Following a heated bidding war, Dear Media prevailed in keeping Claudia and Jackie Oshry’s juggernaut podcast “The Toast” in its fold. Sources say the sisters scored a massive three-year deal that also saw SiriusXM and iHeart gunning for the daily podcast, which has become the leading morning show with millennials and has already surpassed 100 million streams on Spotify alone.
The three-year pact, negotiated by WME and described by insiders as the Oshrys’ biggest yet, covers exclusive ad rights, promotion and production. The show, which runs five days per week, consistently outperforms “Good Morning America” — the most-watched network morning show — in the key Gen Z and millennial demographics, underscoring a measurable shift in daily audience habits away from legacy broadcast to digital-first platforms. YouTube currently streams the video format of “The Toast” exclusively.
“Claudia and Jackie have built ‘The Toast’ into a pop culture powerhouse with a loyal and engaged cult following of listeners and viewers,” Dear Media founder and CEO Michael Bosstick said. “At Dear Media, we are committed to amplifying visionary creators whose platforms extend far beyond audio, and this renewal reflects that mission as we continue our partnership and support ‘The Toast’s’ growth across entertainment, live experiences and more.”
The sisters said in a statement that the new deal will give them “the chance to take ‘The Toast’ further than we ever imagined.”
Since launching in 2018, the Oshrys are credited with helping shape what the modern-day morning show looks like and have cultivated a fiercely loyal audience that has turned them into one of digital media’s most powerful duos. What started as a daily ritual for millions of listeners has spawned a digital empire for the sisters. Since ‘The Toast’s’ inception, the sisters have launched Toast News Network (TNN), now home to a slate of hit shows featuring Josh Peck and Ben Soffer (“Good Guys”), Shannon Ford (“Probably a Podcast”) and “The Readheads Book Club” (Jackie Oshry, Margo Oshry, Dana Webman, Rebecca Rittenberg).
On the brand front, the sisters also created Spritz Society, a sparkling canned cocktail featured across TNN and on Bravo’s “Southern Charm.” In 2022, Bosstick took a financial stake in Spritz Society.
The sisters have branched out from the studio and hit the road with sold-out live events like Girly Swirlies Night Out!, expanding their reach beyond the podcast, which has become a force with young female audiences.
Attorney Jessica Marlow at Weintraub Tobin also represented the sisters in negotiations with Dear Media.
