500 Episodes Strong: Rob Schwartz and the Moment that Sparked Breaking & Entering Advertising
Five hundred episodes. That’s where Breaking and Entering Advertising just landed.
In podcast years, that’s ancient. Most shows don’t make it past 20. Fifty means staying power. Five hundred means legacy.
To mark the moment, host Geno Schellenberger called in Rob Schwartz, the ad world’s self-appointed coach and one of the people who helped kick this whole thing off. Schwartz, the former TBWA\Chiat\Day Executive Coach, is the kind of creative who’s seen everything, done everything, and still shows up hungry. He’s also the one who convinced Geno to take the podcast full time, turning it from a scrappy side project into a real-deal media company on Madison Avenue.
The two sat down to unpack what they’ve learned, from 27 years in the business, from 500 conversations behind the mic, and from the chaos that is advertising itself.
Lesson One: Show Up
Schwartz started with something simple. “Show up,” he said.
Not metaphorically. Physically. Mentally. Be in the room.
He tells this story from a Pepsi Izzy pitch. There was a young copywriter hanging around the office, just close enough to get noticed. Schwartz saw something funny scribbled on the wall, a line that would end up driving the campaign across TV, trucks, and social. The kid got to pitch it himself.
“That doesn’t happen over Zoom,” Schwartz said. “Opportunity shows up when you do.”
Lesson Two: The Idea Is in the Field
Schwartz hates briefs that live and die in PowerPoints. His advice? “Go take the factory tour.”
When he was working on Nissan, he and his team ditched the boardroom for the design floor. They talked to the people who actually built the cars. Out of that came the line that defined the Xterra: Everything you need. Nothing you don’t.
Same approach with McDonald’s. His team spent time in French McDonald’s, watching kids text each other while sitting shoulder to shoulder. “The idea,” he said, “is often in the restaurant.”
Lesson Three: Born from Necessity
The origin story of Breaking & Entering isn’t glamorous. It’s pandemic survival.
March 2020. Geno’s a senior at the University of Illinois, freshly hired at Edelman, and then the world shuts down. The start date gets pushed nine months.
“I was stuck in my parents’ basement,” he said. “So I started hitting record.”
He cold-emailed creatives, asked for advice, and used a snowball trick, every guest had to name three more people to talk to. One of those early guests was journalist Brian Breaker.
By the end of the year, the show had a mission: help people break in and thrive in advertising. The name came from a friend who said getting a job in the industry felt like “pulling off a grand heist.”
Four years later, it’s more than a podcast. Breaking & Entering Media is now a creative company telling the good stories about a business that can be cynical and chaotic. Schwartz calls it “the MTV of B2B.”
Lesson Four: Be a Sniper, Not a Shotgun
When the talk turned to breaking in today, both agreed: focus is everything.
“You can’t spray your portfolio everywhere,” Geno said. “You need to pick your target. Be a sniper, not a shotgun.”
The 500th Episode
The milestone episode is part career seminar, part confessional. It’s two people who love this business dissecting what keeps them in it — the obsession, the lessons, the mistakes, the wins.
They talk about the future, too: SNL-style variety shows, city tours for aspiring creatives, and the next wave of Breaking & Entering projects that blur the line between media and movement.
“Five hundred is incredible,” Geno said. “But we’re just getting started.”
Listen to Episode 500 on YouTube or Spotify. Rob Schwartz’s full list of 27+ lessons is on his Substack, Rob Schwartz Helps, and on LinkedIn.
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