Rony Castor, Group Creative Director at BarkleyOKRP, joins the Breaking and Entering Advertising Podcast to break down his journey from getting laid off in 2008 to leading award-winning campaigns.

Rony shares how Mad Men pushed him toward advertising, why portfolio school still matters, and what it actually takes to “figure it out” as a creative. He walks through his time at agencies like FCB, DDB, Havas, and Goodby, and the campaigns that shaped his career including “Not a Gun” and “Driving While Black.”

This episode covers breaking into advertising with no clear path, why it took 5–6 years to feel confident as a creative, the importance of having a strong partner, how great ideas actually get made under pressure, what separates good creatives from great ones, and why knowing how to get things done matters more than anything.

If you are trying to break into advertising or level up your creative career, this is a direct look at what the path really looks like.

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🏆 Check out the Crowbar Awards to break into advertising https://www.crowbarawards.com/

🤝 Work With Us - Email: [email protected]

What does it actually take to break into advertising in 2026?
Andre Gray, Chief Activation Officer and Head of Culture & Entertainment at Havas Lynx New York, joins the Breaking and Entering Advertising podcast to unpack why the old playbook is dead, why most agencies are behind, and why not knowing everything might be your biggest edge.
From growing up in San Francisco to sleeping on a couch in Paris chasing a career in advertising, Andre shares the real story of how he broke in and what he’s learned as a creative leader navigating an industry that’s changing in real time.
This conversation dives into the gap between culture and corporate marketing, why we no longer live on the same internet, and why emerging media is often more “true” than legacy platforms.
Andre also breaks down:
Why advertising won’t exist the same way in the next few years
The difference between objective truth and what agencies sell
How young talent can win in a system that hasn’t caught up
The two skills that matter most when breaking in today
Why relatability and trust beat resumes every time

More from Breaking and Entering Media:💼 Follow on LinkedIn⁠ https://www.linkedin.com/company/breaking-entering-podcast/⁠📖 Read our Publications⁠ https://www.breaking-entering.com/blog⁠💬 Join our Unlocked GroupMe⁠ https://groupme.com/join_group/102437585/xg5Z5tei⁠✉️ Subscribe to The Vault⁠ https://breakingandenteringadv.substack.com/⁠📹 Subscribe to our :60 Advertising News Videos⁠ https://breakingandentering.beehiiv.com/⁠🏆 Check out the Crowbar Awards to break into advertising⁠ https://www.crowbarawards.com/⁠🤝 Work With Us - Email: ⁠[email protected]⁠

Steve Scutellaro, CEO of StrawberryFrog, joins the Breaking and Entering Advertising Podcast to talk about the agency’s next chapter and the future of independent shops.

In this episode, Steve shares how the 26-year-old agency operates as a boutique, senior-led team working closely with brands. He discusses how agencies can stay relevant as AI and self-service media platforms reshape the industry, why smaller agencies can still compete with holding companies, and what he is focused on in his first months as CEO.

Steve also offers advice for the next generation entering advertising, including why writing remains the most important skill and why starting your career at a smaller agency can accelerate learning.

More from Breaking and Entering Media:

💼 Follow on LinkedInhttps://www.linkedin.com/company/breaking-entering-media 

📖 Read our Publications https://www.breaking-entering.com/blog

💬 Join our Unlocked GroupMe https://groupme.com/join_group/102437585/xg5Z5tei

✉️ Subscribe to The Vault https://breakingandenteringadv.substack.com/

📹 Subscribe to our :60 Advertising News Videos https://breakingandentering.beehiiv.com/

🏆 Check out the Crowbar Awards to break into advertising https://www.crowbarawards.com/

🤝 Work With Us - Email: [email protected] 

On this episode of The Breaking and Entering Podcast, Geno sits down with PJ Pereira. He's the founder of Silverside AI, the agency behind some of the most controversial ads to come out this past year - the Coca-Cola holiday spot, and the Svedka Super Bowl spot. The two spots have one thing in common - they're both fully generated by AI.

Pj has heard all the comments, and he joins us to give his point of view. Tune in for Breaking and Entering's most loaded interview yet.

More from Breaking and Entering Media:💼 Follow on LinkedIn⁠ https://www.linkedin.com/company/breaking-entering-podcast/⁠📖 Read our Publications⁠ https://www.breaking-entering.com/blog⁠💬 Join our Unlocked GroupMe⁠ https://groupme.com/join_group/102437585/xg5Z5tei⁠✉️ Subscribe to The Vault⁠ https://breakingandenteringadv.substack.com/⁠📹 Subscribe to our :60 Advertising News Videos⁠ https://breakingandentering.beehiiv.com/⁠🏆 Check out the Crowbar Awards to break into advertising⁠ https://www.crowbarawards.com/⁠🤝 Work With Us - Email: ⁠[email protected]⁠

AGENCY BREAK IN: THE LARGEST AGENCY IN SAN DIEGO - THE SHIPYARDMore from Breaking and Entering Media:💼 Follow on LinkedIn⁠ https://www.linkedin.com/company/breaking-entering-podcast/⁠📖 Read our Publications⁠ https://www.breaking-entering.com/blog⁠💬 Join our Unlocked GroupMe⁠ https://groupme.com/join_group/102437585/xg5Z5tei⁠✉️ Subscribe to The Vault⁠ https://breakingandenteringadv.substack.com/⁠📹 Subscribe to our :60 Advertising News Videos⁠ https://breakingandentering.beehiiv.com/⁠🏆 Check out the Crowbar Awards to break into advertising⁠ https://www.crowbarawards.com/⁠🤝 Work With Us - Email: ⁠[email protected]⁠

In this episode, we sit down with Joaquín Mollá, co-founder and Chief Creative Officer of The Community. From Buenos Aires to building one of the most culturally influential agencies in the world, Joaquín shares how identity, instinct, and artistic obsession shaped his path.

Recognized as a Hispanic Heritage Month Icon by The Advertising Club of New York, Joaquín reflects on what it really means to create work that resonates across cultures without diluting its soul. We talk about the power of community in creativity, the difference between trend chasing and truth telling, and why some of the industry’s biggest awards from Cannes Lions to D&AD matter less than the human impact behind the work.

This is a conversation about legacy, leadership, and building ideas that move people, not just metrics.

More from Breaking and Entering Media:💼 Follow on LinkedIn⁠ https://www.linkedin.com/company/breaking-entering-podcast/⁠📖 Read our Publications⁠ https://www.breaking-entering.com/blog⁠💬 Join our Unlocked GroupMe⁠ https://groupme.com/join_group/102437585/xg5Z5tei⁠✉️ Subscribe to The Vault⁠ https://breakingandenteringadv.substack.com/⁠📹 Subscribe to our :60 Advertising News Videos⁠ https://breakingandentering.beehiiv.com/⁠🏆 Check out the Crowbar Awards to break into advertising⁠ https://www.crowbarawards.com/⁠🤝 Work With Us - Email: ⁠[email protected]⁠

This week, we are breaking into FIVE difference advertising agencies across the city of San Francisco. Today, Goodby Silverstein & Partners, one of the most iconic ad agencies of the century. We sit down with Chief Creative Officer, Margaret Johnson to talk the impact GSP has had on the industry. Every agency we visited this week was born out of GSP. At least one founder from Erich & Kallman, Barrett Hofherr, BSSP, and Venables Bell + Partners worked at Goodby at one point in their career. Chew on that!

More from Breaking and Entering Media:💼 Follow on LinkedIn⁠   / ⁠  📖 Read our Publications⁠ https://www.breaking-entering.com/blog⁠💬 Join our Unlocked GroupMe⁠ https://groupme.com/join_group/102437...✉️ Subscribe to The Vault⁠ https://breakingandenteringadv.substa...📹 Subscribe to our :60 Advertising News Videos⁠ https://breakingandentering.beehiiv.c...🏆 Check out the Crowbar Awards to break into advertising⁠ https://www.crowbarawards.com/⁠🤝 Work With Us - Email: ⁠[email protected]⁠

This week, we are breaking into FIVE difference advertising agencies across the city of San Francisco.

Today, Venables Bell and Partners, whose guiding principle is "Do right by people."

We sit down with Founder and Chairman, Paul Venables, and Partner and Chief Creative Officer to talk forging successful young creatives, advancing advertising from San Fran, and more.

More from Breaking and Entering Media:💼 Follow on LinkedIn⁠ https://www.linkedin.com/company/breaking-entering-podcast/⁠📖 Read our Publications⁠ https://www.breaking-entering.com/blog⁠💬 Join our Unlocked GroupMe⁠ https://groupme.com/join_group/102437585/xg5Z5tei⁠✉️ Subscribe to The Vault⁠ https://breakingandenteringadv.substack.com/⁠📹 Subscribe to our :60 Advertising News Videos⁠ https://breakingandentering.beehiiv.com/⁠🏆 Check out the Crowbar Awards to break into advertising⁠ https://www.crowbarawards.com/⁠🤝 Work With Us - Email: ⁠[email protected]⁠

This week, we are breaking into FIVE difference advertising agencies across the city of San Francisco.

Today, BSSP. A small shop tucked away in Sausalito, the idyllic outskirts of San Francisco.

We sit down with CEO Tracey Faux Pattani, Partner & Executive Strategy Director Jake Bayham, and Partner & Executive Creative Director Sinan Dagli, to talk bouncing back, winning business and a few teasers for our boat ride later on in the day.

More from Breaking and Entering Media:💼 Follow on LinkedIn⁠ https://www.linkedin.com/company/breaking-entering-podcast/⁠📖 Read our Publications⁠ https://www.breaking-entering.com/blog⁠💬 Join our Unlocked GroupMe⁠ https://groupme.com/join_group/102437585/xg5Z5tei⁠✉️ Subscribe to The Vault⁠ https://breakingandenteringadv.substack.com/⁠📹 Subscribe to our :60 Advertising News Videos⁠ https://breakingandentering.beehiiv.com/⁠🏆 Check out the Crowbar Awards to break into advertising⁠ https://www.crowbarawards.com/⁠🤝 Work With Us - Email: ⁠[email protected]⁠

This week, we are breaking into FIVE difference advertising agencies across the city of San Francisco.

Today, Barrett Hofherr, the "Makers of Momentum."

We sit down with Partner and Chief Creative Officer, Jamie Barrett, Partner and Chief Strategy Officer, Matt Hofherr, and Partner and Executive Creative Director, Todd Eisner to talk San Francisco, Yellow Door, and a whole lot of advertising.

More from Breaking and Entering Media:💼 Follow on LinkedIn⁠ https://www.linkedin.com/company/breaking-entering-podcast/⁠📖 Read our Publications⁠ https://www.breaking-entering.com/blog⁠💬 Join our Unlocked GroupMe⁠ https://groupme.com/join_group/102437585/xg5Z5tei⁠✉️ Subscribe to The Vault⁠ https://breakingandenteringadv.substack.com/⁠📹 Subscribe to our :60 Advertising News Videos⁠ https://breakingandentering.beehiiv.com/⁠🏆 Check out the Crowbar Awards to break into advertising⁠ https://www.crowbarawards.com/⁠🤝 Work With Us - Email: ⁠[email protected]⁠