June Diane Raphael and Jessica St. Clair launched their podcast, The Deep Dive, in the midst of the pandemic as a way to compensate for the loneliness and disconnect of lockdown.
Each week, the two longtime friends and creative collaborators discuss their pursuit of joy amid a bevy of challenges both relatable (motherhood, aging) and aspirational (finding the correct poolside attire for Miami Beach Pride). Doing the podcast helped lift the actresses out of their own post-lockdown voids, and their motto — “Let Us Live!” — echoes through Apple reviews posted by their ever-expanding listening community.
More from The Hollywood Reporter
When the abrupt work stoppage of this summer’s double strike threatened to trigger a similar existential crisis, they were ready with an antidote: They launched the Deep Dive Academy of Significance.
“We started a virtual school, and that is one of the most insane things I think I have ever said,” St. Clair says with a laugh.
The academy is their take on a Patreon — bonus content, for $8.99 a month, tailored to their unique blend of sincerity and satire. And, true to their decades of experience working in film and television — Raphael first broke out after co-writing the screenplay of 2009’s Bride Wars with Casey Rose Wilson and spent the past seven years starring on Netflix’s Grace and Frankie; St. Clair co-created and starred in USA’s Playing House — they have infused it with a certain level of artistry. The academy releases instructional videos on everything from cat-eye makeup to baking the perfect tomato tart, offers a “student portal” on which to submit coursework, and is overseen by their newly formed Headmistress personas, the inspiration for which, says Raphael, comes to them from the beyond. Adds St. Clair: “This started as my baby, but it was June’s idea to lean further into the school aspect and to create these sort of turn-of-the-century Headmistri characters — like any good marriage, we split up our tasks.”
Elements of both the academy and the podcast touch on topics that could be considered wellness-adjacent. St. Clair and Raphael are uninhibited in discussing the machinations of modern womanhood and life in the public eye, never too shy to share about a beauty procedure or discuss the power of a good set of highlights. But they’re deliberate in their focus on how women can open up their lives, as opposed to restricting themselves.
“God bless Gwyneth Paltrow and Goop and keep them well, but what I love about what we’re doing is that it’s partly a satire of all those places that tell you if you just get or do this one thing, everything will be OK,” says Raphael. “The promise of wellness or an ideal form of living as a woman is totally empty. We’re doing these lessons, but we’re using them as a recommitment to each other and our community.”
They point to the academy’s book club, which launched with former Goop CCO Elise Loehnen’s On Our Best Behavior: The Seven Deadly Sins and the Price Women Pay to Be Good. After reading the chapter on sloth, they asked students to submit photos of the mess in their homes, along with a blurb about what they were doing instead of cleaning. “It was so beautiful and healing to read,” says St. Clair. “It really changed us and the way we’re looking at our own messiness. A lot of wellness is really a product of capitalism that says you always have to be optimizing. It’s nice to do things that are just about enjoying yourself.”
Here, the Headmistri talk about what they’ve learned from their podcast and each other.
You launched the academy on July 1, about two months into the WGA strike and 10 days before SAG; how do you feel about that timing?
St. Clair: I feel like we’re busier than ever.
Raphael: The timing of creating the academy, and now having a way to be creative, to have an outlet during all this, to have full control of something, has been amazing.
St. Clair: We started as such little scrappers in New York, never getting paid, and creating our own content. There’s something about it, when everything is stripped from us, we always return to our roots and that makes me really happy. Because no matter what corporations decide to do or not do, we will always have ourselves — and each other.
It seems like it’s also offering an outlet to other creatives you know and are friends with.
St. Clair: That’s what’s really beautiful about the academy, is we have built this community. And we’re calling on our friends too. God bless my best friend Josh Levine, who is normally in the writers room of amazing shows and now happens to be free, so he’s editing every single one of our videos. At one point, I did see him put his head down on his desk and say quietly to himself, “Oh, I’m in it for the long haul.”
I know that you started getting the idea for all of this before the strikes hit, but has it changed the way you’re approaching your careers? Like, you’re not necessarily waiting around for someone to greenlight something.
Raphael: Having what is essentially a subscription service for our own content, and having full control over it without having to answer to anybody and being able to keep the profit — that’s empowering. My solidarity with my unions has never felt stronger because I have seen what it’s like to do something entirely on your own, without any networks giving you permission or taking the bulk of the money. That’s made it a really wonderful project to work on.
Tell me a little bit more about what the initial vision was.
St. Clair: What we really wanted to do, as opposed to being like “Here’s our content we’re performing for you,” we wanted to expand the Deep Dive experience, which is that we are all friends and learning how to get more joy out of life together. We already have our live experiences, which are equally insane, like our pickleball tournaments. June handles those, and there’ll be more of that to come.
Raphael: The thing I love so much about having founded an institute of higher education — and obviously, our accreditation is pending — is that women in particular can get bogged down in, “Am I allowed to do this? Am I allowed to call myself this or that?” So of course it is hilarious that we’ve founded a school but it is also deeply soul-satisfying. It’s weirdly healing. Yes, it’s a bit, yes it’s super funny, but in its own subversive way I feel very good about taking up space in this way.
So being a headmistress comes naturally?
St. Clair: It’s an easy role for June to fill. The students were originally really afraid of June, which makes sense because I’m often like the daddy serving ice cream for dinner. In our friend group, which also includes Casey [Rose Wilson] and Danielle [Schneider] of Bitch Sesh, June tells us what to do. We have strict dress codes for events. She told me at one point my hair was too long. Now she’s gone back on that, but I’m the only one in the group who can wear my hair this long. People would say, that’s strange, why would you let your friend tell you what to do? But people actually like to be told what to do, it makes them feel safe among chaos and uncertainty.
Raphael: I will say, and I’m happy to put this in print, that in our friend group Kulap Vilaysak is often the Dick Cheney to my George W. Bush. A lot of the edicts are coming down from her, but I’m the one that says them out loud. So I take a lot of heat for that. But as Jess knows, I’m a big softie, and I think the sort of gameplay of wanting to be told what to do, being scared of being on academic probation, is really fun. It’s an improv game we’ve been playing with our students, but it’s also quite real. Everyone is playing along.
I just did a live show for my other podcast How Did This Get Made — I didn’t even tell you this, Jessica — and we had a question and answer portion and a woman raised her hand and said, “This question is for Headmistress Raphael.” Like yes, we could have done a Patreon, something that is just extra content and that’s great because I subscribe to a lot of those and I think it’s wonderful for the hosts and artists to have more cash in their wallets. But I’m really proud of this because we have found a new framework for bonus content that’s much more interactive.
St. Clair: I don’t think you’re gonna find this stuff on Goop. And you know, I’m never gonna dry brush. That’s just not available to me. But I loved reading everyone’s responses to the book club prompt about what they were doing instead of cleaning: ‘I sat outside and drank a martini, I played with my son, I scrolled through TikTok.’
It feels like your mission is more to expand people’s lives than to close them in …
Raphael: Yes, and that’s very powerful to me. Life is messy. Life is unexpected. There’s fucking wildfires that wipe out an island. There are so many reasons for deep sadness and there’s no amount of creams to put on your face to get around the deep grief that is available to us at all times. But learning from each other, in whatever ways we have to offer, is why we started doing The Deep Dive. That was the moment we found ourselves in and we needed the connection.
To go back to the discussion of capitalism, and acknowledge that we do live in a capitalist society — do you think you could be charging more for the academy? You should see what Goop charges for things.
Raphael: I mean, listen. I don’t doubt it. We do want to grow. We want our listeners and our students to tell their friends about the podcast and the academy. But we want it to be accessible. We didn’t want to price out people who couldn’t afford the monthly tuition. We also have financial aid available. We feel really good about what we’re charging, because it’s what makes sense for us to be able to devote our time to it, but also it feels like the majority of our listeners can afford it.
St. Clair: Completely. But I’ll give you this: We have to pay for our eyelash extensions at the end of the day. That’s important.
A version of this story first appeared in the Aug. 23 issue of The Hollywood Reporter magazine. Click here to subscribe.
Best of The Hollywood Reporter