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.

In this 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.

In this episode, Tom sits down with Jeff Perkins, CEO of Soundstripe, to talk about gaming LinkedIn to escape career purgatory. Jeff shares how changing his title from "Marketing Manager" to "Executive Leader" suddenly had recruiters calling about CEO roles instead of lowball offers. They discuss the brutal reality of transitioning from CMO to CEO and why Soundstripe built an AI music supervisor. (Spoiler: because scrolling through 58,000 songs to find the perfect track is soul-crushing.)

In this no-holds-barred episode, Kent Zimmerman and Tom Hootman dive deep into the gritty realities of the retail world. From the rise and fall of malls to the chaotic dance with digital transformation, expect candid stories and hard truths. Kent shares his in-house marketer perspective, especially on what makes agency sales pitches stand out or fall flat.

Jeff Allen, CEO at OuterBox, gets real about the messy truth of leadership transitions—the trust you have to rebuild from scratch, the pitches that go sideways in unexpected ways, and why putting your team's wins before your own ego actually works. No corporate fluff, just the unvarnished stories that shaped his career.

What you'll get:
-Why new leadership is basically starting over (even when you think it isn't)
-The pitch moment that defied expectations—and still led to success
-How to win by making other people look good
-Real talk for young professionals trying to break through

Less LinkedIn motivation, more honest conversation about what actually happens when you're figuring it out as you go.