Don't Worry I'll Ask With Isaac Rochell

This is a proper see you later. Season One is officially wrapped, and it’s time to rest, reset, and gear up for Season Two. I’m beyond grateful for what we’ve built so far—the interviews, the conversations, the moments. And the wildest part? We’re just getting started.

Josh Barbour, better known as Dad Challenge Podcast, has built an online following by calling out family vloggers and influencers he believes exploit their kids against their will, whether they realize it or not. But is he just as guilty of bullying the people he criticizes? Isaac pushes Josh on where he draws the line, whether he’s gone too far, and how he views himself within the influencer industry.

Robyn DelMonte (better known online as @GirlBossTown) joins Isaac Rochell for a heartfelt and unfiltered conversation about grief, healing, relationships, and the wild ride of navigating a career that started on TIkTok. Robyn opens up about losing her mom before adulthood, how that experience shaped her career and outlook on life now that she’s older, and how she met her now boyfriend after bonding together at a grief camp. She and Isaac also dive into toxic relationship patterns, the pressures of dating in your late 20s, and Robyn’s ongoing love-hate relationship with TikTok’s algorithm.

Isaac opens up about his recent visit to the White House, and why it became one of the most polarizing moments of his public life.

After meeting press secretary Karoline Leavitt, Isaac posted a photo of the two of them together and faced a wave of backlash from his followers for doing it. The post, which was meant to signal open dialogue across party lines, was quickly misunderstood and criticized, forcing him to take it down within 45 minutes and reflect on how even the intent to listen can spark outrage.

What does it really mean to sit at the table with someone you disagree with? What responsibility comes with platforming controversial voices? And how do you navigate the tension between personal conviction and public reaction?

Grace O’Malley never planned to be in the middle of one of the most talked-about podcast breakups on the internet. But after her public falling out with Brianna Chickenfry and her dramatic exit from Barstool Sports, Grace found herself in unfamiliar territory: on her own, with everything up in the air. Isaac Rochell talks with Grace about the behind-the-scenes tensions that built up, and what it really felt like to have her personal friendship become internet entertainment. Grace shares how Alex Cooper’s call to host her own podcast changed everything after the fact, and learning to trust her own voice for the first time (even though that shit is cheesy as hell).

Senator Cory Booker sits down with Isaac Rochell for a wide-ranging conversation about what he’s hopeful about in America - and what’s breaking his heart. From systemic injustice to partisan division, Booker challenges the idea that we’re too far gone, arguing instead for a kind of moral leadership rooted in empathy, unity, and love. Drawing from his days as a college tight end, Booker uses football as an analogy to break down the state of American politics—arguing that the real danger isn’t left vs. right, but a team that’s too busy fighting in the huddle to come together and score. This episode is about moral leadership, spiritual integrity, and showing up like a teammate—even when it’s hard.

Dom Gabriel rose to fame on Netflix’s Perfect Match, but his story runs much deeper than reality TV. Dom—who we’re now calling Dominique after this episode—opens up to Isaac Rochell about growing up in Toronto with a single mom, the pain of being abandoned by his father, and how that experience shaped his drive to protect the people he loves.

He talks about becoming the man of the house at just 10 years old, why he paints his nails, and why real masculinity is about showing up—not showing off. Dom also reflects on growing up in a rough neighborhood—including getting stabbed outside a McDonald’s—how he found the strength to keep going after a near-death experience, and how it all shaped his definition of what it means to be a man.

Can people change? Brooke Schofield sits down with Isaac Rochell for her first in-depth conversation about the resurfaced tweets from 2013. This conversation isn’t about defending the past—it’s about owning it, learning from it, and pushing forward with humility.

When old tweets resurfaced—tweets Brooke posted at 16 defending George Zimmerman and the killing of Trayvon Martin—they triggered a wave of backlash that threatened to end her career. As the co-host of Cancelled, a podcast built around confronting culture and controversy, Brooke suddenly found herself on the receiving end of the very thing she often talks about: being cancelled.

Isaac brings his unique perspective as a Black man and father into the dialogue, creating space for accountability and honest reflection. Together, they talk about her upbringing in Arizona and how that environment shaped her early—and deeply misguided—views.

This isn’t a redemption arc, and it’s not a takedown—it’s a real-time look at how someone comes to terms with harm they’ve caused, learns from it, and tries to do better moving forward.

California Governor Gavin Newsom sits down with Isaac in downtown Los Angeles—just blocks from the ICE detention center at the center of recent protests—to discuss the immigration raids in and around the city and what he views as executive overreach by the Trump administration. Governor Newsom opens up about what’s really happening behind the scenes, the human cost of ICE tactics directed by the administration, and why he believes California is ground zero for the country’s future. He also shares what Democrats need to do differently, what Republicans are saying behind closed doors, and why he continues to engage with people who don’t agree with him—including Trump himself.

OG YouTuber Kyra Sivertson sits down with Isaac to talk through everything — from her rise with OKbaby, to the deeply personal breakup with Oscar, to the internet firestorm that followed. Kyra opens up about the infamous breakup video and how she ended up in a relationship with Preston, her former best friend’s partner. She addresses rumors of being in threesomes, losing her audience and identity as an influencer, and what it’s like to become a target of online snark pages. For the first time, she walks us through her side of the timeline and what she's learned in the chaos.