Sarah Collinson, CEO of Havas New York, joins the Breaking and Entering Advertising Podcast to talk about what it takes to break into advertising at a time when there are fewer roles and higher expectations than ever.

She shares how she built a high-performing agency culture, why leadership and communication matter more than process, and how her team continues to win major clients while prioritizing people.

The conversation covers the reality of entry-level roles changing due to AI, what young professionals should focus on instead, and why becoming an expert in your client’s business is still the fastest way to stand out.

They also get into pay gaps in the industry, the challenges around maternity leave, and what agencies need to do to better support talent long term.

If you are trying to break into advertising or lead within it, this episode gives a clear view of what works now.

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

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Brian Collins, co-founder of COLLINS, joins the show to break down how design actually drives business transformation. COLLINS has won the Ad Age Design and Brand Agency of the Year or Business Transformation Agency of the Year seven times, and has helped shape brands like Spotify, Airbnb, Robinhood, and The Coca-Cola Company.

In this conversation, Brian explains why advertising makes things famous while design makes them useful, and how the best brands win by doing both. He shares his philosophy of “making the future irresistible so it becomes inevitable,” and what that looks like inside COLLINS, a consultancy-studio hybrid that helps companies imagine and build their next chapter.

We get into the Up&Up transformation at Target, how great packaging should live in your home, and why most brands are designed to sell instead of to last. Brian also breaks down what actually builds long-term client relationships, the role of trust in creative work, and the difference between having a job and building a career.

If you care about branding, design, and where the industry is going next, this episode is a masterclass from one of the most respected thinkers in the space.

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

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

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

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

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Rick Brim has won over 100 Cannes Lions and helped shape one of the most iconic creative agencies in the world. He played a key role in building Adam&EveDDB and bringing campaigns like John Lewis’ holiday ads to global attention, turning them into cultural moments that drove real business impact.

In this conversation, he breaks down what actually makes great advertising and why so much of the industry gets it wrong. He talks about the danger of chasing awards, how momentum can transform an agency overnight, and why creativity should be treated as a serious business tool rather than surface-level output.

Rick shares what it was like working on high-pressure campaigns that the public reacts to in real time, how to lead creative teams without pretending to have all the answers, and why vulnerability and curiosity matter more than hierarchy. He also explains why most ads don’t last, what makes certain ideas endure for years, and how the best work often comes from doing what you personally find interesting rather than trying to impress others.

The conversation also covers his decision to launch Ace of Hearts, what he believes the future of agencies looks like, and what advice he would give to anyone trying to break into advertising today.

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]⁠

Geno sits down with Ted Markovic, Global Head of Advertising & Creative Ops at Canva, to break down how one of the world’s fastest-growing brands actually runs creative. From building a 150-person in-house team to working seamlessly with agencies, Ted shares the systems, expectations, and communication required to get great work. If you want to understand how modern brands scale creativity and become better clients, this is the playbook.

Join the show today for an exclusive episode with the Co-Founder and Chief Creative Officer at JOAN. She goes in-depth about the Dr. Bronner's campaign for this quarter's Crowbar brief.You'll hear from the winners, Carolina Versolato and Jane Wineman, both soon-to-be advertising graduates from the University of Miami.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]⁠

Daniel Portrait, founder of Kamp Grizzly, breaks down how the agency evolved from a small Portland studio into a global creative partner for brands like Apple, Adidas, Uber Eats, HBO, and Amazon.
In this conversation, he explains how Kamp Grizzly grew over 20+ years into an 80+ person agency and how their approach to experiential marketing and IRL activations has become central to modern advertising.
He shares why brands are investing more in real-world moments that scale digitally, along with the thinking behind campaigns like Uber Eats’ Halloween film.
Daniel also gets into what agencies need to win in a creator-driven, AI-influenced industry, why “joy” is becoming a KPI, and what he looks for when hiring the next generation of creatives.
Throughout the episode, he shares lessons from working with top brands and why having a strong point of view continues to separate great creative work from the rest.

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/

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

🤝 Work With Us - Email: [email protected] 

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.

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]

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]⁠