is a huge need for women. Endometriosis care is a great example. A lot of women are silently suffering with endometriosis, have a very hard time actually getting diagnostic proof that they have it.

And it feels like a very invasive surgery to deal with it. And just saying that like the stats are out there that so many women are suffering with this and they absolutely deserve solutions. But when you ask women who are, 35 years into having really painful periods, they may not feel immediately motivated to change that. So there's a lot of socialization that comes with kind of us just accepting that.

periods are painful or that it's supposed to be this way. And I worry that that's a bit of an insidious, know, that's a hard issue for us to solve. But it's something that's important to acknowledge that just because the need is very evident and obvious and well researched, that doesn't necessarily mean that women are going to be lining up to solve it. And there's a lot of hard truth around that, but it's been something I've learned and it feels like very prominent with this audience in particular.

Amy Boyle (amyboylephoto) (16:28)

And then the other thing you mentioned is sharing the research that you did and having that be open knowing that just in general, how you keep that kind of data close to the vest, that's our proprietary, all these different things. How has that been received and what would you have to say to that?

Ellen Wilcox (16:48)

Thank you. appreciate that. And we've certainly seen a lot of benefit at Listen from sharing it and distributing it widely. I've seen maybe two different camps or two different ways it's been received. One is I've gotten a number of folks writing in just saying this really either gave voice to an experience I had, but never had like the words or validation to share, which I really appreciate. I heard stories like this really fostered a cool conversation between me and my mom.

I think I was able to ask her questions and I love that feedback. Bringing this work into traditional venture capital circles is also interesting. I was at an event that was directed toward VC investors and I always, anywhere I go, I bring a little packet of zines because we have physical printed copies of the report. And I was in a small networking circle with a few male investors and two of them responded in a way that I thought was very representative of the challenge of working in this space.

One interrupted me about halfway through me talking about the work and said, Whoa, whoa, whoa, you don't look like you're in midlife at all. You don't need to be worrying about any of this stuff yet. You're far too young. And my first reaction was like, one, why are we making comments about how old I look or don't look? The second feedback I had on that was I, I wholeheartedly believe that as an investor, you must be able to not only invest in things that you

personally understand or have personally gone through. I think that's where venture capital fails is when it relies on personal experiences of investors because we'll never have a big enough team to wholly represent the needs of humanity. And so as venture capitalists, I think it's our responsibility to figure out how to get an informed point of view on areas that we aren't personally experiencing. So that was my reaction to that one. The second person in that circle grabbed a report.

was said he was very excited and he was gonna share it with his wife. And that, my reaction to that was, well, frankly, your wife, I guarantee, does not need to read this report. Maybe it will feel representative to her. Maybe it won't. But really, this is for you. This is for us. This is for our investing community who maybe don't know how to educate themselves or demystify this life stage and build conviction in it. This is not built for,

women to understand their personal experience, even though it maybe had that effect on some people. And I just think that both of those reactions, nothing against these folks that said them, I just think is representative of so many conversations I had with women's health founders who say they get into the room with funders or other investors, typically male investors, and spend 28 of 30 minutes, precious minutes with an investor.

saying why this company matters and why women's health is important to invest in or educating them on the women's body and what even is endometriosis. And then you have two minutes at the end of the pitch to share all of the wonderful work you've done, the traction you've built, your unit economics, your supply chain, to go through all of the business that you have built around that issue. And it just became clear to me again, I think the mandate for us and why I feel so passionate about listening applied to venture capital.

is that we must be able to listen because that's really where investing in untapped and amazing opportunities is going to lie, is being able to very quickly get smart and very quickly build conviction in people and topics and subjects that we don't maybe personally have experiences in.

Amy Boyle (amyboylephoto) (20:20)

I love all the data and points that you're gathering, the information that you're gathering from all these women. Now,

For our listeners who maybe some are in the venture capital space, maybe some are curious about how to invest, but maybe just in investing in themselves, what kind of advice do you have to our listeners for being heard, being seen, ⁓ that sort of experience to make things different from themselves?

Ellen Wilcox (20:52)

Great and hard question. I do think that we talk a lot at Listen about seeking out companies that have momentum. And I think about that even from my personal experience and you're in a job interview or you're pitching yourself, you know, how do we think about telling us telling the phenomenal parts of us to borrow your language? And I do think about

whether it's pitching a business or pitching yourself, kind of what are your points of momentum? How do I share my momentum story? I think I see a lot of women that I talk to that are navigating even careers say, well, my path isn't linear. It's not logic. It's like they're out that the thing they did, the way they started their career wasn't relevant to what I'm doing today. And I think that the beauty of the modern career is that we're all having portfolio careers.

Very few people in this world now are starting somewhere and working in the exact same company for 35 years until they retire. And that in my mind gives us the gift of really owning the story that we tell and finding connection points between all those different components of life or your career or work or home or whatever. How do you tell that momentum story? And so I think about a lot of times like when we see, early stage brands pitching us,

What parts of your story or your business are you most proud of and what are signals that this is a momentum, that the moment is now and now is the time to either invest in me or invest in the business. How do you build those proof points? So I think a lot about momentum, both kind of personally and professionally.

also, I was given feedback

really early on. Funny, when I was in business school, did a startup with some, some friends and peers. And it just so happened that everybody on the team was very tall and you can't see me in this podcast, but I'm like five, five. I'm pretty average. but I was, I was with a team that was quite tall and a woman gave me feedback in our presentation that was extremely helpful, which was, Hey, you look really small up there.

And it would behoove you to, when you speak, take a step forward. So step away from the group, physically take a step away from, you know, the peers that you're with, and it will help you visually take up space. And I think that sets such a small little indicator of if you're in a room of tall people, which you could use that as a euphemism for literally anything, like how do I make myself stand a little bit apart or take a little bit more space or take a little bit more ownership to differentiate and be heard?

How do I create the conditions for other people to hear me? It's not only about what I say, it's also about kind of how I'm showing up. And I think about that a lot. It's a bit of an analogy now for me too, for other settings that does still apply, but I thought that was great feedback.

Amy Boyle (amyboylephoto) (23:33)

Yes. Just step forward. then like to your point that I mean, that says so much about ownership right there, just in body language. And the other thing that you had mentioned in there is, you know, owning your nonlinear story. mean, this podcast, if you went back 50 episodes, that is exactly what we end up talking about. Every single woman who's been on this show has a story. And the ones that tell the best story are the ones that find the through line.

out of chaos and it's the biggest squiggle. And I actually took a design thinking course in grad school. And one of my slides when I had to pitch my personal brand was this complete wriggle. I'm like, here's my timeline. Here's what I thought, here's what I am. And then I got to say, and it wouldn't have it any other way. And that was like the thing that, know, out of all the other things I said to your point about like standing forward is like owning it

our story is what makes us unique. possibilities are endless when we own that. So I love the fact that that's things that you're not only learning for yourself, you're learning from the people and the companies that you're listening to.

and also convincing a ⁓ group, a demographic of business folk that might go, this is the way we've always done it, and show them how to think differently. Bravo.

Ellen Wilcox (24:55)

I totally agree with you. think the, the, the, has to make sense to you if it's going to make sense to other people. And so I do think that some of the work to be done in storytelling careers like that is actually just you believing that it's true. Like you understanding that you've gained such an amazing, you know, amazing diversity of perspectives and experiences across these jobs and deeply believing that story. Because I think women in particular, and this is a great quality, by the way, have a hard time telling stories they don't believe.

and believe in. And so I think some of that work to be done is actually whiteboarding it out for yourself and saying, this is what makes me who I am. All of these, these experiences tethered together. if you, know, telling that passionate story for yourself, it really, it both exudes interest and clarity for the listener, but it also exudes confidence for you saying, ⁓ hell yeah, this, she knows how to do it. She clearly has.

is self-reflective and aware and able to masterfully pull from one part of her life to another. think that's just that ability to do skill transference from one part of life to another is an amazing skill that many women have.

Amy Boyle (amyboylephoto) (26:06)

We've kind of chatted about this a bit, but how would you define phenomenal? What is phenomenal to you?

Ellen Wilcox (26:16)

I think that for me, maybe this is maybe more of a values-based response. But one of the superpowers that I reflect on, I feel really grateful to have, is that I am simultaneously extraordinarily driven and I can be intense, but I'm also extremely content. And so I think there is real power in when I think about

phenomenal and when you asked me the hardest question to reflect on in our prep call around what makes you phenomenal, which made me want to shrink from the inside out. One of my reflections and I took myself back and said, what do I really appreciate about myself? I do think it's that it's that I'm, I'm ambitious. I am driven. feel extremely intrinsically motivated. I love to work hard, but I feel like I see a lot of peers or,

colleagues or humans struggle to know how to like turn off that ambition and not be looking for something else that you don't have. And in some ways, I think that's what it means to live a phenomenal life is both feeling very driven and very growth mindset oriented and always wanting to be better and wanting more while not letting that desire for more keep you from appreciating what you have. And when I think about how I want to live phenomenally, I do think it goes back to that balance of

always working hard, having high integrity and high drive, but not letting it get in the way of gratitude and contentment, like an ability to access joy on a daily basis and in life. And I think that's, I don't know how to put that in words, but to me, like, phenomenal is both of those things at one time.

Amy Boyle (amyboylephoto) (27:57)

I love that. The thing of like having everybody define this is that there is a very different definition for everybody, but there are common threads. And it's, my little listening exercise is like, what is it when we finally come to own that? Because it takes time to do it. It's like that stepping forward in a group where if maybe I'm, you know, I'm also like five, three on a good day with the right shoes. So, ⁓

You know, it's like, ⁓ yeah, I can do this. How can I do that? And where does that take me? I love it. And as far as our listeners learning more about you, learning more about Listen getting in touch, what's the best way everything will be listed in our show notes.

Ellen Wilcox (28:39)

Awesome. Listen's pretty active. We oftentimes think of Listen as a brand in and of itself. So we're fairly active on LinkedIn and other socials like Instagram. ⁓ So definitely recommend following Listen or Listen Ventures in those areas. And LinkedIn's a great place to find me as well. And I love meeting women. think being in community with women across a variety of categories and areas of life is really important. So

always excited to meet women that are living and breathing day-to-day life like we all are trying to and doing it in an interesting and phenomenal way. So LinkedIn is probably the best place to find me for that.

Amy Boyle (amyboylephoto) (29:19)

Excellent. Well, like I said, I'll have everything listed and linked in the show notes, the blog post that follows and any social things from there. And it's just been tremendous to chat with you today. We barely scratched the surface. There's like a series long years of, ⁓ that was a topic, could have gone deep on that. So, come back for more, get in touch with Ellen. You're gonna wanna have more conversations

Thank you for sharing your time with us today.

Ellen Wilcox (29:48)

Thanks, Amy. I think that the, we've nerded out on this before, but I think that asking great questions is a really hard and really beautiful and rewarding job. So I'm so grateful that you've chosen to ask them in a public setting so that you can share that insight and curiosity with other people. So thank you for making the space for all of these wonderful and phenomenal women.

Amy Boyle (amyboylephoto) (30:07)

My pleasure. Well, as I often say in my sign off is more later, we will definitely circle back.