Jessica St. Clair and June Diane Raphael’s podcast offshoot offers a subversive take on wellness

June Diane Raphael and Jessica St. Clair launched their podcast, The deep divein the midst of the pandemic, as a way to offset the loneliness and disconnection of the lockdown.

Each week, the two longtime friends and creative collaborators discuss their quest for joy amid a slew of challenges that are both relatable (motherhood, aging) and aspirational (finding the right pool attire for Miami Beach Pride). Creating the podcast helped the actresses emerge from their own post-lockdown void, and their motto: “Let Us Live!” — echoes in Apple reviews posted by their ever-expanding listening community.

When the abrupt work stoppage due to 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’s one of the craziest things I think I’ve ever said,” says St. Clair, laughing.

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 in film and television, Raphael first broke out after co-writing the 2009 screenplay. Bride Wars with Casey Rose Wilson and has played on Netflix for the past seven years Grace and Frankie; St. Clair co-created and performed in the US To play House – they added a certain level of artistry to it. The academy releases how-to videos on everything from cat-eye makeup to baking the perfect tomato pie, offers a “student portal” where they can submit courses, and is overseen by their newly formed Principal personas, whose inspiration, says Raphael, comes to them from outside. Adds St. Clair, “This started as my baby, but it was June’s idea to dive further into the school aspect and create these turn-of-the-century Headmistri characters like this — like any good marriage, we divided up our duties.”

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 shy about talking about a beauty procedure or discussing the power of a good highlight sequence. But they are deliberate in their focus on how women can open up their lives, rather than limiting themselves.

“God bless Gwyneth Paltrow and Goop and keep them healthy, but what I love about what we do is that it’s partly a satire on all those places that tell you if you just get or do this one thing everything will be alright come. says Raphael. “The promise of well-being or an ideal form of life as a woman is completely empty. We do these lessons, but we use them as a renewed commitment to each other and to our community.”

They point to the academy’s book club, which started 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 laziness, they asked the students to send in pictures of the clutter in their home, along with a brief description of what they did instead of cleaning. “It was so beautiful and healing to read,” says St. Clair. “It really changed us and the way we look at our own messiness. A lot of well-being is actually a product of capitalism that says you should always optimize. It’s nice to do things that are just about having fun.”

Here, the Headmistri talk about what they’ve learned from their podcast and from each other.

You launched the Academy on July 1st, about two months after the WGA strike and ten days before SAG; What do you think about that timing?

St Clair: I feel like we’re busier than ever.

Raphael: The timing of setting up the Academy, and now having a way to be creative, to have an outlet during all of this, to have complete control over something, was amazing.

St Clair: We started as small scrappers in New York, never got paid, and created our own content. There is something in it, when everything is taken from us, we always return to our roots and that makes me very happy. Because no matter what companies decide to do or not do, we will always have ourselves – and each other.

It seems like it also provides an outlet for other creatives you know and are friends with…

St Clair: That’s the beauty of the Academy: we’ve built this community. And we also appeal to our friends. God bless my best friend Josh Levine who is normally in the writers room of great shows and now happens to be free so he edits all of our videos. At one point, I saw him lay his head on his desk and quietly say to himself, “Oh, I’m in it for the long haul.”

I know you got the idea for all this before the strikes hit, but has it changed the way you approach your career? For example, you don’t necessarily wait for someone to give something the green light.

Raphael: Having what is essentially a subscription service for our own content, and having complete control over it without being accountable to anyone and being able to keep the profits – that’s empowering. My solidarity with my unions has never felt stronger because I’ve seen what it’s like to do something all by yourself, with no networks to give you permission or take most of the money. That really makes it a wonderful project to work on.

Tell me a little more about what the original vision was.

St Clair: What we really wanted to do, rather than say this is our content that we perform for you, we wanted to expand the Deep Dive experience, which is that we all be friends and learn how to get more joy out of life together . We have all of our live experiences, which are just as insane as our Pickleball tournaments. June handles this one, and more will follow.

Raphael: What I love about having founded one Institute of Higher Education – and of course our accreditation is being processed – is it the case that women in particular can get bogged down in this, can I do this? Can I call myself this or that? So of course it’s hilarious that we started a school, but it’s also very satisfying for the soul. It’s strangely healing. Yeah it’s kind of, yeah it’s super funny, but in its own subversive way I think it’s really good to take up space like this.

So being a director is obvious?

St Clair: June can easily fill this role. The students were initially very afraid of June, which makes sense because, like Dad, I often serve ice cream for dinner. In our group of friends, which also includes Casey (Rose Wilson) and Danielle (Schneider) from Bitch Sesh, June tells us what to do. We have strict dress codes for events. She told me at one point that my hair was too long. Now she has come back to that, but I am the only one in the group who can wear my hair that long. People would say, that’s strange, why let your friend tell you what to do? But people actually like being told what to do; it gives them a safe feeling between chaos and uncertainty.

Raphael: I will say, and I’m happy to put this in print, that in our group of friends, Kulap Vilaysak is often my George W. Bush’s Dick Cheney. Many edicts come from her, but I am the one who pronounces them aloud. So I need a lot of heat for that. But as Jess knows, I’m a big softie, and I think the kind of game where you want to be told what to do, and dread academic probation, is really fun. It’s an improvisational game that we played with our students, but it’s also very real. Everyone plays 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 have a Q&A section and a woman raised her hand and said this question is for Principal Raphael . Yeah, we could have done a Patreon, which is something that’s just extra content and that’s great because I subscribe to a lot of that and I think it’s great for the hosts and artists to have more money in their pockets. But I’m really proud of this because we’ve found a new framework for bonus content that’s much more interactive.

St Clair: I don’t think you’re going to find this stuff on Goop. And you know, I never dry brush. That’s just not available to me. But I enjoyed reading everyone’s reactions to the book club prompt about what they were doing instead of cleaning: “I sat outside and had a martini, I played with my son, I scrolled through TikTok.’

It feels like your mission is more about expanding people’s lives than trapping them in…

Raphael: Yes, and that is very powerful for me. Life is messy. Life is unexpected. There are goddamn wildfires destroying an island. There are so many reasons for deep sadness and there are no creams you can slather on your face to bypass the deep sadness that is always available to us. But learning from each other, in any way possible, is why we started doing The Deep Dive. That was the moment we were in and we needed the connection.

To return to the discussion of capitalism, And recognize that we live in a capitalist society – do you think you could charge more for the Academy? You should see what Goop charges for stuff.

Raphael: I mean, listen. I do not 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 pay people who couldn’t pay the monthly tuition fee in the price. We also have financial aid available. We feel really good about what we charge because it makes sense that we can spend our time on it, but it also feels like the majority of our listeners can afford it.

St Clair: Complete. But I’ll give you this: We have to pay for our eyelash extensions at the end of the day. This is important.

This story first appeared in the Aug. 23 issue of The Hollywood Reporter magazine. Click here to subscribe.