In this episode, I sit down with longtime creative leader and newly minted agency founder, Chris D’Amico, to discuss big career moves, the evolving creative landscape, and the power of clarity. Chris has built a standout career in advertising, creative direction, and brand storytelling—working with brands like Taco Bell, Dunkin’, and many more.
Now, he's channeling all of that experience into CAPTAIN, a strategic and creative studio helping ambitious founders and executives find their voice and category. Chris brings wisdom, humility, and bold insights on what it means to lead, evolve, and stay true to your creative instincts (no matter where you are in your journey), as well as what it takes to break into the business.
🔍 What We Talk About:

How to make your brand “terribly tangible”
Why clarity is a strategic superpower
The real role of a creative director (and how the job is evolving)
Why even seasoned leaders need co-captains
The benefits and challenges of starting your own agency
How AI and modern tools are changing the creative industry
Advice for breaking into advertising today—and what Chris looks for in new talent
Why your life experience is just as important as your portfolio
Building your personal brand with purpose and authenticity
The power of mentorship—even digital ones

💡 Key Takeaways:
“Your network is everything.” Chris is a serial connector who believes in networking with intention, reciprocity, and purpose.
Start sooner. Chris shares that he waited too long to start his own thing—and encourages others to bet on themselves earlier.
Execution is being commoditized. Strategy and upstream creative thinking are more valuable than ever.
Even captains need captains. Leadership can be lonely. Finding partners, advisors, or co-pilots can make all the difference.
The best ideas still win. Amid all the noise and new tools, great storytelling and authenticity still rise to the top.
🔥 Memorable Quotes:
“Your network is everything… 80 to 90% of your future business will come from it.”
“I probably should have started a lot earlier. But that’s okay. You start when you’re ready.”
“Creative direction is not about art—it’s about solving problems.”
“Be interesting and be interested.”
🎯 Listen to this episode if you are:

A founder or executive looking to level up your brand strategy
A creative professional considering the leap to entrepreneurship
An aspiring designer or storyteller wanting to break into the industry
Curious about how branding, clarity, and leadership intersect
Seeking inspiration on how to reinvent your career after 20+ years in the game

🔗 Links from the show:

Chris D’Amico - https://www.linkedin.com/in/chrisdamico/ 
CAPTAIN - https://www.wearecaptains.com/ 
Chris Do - The Futur
Play Bigger book - https://www.playbigger.com/ 
How I Built This - https://wondery.com/shows/how-i-built-this/ 
The CMO Podcast - https://www.linkedin.com/in/jimstengel/ Music by Lidérc.

#careerjournies #careerstories #careerlessons #careeradvice #theunderswell #advertising #marketing #professional

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