B. Simone has been known as the loud, funny, and sometimes polarizing figure who broke out on Vine before building a multi-platform brand.
Her name has trended as much for her jokes as for her controversies, from the 2020 plagiarism scandal tied to her book Baby Girl: Manifest the Life You Want, to the viral “9-to-5 job” comments, and a resurfaced 2017 interview clip that drew backlash for transphobic remarks.
Now, through her podcast Let’s Try This Again, Simone is taking control of her own narrative—leaning into the messy parts but turning them into meaningful conversations.
That evolution hasn’t been accidental. It’s been shaped in part by Kaitlin Dryden, the Los Angeles–based audio producer and engineer who has worked on over 15 shows and 700 episodes since 2021. Dryden has been key in channeling the comedian’s unpredictable energy into something polished.
“Organized chaos is the best way to think about it—have the structures in place to get the job done but then let her fly,” Dryden said on Tuesday, September 2. “What I love about B. is her authenticity. What you see on screen is what you get in real life.”
Simone first gained attention on Vine, where she mastered the art of making people laugh in six seconds. That comedic timing carried over into Instagram sketches, stand-up, and television appearances.
But as Dryden points out, podcasting offers a different layer. “B. does her due diligence in research beforehand, but she lets it ride in the moment,” Dryden explained. “She’s a comedian and does well reacting in real time. Plus, she’s very inviting and knows how to adjust herself to get guests to open up more.”
Episodes often swing from hilarious banter to deeply personal disclosures. Actress Jasmine Luv, for example, broke down in tears while sharing how rejection in Hollywood shaped her journey. The balance of laughter and vulnerability is what has kept Simone’s audience engaged, even after public missteps.
Part of that shift comes from the way Dryden runs the room. She compares it to working at a restaurant—welcoming guests, asking about their day, getting them comfortable before recording. “I’ve been in studios before where we were able to play music while the guest came in, and we’d research what they liked. Having their favorite album playing always disarmed them and made them feel at home,” she said.
That intentional hospitality matters most when first-time guests are in the chair. “I always reassure first-time guests to be as calm as possible and speak from the heart,” Dryden noted. “When guests ask for questions beforehand, I hesitate because then they start scripting themselves, and the tape never sounds good.”
This atmosphere has allowed Simone to show a different side of herself—one less concerned with going viral, and more focused on building trust.
That matters because Simone’s career has been defined as much by backlash as by her hustle. The plagiarism accusations in 2020 forced her to confront questions about authorship and credibility. The “9-to-5” comments led to accusations of being out of touch, especially after she later admitted she was cutting back on luxury spending to invest in her new app. And the resurfaced remarks from 2017 drew widespread condemnation for being transphobic.
Those moments could have ended a career. Instead, Simone is trying to address them by leaning into transparency. On Let’s Try This Again, she speaks openly about faith, surrender, and mistakes—topics that wouldn’t have landed during her Vine era.
Per EEW Magazine, in conversation with actress Bresha Webb, she admitted, “I surrender what I thought the idea of my life should be, my platform, everything. Whatever You [meaning God] want, at this point, is what I want. Because I don’t want to be outside of His will. The disobedience, it’s not worth it.”
Her willingness to bring both the jokes and the honesty is what makes the podcast resonate. Fans frequently leave comments like “this changed my outlook” or “this is what I needed to hear today,” according to Dryden.
The growth is ongoing. Simone and Dryden are already thinking bigger—live shows, spin-offs, and an app designed to expand the Let’s Try This Again experience. “B. thinks big and so do I,” Dryden said. “Nothing is off the table and we all see a massive movement happening around Let’s Try This Again. Live shows, spin-offs, bigger guests. The LTTA App is just the beginning.”