Kristin Cavallari Makes Money Move After Ex Jay Cutler Jail Stint

Kristin Cavallari continues to thrive following the end of her union with Jay Cutler. 

The TV personality recently secured a multi-year deal for her podcast. This significant achievement occurred just over a week after her ex-husband completed his prison stint in Tennessee.

Kristin Cavallari and Jay Cutler tied the knot in 2013 and welcomed three children before their union crashed in 2020. They finalized their tumultuous separation in 2022, but that hasn't stopped them from throwing jabs at each other.

According to new reports, Cavallari's collaboration with Dear Media continues with a multi-year deal that exceeds seven figures for her "Let's Be Honest" podcast. Michael Bosstick, founder and CEO of Dear Media, confirmed the news, raving about Cavallari's years-long success.

"We're thrilled to continue our partnership with Kristin. From the first episode, 'Let's Be Honest' has connected with audiences—many of whom have grown up alongside her—through her signature honesty and relatability," Bosstick gushed. He applauded Cavallari, noting his excitement for her next chapter.

Cavallari's podcast debuted in the fall of 2023, following her "Laguna Beach" rewatch podcast, according to Variety. At the time, the host confessed that she used to keep the public at arm's length. However, her "Let's Be Honest" podcast allowed her to connect with fans in a comfortable space.

When Cavallari launched her podcast, she noted that it would offer a refreshingly honest take on her life and feature guests she personally chose. She vowed that everyone who appeared on her show would be someone fans would love and get valuable takeaways from.

True to her words, Cavallari has welcomed several A-listers on her podcast, who have shared their vulnerabilities with her audience. The list included NFL superstar Travis Kelce, The Bella Twins (Nikki and Brie Garcia), fashion designer Rebecca Minkoff, and renowned chef Bobby Flay.

The popularity of Cavallari's show skyrocketed over the last two years to the point that she launched a multi-city tour. She took her podcast on the road to connect with guests and fans, but her successes don't end there.

In 2026, Cavallari is reportedly set to participate in the "Laguna Beach" reunion, both as a star and an executive producer.

Cavallari's multi-year deal was announced over a week after her ex-husband, Cutler, completed his stint at a Tennessee jail. PEOPLE confirmed that he was released early on Wednesday, October 1, after serving two and a half days in custody.

The short jail sentence began on September 29 after Cutler pleaded guilty to a misdemeanor DUI charge and received a four-day sentence and a $350 fine. The Blast covered the story, reporting that he was punished for an incident that occurred on October 17, 2024.

Cutler had rear-ended another vehicle and allegedly tried to cover up the incident by offering the other party $2,000 to avoid police involvement. When authorities arrived, they noted the former NFL player checked all the boxes for DUI, but he reportedly refused to undergo a sobriety test.

A month before reporting for his brief stint in jail, The Blast shared that Cutler had called out his ex-wife for allegedly lying. He explained on an August episode of the "Take It Outside" podcast that he couldn't have divorced Cavallari without giving her a single penny.

Cutler stressed that it wasn't logical for a Tennessee judge to consider his illustrious NFL career, the length of his marriage, and his three kids, and then decide to award Cavallari nothing. Although he refused to reveal the sum she allegedly earned, he noted it was enough to keep her settled for life.

The former athlete's words followed Cavallari's claims that her successes weren't built with her ex-husband's support. "I have never gotten a penny from my ex-husband. I didn't get any money from our divorce," she told fans on a podcast episode.

Cavallari's claims about not receiving money from her ex-husband weren't the only allegations she has dropped since their divorce. The Blast reported in 2024 that she reflected on her weight loss while filming the "Very Cavallari" show.

The reality TV star claimed she became "skin and bones" despite eating healthy because of her tumultuous relationship with Cutler. "I was so unhappy and so stressed out. And you guys, that was just stress. That was being in a really unhappy marriage," Cavallari told fans.

Cavallari added that she "looked like sh-t" and was shocked when she saw throwback pictures of herself. She implied divorce was the best thing for her mental and physical well-being, noting that she looked and felt "so much better now."