On Brand with Nick Westergaard – Details, episodes & analysis

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On Brand with Nick Westergaard

Nick Westergaard

Business

Frequency: 1 episode/7d. Total Eps: 600

On Brand helps you tell stronger stories and build better brands. Each week, host Nick Westergaard, author of Get Scrappy and Brand Now, interviews marketing and communication thought leaders and innovators from brands like Ben & Jerry’s, Microsoft, LinkedIn, Meta, Crayola, Beats by Dre, Southwest Airlines, Reddit, Spotify, and MailChimp. Watch the full, in-depth conversations and get actionable insights to help you and your brand stand out in a crowded, distracted world. For show notes and more, please visit http://onbrandpodcast.com.

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https://tunein.com/radio/On-Brand-p967623/
366 shares
https://www.branddrivendigital.com/feed/podcast/
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http://app.stitcher.com/browse/feed/40156/details
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https://twitter.com/seancarp
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https://twitter.com/deniseleeyohn
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Ron Johnson on Steve Jobs & Building the Apple Store

Episode 633

Monday, September 21, 2026 • Duration 34:38

Before the first Apple Store opened, the experts said it would fail within a year. But Ron Johnson saw a different story. As the retail pioneer who worked directly alongside Steve Jobs to build the Apple Store from scratch, Ron transformed retail from a simple transaction into an immersive experience. He also pioneered Target's famous high design partnerships and founded Enjoy. In this episode, we take a look at what it really takes to build a physical space and leadership lessons learned directly from Steve Jobs.

What You’ll Learn in This Episode
Why Apple delayed its retail launch six months to redesign around the digital hub
How Steve Jobs applied Pixar storytelling principles to physical store design
Why total trust and customer experience matter more than online transaction speed
What direct-to-consumer brands get wrong when attempting physical retail expansion

Episode Chapters
(00:00) Intro
(01:08) Challenging the Dot-Com Retail Consensus
(05:07) Co-Creating Space in a Secret Warehouse
(09:31) Designing for Ease of Use and Tactile Discovery
(12:07) The Digital Hub Rewind
(17:23) Focus and Execution Lessons from Steve Jobs
(21:50) The Reality of Modern Omnichannel Retail
(28:39) A Brand That Made Ron Johnson Smile

About Ron Johnson
Ron Johnson is a retail pioneer best known for co-creating the Apple Store alongside Steve Jobs, where he served as Senior Vice President of Retail Operations. Throughout his career, he has transformed customer experiences across major brands, pioneering Target’s famous high-design partnerships, leading JCPenney, and founding Enjoy. His upcoming book, Shop Different, details the leadership, design, and innovation principles behind some of the world’s most iconic physical spaces.

What Brand Has Made Ron Smile Recently?
Ron Johnson highlighted Sixt, the European car rental company, for its energetic branding, bright orange store design, and clever marketing that consistently features a subtle, engaging wink.

Resources & Links
Connect with Ron on LinkedIn.

Learn more at Ron’s website.

Check out his book, Shop Different.

Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.

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Can You "Rewild" the Corporate Mind?

Episode 632

Monday, September 14, 2026 • Duration 31:14

What if the biggest threat to your organization isn't disruption from the outside, but the way you operate inside? Tom Dennis argues that many companies have become overcontrolled and disconnected from the things that make organizations resilient: trust, adaptability, and human connection. A former Royal Marines officer, he's the founder and CEO of Serenity and Leadership and author of Rewilding the Corporate Mind.

What You’ll Learn in This Episode
Why relying on rigid control creates hidden organizational fragility
How Nelson’s naval strategies offer a modern template for leadership trust
What self-awareness reveals about your unconscious management habits
Why psychological safety drastically reduces costly operational mistakes
How setting up the right environment allows you to step back and let go

Episode Chapters
(00:00) Intro
(01:17) Rewilding as a Business Metaphor
(03:33) Military Strategy and Delegated Initiative
(07:52) The Power of Leadership Self-Awareness
(10:46) Overcoming the Urge to Micromanage
(13:27) Cultivating Psychological Safety
(19:34) Navigating Cultural Resistance at the Top
(24:40) A Brand That Made Him Smile

About Thom Dennis
Thom Dennis is a former Royal Marines officer and the founder and CEO of Serenity in Leadership. With over 30 years of experience helping executives rethink how they lead, Thom is the author of Rewilding the Corporate Mind. He specializes in helping organizations move away from rigid command-and-control structures toward cultures built on adaptability, psychological safety, and trust.

What Brand Has Made Thom Smile Recently?
Thom smiled thinking about Cadbury’s classic gorilla drum-solo commercial set to Phil Collins. While he laments how corporate acquisitions changed the company’s original Quaker-led approach to caring for people, the pure joy of that iconic campaign still stands out.

Resources & Links Connect with Thom on .

Great Technology Isn't Enough

Episode 631

Monday, September 7, 2026 • Duration 30:21

AI may be everywhere, but Brian Herr says the technology itself isn't the competitive advantage. The real moat, he argues, is data, distribution, and trust. As founder and CEO of Starting Blocks and managing partner at HHI Advisory Group, Brian helps startups, scale ups, and portfolio companies grow while also advising organizations on secure adoption.

What You’ll Learn in This Episode
How data distribution and trust serve as true competitive moats in the AI era
Why software wrappers fail without core business fundamentals and strategy
How transparent, auditable AI processes protect brand credibility and trust
How agile small teams leverage AI augmentation to outperform larger competitors
How shared AI knowledge networks accelerate cross-functional team velocity

Episode Chapters
(00:00) Intro
(00:55) Defining the AI Moat
(03:11) SAAS-pocalypse and Business Fundamentals
(05:53) Building Trust in Technology
(09:30) Responsible AI in Practice
(12:28) Balancing Speed and Trust
(17:23) Effective AI Startup Strategies
(21:45) What We Overestimate in AI
(24:18) Brand That Made Brian Smile

About Brian Herr
Brian Herr is the founder and CEO of Starting Blocks and managing partner at HHI Advisory Group. With extensive experience as an operator, executive, advisor, investor, and scout, Brian guides startups, scale-ups, and portfolio companies through growth and secure technology adoption.

What Brand Has Made Brian Smile Recently?
Filmlink, a Detroit-based company, made Brian smile recently by solving distribution and visibility challenges for the independent film industry. Their scrappy, enthusiastic approach to building a brand that connects independent filmmakers with audiences creates authentic support and excitement.

Resources & Links
Connect with Brian on LinkedIn.

Emergent Leadership Beats Overwhelm

Episode 630

Monday, August 31, 2026 • Duration 33:22

Leaders have more advice, tools, and resources than ever. So why are so many still overwhelmed? Don Gregori says we've been missing the bigger picture. He's the COO of First Factory and author of The Emergent Leader, a book about leadership, self-mastery, and building a strong brand. We're talking about what it takes to become a leader and build something that really lasts.

What You’ll Learn in This Episode
How building yourself and building a brand are the exact same project
Why empathy needs to be treated as a hard skill for managers
What separates "emergent" leadership from static management models
How to avoid getting overwhelmed by the sheer volume of new tech tools
Why AI should serve the individual rather than replace human judgement

Episode Chapters
(00:00) Intro
(00:46) Building Yourself vs Building a Brand
(04:30) Empathy as a Core Management Skill
(06:08) Defining the Emergent Leader
(09:34) Navigating Modern Information Overload
(12:32) Managing Stress and Fear in Leadership
(18:33) The Theater and Business Connection
(22:34) Managing AI and the Human Element
(28:44) A Brand That Made Don Smile

About Don Gregori
Don Gregori is the Chief Operating Officer of First Factory, a nearshore software development firm, and the author of The Emergent Leader. With a background spanning technology, strategy, and the performing arts, he focuses on self-mastery, organizational culture, and navigating rapid industry change through empathetic leadership.

What Brand Has Made Don Smile Recently?
During a recent trip to Maine, Don was brought a smile by Gelato Fiasco—a local favorite in Brunswick—and Middle East Coast, a regional brand making exceptional tahini-forward hummus.

Resources & Links

Connect with Don on LinkedIn.

The Woman Behind the Aflac Duck

Episode 629

Monday, August 24, 2026 • Duration 31:43

What can happen in 30 seconds? For Linda Kaplan Thaler, quite a lot. She’s the creative force behind some of the advertising world’s most unforgettable ideas, from the Aflac duck to “I don’t want to grow up, I’m a Toys R Us kid.” Now, in her new book, My Life in 30 Seconds, Linda looks at the small moments that can change a career or even a life. She’s here to talk about creativity, resilience, leadership, and why sometimes the smallest ideas can make the biggest impact.

What You’ll Learn in This Episode
How distilling complex messages into 30-second constraints drives massive brand awareness
Why adopting an improv “yes, and” mindset unlocks breakthrough team creativity
How taking bold, fearless pitches to conservative clients can rescue dying brands
Why replacing standard networking with “nice working” yields long-term career returns
How human creativity retains its edge in an era of rapid AI adoption

Episode Chapters
(00:00) Intro
(00:49) Welcome Linda Kaplan Thaler
(02:42) The Power of 30-Second Distillation
(03:43) Pitching Herbal Essences and Bold Ideas
(06:46) Writing the Iconic Toys R Us Jingle
(10:55) Applying Improv Rules to Business Creativity
(11:51) Creating the Aflac Duck
(16:23) Building Agency Culture Through Kindness
(18:13) Human Creativity in the Age of AI
(23:12) The Difference Between Networking and Nice Working
(24:28) A Brand That Made Linda Smile

About Linda Kaplan Thaler
Linda Kaplan Thaler is a legendary advertising executive, author, and speaker responsible for some of the most iconic pop-culture campaigns in history, including the Aflac duck and the Toys R Us jingle. As the co-founder of the Kaplan Thaler Group, she helped build one of the fastest-growing agencies in the United States, scaling it from scratch to over a billion dollars in billings. A master of message distillation and creative leadership, her latest book, My Life in 30 Seconds, explores how micro-moments and rapid insights shape extraordinary careers.

What Brand Has Made Linda Smile Recently? Recently, Linda has been smiling at Progressive Insurance for their long-running campaign warning homeowners not to turn into their parents. She loves the humor and stand-up performance driving the spots, pointing out that even when an ad makes you laugh before you remember the exact name, the sheer joy and entertainment value make it stand out in a low-interest category.

Why AI Is a Mirror and Not a Tool

Episode 628

Monday, August 17, 2026 • Duration 30:54

Most conversations about AI focus on the technology. David Dean thinks we're looking in the wrong place. In his new book, An Inbox Between Us, AI and the Reality of Modern Work, he argues that AI is acting like a mirror, revealing the hidden workarounds, decision-making, and human judgment that have always kept organizations running. Today, we're talking about what leaders can learn from that reflection.

What You’ll Learn in This Episode
Why AI functions as an organizational mirror that exposes hidden workarounds and human judgment
How the majority of workers operate as AI survivalists rather than power users
The hidden cost of the retry tax when over-relying on automated outputs
Why human intuition and lived consequence remain irreplaceable in critical decision-making
How to avoid industrializing existing workplace dysfunction with new technology

Episode Chapters
(00:00) Intro
(00:36) AI as an Organizational Mirror
(05:11) Navigating the Productivity Maxing Trait
(09:01) The AI Survivalist and Adoption Realities
(11:19) Understanding the Hidden Retry Tax
(13:21) How Organizations Rely on Workarounds
(17:20) Tech Problems versus Behavioral Problems
(19:56) Why Human Judgment Outlasts Automation
(23:40) Authenticity as the Ultimate Leadership Skill
(25:19) A Brand That Made Him Smile

About Bill Sherman
David Dean is an author, productivity solution designer, and change management practitioner focused on the intersection of human behavior and emerging technology. In his book, An Inbox Between Us: AI and the Reality of Modern Work, he examines how enterprise technology impacts ground-level teams across HR, finance, and operations. Drawing on years of experience analyzing workplace workflows, David helps organizational leaders navigate digital transformation by focusing on human judgment, authentic leadership, and practical operational discovery.

What Brand Has Made David Smile Recently?
A brand that made David smile recently is Marvel. After taking his son to see the newest Spider-Man movie, he appreciated how the brand continues to craft engaging experiences that bring families together and build lasting memories.

Five Thought Leadership Avatars for Scaling Ideas

Episode 627

Monday, August 10, 2026 • Duration 31:44

What does it really take to turn expertise into influence? My guest this week has spent the last two decades answering that very question. Bill Sherman is the COO of Thought Leadership Leverage and co-author of the Thought Leadership Handbook. His journey into thought leadership began with a simple question from a Fortune 500 executive. How do I scale the ideas in my book? Since then, he's helped organizations and experts transform ideas into impact.

What You’ll Learn in This Episode
Why practice matters more than how in thought leadership
The five distinct avatars of thought leadership
How the growth-minded CEO opens new doors
Why silence in a noisy world is never neutral
How to simplify complex concepts so they stay memorable

Episode Chapters
(00:00) Intro
(01:35) The Five Thought Leadership Avatars
(05:13) Breaking Down the Avatars from CEO to Legacy
(08:25) Matching Strategy to Your Personal Brand
(14:03) Why Ideas Can't Speak for Themselves
(17:49) Creating a Platform Identity for Your Work
(23:43) Why Silence is Never Neutral in Turbulent Times
(29:32) A Brand That Made Bill Smile

About Bill Sherman
Bill Sherman is the COO of Thought Leadership Leverage and co-author of the Thought Leadership Handbook. Over the last two decades, he has helped organizations, Fortune 500 executives, and independent experts scale their ideas, transform insights into strategy, and build sustainable impact. He also co-hosts the Thought Leadership Podcast, where he explores the mechanics of turning deep expertise into widespread influence.

What Brand Has Made Bill Smile Recently?
Bill recently smiled at Pirate Ship, an online shipping service that simplifies sending author copies of his book right from his front door. He loves their delightful, pirate-themed user interface and how effortlessly the service eliminates the hassle of traditional post office runs.

Resources & Links
Connect with Bill on .

The AI Brand Speed Trap

Episode 626

Monday, August 3, 2026 • Duration 30:38

What if AI isn't just changing marketing, but changing what a brand actually is? Melissa Jackson-Parsey has spent her career helping some of the world's most recognizable organizations reinvent themselves at the intersection of strategy, creativity, technology, and experience. As Global Chief Strategy Officer at RGA, She leads a worldwide team shaping brands for the intelligence age, from rebooting Android to launching the new sports streaming brand from ESPN, Fox, and Warner Brothers Discovery.

What You’ll Learn in This Episode
Why building brands for AI agents requires context over cleverness
How to shift marketing focus from single campaigns to generating intelligent systems
The critical difference between bottom line efficiency and top line growth in the AI age
Why modern talent needs to evolve from T-shaped to M-shaped expertise
How the craft of human taste prevents brand slop

Episode Chapters
(00:00) Intro
(00:45) What Endless Tech Evolution Hasn’t Changed About Brand Building
(02:06) Encoding Brands for Machines, Agents, and Markdown Files
(06:05) How AI is Changing What a Brand Actually Is
(08:36) Moving from Making Campaigns to Making Intelligent Systems
(12:08) Human Value, Critical Thinking, and the Role of Taste
(16:33) The Biggest Strategic AI Mistake Brands Make Today
(20:12) Cultivating M-Shaped Talent and the Future of Skillsets
(24:41) A Brand That Made MJP Smile

About Melissa Jackson Parsey
Melissa Jackson Parsey is the Global Chief Strategy Officer at R/GA, having worked at the forefront of brand, innovation, and experience design across three continents. She leads a global team of strategists, designers, coders, and writers, accountable for shaping brands and experiences that add value to people and businesses. In the past year, they’ve rebooted the world's largest operating system brand, Android, and created the much-anticipated live sports streaming brand from ESPN, Fox, and Warner Bros. Discovery. Over the course of her career, she’s led brand transformation initiatives for a broad array of organizations, including Microsoft, Under Armour, Google, IBM, the UN, and for Dwayne (The Rock) Johnson’s portfolio.

Uncommon Leadership in Times of Change

Episode 625

Monday, July 27, 2026 • Duration 29:29

What if the qualities we call “uncommon leadership” are actually the ones that should be ordinary? After leading at IBM, AT&T, Pitney Bowes, SuperValu, and Walmart through decades of transformation, Keith Wyche argues that the leaders who endure aren't simply the smartest or the most innovative—they're the ones who consistently lead with integrity, humility, and trust. His new book, Uncommon Leadership, is both a call to higher standards and a practical guide for leading people through change.

What You'll Learn

The four Rs required to guide teams through rapid industry transformation
Why trust equals character times competency times consistency
How to distinguish real character from captivating charisma in executive selection
The simple question frontline associates need to be asked during store visits
How managing imbalance replaces the impossible myth of work balance

Episode Chapters

(00:00) Intro
(01:10) Leading Through Decades of Corporate Transformation
(01:52) The Four Rs of Navigating Organizational Change
(03:04) The Steep Decline of Trust in Modern Leadership
(04:49) The Simple Formula for Building Real Trust
(06:05) Why True Leadership Demands Character Over Charisma
(11:10) Moving Beyond Results to Value Human Capital
(12:38) How Vulnerability and Listening Transform Team Culture
(18:17) Simplifying What Matters Most in Strategic Communication
(20:27) Managing Imbalance to Protect Energy and Prevent Burnout
(22:25) Planting Trees and Building a Lasting Leadership Legacy

About Keith Wyche

Keith Wyche is a seasoned corporate executive and author who has led major operational transformations across global organizations, including IBM, AT&T, Pitney Bowes, Supervalu, and Walmart. With decades of executive leadership experience, he focuses on helping leaders navigate disruptive change, cultivate authentic trust, and build cultures grounded in character, humility, and human capital. His latest book, “Uncommon Leadership,” provides a practical guide for modern leaders striving to elevate organizational standards and leave a lasting legacy.

Mortal Kombat Madness Over Mediocrity

Episode 624

Monday, July 20, 2026 • Duration 31:44

How do you go from producing Dirty Dancing to building the global Mortal Kombat franchise? Today’s guest, legendary producer Larry Kasanoff, has raised over a billion dollars by embracing what others call a little bit crazy. He has shaped the entertainment landscape by constantly fighting the current of mediocrity. Today, we are breaking down how to lead through massive industry shifts and build brands that stand the test of time.

What You’ll Learn in This Episode
How to identify the core essence of a brand so you can stretch it across different media successfully
Why fostering a state of play is essential for leading creative teams and sparking innovation
The importance of asking anyone anything to advance your projects and overcome creative barriers
How to balance emerging technologies like AI with the enduring human elements of storytelling
Why embracing a touch of the madness helps you fight the pull of mediocrity in your work

Episode Chapters
(00:00) Intro
(01:08) Finding the Essence of Enduring Global Brands
(04:41) Protecting the Brand and Knowing When to Say No
(06:24) Embracing a Touch of the Madness in Leadership
(08:13) The Create Ask Play Framework
(10:20) The Origins of a Touch of the Madness
(14:08) Balancing New Technologies with Timeless Storytelling
(16:49) Leading Like a Visionary and the Value of Play
(26:51) The Brand That Made Our Guest Smile

About Larry Kasanoff
Larry Kasanoff is a legendary producer who has raised over a billion dollars and shaped the entertainment landscape. He is known for building enduring global franchises across movies, video games, theme parks, and music, including the massive Mortal Kombat brand. Beginning his career as head of production at Vestron, he greenlit the Academy Award-winning film Platoon and has since led major tech shifts in the industry. Larry is the author of A Touch of the Madness, where he shares his philosophy on fighting mediocrity and taking bold creative risks.

What Brand Has Made Larry Smile Recently? Larry recently smiled thinking about Sennelier, a historic French brand of pastels. As someone who enjoys drawing, he visited their store in Paris and was captivated by the brand’s enduring story. Now, whenever he sees his Sennelier pastels on his work table, it brings a smile to his face.

On Brand with Nick Westergaard – Details, episodes & analysis

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On Brand with Nick Westergaard – Details, episodes & analysis

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