Debbie Millman (@DebbieMillman) is a design and branding industry impresario. She will, at any given moment, be involved in a multitude of projects and roles across the profession. For nearly 20 years, she’s been the President of Sterling Brands, a design and brand strategy firm based in New York, Los Angeles, and San Francisco.

Since 2005, she’s hosted Design Matters, one of the most successful radio shows (now podcasts) about design and creativity. She also founded and chairs the Master’s in Branding course at the School of Visual Arts in New York, and has authored numerous books.

In this episode, Debbie speaks about the structure and workflow of Sterling — now a corporate agency, how she stays energized across her many endeavors, and how she’s still working to overcome awkwardness in her life and career. We also get to hear the story of how Debbie and Prescott first met.

Cover photo by John Madere

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Show Notes & Links

  • Design Matters was recognized as an iTunes Best of 2015 show. Amazing achievement.
    iTunes best of 2015

    Design Matters is among the iTunes Best of 2015

  • Prescott discovered Design Matters while working a crappy job working for a startup marketing firm.
  • Helvetica, by Gary Hustwit
  • Prescott is standing on the shoulders of giants with his podcast
  • Debbie describes herself as a brand consultant, wannabe artist, and chair of the MFA Master’s in Branding at SVA
  • Debbie and her partners at Sterling sold to the business Omnicom in 2008
  • Sterling defines itself as a Brand Consultancy with three disciplines – Design, Strategy, and Innovation
  • DeeDee Gordon runs Innovation from Los Angeles; Austin McGhie runs Strategy from San Francisco
  • Sterling acquired Philippe Becker in San Francisco, joining that to their studio.
  • Simon Lince is Sterling’s Chief Creative Officer in New York, with four Creative Directors under him. Same with Philippe Becker in SF.
  • Sterling consciously went to the traditional advertising agency model, rather than a “bullpen” model, with lots of cross-disciplinary work. It was “less deliberate”.
  • “Institutional knowledge” is important for growth within an agency. Helps to serve clients year-on-year.
  • Design strategy entails asking questions: What is the brand? What is the criteria for success? What is the “whitespace” we want to uncover? Can we own that space? What is the dynamic for change within an organization? etc.

“Common vocabulary does not always equate to common behavior.”

—Debbie Millman

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“The only people that really like brand design changes are brand designers.”

—Debbie Millman

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“Ambiguity is never seen positively.”

—Debbie Millman

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“I don't even know that I was a fully formed human being when I was 30.”

—Debbie Millman

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  • All The Wrong People Have Self-Esteem by Laurie Roselwald on Amazon
    All The Wrong People Have Self-Esteem by Laurie Roselwald
  • Adult Onset Awkwardness

“Getting your first job out of college is like starting kindergarten all over.”

—Prescott Perez-Fox

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“We are what we repeatedly do. Excellent, then, is not an act but a habit.”


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“Multitasking is the enemy of focused creativity.”

—Debbie Millman

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  • Debbie is now ashamed of her past pride as a multi-tasker

“When the going gets tough, we go to Facebook.”

—Debbie Millman

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  • Multi-tasking is usually “rapid-switching”
  • Lisa Grant, Debbie’s better half at Sterling
  • J’aime Cohen, original SVA dir. of operations
  • Mark Dudlik, current SVA partner in crime
  • Curtis Fox, producer for Design Matters
  • Energy management is more important than time management.



  • Copy the habits of small studios and create “in-house studios” within the larger agency
  • Allow strong personality to exist and thrive in a company; build a culture as such
  • Prepare strategy and challenges during proposal/pitch stage. Don’t wait until you’ve won it.
  • Want something done? Ask a busy person — they have less time to procrastinate.
  • Learn what you’re good at. Production/details? Coming up with ideas?


  • Celebrate small victories, such as winning a new project or client
  • Sleep a lot. 8 hours at least.
  • Eat better. (better than soda, candy, cigarettes, that is.)
  • Read constantly.

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About the author: Prescott Perez-Fox

Prescott Perez-Fox is a graphic designer, brand developer, and educator with 18+ years experience in branding, packaging, graphic design, and web design. He runs The Busy Creator.

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