

On Brand with Nick Westergaard
Nick Westergaard
On Brand helps you tell stronger stories and build better brands. Each week, host Nick Westergaard, author of Brand Now and Get Scrappy, 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.
For show notes and more, please visit http://onbrandpodcast.com.
Episodes
Mentioned books

Oct 13, 2025 • 31min
World-Building Brands in an AI Era
Geoff Cook’s career took off the night he met MoMA’s CMO—and helped create the iconic MoMA QNS brand. Since then, he’s shaped brands from MILK and NeueHouse to Times Talks, JFK Terminal 4, and the Prince Estate. Partner at Base, mentor at TechStars, and global culture expert, Geoff shares how bold branding can leave a lasting cultural impact.
What You'll Learn in This Episode
- How a single encounter can launch a career and define a creative trajectory
- Why human connection is at the heart of every successful brand experience
- The concept of “world-building” in branding and how it fosters community
- How to balance AI as a tool without losing creative originality
- Key considerations for branding early-stage companies and preserving cash
Episode Chapters
(00:00) Intro
(00:33) Geoff Cook’s career breakthrough at MoMA
(02:10) Early lessons from DKNY and international branding
(04:07) Culture-driven branding from Milk to global institutions
(07:40) Translating cultural expertise to JFK Terminal 4
(10:09) World-building brands to foster human connection
(12:19) AI in creative work: opportunities and guardrails
(20:12) Mentoring early-stage companies and branding pitfalls
(26:27) Brands that make Geoff smile
About Geoff Cook
Geoff Cook's career catapulted on the night he met MoMA’s CMO at a Base party in Manhattan, where he discussed developing the institution’s new branding for its temporary museum in Queens. The project, MoMA QNS, was the first in a string of iconic brands he has helped to create, including MILK, NeueHouse, JFK Terminal 4, Iconiq, The New York Times' Times Talks & Food Festival, the Prince Estate, and countless others. Geoff approaches branding with a sharp understanding of business strategy and a finger on the pulse of global culture (he speaks four languages and savors local flavor everywhere he travels). As a partner at Base, Geoff asks companies big questions and helps answer them with unexpected, visionary solutions. The result is very often a profound cultural impact. Geoff also puts his branding acumen to use as a mentor at renowned tech accelerator, TechStars, and serves as a board member at Sentral.
What Brand Has Made Geoff Smile Recently?
Geoff is impressed by On, a Swiss-based athletic brand. He admires how On builds a cohesive, coherent world through product design, store experiences, and creative campaigns that surprise and delight. The combination of Swiss precision and playful, culturally relevant marketing makes On a standout in his eyes.
Resources & Links
Connect with Geoff on LinkedIn.
Check out the Base Design website and Instagram.
Here's the Design Week article on AI we discussed.
Listen & Support the Show
Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.
Rate and review on Apple Podcasts and Spotify to help others find the show.
Share this episode — email a friend or colleague this episode.
Sign up for my free Story Strategies newsletter for branding and storytelling tips.
On Brand is a part of the Marketing Podcast Network.
Until next week, I’ll see you on the Internet! Learn more about your ad choices. Visit megaphone.fm/adchoices

Oct 9, 2025 • 40min
Taylor's Version, Bonus Track! Showgirl Spotlight
In this special bonus episode of On Brand: Taylor’s Version, now that The Life of a Showgirl is out in the world, we’re asking: what does this new era tell us about Taylor Swift? To explore, I’m joined by Joanna Weiss, editor of Harvard Magazine, journalist, and co-author of Taylor Swift: Album by Album, a deep dive into every era. Together, we’ll unpack how Showgirl fits into Taylor’s evolution and what this chapter reveals about her storytelling, strategy, and brand.
What You’ll Learn in This Episode
How Life of a Showgirl fits into Taylor Swift’s evolution as an artist and storyteller
Why some fans are divided on this album — and what that says about the expectations Taylor sets with each new era
How Taylor balances real-life inspiration with fiction and character-driven songwriting
What her creative process and relentless work ethic reveal about brand storytelling and reinvention
Why Taylor’s storytelling genius is as much about community and connection as it is about the music
Episode Chapters
(00:00) Intro
(00:47) Welcome Joanna Weiss
(04:24) How the book Taylor Swift: Album by Album came together
(07:02) Early takes on Life of a Showgirl
(11:04) What makes an “era” — and how Showgirl fits in
(19:18) What Taylor’s saying with this album
(25:23) Her creative process and work ethic
(30:37) Money, power, and independence
(33:20) The Taylor song that makes Joanna smile
About Joanna Weiss
Joanna Weiss is the editor of Harvard Magazine, a contributing writer for Politico Magazine, and a former columnist for The Boston Globe. Her work has appeared in The Atlantic, Slate, The Economist, and many other outlets. After chronicling her own Eras Tour experience for Boston’s NPR affiliate WBUR, Joanna dove deeper into the Swiftiverse as co-author of Taylor Swift: Album by Album (Quarto Books), which explores each of Taylor’s eras in detail. In addition to her journalism career, Joanna fronts a rock band she formed with five fellow moms — a story captured in her Boston Magazine feature “For Those Moms About to Rock,” now optioned for film by 20th Century Studios.
What Taylor Era Has Made Joanna Smile Recently?
When asked which Taylor song or era makes her smile, Joanna picked “Love Story.” Despite everything that has come since, she still returns to that song for its sheer emotional clarity — a bedroom-written, 20-minute burst of teenage storytelling that still captures the universal thrill of hope, love, and happily-ever-after energy that defines so much of Taylor’s work.
Resources & Links
Connect with Joanna on LinkedIn and her website
Check out her new book, Taylor Swift: Album by Album
Listen and Support
Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.
Rate and review on Apple Podcasts and Spotify to help others find the show.
Share this episode — email a friend or colleague this episode.
Sign up for my free Story Strategies newsletter for branding and storytelling tips.
On Brand is a part of the Marketing Podcast Network.
Until next week, I’ll see you on the Internet! Learn more about your ad choices. Visit megaphone.fm/adchoices

Oct 6, 2025 • 31min
The Power of Productive Tension in Branding
What makes a brand unforgettable instead of overlooked? Tom Miner knows. As Head of Global Social Media at Crocs, he helped drive one of today’s biggest brand turnarounds. Now author of Social First Brands, Tom shares how embracing productive tension, making personality your secret weapon, and riding trends that matter can turn comments into real community.
What You’ll Learn in This Episode
Why Crocs’ turnaround shows the power of leaning into brand polarity
How to know if brand tension is productive instead of problematic
What it really means to be a “social first” brand—and why fearlessness is key
Why unhinged marketing works for some brands and flops for others
The difference between comments, engagement, and true community
Episode Chapters
(00:00) Intro
(00:35) Welcome to Tom Miner
(01:22) Crocs as a brand turnaround case study
(04:41) Embracing polarity and productive tension
(09:08) What it means to be a social first brand
(13:21) Fearlessness and comfort levels in social strategy
(15:32) Unhinged marketing and authentic brand personality
(18:18) Comments versus true community
(22:43) Liquid Death as a social first example
(25:10) The brand that made Tom smile
(27:10) Where to learn more
About Tom Miner
Tom Miner is a social media strategist and the author of Social First Brands. As the former Head of Global Social Media at Crocs, Tom helped lead one of the most remarkable brand turnarounds in recent years, taking the shoe from internet punchline to cultural icon. Based in Denver, Tom now consults with organizations worldwide—from household consumer names to international B2B enterprises—helping brands move beyond chasing trends to creating genuine, lasting connections with their audiences.
What Brand Has Made Tom Smile Recently?
Recently, Tom found himself impressed by PopSockets. Long known for their stick-on phone grips, the brand has reinvented itself with MagSafe-compatible products and a renewed sense of fun on social media. A standout moment was a TikTok reaction video where the founder surprised a customer who lost her phone in the ocean. The mix of humor, generosity, and leadership buy-in reminded Tom why surprise-and-delight marketing still matters.
Resources & Links
Connect with Tom on LinkedIn.
Learn more about Tom Miner.
Check out Social First Brands on Amazon.
Listen & Support the Show
Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.
Rate and review on Apple Podcasts and Spotify to help others find the show.
Share this episode — email a friend or colleague this episode.
Sign up for my free Story Strategies newsletter for branding and storytelling tips.
On Brand is a part of the Marketing Podcast Network.
Until next week, I’ll see you on the Internet! Learn more about your ad choices. Visit megaphone.fm/adchoices

Oct 2, 2025 • 36min
Taylor's Version, Pt 4: Swifties & Storytelling
In this episode of On Brand: Taylor’s Version, we’re joined by Ann Handley — Wall Street Journal bestselling author, Chief Content Officer of MarketingProfs, and one of IBM’s ‘7 people shaping modern marketing.’ Ann brings not just her marketer’s eye but also her mom’s heart to the Swiftiverse. We’ll explore how Taylor’s storytelling fuels parasocial relationships, why The Eras Tour transformed casual fans into rabid ones, and what smart marketers can learn from the savviest hitmaker of our time.
What You’ll Learn in This Episode
How Taylor Swift’s storytelling makes the personal feel universal—and what marketers can borrow from that.
Why parasocial relationships don’t have to be clinical, and how Taylor transforms them into community.
The genius of anticipation, reveals, and Easter eggs in building long-term fan trust.
What the Eras Tour can teach marketers about creating inclusive, unforgettable experiences.
How Ann Handley’s own fandom grew from casual listener to full-on Swiftie devotion.
Episode Chapters
(00:00) Intro
(01:20) Swiftie Story Prompts and the Tortured Poets Era
(03:14) Standing Up as a Swiftie
(05:40) Taylor as Writer, Storyteller, and Cultural Icon
(08:07) Making the Personal Universal
(11:00) Marketing Lessons from Taylor Swift
(19:25) The Eras Tour as Community Experience
(29:41) The Taylor Songs and Albums That Make Ann Smile
About Ann Handley
Ann Handley is a Wall Street Journal bestselling author, digital marketing pioneer, and Chief Content Officer at MarketingProfs. Named by IBM as one of seven people shaping modern marketing, Ann is a trusted voice on content, storytelling, and building authentic connections with audiences. She is the author of Everybody Writes, now in its second edition, and a frequent keynote speaker at marketing and business events worldwide. Through her popular newsletter, Total Annarchy, and her leadership at MarketingProfs’ B2B Forum, she continues to inspire marketers to approach their work with clarity, creativity, and heart.
What Taylor Era Has Made Ann Smile Recently?
Ann lights up when she talks about Taylor Swift’s most recent projects—The Tortured Poets Department and Midnights. She especially loves “Fortnight,” with its Post Malone collaboration and typewriter aesthetics (a nod to her own collection of typewriters), and “Mastermind” from Midnights, which she admires for its playful storytelling. For Ann, these albums are on constant repeat, blending artistry, narrative, and joy in ways that fuel both her fandom and her creative spirit.
Links & Resources
Connect with Ann on LinkedIn
Check out her website and newsletter
Speaking of connecting with community, don’t miss the MarketingProfs B2B Forum
Listen & Support the Show
Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.
Rate and review on Apple Podcasts and Spotify to help others find the show.
Share this episode — email a friend or colleague this episode.
Sign up for my free Story Strategies newsletter for branding and storytelling tips.
On Brand is a part of the Marketing Podcast Network.
Until next week, I’ll see you on the Internet! Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 29, 2025 • 34min
How AI Is Rewriting Answer Optimization
Few business thinkers have shaped customer experience and marketing as profoundly as Jay Baer. A 7th-generation entrepreneur, best-selling author, and creator of six multi-million-dollar companies, he’s helped more than 700 brands, from Nike to the United Nations, grow and connect with customers in ways that matter. Now, he’s challenging everything marketers think they know about “owned” digital land, AI, and the future of content strategy.
What You'll Learn
Why the old rule of “never build on rented land” may be past its prime
How AI is shifting marketers from search optimization to answer optimization
Why breadth of authority matters more than backlinks in today’s landscape
How to atomize your awareness across platforms and nodes of trust
What AI can and can’t replace when it comes to creativity and customer experience
Episode Chapters
(00:00) Intro
(00:47) Welcoming Jay Baer back to On Brand
(02:26) A dramatic reading of “Never build your house on rented land”
(05:17) The declining importance of websites in an AI world
(06:00) From search optimization to answer optimization
(08:38) Atomizing awareness and saying yes to more opportunities
(14:13) What AI can’t do—and why bold ideas matter more than ever
(17:36) Customer experience, hyper-personalization, and efficiency gains
(22:19) What to do with the capacity AI creates
(23:29) Personal branding, tequila, and why authenticity wins
(27:19) The AI dating app that made Jay smile
(29:57) Where to find Jay online
About Jay Baer
Jay Baer is a business growth and customer experience strategist, author, and advisor who has helped more than 700 brands, including Nike, Oracle, IBM, and the United Nations. A seventh-generation entrepreneur, he has built six multimillion-dollar companies and written seven best-selling business books, earning recognition as a Professional Speakers Hall of Fame inductee and a Global Guru in marketing and customer experience. Beyond the stage and boardroom, Baer is also the world’s second most-popular tequila educator, blending sharp business insight with an engaging style that makes him one of the most sought-after voices in modern marketing.
What Brand Has Made Jay Smile Recently
Jay pointed to Valor, an AI-driven dating app that runs simulated dates between AI versions of potential matches before introducing people in real life. While he’s not on the app himself—he just celebrated his 33rd wedding anniversary—Jay says the concept makes him smile because it cleverly uses AI to cut through the awkwardness and false starts of early dating.
Resources & Links
Connect with Jay on LinkedIn.
Check out his website JayBaer.com.
And, of course, check out his work as the second-most popular tequila educator on Instagram.
Listen and Support the Show
Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.
Rate and review on Apple Podcasts and Spotify to help others find the show.
Share this episode — email a friend or colleague this episode.
Sign up for my free Story Strategies newsletter for branding and storytelling tips.
On Brand is a part of the Marketing Podcast Network.
Until next week, I’ll see you on the Internet! Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 25, 2025 • 48min
Taylor's Version, Pt 3: Eras & Education
In this episode of On Brand Taylor's Version, we're joined by Stephanie Burt, poet, critic, and professor of English at Harvard University. Stephanie made headlines when she created and taught one of the very first college courses on Taylor Swift at Harvard, Taylor Swift and her world. We discuss what it means to study Taylor seriously at Harvard, why her storytelling resonates so widely, and what we can all learn from her profound cultural impact.
What You’ll Learn in This Episode
How Taylor Swift’s approach to storytelling parallels the way we relate to literature and life, making her English-teacher-like to her fans
The narrative techniques and structural choices that make her songwriting resonate across diverse audiences
How she revisits, rewrites, and evolves previous stories in her music to deepen character and theme
The role of collaboration, marketing, and audience awareness in building a fan community that scales from niche to mainstream
How joy, friendship, and shared experiences are expressed in her music, and why songs like 22 continue to resonate
Episode Chapters
(00:00) Intro
(01:12) Taylor Swift as an English Teacher: Literary Language and Fan Connection
(05:30) Building Fan Communities and Shared Experiences
(10:22) Storytelling Techniques: Point of View, Character, and Rewriting Songs
(18:10) Revisiting and Evolving Previous Stories: Love Story and Forever & Always
(25:12) Adult Love, Partnership, and Feminist Storytelling
(32:01) Niche Fan Communities, Mainstream Appeal, and Marketing Savvy
(38:22) Collaboration and Craft: Working with Musicians and Audiences
(40:01) Guest’s Favorite Taylor Song: 22 and Closing Thoughts
About Stephanie Burt
Stephanie Burt is the Donald P. and Katherine B. Loker Professor of English at Harvard University. She specializes in 20th- and 21st-century poetry, science fiction, and the intersections of literature with other arts. Her work has appeared in The New York Times Book Review, The London Review of Books, Slate, and The Times Literary Supplement. Burt is the author of several acclaimed books of poetry and literary criticism, and her upcoming book, Taylor’s Version: The Poetic and Musical Genius of Taylor Swift, explores the artistry and cultural impact of Taylor Swift. At Harvard, she teaches courses including “Taylor Swift and Her World,” which has drawn widespread attention for its innovative exploration of music, poetry, and popular culture. She currently serves as co-editor of poetry for The Nation and is a recipient of a Guggenheim Fellowship.
Resources & Links
Check out Stephanie's new book Taylor's Version: https://www.amazon.com/Taylors-Version-Poetic-Musical-Genius/dp/154160623X/ref=tmm_hrd_swatch_0
Listen & Support the Show
Watch or listen on Apple Podcasts → https://podcasts.apple.com/us/podcast/on-brand-podcast-about-branding/id1113563080?mt=2
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Rate and review on Apple Podcasts → https://podcasts.apple.com/us/podcast/on-brand-podcast-about-branding/id1113563080?mt=2
Rate and review on Spotify → https://open.spotify.com/show/2Hq9fjctcpm3YKlJFuXmRk
Share this episode — email a friend or colleague → mailto:?subject=Check%20out%20this%20podcast%20episode&body=I%20thought%20you%20might%20like%20this%20podcast
Sign up for my free Story Strategies newsletter → https://www.nickwestergaard.com/email/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 22, 2025 • 32min
Creative Swings, Not Cracker Barrel
What do Hot Wheels, Disney, Burton, and WWE have in common? They’ve all had Mark Michaylira driving their brand forward. With two decades of creative leadership behind some of the world’s most beloved names, Mark knows how to make work that’s not just bold and joyful but rooted in culture—and powerful enough to move business.
What You’ll Learn in This Episode
- How to build authentic brands by starting with humanity and understanding your audience
- Why taking creative risks—and even failing—can move brands forward
- What it means to create joy and edge in storytelling across very different industries
- How Friends Everywhere is rethinking the agency model with cultural insiders and seasoned creators
- The role of AI as a creative tool and why transparency matters in its use
Episode Chapters
(00:00) Intro
(00:35) Starting with humanity in brand building
(03:15) Lessons from Cracker Barrel and Gap missteps
(05:55) Leading creative teams through swings and misses
(09:30) Creating joy and edge across brands like Hot Wheels, Disney, Burton, and WWE
(12:18) The Friends Everywhere model of cultural insiders and seasoned creators
(16:38) The role of AI as a creative tool, not a replacement
(22:12) Advice for emerging creatives
(24:31) The brand that’s made Mark smile
About Mark Michaylira
Mark Michaylira is Creative Director at Friends Everywhere, where he also leads agency growth for the independent partner to visionary teams building beloved brands. He previously led Global Brand Creative for Mattel’s vehicle portfolio, including Hot Wheels, Matchbox, and Disney Pixar Cars, overseeing disruptive, culture-driven campaigns for some of the world’s biggest toy brands. Earlier in his career, he built creative for Burton Snowboards, Disney, WWE, DreamWorks, Warner Bros., and Levi’s. With more than two decades of experience across creative direction, brand strategy, experience design, and integrated campaigns, Michaylira has shaped work that blends bold ideas with business impact. He is based in Long Beach, California.
What Brand Has Made Mark Smile Recently?
Mark shared Bug Assault, a quirky brand that sells salt-powered fly blasters. What made him smile wasn’t just the product—it was how the brand solved a real problem with humor, storytelling, and an unexpected creative twist. Their branding struck the right balance of playful and educational, proving that even pest control can be memorable when approached with imagination.
Resources & Links
Connect with Mark on LinkedIn →
Friends Everywhere website →
Bug Assault website →
Listen & Support the Show
Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.
Rate and review on Apple Podcasts and Spotify to help others find the show.
Share this episode — email a friend or colleague this episode.
Sign up for my free Story Strategies newsletter for branding and storytelling tips.
On Brand is a part of the Marketing Podcast Network. Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 18, 2025 • 44min
Taylor's Version, Pt 2: Fearless Focus
In this episode of On Brand: Taylor’s Version, we’re joined by Emily Campion — Henry B. Tippie Fellow and Associate Professor at the University of Iowa’s Tippie College of Business. Emily’s research explores how organizations hire and develop talent. But today, she’s here to talk about something decidedly more human: Taylor Swift’s relentless work ethic, authentic leadership, grit in the face of setbacks, and her ability to balance it all with self-care.
What You’ll Learn in This Episode
Why Taylor Swift is the ultimate case study in relentless work ethic and focus
How authenticity fuels leadership and builds trust with fans — and employees
What Taylor’s grit teaches us about resilience, reinvention, and leading through setbacks
The role of self-care in sustaining high performance over the long haul
Why leaders need to balance hustle with humanity
Episode Chapters
(00:00) Intro
(02:15) “Taylor Inc.” and the ultimate one-person company
(04:40) Emily Campion on studying work ethic and leadership through Taylor Swift
(08:30) Taylor’s relentless productivity and lessons for business leaders
(14:05) Authenticity as strategy vs. sincerity
(19:20) Grit, comebacks, and leading through setbacks
(25:45) Boundaries, rituals, and Taylor’s approach to self-care
(32:10) Leadership lessons leaders can apply today
(38:15) Emily’s Taylor smile: Stay Stay Stay on ukulele
About Emily Campion
Emily Campion is a Henry B. Tippie Fellow and Associate Professor at the University of Iowa’s Tippie College of Business. Her research focuses on staffing procedures, the use of machine learning and natural language processing to improve these systems, and ways to mitigate employment discrimination. Her work has been published in leading academic journals, and she currently serves on the editorial boards of Journal of Applied Psychology and Personnel Psychology, where she recently co-edited a special issue on machine learning in selection.
What Taylor Era Has Made Emily Smile Recently?
For Emily, the Taylor song that’s made her smile recently is “Stay Stay Stay” from Red (Taylor’s Version). She first loved it while learning the ukulele, and even though she jokes she won’t be a famous ukuleleist, the song’s plucky energy and Taylor’s laugh at the end never fail to make her beam.
Resources & Links
Connect with Emily on LinkedIn.
Check out Emily’s University of Iowa faculty page.
Listen & Support the Show
Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.
Rate and review on Apple Podcasts and Spotify to help others find the show.
Share this episode — email a friend or colleague this episode.
Sign up for my free Story Strategies newsletter for branding and storytelling tips.
On Brand is a part of the Marketing Podcast Network.
Until next week, I’ll see you on the Internet! Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 15, 2025 • 33min
TikTok and the Future of Storytelling
Few platforms have changed culture as quickly—or as globally—as TikTok. Khartoon Weiss, VP and GM of North America and Global Business Solutions, is at the center of it, helping brands and businesses connect with audiences in ways that are creative, authentic, and impactful. From scaling Spotify to leading top agencies, she’s built a career on turning bold ideas into cultural movements—and now she’s shaping the future of TikTok.
What You’ll Learn in This Episode
How TikTok has broken the traditional brand storytelling arc
Why authenticity and “real production” outperform polish on the platform
How content, commerce, and search converge on TikTok
Why short form content can still drive loyalty and long-term brand love
What brands like Chipotle, McDonald’s, and Gap are doing right on TikTok
Episode Chapters
(00:00) Intro
(00:38) Why TikTok has changed brand building
(02:12) Stewarding TikTok’s brand and helping other brands grow
(03:34) Unlearning traditional storytelling on TikTok
(06:01) Authenticity over polish with examples from Chipotle and McDonald’s
(10:20) Content, commerce, and the rise of search on TikTok
(14:04) Can short form content build brand loyalty
(21:08) Brand safety, trust, and TikTok’s uncertain future
(24:48) Lessons from scaling brands at Spotify, agencies, and TikTok
(27:09) The that made Khartoon smile recently
About Khartoon Weiss
Khartoon Weiss is the VP and GM of North America and Global Business Solutions at TikTok. She previously led global revenue at Spotify, served as Chief Marketing Officer and Managing Director at MDC Partners and Mediacom North America, and was a VP at iHeartMedia. She began her career at BBDO, Ogilvy, and Grey Worldwide. Weiss has been recognized by Campaign’s “40 Over 40,” AdAge’s “40 Under 40,” and AdWeek’s “Top 50.” She completed executive education at The Wharton School and lives in New York City with her husband and two rescued cats.
What Brand Has Made Khartoon Smile Recently?
Khartoon pointed to Gap as the brand making her smile lately. She praised the retailer for collaborating authentically with creators, staying true to its roots, and showing up on TikTok in ways that feel natural and culturally relevant. For her, Gap’s bravery and creativity prove that when brands lean into community and culture authentically, audiences instantly recognize it—even without the logo.
Resources & Links
Connect with Khartoon on LinkedIn.
Learn more about TikTok for Business.
Listen & Support the Show
Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart.
Rate and review on Apple Podcasts and Spotify to help others find the show.
Share this episode — email a friend or colleague this episode.
Sign up for my free Story Strategies newsletter for branding and storytelling tips.
On Brand is a part of the Marketing Podcast Network.
Until next week, I’ll see you on the Internet! Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 11, 2025 • 43min
Taylor's Version, Pt 1: Swift Strategy Secrets
In our first episode of On Brand: Taylor’s Version, we’re joined by Sinéad O’Sullivan — aerospace engineer turned business strategist, former head of Strategy at Harvard Business School, professor, and co-founder of a global investment fund. She’s advised everyone from NASA to prime ministers … and she also happens to be in the top 0.01% of Taylor Swift fans worldwide. Her new book, Good Ideas and Power Moves: Business Lessons from Taylor Swift, hits shelves this week — and she’s here to share why Taylor isn’t just a pop star, but one of the sharpest strategists of our time.
What You’ll Learn in This Episode
Why “doing strategy” is more than PowerPoints and wish lists
How Taylor Swift creates interlinked universes across her albums
What it means to be anti-fragile and thrive in chaotic environments
How storytelling can be leveraged as a business strategy
Why Taylor Swift is her own product and outperforms traditional companies
Episode Chapters
(00:00) Intro
(01:00) Getting Started with Taylor’s Version
(01:35) Reputation Era Story Prompt and Misunderstandings
(03:40) Doing Strategy the Taylor Way
(08:10) Building Worlds Not Products
(12:30) Lessons for Brands and Community
(17:50) Fearless Era Story Prompt and Courage
(24:20) Anti-Fragile Moves and Thriving in Chaos
(28:10) Timing, Reverse Acquisitions, and Big Picture Strategy
(38:30) Where to Connect with Sinéad
About Sinéad O’Sullivan
Sinéad O’Sullivan is an aerospace engineer turned business strategist, former head of strategy at Harvard Business School, professor, writer, and co-founder of a global investment fund. She has advised organizations from NASA to prime ministers and is the author of Good Ideas and Power Moves: Business Lessons from Taylor Swift. O’Sullivan has a BA in engineering, an MSc in finance, and a PhD in strategy.
What Brand Has Made Sinéad Smile Recently?
Sinéad shared that she’s been smiling at the creative universe built around Barbie. From specialty cars to Airbnbs, the way Barbie has expanded into a full cultural ecosystem reminded her of the worlds Taylor Swift builds with her albums—demonstrating creativity, collaboration, and clever brand storytelling.
Resources & Links
Connect with Sinéad on LinkedIn.
Sinéad’s website.
Sinéad’s Substack.
Sinéad’s new book, Good Ideas and Power Moves: Ten Lessons for Success from Taylor Swift.
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