S5E3: How Faye Keegan of Dipsea is Empowering Women Using Audio-First Content with Sex-Positive Narratives

Welcome to The Room Podcast. I'm Claudia Laurie, co-CEO and founder of Pryve.

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We are so excited to welcome you back to The Room. On today's episode, we sit down with Faye Keegan, co-founder and CEO of Dipsea. Dipsea is a platform that is rethinking sexual wellness and audio content. It's where storytelling meets sexual wellness. With a subscription, users can access hundreds of audio stories designed to enhance and help people with discovery and wellness. Every Dipsea story is consensual, feminist, and sex-positive original production created by Dipsea's in-house team of storytellers. The Dipsea library also includes cozy sleep scenes and wellness sessions. On today's conversation with Faye, we discuss Faye's early career journey and what it took to go from investing to software engineering, to founding Dipsy. We also discuss Dipsy's early fundraising journey, especially for the space that they're operating in, and finding product market fit for a new user experience and form factor. Let's open the door.

Hey, thank you so much for joining us today in the room.

Yeah, I'm so excited.

We're gonna start at the beginning of your own personal journey. We're curious both where did you grow up and as a kid, did you always think you were gonna become a founder?

I don't know, do kids know what founders are these days? Maybe you guys did. I'm not sure that I had that terminology at the time, but no, I don't think I always wanted to be a founder. I think at some point in college I decided I want to work in finance, which I don't really do, but sometimes I feel like I do still think a lot about financing my company, although definitely a pretty big departure working at a hedge fund, but definitely didn't have the language for founder. I think I was a natural, I don't know, leader. That sounds really arrogant, but a way to speak of my friends that could call me like CEO of Campy Weekend. I was time checking people. So maybe it's just in my blood. I don't know. You alluded to your hedge fund.

Fund. For listeners, full context there, you went to Dartmouth for undergrad— go Big Green— where you majored in economics and minored in English. And then after undergrad, you did find yourself at Bridgewater, which is kind of a famous hedge fund, and they're famously known for this policy, what people call radical transparency. Curious about what was that experience like for you and how that informs your leadership style today.

Working at Bridgewater was extremely formative for me personally, professionally. Still to this day, a lot of my closest friends worked at Bridgewater, met through Bridgewater, or are still there. It definitely informed a lot of my leadership style, but I do think a lot of what draws people at Bridgewater, what drew me to Bridgewater, is already having that style to an extent, already wanting that feedback, wanting that personal growth and development. On the margin, being more welcome to, like, experience pain to get there versus other methods. But I definitely think that there's drawbacks to styles like that. It's a community and culture doesn't work for everyone. And when you create extremes in culture like that, no matter what they are, there's ways of doing this, you also can be exclusionary and just not let everyone succeed in that environment. So it was great for me. I really liked it. I'm not trying to replicate it, but trying to learn from it and have it also take the good parts with me while I'm building Dipsy.

What was a lesson that you have taken with you that you have implemented in the Dipsy culture?

The Bridgewater principle would be like, feedback is a gift. It's really hard to get better if you don't give them that feedback. Also, it's really hard for people to realize what they're doing well if you don't give them that feedback. So, if you can create a culture where people feel like it's easy, that those channels are open, then I think you actually can have a lot more personal growth across the board. And I definitely think that Gina and I, my co-founder, try to model that a lot. I think it's really hard to instill that in a top-down way. You have to live that. Culture in your way you work with each other as well, not just downward. So I think that we have a really collaborative, open relationship, and then through the beginning it was just informally how we built it. Now we try to institutionalize those things as well.

That's a great perspective. I think as all of us are figuring out our career and trying to grow, one of the best ways to level up is to be really honest about where you need to. And whether that be someone like your mentor or your boss telling you, also just having that recognition for yourself of where you can grow and being intellectually honest about it makes a lot of sense.

Bridgewater has one way in that there's tons of different Networks that work too, knowing where you're strong and where you're weak can be very empowering. I like to be way more successful than if you are not honest yourself about that shape.

Ultimately, you did pivot out of Bridgewater and went into software engineering, which I believe you pivoted into through taking a coding boot camp. What inspired this career shift?

Yes, so I was at Bridgewater, I started coding just in my job fortuitously. I worked on a team that supported the CEO, CIO directly, and he was very interested in the tools that Bridgewater used to do research. So it's not just research itself, but how do you build the best world-class tools to like empower those researchers, those investment analysts to produce that alpha. And because of that, Bridgewater had an internal Palantir team, and I was working with the Palantir team as like a client essentially of the new tools, helping them like beta their new software. It's like, wow, this part of my job is really fun, and I'm feeling more amped about this than whatever I was researching Australian housing, you know, the US shale boom, and I was like, I feel like that I'm probably not doing the right thing for me in my career right now. So I kind of started product management, like the idea of that even, at Bridgewater. Started coding a little bit there in honestly Palantir-specific languages that's only used at Palantir for their tools, so not super helpful. I was like, okay, I gotta go learn some like real coding. So I went to coding boot camp, learned a lot there, but really learned a lot more on the job at my next startup when I joined Neighborly in 2015.

So you leave Bridgewater and you're at Neighborly as a software engineer. At some point you stumble upon the idea for Dipsy. What was the initial aha moment? Walk us through that period of time for you.

So I was at Neighborly, it was like a fintech startup, so I was coding, actually learning how like production code gets shipped, really leveling up there, but also being exposed to product management, able to leverage some of my finance background because it was a fintech company. Which was awesome. But while I was there, I was getting more and more obsessed with this idea that actually came from my co-founder, Gina, where she was very inspired by apps that were new at the time, Headspace, Calm, that were able to create audio content that was effective at allowing listeners to shift their mood and their moment. So for Calm and Headspace, those moments are, I can't sleep, I'm stressed out before a meeting, I've started my day and I'm already feeling anxious, how do I approach my day positively? And by taking this sort of content and making it audio, making it premium, making it discoverable in a way that's accessible. They were able to really open up the field of meditation that was very niche to this broader mainstream audience. And so the tool was interesting, the business model was interesting, and we were like, what if we did something like this but for a totally different use case? And we were both interested in this idea of sexual wellness and that no one had taken this kind of product-first approach to female sexuality and desire. And that for us, unlocking that was so much more than unlocking that 15 minutes, that connection with your partner, but empowered you in your life more broadly. And so That was the product inspiration, the passion, and then just did a ton of research. We read a bunch of books about the psychology of female sexuality and desire. We did a lot of product research. I did a lot of market research on the romance industry, and all those things came together at the right time for us to be like, "Yeah, let's do it. Let's quit our jobs and get this thing going." And how did you meet Gina? Gina's a totally social friend. I feel like so many founders have previously professionally worked with their co-founder, which makes a lot of sense 'cause it's a really big leap, but my— roommate grew up with Gina, my roommate in San Francisco. So it was a random SF meeting. Literally the idea of Dipsy began over many bottles of red wine in the kitchen and eventually everyone going to bed and me and Gina are still like, "But what if this? And have you heard about that? And what about this product inspiration?" And people would be like, "You gotta shut up about this or just start this company because we can't hear about it anymore." That's awesome.

Truly an organic origin story there. Would love to double-click a little bit and for our listeners who might not be familiar with Dipsy, Could you tell us a little bit more about what Dipsea's core product is?

Dipsea is really where storytelling meets sexual wellness. We're taking like a mind-first approach to female sexuality and the power of story is the way to do that. So we offer sexy stories, literally 15 to 25 minute audio stories who are designed to turn you on, to unlock that side of yourself, whether that means with yourself, to your self-pleasure practice, connect with a partner, pregame date, tap into that more accessibly. And we also offer sleep and wellness, everything from like educational to breathwork. So all kinds of things.

You have this idea, you start building this product, and obviously venture capital is part of your founding journey. You raised venture capital from well-known investors such as Thrive Capital and Maveron. Could you tell us a little bit about that early fundraising journey? Who wrote your first check?

A lot of people were like, "You'll never raise venture capital." I literally emailed someone who was a VC investor who I knew, and they were like, It's never gonna happen. Wouldn't advise you to try. And I was like, thank you for that feedback, but I'm gonna go for it. I guess I might as well. And the first check came from Eric Stromberg at Bedrock. He was such a great fit. He was so savvy business. He didn't care that every week, every second— it's like less unusual to be talking about sexual wellness, but at the time it was more maybe groundbreaking. And he had a background. He was previously the founder of a company called Oyster, which is like Netflix for books. And so he'd seen firsthand the voracity and the size of the romance market. So he had a really strong belief in the consumer and that why couldn't you take this— romance is by far the best-selling genre in literature. It's like why bookstores are open. It's like all the top readers in the world are reading romance in terms of volume. Why couldn't you take this kind of outdated motif format product, um, unbranded space and create a premium millennial version of it? He was the first check-in because of that background, I think, and that belief in romance where even today when we're talking to venture capitalists, they're like, "Really? Romance?" It's like, "Yes, bigger than every other genre." Even for myself, I remember how big Twilight was when we were all in middle school.

And I think that's very much an early indicator of the interest in that genre.

People can define romance what they want, but that's the core of so much the content that we consume is romance, relationships between people, is that spark and that flirtation. That's why we're both in as well.

Going back to your early journey with Gina, what advice would you give fellow founders who are just starting to think through an idea with a friend?

I think who that friend is matters a lot. I feel like I really lucked out. I can't imagine a better partnership because a lot of times being a founder is really hard and it's lonely and there are like high highs, but there are low having someone there who you love and trust and want to work with every day makes a huge difference. Like, most startups fail. That's the reality.

That's definitely something we evaluate as a part of our investments, is the strength of that co-founder relationship. Did they meet because someone told them they should meet, and how long have they known each other? Did they meet inside the founding journey? Did they meet outside the founding journey? And different people have different philosophies on what makes great co-founder pairings. But what really resonated with what you said was that there's high and low lows, and you do need someone who's going to pick you back up because sometimes those lows are different for different people. And it's great to have someone who can complement and be there when maybe you're having a bad day or they're having a bad day.

Another thing about Gina and I as a team is that we just have really different backgrounds, and both of those were hugely impactful for the product we were building. Neither of us have backgrounds in creating erotic content, but that hasn't really stopped us. My background was really in finance, but I think more broadly in analytics and in research. Whether you're making content or building a product, that data-informed approach is huge in knowing what kind of content to make, when to serve it to people, what kind of content converts versus engages versus retains. At its core, Dipsy is building an understanding of how people consume this kind of content that doesn't exist anywhere else. My co-founder's background really is in brand strategy and design, and especially in the space, brand was such a crucial lever for us to break into all the places we're in, like where we can advertise, be in the App Store, but also get that funding that we could build that brand and people could trust us to protect it. I think those pieces together, which are so different and so crucial to the company we're building, also makes a big difference.

Absolutely. And having both of those two superpowers has helped you guys build from where you were, from just that idea on a couch, to today. And I noticed online in 2019 that you had said that Dipsy app had 325,000 app downloads. I can only imagine what it is currently. What was the process like finding that product-market fit? For this unconventional user experience?

It was really crucial to launch, get out there. I think it's really scary, and I think there are a lot of reasons that it's even scarier to launch when you know it's not perfect. But we just had so much to learn about the product and what people wanted because it was so new. And we had so much to learn about what to make, like what kind of content really resonated with people, what voices, what storylines, what length of story, how to describe them, and Those kinds of things we couldn't just sit in a room and guess. So we started with 60 total stories and we launched with an app that me and one other engineer built in 6 months. And so it was like scrappy. I don't think it would hold up to my bar today, but the point was that we wanted to get something out there to see how people actually used it. We did beta testing and test flight that stuff too, but it's not the same thing as will people pay for this stuff? Like what kind of story will they also do and then subscribe? It's really for them asking a couple hundred people what they liked. And then just being really honest what was working, what was not, and trying to be less precious about what our favorite stories were and trying to hold the high bar and have our brand lens and make sure we were creating content that always felt quality and true to what we were. And then listening to all the user feedback we're getting, both from qualitative interviews and the data. Doesn't lie.

It's so funny how you mentioned you do need to wait until you can get someone to pay for a product to like really understand feedback. No matter how many user interviews you do, you'll hear something very different from what the actual user behavior is. So it's interesting to hear that's certainly the case in consumer as well. You mentioned that it took a little bit of time to hit stride, which I think is the case for every founder and those like myself who are in that journey getting there. It's often quite daunting. But I think sort of distribution marketing is a huge part of being able to hit that stride. And I think what's really interesting is that there are a lot of marketing restrictions around sensitive topics such as cannabis. Or even sex. How have you leveraged traditional or untraditional methods for growth given these restrictions?

Whether you're looking at any of these institutional ad platforms, the policies that are written there are generally outdated. Their sexual wellness policies are not their highest priority, and they're written to be like purposely ambiguous so they have discretion, and they're probably written 5 years ago. And if you're in a space like this or any other space where you're pioneering, you're gonna have to just take risks and see yeses and nos. I think the only way that we've been able to protect ourselves from that is because we had a really strong mission that our product was attached to. We could get into the room with someone and explain it, they'd understand that we held everything in our app to an extremely high bar in terms of content, that it was all so well done. But I think there are tons of companies that probably do those things and can't advertise on those platforms because of outdated policies. And partially we're lucky because we're content and humans or humans, current society culture has this sort of strange bar for content. The kinds of content that you can consume on HBO Game of Thrones can be extremely visually graphic, sexually violent content, and that's okay, but I can't use the word erotica in ads. It's okay, sure, whatever. So I think content's in this kind of weird in-between space for all these platforms as well. So you get in that way where a lot of other sexual wellness brands who are doing physical products, for example, those barriers are really high for them.

You mentioned that your mission alignment was super core and you think was critical in being able to teach people why Dipsea needed to exist, both to investors but also on cross-platform promotion. You guys have over 3,000 reviews on the App Store today, and I was struck by the tone of them. As we know from our pods, reviews really matter on App Store ranking and all that. I was touched by the comments that were being shared openly about these sensitive topics for people on the App Store, and a central theme that I was picking up on was empowerment. One reviewer noted that, quote, "I've never felt my sexuality respected to and catered to before, and it's so beautiful and relieving." Another person wrote, "This app is freeing and empowering. I recommend it to every single one of my friends." I'm curious about how Dipsea thinks about the empowerment and how their user base and kind of women in general can be more open to what they need emotionally and physically.

We're on a mission to allow women to tap into their sexuality more accessibly and on their own terms. And that impact is so much greater than the bedroom. And I think it unlocks joy and confidence throughout all the parts of a person's life. It allows them to understand that what they want is important, what they enjoy is important, what they don't want is important, how to set boundaries in a relationship that's romantic or otherwise. There's so much content that you're being exposed to all the time that is sexual in nature that does not have that perspective, that is treating these topics frivolously or at worst violently. And we are taking a totally different lens, like a female gaze, to what we're doing. It really resonates with people. It resonates with people whether you're just like, "Oh my God, I've never actually listened to content like this before," or you're working through personal trauma, or you're first— you're exploring your sexuality, you're figuring out whether you want to be in an open relationship or a close relationship, that listening to somebody having that experience is so much more educational. It's so much more close to how people actually learn than reading a blog post about 10 steps how to set boundaries with your partner, how to dirty talk, how to know if you're gay. Our users are so passionate about what we create and they tell us and they use words that we use to describe our content, having never heard us talk about it. So it's really, really beautiful. I love reading them too.

I am going to start doing that when I'm having a bad day. I'm just going to go read your App Store reviews.

They're so good. We also do interviews with our users every couple months. We're doing them right now. And it's like, oh my god, you read the transcripts and I cry at my desk. I got to lock it up, get it together. It's been 4 years since we started this thing. But it still really is so touching. And again, it makes all the hard work worth it.

Just hearing you share that story too, I think the incredible thing about the shifting landscape and the conversation about women's sexual health and wellness and then just in general, the kind of companies that are getting funded these ways versus even 3 years ago, 5 years ago, we're unlocking and actually serving a population who has not previously had people innovating. So it's really cool to see that Dipsy is doing that. We talked a lot about kind of Dipsy's core mission, your founding journey with Gina, and some of the incredible growth that you all have faced, but we haven't touched a lot on the vertical that you're in, which is audio. And audio is a pretty hot topic in general right now, and you have been building the foundation in audio-first stories since inception. So how does Dipsea think about the future for audio platforms and audio creators?

We think about audio honestly a lot more as its power as a creative medium. I think that audio is super immersive. It can be really well done. If it's not well done, you can really tell. Listeners are getting more and more good at discerning sound quality. First of all, their headphones are all getting a lot better, so that helps. Their speakers are getting better. But I think also the more audio you hear, the more you're like, why is there this weird room tone? And like, why is the volume not does it correctly. And so actually creating premium stuff there will be like more and more important as listeners get more experience. More importantly, as a creative format, it allows us to create a blueprint for our listeners' imagination. And I think in this space, but in many spaces for fictional storytelling in general, audio is a really compelling medium. A lot of the audio people consume today is nonfiction. It's podcasts. It's like old-timey radio drama to an extent. It's also going to have a revolution and we're a part of that as well.

I am curious what your take is on platforms that are social in nature for audio, cuz Dipsea for obvious reasons is a closed experience for their users. Then in contrast, we have Clubhouse, which is trying to make audio social. Do you have a take on social audio?

For the same reasons that it's a good fictional storytelling medium, it's a really good social medium. It allows you to get to know people. We thought a lot about social features and audio, and like you said, it's really important that our space on our app feels protected and private. And so probably not soon, but something about hearing a voice note, even the way people are texting back and forth now with so much more audio, you're already moving a lot more of your social commentary into audio space and consuming more of it.

We chatted a little bit about the future of the audio medium in general. Are there any sort of upcoming exciting things that listeners can expect to see on the Dipsea platform?

Our first non-audio stuff in the app, which is pretty exciting, a few weeks ago. Obviously people consume erotic content in written format all the time, and it's the most common way to consume it. So it's not like it's that big of a risk. People definitely like it. Whether they like it on our app is maybe more of the risk. It's our first time doing anything at all that's not audio. All startups are really fun, but our startup is really fun because it's not just tech people, it's also creative people who are like writers and editors and producers.

That's awesome. And the past year has definitely been a crazy time and yet definitely an exciting one. The past 4 years have been incredibly exciting for Dipsy.

But what's next for yourself? More Dipsy. Dipsy till I die. Can't get enough Dipsy. We're so excited for the future of Dipsy. We're so excited to expand the kind of content we're making. Probably with an audio, even more different kinds of formats, and also written as well. I think there are so many ways to, to address the subscriber, expand what we're doing, and stay true to our mission.

We are so excited for you, Fei. As we're coming up on time, we have a hero question that we ask to all of our guests. We ask that the answer be in the professional context, so no moms or sisters, even though we love family. But the question is, who is a woman in your life that has had a profound impact on you and your career?

I've come from two fields which are largely dominated by men. I've never been managed by a woman. Dipsy is by far the most female-oriented team I've ever been on, which also makes it very fun and very unusual among tech startups in Silicon Valley. But I don't know, I never really worked close to other women until Dipsy, like in a serious way. When I was at Bridgewater, there was like very few women on the team. I was the only female intern on the investment side. The leadership was also like most of them men, but the women who were there were like such insane badasses, Karen Carniel Tambor being the one who really comes to mind, who's actually now much more— she's still there and she's still crushing. It's like future Bridgewater is obviously Karen. And she always just really inspired me for being so on it. He would talk to her and she just would know what was going on all the time. And also just someone who always made time to talk to junior women starting at Bridgewater. I've tried to be good about that in my career and be mentoring as well and try to pay it forward.

We hope that our listeners all have Karens to look up to. Was there anything that you wanted to touch on or chat about that we didn't?

No, I really enjoyed the conversation. Thank you all for having me on here.

Thank you so much, Faye, for joining us in The Room today.

Of course.

I think this is a call to action for people in finance and tech to have more female managers.

I assume it's better now, but I remember just being the only female intern and being like, oh, this is actually like this.

Thanks for listening to this episode of The Room podcast. We hope you enjoyed today's conversation with Faye of Dipsy. We also hope to see you next Tuesday at 10:00 AM Eastern, 7:00 AM Pacific for another inspiring conversation. Please like, subscribe, follow us on Twitter, Instagram, DM us, leave us a review.

We'd love to hear from you.

In the meantime, we'll see you next week in The Room for another conversation with another groundbreaking founder. See you soon.

Support for The Room comes from Silicon Valley Bank. Silicon Valley Bank understands these questions can keep founders up at night like Claudia. For over 35 years, Silicon Valley Bank has helped high-growth companies through scalable financial solutions, plus insights and expertise that many other banks just can't. Which could be why 50% of US-based venture-backed tech and life science companies bank with SVB. Learn more at svb.com/next. Silicon Valley Bank, built for what's next.

Cooley is a global law firm built around startups and venture capital. Since forming the first institutional venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world. The firm has 60+ years working with VCs, helping form managed funds, make investments, and to handle the myriad of issues that arise through a fund's lifetime. Learn more about the firm at cooley.com and also cooleygo.com. Cooley award-winning free legal resource for startups.

All opinions expressed by Claudia Madison McIlwain McIlwain and podcast guests are solely their own opinions and do not reflect the opinion of the 5EC.

This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.