March 19, 2026

Be Someone to Root For: Michael B. Jordan, Disney & Stripe

Be Someone to Root For: Michael B. Jordan, Disney & Stripe
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Timothy Chalamet won zero Oscars this week. Sinners won four. Michael B. Jordan's humble acceptance speech reminded us what we're actually rooting for—humility, craft, and people who remember where they came from. Meanwhile, Chalamet's campaign flew too close to the sun, turning from "movie star we love" to "guy who thinks he's in the Venn diagram of cultural influencers." We break down what went wrong, why Disney's "Midnight Magic" cruise ad made us cry, and how Staples turned a 22-year-old print specialist into their biggest brand ambassador without fumbling the bag.

This week Sonia sits down with Cynthia McGillis (Head of Marketing at Laribel) to talk through the Oscars' hidden lesson on authenticity, Disney's generational storytelling play, Home Depot accidentally becoming a family destination, and why the $99 AI CMO is a shortcut that misses the entire point of marketing. Plus: Stripe's comms hire proves storytellers are the new CMOs, and why brands that make you want to root for them are the ones building lasting equity.

The big thesis: be the person (or brand) people want to root for. Chalamet lost the plot when he made it about himself instead of the work. Michael B. Jordan won by thanking his mom and the crew. Disney's betting on experiences and family moments that span generations. Staples sent roses to their viral employee instead of a cease and desist. And Stripe's hiring storytellers while startups think a $99 AI agent can replace a CMO. Humility, craft, and gratitude aren't just nice—they're competitive advantages.

We're talking about:

  • Oscars 2025: Why Michael B. Jordan and Ryan Coogler won (humility, crew shoutouts, paying dues), Chalamet's campaign going from beloved to backlash (Venn diagram comment, Kylie Jenner overshadowing Marty Supreme, losing the authenticity), and SAG Awards as the turning point

  • Disney's "Midnight Magic" cruise ad: Up piano music opening, three-generation storytelling (past/present/future), nostalgia without being purely nostalgic, and why companies with generational equity should remind customers of it

  • Disney's family-first pivot: Bluey Disneyland experience, Bluey movie 2026, DisneyVerts (closed content ecosystem for kids vs. TikTok/YouTube Shorts), F1 partnership, ESPN Super Bowl integration, and ticket price reductions signaling recession or accessibility play

  • Staples Baddie phenomenon: Kaden Roland (22-year-old print specialist) going viral with ASMR-style TikToks, Staples sending roses and making it official, employee-generated content done right, and why compensation matters (she's getting paid beyond her salary)

  • Home Depot's accidental family moment: Moms taking kids to Home Depot as a "busy board," Saturday kids' craft hours, New York Post article, and the opportunity for Home Depot to amplify (please don't fumble this)

  • Costco's IVF support: Helping members with fertility treatments, creating future customers, and companies staking territory as family-friendly vs. alienating parents

  • $99 AI CMO disaster: Launching an AI agent to handle SEO, content, social, community, and Twitter auto-replies, Reddit/Hacker News spam bots, and why this misses the entire point of marketing (strategy, positioning, messaging, taste, judgment)

  • Stripe's comms hire: Looking for storytellers with taste, judgment, and founder DNA, ability to design microsites/launch podcasts/write keynotes, and why craft beats AI slop (mini city campaign callback, using AI internally but marketing human connection)

  • AI as a tool vs. AI as a crutch: Linear and Stripe using AI internally (minions fixing buttons, Slack bug tracking) but marketing craft and thoughtfulness, spray-and-pray doesn't work even with AI sparkle emoji, and why storytellers are the new CMOs (Wall Street Journal trend)

  • Founder-led marketing: Why early-stage companies can't skip founder-led comms and sales, fractional marketers as a solution, and the importance of figuring out positioning/messaging/channels before hiring tactics-only roles

  • Claude Ambassadors vs. Pete fumble: Anthropic launching ambassador program after fumbling Pete (the first Claude ambassador who got a cease and desist, then hired by OpenAI), and how acknowledging mistakes builds trust

  • Taylor Swift's gratitude playbook: Constantly thanking fans, special behind-the-scenes moments, and why humility keeps you relevant for 15+ years despite criticism

Plus: Why Zendaya and Tom Holland's relationship feels wholesome vs. Chalamet/Kylie Jenner, Chevrolet's holiday ad callback, Target's gift-wrapping employee moment, and the Monster's Inc marketing theory (laughter beats screams)

guest: Cynthia McGillis – Head of Marketing at Laribel (@CynthiaMcGillis on X, cynthiabellmcgillis.com)