Honestly, the podcast world is a lot like middle school. There are the cool kids, the nerds, and then there are the power players who basically run the cafeteria. When news broke about the dear media the toast deal, it wasn’t just another press release. It was a statement. Claudia and Jackie Oshry didn't just sign a contract; they effectively anchored the "largest female marketplace in audio" for the foreseeable future.
People love to speculate. They want to know the "number." While the exact paycheck remains tucked away in a vault at WME, the details we do have tell a much more interesting story about where digital media is headed in 2026. This isn't just about a 60-minute daily show anymore. It’s a 360-degree ecosystem involving canned cocktails, live tours, and a literal network within a network.
The Three-Year Landmark: Breaking Down the Dear Media the Toast Deal
In October 2025, the industry held its breath. The original 2022 partnership was up, and rumors were swirling that heavyweights like SiriusXM and iHeartMedia were ready to back up the Brinks truck. They didn't. Instead, Dear Media CEO Michael Bosstick managed to keep the "Girly Swirlies" at home.
The new agreement is a massive three-year renewal. It’s a landmark deal because it grants Dear Media exclusive rights to advertising, promotion, and production. But if you think this is just about selling ad slots for Casper mattresses, you're missing the forest for the trees. This deal solidifies the "Toast News Network" (TNN) as a cornerstone of the Dear Media empire.
Why Claudia and Jackie Stayed Put
You've probably wondered why they didn't jump ship to a bigger corporate titan. It comes down to freedom. Dear Media isn't just a distributor; they are an IP incubator. The Oshrys didn't want to be employees; they wanted partners who understood that The Toast is a lifestyle brand.
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Remember Spritz Society? That sparkling cocktail brand isn't some separate side hustle. Michael Bosstick actually invested in it back in 2022. When your boss is also your business partner in your alcohol brand, the "deal" becomes much stickier than a standard talent contract.
What’s Actually Included in the Contract?
Most people think a podcast deal is just: talk for an hour, get paid. In this case, the dear media the toast deal covers way more ground.
- Production and Distribution: Dear Media handles the heavy lifting of getting the show onto every platform, including the massive expansion into Spotify’s video platform.
- Ad Sales: They have the exclusive right to sell the show’s inventory. This is huge because The Toast has one of the most engaged millennial female audiences in existence.
- The TNN Umbrella: This deal doesn't just cover the flagship show. It includes the "Toast News Network," which houses hits like The Good Guys (with Josh Peck) and Probably a Podcast.
- Live Events: Promotion for their "Girly Swirlies Night Out!" residency in NYC and other live tours is baked into the partnership.
The sisters have surpassed 100 million streams on Spotify alone. That kind of leverage allowed their attorney, Jessica Marlow, to negotiate what insiders call their biggest deal to date.
The "360 Model" and Why it Matters
Michael Bosstick has been vocal about how most podcast networks are "doing it wrong." He thinks they focus too much on audio. Dear Media focuses on the person.
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The dear media the toast deal is the blueprint for this. By integrating their social media strategy, their merchandise, and their live experiences, they've created a moat. It’s very hard for another network to come in and disrupt that because the infrastructure is so intertwined.
Honestly, the move from Los Angeles to Austin a few years ago also played a role. Being in a business-friendly environment allowed the network to scale quickly without the overhead of a legacy Hollywood studio.
Does it Change the Show?
Kinda, but mostly no. The "fast five" stories aren't going anywhere. But you’ll notice the production quality is getting sleeker. There’s a bigger push toward video, especially as YouTube becomes a primary search engine for podcast fans.
The deal basically ensures that the Oshrys have the resources to keep doing what they do without worrying about the back-end logistics.
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Moving Forward: Actionable Insights for Creators
If you're watching this deal from the outside and wondering how to apply it to your own brand, there are a few key takeaways. The days of being "just" a podcaster are over. You need to be a brand.
First, own your niche. The Toast doesn't try to appeal to everyone. They speak to millennial women who love pop culture. That specificity is what makes them valuable to advertisers.
Second, diversify your revenue. Don't rely solely on CPMs (cost per thousand listeners). Look at the Oshrys—they have a cocktail brand, a book club, and a merch line.
Third, prioritize community. The "Toasters" aren't just listeners; they are a cult following. They show up to live events and buy the products. That loyalty is the ultimate currency in a 2026 media landscape.
Your Next Steps:
- Audit your "stickiness": If your primary platform disappeared tomorrow, would your audience follow you to a new one? If the answer is no, start building an email list or a community platform immediately.
- Evaluate your partnerships: Are your current collaborators or networks invested in your long-term growth, or just your current download numbers? Look for "360" partners who understand your brand beyond the mic.
- Invest in video: As seen with this deal, video distribution (YouTube and Spotify Video) is no longer optional. Start filming your sessions, even if it's just a "behind-the-scenes" look at first.