A Good Day Series: Fast, Fun, and Very Much Not Boring (Breaking and Entering Media)
A Good Day is back again. Because when you think about it, a life well-lived is simply a collection of meaningful moments. Our series returns to spotlight the people and companies leading with purpose and doing good, one good day at a time.
Geno (left), Jack (right) and Ellie, producer and first ever full-time hire at B&E (middle).
Breaking and entering isn’t about permission; it’s about taking space. It’s what happens when you stop waiting to be let in and start building your own way forward.
If you’ve spent any time on ad-industry internet lately, chances are you’ve crossed paths with Geno Schellenberger, Jack Westerkamp, and the Breaking & Entering crew. Their content moves quickly, doesn’t take itself too seriously, and somehow still manages to convey something meaningful about advertising, creativity, and the people involved.
For our A Good Day series, we caught up with Geno and Jack to talk culture, creative leadership, business pressure, and why “making your own table” matters more than ever.
Breaking & Entering has a unique tone, fast, fun, and creative. How did that identity form?
Breaking & Entering’s tone didn’t come from a brand deck or positioning exercise. It came from who they are as people.
Geno and Jack shared that the energy behind the brand is rooted in growing up together, sharing the same sense of humor, and leaning into what feels natural and sustainable to create.
“If you try to force a tone that isn’t authentic, you burn out quickly. Staying true to ourselves makes it easier to keep creating, and people can feel that.”
A culture that sticks usually mirrors the humans behind it.
If you had to describe your culture as a person, who would it be and why?
When asked to personify the Breaking & Entering culture, Geno didn’t hesitate: Step Brothers energy.
Shake-and-bake with a little John Cena optimism mixed in, courtesy of Jack.
It’s playful, slightly unhinged, and deeply collaborative, the kind of environment where creativity feels lighter, not heavier.
How do you balance authentic creative culture with the business pressures of scaling?
The hardest part of building a creative company? Balancing the business without crushing the work.
Geno and Jack were candid about early mistakes typically made in the industry: prioritizing monetization too soon, letting pressure creep in, and watching creativity suffer as a result.
They shared that pressure kills creativity.
“When you over-index on the business side, the content suffers, and that starts a doom spiral.”
They learned early on that if you focus on making the best product possible, sponsors and partners will come. They’re sticking with content first always.
What do you want people to feel when they engage with your content, and how do you design for that?
“We want it to feel like a roller coaster of emotions, excitement, confusion, fear, optimism, all wrapped around genuinely useful information. Advertising and marketing content doesn’t have to be dry. If people are entertained, they stay. And if they stay, they learn.”
What makes a standout creative leader in 2026?
“Someone who champions good work that’s disrupting, interesting, or entertaining.”
But just as important is creating an environment where people feel safe to be themselves, make mistakes, and experiment. Vulnerability and POV matter more than ever before.
What is one lesson you’d tell new talent about “getting a seat at the table”?
“Make your own table, create your own seat.”
One of Geno and Jack’s strongest pieces of advice for new talent: stop stressing about “getting a seat at the table.”
The knowledge gap in the marketing and advertising industries is smaller than people think. Tools are accessible. Platforms are open. Perspective is powerful.
If you have a point of view and you’re willing to build something, you can get there faster than you expect.
What newsletters, creators, or media do you both follow religiously? - If any?
Industry voices like Rob Mayhew and Joe Meier stay on the radar, along with creator-focused newsletters like Tube Filter that blend creator news and brand storytelling into one feed.
What tool, app, or technology do you use that most people wouldn’t guess?
Jack is a huge Notes app guy. iPhone calendar too. (We know, hot take) He shared that Canva is a big one for Breaking and Entering creatively, as well as CapCut.
Geno said his most used app is Snapchat… for the stories.
In 5 years, what do you hope Breaking & Entering has influenced about the industry?
“We hope we’ve helped make people want to work in advertising and made those already in it feel proud again. A little more positivity, a little less pressure. Just reminding people that this industry can actually be fun.”
No founder story is complete without the team. Geno and Jack gave flowers to Ellie McCarron, Ross Yenrich, and Jack Williamson, the crew helping Breaking & Entering grow fast without losing its soul.
When you protect creativity, build culture around real humans, and stop waiting for permission, good things follow, sometimes faster than you expect.
THIS or THAT with Geno & Jack:
Big idea brainstorm OR tight deadline adrenaline?
G: Big Idea Brainstorm
J: Tight Deadline Adrenaline
Structured to-do list OR organized chaos?
G: Organized Chaos
J: Organized Chaos
Big team energy OR tight-knit crew?
G: Big Team Energy
J: Big Team Energy
Big launch day OR slow, steady growth?
G: Slow, Steady Growth
J: Slow, Steady Growth
Celebration dinner OR crashing on the couch?
G: Crashing on the Couch
J: Celebration Dinner
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