Kristin Cavallari has signed a multi-year, eight-figure podcast deal with Dear Media to expand her “Let’s Be Honest” show, a development that comes amid renewed public tension with her ex-husband Jay Cutler over their divorce settlement. The agreement, reported on October 14, 2025, marks a significant milestone in Cavallari’s media career, highlighting her growing influence in the podcasting industry while navigating ongoing personal disputes.
The deal, valued at over eight figures, will allow Cavallari to broaden the reach of her podcast, which launched in 2023 and focuses on dating, relationships, friendships, and family dynamics. In statements at the time of the podcast’s inception, Cavallari expressed her enthusiasm for the project, noting that she sought a new challenge after the success of her “Back To The Beach” rewatch podcast. She emphasized the freedom to discuss diverse topics and invite guests who could inspire and entertain listeners, aiming to provide real takeaways and laughter.
Cavallari’s journey into podcasting has been complemented by a multi-city tour, where she shared personal dating anecdotes and insights, which was later documented in the E! docu-series “Honestly Cavallari: The Headline Tour,” premiering in June 2025. This expansion into touring and television reflects her ability to leverage her reality TV background, dating back to “Laguna Beach,” into a multifaceted entertainment career. Her openness about post-divorce life and co-parenting has resonated with audiences, adding depth to her public persona.
The timing of this lucrative deal coincides with heightened scrutiny of Cavallari’s past marriage to former NFL quarterback Jay Cutler. The couple, married from 2013 to 2020, finalized their divorce in 2022 and share three children: Camden, 13, Jaxon, 11, and Saylor, 9. Sources previously attributed their split to Cutler’s “unmotivated” demeanor after retirement, but recent attention has shifted to the financial terms of their settlement, sparking public debate.
In August 2025, Cutler alleged on his “Take It Outside” podcast that Cavallari misled her audience by claiming she “didn’t get a penny” from the divorce. He condemned her statements as “irresponsible” and “borderline slander,” stressing that no Tennessee judge would permit such an unequal division of assets. Cutler, who earned approximately $127.9 million during his 12-year NFL career, referenced a 67-page divorce decree to support his claims, underscoring the legal complexities involved.
Cavallari has not publicly addressed Cutler’s allegations, and she was observed evading questions on the matter in September 2025. This silence adds intrigue to the situation, as fans and media speculate on potential responses in future podcast episodes. The conflict underscores the challenges of blending personal narratives with professional endeavors, especially in the context of high-profile divorces and co-parenting arrangements.
Looking ahead, the eight-figure deal positions Cavallari for further growth in the competitive podcasting landscape, potentially leading to new collaborations or media ventures. However, the unresolved tensions with Cutler could impact their co-parenting dynamics and public image, highlighting the delicate balance between personal transparency and professional ambition. As Cavallari continues to share her experiences, her story serves as a case study in modern celebrity, where career achievements often intersect with private struggles.