Gina Gutierrez gets a lot of blank stares when explaining her start-up to people: It’s called Dipsea, and it sells subscriptions to immersive, short-form audio erotica. Venture capitalists, though, get it. They want to capitalize on dual booms in digital audio and sexual wellness, and some view Dipsea as the next Calm or Headspace. The start-up has raised $5.5 million in funding.
Ms. Gutierrez, 29, and her co-founder, Faye Keegan, created Dipsea when they realized that while there were plenty of companies offering tech-enabled vibrators, no one seemed to be addressing the mental aspect of female sexuality. In December 2018, Dipsea began publishing erotica podcasts, saying, “We think it’s downright powerful for people to discover the most turned-on versions of themselves.” The company charges subscribers $9 a month or $48 a year for access to a library of 10- to 15-minute stories in categories like “open relationship,” “hookup,” “crush” and “voyeurism.” Dipsea’s app also offers guides and exercises that can be done alone (“self love sesh”) or with a partner (“erotic meditation”).
Now the company, based in San Francisco, has 16 employees, 180 stories and 300,000 downloads. Ms. Gutierrez boomerangs between “I’ve never done this before” moments, she said, while juggling investor meetings, podcast appearances, script edits, Instagram caption-writing sessions and “Sacred Planning” meetings. She also has to deal with borderline puritanical rules from the big tech platforms while brainstorming about hunks, discerning what a hug sounds like, and puzzling over why people are so into stories about threesomes.
6:30 a.m. I hate the notion that the most successful people are up at 4:30. No thanks. I work on the couch for an hour before heading into the office.
9:35 a.m. My adrenaline surges when our social media and content manager, who started less than two weeks ago, Slacks me to say she has an urgent personal update. That’s never good.
She tells me she’s accepted another role. I’m shocked. We care so much about Dipsea being a great place to work, and have had zero attrition. So, 35 minutes into my workweek I’m dealing with my first “I’ve never done this before.”
The idea of kicking up the hiring process again so quickly after we’ve ended it makes my head spin. I spend the morning figuring out the transition plan. I really don’t want to go back to writing Instagram captions in the back of Lyfts between meetings.
2:30 p.m. I owe my editing team the final signoff on this week’s scripts before they pass them to the producers for recording. A section of dialogue on this one reminds me of a part from “A Star Is Born.” I send the movie scene to the team as an awesome example of realistic dialogue.
4 p.m. I hole up in a room with Faye and two other executives to brainstorm. We block 30 minutes per idea, throw out thoughts, sketch out designs, argue trade-offs. One idea we come up with is so good, I stand up to dance.
6:45 p.m. I debate bailing on plans to see “Hustlers” with some colleagues because I’m so behind. But I go. It’s an important piece of content for women right now, for God’s sake! I’m back at my computer on the couch by 9:45.
11 p.m. Quick Slack to Faye about a lead for the social media manager role before I shut my computer. I’m tired. When’s the last time I had a sip of water? Did I eat lunch today?
10 a.m. I talk with our audio production team about an article on aftercare, which is essentially affection and communication after sex. It’s the default in the BDSM community, but a good ideal to aspire to in all sexual encounters. We talk about not ending our stories too abruptly.
11 a.m. We have a monthly meeting called “Postpartum” where we discuss what we learned from our last month of stories and how people reacted. Most of our narratives are crafted so a female listener can identify with the woman, but one of our recent stories is about three men at a gay club, and we discuss whether listeners identify with one character, or if they’re more of a voyeur, excited to have eyes into the whole relational dynamic.
1:15 p.m. Over tacos I get book recommendations for my upcoming vacation — the first real one I’ve taken since starting Dipsea — from our content editor and writer. The whole team is voracious. Books lie in stacks around the office, especially Dipsea-relevant reads like “Conversations With Friends,” and “A Billion Wicked Thoughts.”
2:50 p.m. A construction company works in our building and I chat with one of the workers in the elevator. The contrast between their mostly male, neon-vest-wearing crew with our almost all-female team of erotic content creators is funny, but we’re strangely symbiotic.
9 a.m. I get coffee with an investor that we’ve been talking to since our seed round. Meetings like this are a mutual way to keep the relationship warm even when we’re not actively raising.
10 a.m. At the office, Mel Scott, our head of growth, tells me she’s spoken to a few podcast hosts who are going to run our ads. This is exciting. Facebook makes it very challenging for us to advertise as a sexual wellness business, and it’s frustrating. Sometimes our ads perform really well; other times we discover something was disconnected. Ads that were approved mysteriously get disapproved, and we’re left guessing why.
10:05 a.m. Faye and I have a weekly one-on-one meeting we call “Sacred Planning” to remind ourselves never to book another meeting over it.
11 a.m. The founders of an A.S.M.R. app visit our office to learn about how we create our content. I’m curious to learn about their work, too. One of them says the most polarizing A.S.M.R. sound is “mouth sounds.” I tell him mouth sounds can be tough for Dipsea listeners, too.
2 p.m. Our editorial team presents a plan for a new process of developing scripts. No one has ever made exactly what we’re making, so it’s a constant learning game with no instruction manual.
3 p.m. I sit in on a “Hooked on Sonics” meeting, where our storytelling lead and one of our producers talk to the rest of the team. This one covers what feelings sound like: A hug being akin to the sonic experience of going underwater, or anxiety as a high-pitched ring.
6:30 p.m. The entire company goes to a breath-work class at Chorus Meditation. You breathe in a fast, rhythmic way that oxygenates your brain, activating your parasympathetic nervous system and relaxing you. The crazy part is, it can also have effects like tingling, visual experiences or semi-lucid dreams.
I wake up in a jolt, even though I feel mentally present: An hour has passed and it felt like 20 minutes. My body feels amazing, slow and quiet. We all eye each other, while the instructor wraps up, mouthing, “Cool, right?”
10:25 p.m. Faye texts me asking to borrow a shirt. I wonder how many other co-founders sign off with a “Night love you.”
10 a.m. All-hands meeting. As our analyst presents which story tags performed the best, the team debates the underlying reasons. We know stories tagged as “group” or “threesome” are highly rated, but we don’t necessarily know why. The novelty? The explicitness? What are the creative differences between “crush” and “hookup” stories? They seem to overlap a lot, so what makes one more successful than the other?
1:45 p.m. I take a call with an investor who’s been persistent. He describes Dipsea as part of the “N.S.F.W. space,” which tells me I have to take a step back and explain our perspective on sexuality: We’re not interested in creating an erotic utility, we’re interested in empowering women with content designed for their pleasure. To his credit, he understands the difference.
4 p.m. “Hunks Brainstorm” session. The editorial team discusses stereotypes about attractive men that still feel relevant, or that we can modernize. A college athlete isn’t necessarily interesting without some other underlying reason. (Ah! Maybe they’re fed up with the extortive system they’re a part of and lean on a female confidante. She sees his depth in a way that her peers don’t get to. Write that down!)
We talk about the way that passionate people are attractive, and especially so if they’re a bit unattainable because of their focus.
Every “Fireman!” is met with an, “O.K., but why?”
5 p.m. I join Faye and Mel to figure out how to meet our greater goals for the quarter. Five hundred Post-its and two hours later, we take a step back to admire our work.
12 p.m. I meet with Mel to review the past week: how we spent marketing dollars, where it’s working best, trends we’re not sure what to do with yet. There’s one international market that’s going gangbusters.
12:45 p.m. We always order in and eat Friday lunch together.
5 p.m. I find a quiet booth for an interview with Tristan Taormino, host of the podcast Sex Out Loud, which I just found out is airing live. The host, a sex educator who really knows her stuff, gives us advice on creating content for older listeners, shares her favorite story (“Virgo Season”), and asks how I deal with running a women-focused company while also navigating the world of venture capital. I say it took me some time to realize I was more than one thing in different contexts, and that that’s O.K.
6:50 p.m. I find myself alone at Bamboo Hut, a tiki bar, with a blue salt rim mai tai in front of me. I’m evaluating whether this bar will fit our loose holiday party theme of “dive bar fancy.” The bartender tells me that yes, the lamps over the bar are real taxidermied puffer fish.
7 p.m. A friend texts, “‘Blue Salt Rim’ should be the name of a Dipsea story!” It’s a joke I probably hear once or twice a week but still haven’t gotten tired of.
Interviews are conducted by email, text and phone, then condensed and edited.