New York: Claudia and Jackie Oshry, the dynamic sister duo behind The Toast Podcast, have officially inked a three-year deal to continue under the umbrella of Dear Media. This move marks a major milestone for the popular daily show and underscores how top podcasts are making power moves in today’s media landscape.
The Deal in a Nutshell
According to Variety, the new agreement ensures that The Toast remains with Dear Media for at least the next three years. Industry sources say competing buyers like SiriusXM and iHeart had also shown interest, making the deal a competitive win for Dear Media.
As part of the agreement, Dear Media retains exclusive advertising rights for all shows under the Toast News Network. The sisters also step into advisory roles across the network’s growth and future content direction.
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Why This Matters
1. Stability & Growth for The Toast
Podcast creators often face uncertain revenue or distribution deals. For Claudia and Jackie, signing a multi-year contract gives them breathing space to plan, experiment, and grow without constantly worrying over “what next?” It means more security and potentially more creative freedom under a trusted partner.
2. Strengthening Dear Media’s Podcast Roster
Dear Media continues expanding its hold in the podcast realm. Adding The Toast solidifies its position in the pop culture and news commentary niche, making it more attractive to advertisers and listeners alike.
3. Strategic Influence & Network Expansion
The Oshry sisters’ advisory roles hint at something bigger: they won’t just be talent, but architects. Their insight into their audience, trends, and format can inform new launches or programming decisions across Dear Media’s portfolio.
Also, by securing exclusive ad rights across Toast’s network, Dear Media locks in monetization potential – a smart move in an industry where ad revenue is king.
What to Expect Next
For listeners, the deal means The Toast likely stays on familiar platforms, with consistent quality and output. But it also opens doors for new formats, spin-offs, guest expansions, or crossovers within Dear Media’s ecosystem.
Behind the scenes, the sisters will likely work more closely with Dear Media on marketing, creative direction, and even show strategy. Their voices won’t just be heard in episodes — they’ll shape the network’s trajectory.
A Human Take
What makes this deal especially exciting is that Claudia and Jackie are branching deeper into ownership, not just hosting. Many podcast hosts remain voices; fewer become stakeholders or decision-makers. Their transition signals growth not only for them personally, but for the medium: that podcasters can become partners, not just talent.
Imagine 2028: The Toast might have spawned sub-shows, branded series, or even new podcasts under the Oshry-Dear Media joint vision. This deal isn’t just about staying put — it’s about scaling upward.
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The Toast’s new three-year deal with Dear Media brings assurance, ambition, and fresh opportunity to one of podcasting’s big names. For fans, it means continuity with a chance for exciting evolution. For industry watchers, it’s proof that smart deals — not just good content — will shape where podcasting heads go next.
Stay tuned to this space — I’ll be updating you on new episodes, spin-offs, and behind-the-scenes moves. And of course, subscribe to The Toast if you haven’t — it’s poised for an even bigger rise.
