Sophie Hunter is the founder of Sorella Creative and a social media strategist who's worked in fast fashion and now thrives as a freelancer. She joins us to talk about the BRUTAL reality of catastrophizing your way through a marketing career, and somehow succeeding anyway.

Sophie's story is a masterclass in authentic self-awareness. She shares why marketing yourself feels "icky" even when you're literally a marketer, how she went from Brutal by Olivia Rodrigo energy in fast fashion to Hand in My Pocket balance in freelance, and why she keeps a folder called "REMEMBER" filled with screenshots of nice comments for when imposter syndrome hits hard.

She breaks down the unexpected challenges of going freelance (spoiler: it's not the work, it's the micromanaging clients who want pink heart emojis), why ChatGPT can write your content but shouldn't, and why maybe your new year's resolution should be "boundaries", too. 

Plus, learn why the Smiths will always transport her back to her Tumblr days.

Brian Talbot's career is a masterclass in flexibility: from trying to be a "radio god" and selling ad time to becoming a voiceover artist and now a high-level Fractional CMO. He joins Tom to prove that in every role, especially sales and marketing, the most critical asset is simply being yourself.

Brian dives into why authenticity is the only differentiator left in the age of AI, and how he learned to embrace his own voice (literally, by inventing a "Brian's normal voice" character). We discuss why setting boundaries with clients is not only acceptable but essential for long-term partnership, and why CEOs need to stop viewing marketing as a black hole.

Plus, Brian breaks down his successful scaling framework, the Market, Message, and Map, and shares the tough conversations required to get leadership buy-in and turn a team's Net Promoter Score around.

Lisa Levey, a veteran reality TV producer and editor who's worked on Real Housewives of New Jersey, Bravo shows, and more, joins us to talk about the brutal reality of freelance life, why AI can't edit reality TV yet, and the stories nobody asks about.

Lisa's journey is a masterclass in sustainable creative hustle. She shares why living in constant fear is actually her superpower, how she's never had a traditional job, and why the process of making TV matters more than the finished product everyone obsesses over.

She breaks down what really happens behind the NDA-protected walls of reality TV, why everyone wants to know about the Housewives but nobody asks about the thousands of hours of footage it takes to make a 30-minute episode, and how she's built a career without ever feeling secure.

Hear Lisa get incredibly real about her side project, The Otherhood Collective, which tells stories about family, parenthood, and the paths that don't fit into society's neat little boxes. Plus, learn why her theme song is "Work Bitch" by Britney Spears and why that's actually perfect.

James Grixoni, a veteran actor and the Deputy Chad you loved on Twin Peaks: The Return, joins us to talk about the brutal necessity of self-marketing in a creative career, and the single, beautiful time that rule didn't apply.

James’ story is a masterclass in why "ignorance" and authenticity can be better tools than ambition. He shares a core B-Sides lesson: true collaboration means opening up your vision and letting the universe work for you, rather than being the "lead singer" who controls everything. He also breaks down how his authentic self, his true personal brand, showed up in the Lynch audition room, where he simply had to pass a "vibe check" based on who he was, not what he had marketed.

Hear James keep it incredibly real about the time he walked into an audition not knowing he was trying out for David Lynch, the beautiful, chaotic philosophy behind Lynch’s casting process, and why the ultimate career compliment is just being trusted to be yourself. Plus, hear about his current fan-fiction series, The Blue Rose.

Susan Wenograd's digital marketing career started at Circuit City, back when that was still a thing. Now she's the Sr. Director of Paid Media at Mixtape Digital and runs a thriving candle company on the side. Tom and Susan talk nightmare travel stories, managing ADHD in marketing, why clients who manage their own accounts are the hardest to win over, and how she accidentally built a business while grieving a friend.

Audrey Finney ran Hero Conf, a paid media conference, for years before trading digital marketing for Memphis barbecue, craft beer, and Social Cantina. Now she owns 10+ restaurants through Finney Hospitality Group, plus a car wash!

We talk about the stuff that shaped her career: navigating feedback without letting it destroy you (thanks, Tim McGraw), the Hero Conf attendees who tried to cancel her over a panel, and why being book smart means nothing if you can't read a room. Plus: the time she had to emergency-MC an event at 22 years old despite hating the spotlight, why restaurant people can do anything, and the Peter Principle trap that kills subject matter experts.

Audrey keeps it real about diversity efforts nobody saw, the energy-zapping relationships you need to cut loose, and why solid C students can become business geniuses. 

Fair warning: Contains strong opinions about yogurt parfaits, possums, and whether Taylor Swift's new album slaps.

Megan Maguire left a Senior VP gig at a major agency to start her own thing in 2024. "Probably crazy," she admits. But also? No regrets.

We talk about the stuff LinkedIn won't let you say out loud: the daily anxiety of betting on yourself, why her house painter uncle's "there's only one way to paint a house" philosophy shaped her entire career, and how she became the self-proclaimed Lobster Queen of Martha's Vineyard (five-pounders in an hour, baby).

Megan keeps it real about agency politics, the myth of linear success, and choosing your own flavor of crazy as a founder. 
Plus, the restaurant-to-marketing pipeline remains undefeated on this show.

Fair warning: if you're thinking about making a leap, this one might be the nudge you need.

On this week's episode, Tom sits down with Aaron Levy to dive into the messy, human side of agency life that nobody talks about at conferences. They explore:

• Aaron's career soundtrack featuring Wu-Tang and Spice Girls wisdom
• Pitch horror stories, including Aaron's legendary meltdown where he turned into a "straight up cartoon character"
• Why success isn't measured by how many people you manage but don't actually know
• Why hiring restaurant workers is the ultimate agency hack
• The transformative power of executive coaching when you're tired of being the office curmudgeon

On this week's episode, Tom and Dean discuss how Dean built his online personal training business, Dean Turner Training, from the ground up, one tweet at a time. They chat about the surprising pros of getting roasted, why the pursuit of perfection is often just fear in disguise, and how Dean’s most successful clients are the ones with an internal fire, not an external deadline. They also get into why Dean doesn't work with brands, why his body is his business card, and how Dean discovered a way to find a blue ocean in the red waters of online fitness. 

(Make sure you start with Part 1!)
In this two-part episode, Tom sits down with Kayla Kurtz, VP of Sales at Forthea, to dive into the wild world of agency pitching and sales war stories. Kayla shares her career soundtrack (heavy on Taylor Swift and Paramore) and breaks down why she's stuck with agency life across five different shops. They swap horror stories about prospects who ghost after demanding urgent timelines, the awkwardness of remote pitching, and that time Cintas tried to recruit Kayla mid-pitch. Plus, Tom admits he still can't pronounce "Chappell Roan" correctly because apparently no one says it out loud in his circles.