Olivia Wilde
Armchair Expert with Dax Shepard
Armchair Umbrella
4.6 • 70K Ratings
🗓️ 29 June 2026
⏱️ 145 minutes
🧾️ Download transcript
Summary
Olivia Wilde (The Invite, Booksmart, and Don’t Worry Darling) is a director, actor, and filmmaker. Olivia joins Armchair Expert to discuss being raised by war-correspondent parents, growing up too fast on the Georgetown campus, and finding her footing at boarding school. Olivia and Dax talk about learning the wrong lessons in LA audition rooms, leaving The OC to chase movies, and making the jump from directing music videos to Booksmart. Olivia explains why the most personal work is usually the best work, how parenting teaches patience and humility, and why we need to relearn the art of disagreement.
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Transcript
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| 0:00.0 | Welcome, welcome, welcome to Armchair Expert. I'm Dax Shepherd. I'm joined by Lily Padman. Hello. And today we have Olivia Wilde. Olivia Wild. I'm such a fan. Yes, me too. I've talked about her a lot on here. I think she's such a gangster director. She directed, Don't worry, darling. The name that I... The name alludes you a few times in this episode. That I never get right in the interview. Book Smart. She also directed it was incredible. And then as an actor, Tron, Cowboys and Aliens House. And she's a new movie out, her third movie that she's directed, called The Invite, which you and I saw, |
| 0:39.3 | and we fucking love it so much. And we're doing a little The Invite Week. So this is guest |
| 0:46.5 | one of The Invite Week. Please enjoy Olivia Wild. This podcast is brought to you by Squarespace. |
| 0:53.5 | I feel like Spring always does this thing where you realize you've been thinking about something for a long time. |
| 0:58.4 | And suddenly it feels like, okay, maybe I actually do something with it. |
| 1:02.5 | Totally. It's less pressure, but more like readiness. |
| 1:05.9 | Yeah, like you've been sitting on an idea or a project or even just a perspective you care about. |
| 1:10.0 | And now you're like, |
| 1:11.0 | maybe this deserves to exist somewhere outside of my own head. In May being Mental Health |
| 1:14.9 | Awareness Month, there's already this broader conversation happening. People are more open, |
| 1:19.0 | more curious, more willing to engage. Which is where something like Squarespace comes in. It makes |
| 1:23.8 | that jump from idea to actual thing feel way less overwhelming. |
| 1:28.0 | You can build a site that looks good, works well, and actually reflects what you're trying to put out there. |
| 1:33.6 | And it's not just hypothetical. |
| 1:35.1 | Wabiwob literally used Squarespace to build our site. |
| 1:37.7 | Yeah, and Wabiwob is not trying to spend 40 hours figuring out web design. |
| 1:41.9 | It just worked. |
| 1:43.0 | Which is kind of the point. |
| 1:44.0 | So if you've been sitting on something and waiting for the right moment, this might be it. |
| 1:48.4 | Head to Squarespace.com slash Dax for a free trial. |
| 1:51.7 | And when you're ready to launch, use offer code Dax to save 10% off your first purchase of a website or domain. |
| 1:59.0 | He's an object expert. He's an... of a website or domain. |
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