#108: A New Playbook for Standing Out in Advertising | Jack Westerkamp & Geno Schellenberger, Co-Founders of Breaking & Entering Media cover art

#108: A New Playbook for Standing Out in Advertising | Jack Westerkamp & Geno Schellenberger, Co-Founders of Breaking & Entering Media

#108: A New Playbook for Standing Out in Advertising | Jack Westerkamp & Geno Schellenberger, Co-Founders of Breaking & Entering Media

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 Breaking into advertising can be tough—and standing out once you’re in is even tougher. But two young creatives are showing there’s a new path.

In this episode, Jack Westerkamp and Geno Schellenberger, co-founders of Breaking & Entering Media, join Jason to share how they built one of the most energetic and attention-grabbing brands in the industry by combining cultural instinct, social-first thinking, and a healthy disregard for the “traditional” career playbook.

They share how a pandemic Zoom interview series turned into a movement: raising their first $50K from friends and family, moving to New York on a leap of faith, bootstrapping their first office, and building momentum through daily content like Whiteboard News, Super Bowl coverage, and agency tours. Jack and Geno also open up about learning to run a media company for the first time—from managing a team, to keeping content fresh, to navigating an industry where algorithms, attention, and expectations shift constantly.

Key Takeaways:
✅ Energy is a differentiator—fun and momentum cut through a jaded industry
✅ Great content wins when it’s built for the busy professional: fast, social-first, and useful
✅ When the fall isn’t far, risk becomes a competitive advantage for young marketers
✅ Trust, instinct, and consistency matter more than having a five-year plan

Memorable Moments:
💡 “If someone gives you 60 seconds, you better give them something worth it.”
💡 “We didn’t have a master plan—we just believed there was something there.”
💡 “It’s not illegal to have energy in advertising.”
💡 “Life’s not about finding yourself. It’s about creating yourself.”
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