109: Counting Sheep to Marketing Virality with Peter Freedman

The Power of Weird: How Calm Used Quirky PR to Go Mainstream

Before Calm became one of the most recognizable wellness apps in the world, it was a nine-person startup in a tiny San Francisco apartment with a big problem: no one knew it existed. That’s when they brought in Peter Freedman, founder of Thinking of Think, a creative PR and guerrilla marketing firm known for turning offbeat ideas into global attention.

In this episode of the Marketing Umbrella Podcast, we sit down with Peter to unpack the viral campaigns that helped Calm stand out in a crowded market. From an AI-generated Brothers Grimm fairy tale to an eight-hour film of sheep standing in a field, Peter shares how calculated weirdness—and a lot of heart—became Calm’s secret weapon.

Peter also breaks down his 10 Golden Rules of PR and guerrilla marketing, explains why humor builds trust faster than a press release ever could, and makes the case that playing it safe is now the riskiest strategy of all. Whether you're building a brand from scratch or looking to reboot your messaging, this conversation will challenge the way you think about attention, emotion, and what it really takes to stand out today.

Key Takeaways:

• Weird Wins Attention. In a crowded market, quirky, unexpected ideas can be more powerful than polished ones.
• “Weirdness and celebrities” are the two things that still get media attention, but weirdness is cheaper, repeatable, and limitless.
• Rolling Thunder Beats One Big Bang. Consistent, creative content outperforms one-off stunts.
• Emotion Drives Sharing. People share what makes them feel something—especially humor and joy.
• Not All PR Is Created Equal. There are two kinds of PR. 
  • Traditional PR: Product-focused, informative, and effective for launches—but risks becoming stale.
  • Quirky/Guerrilla PR: Creative, ongoing, shareable, and ideal for staying top-of-mind post-launch.
• The main barrier is fear, not fit. Brands that embrace this creativity early tend to be perceived as cool, approachable, and human.
• Risk Is Relative. In today’s noisy world, playing it safe is the real gamble.
• Delight Builds Loyalty. People remember how a brand made them feel. Entertainment creates lasting impressions.

Peter reminds us that standout marketing doesn’t always require a big budget, just bold ideas, emotional resonance, and a willingness to break the mold. In a world overloaded with noise, the brands that dare to be different are the ones we remember.

As a closing thought: “The best ideas don’t blend in. They break through. Quirky marketing works because it dares to be memorable in a world that forgets fast.”

Listen to the full conversation here:

• YouTube: https://www.youtube.com/@frintmedia
• Apple Podcast: https://podcasts.apple.com/us/podcast/the-marketing-umbrella-podcast/id1564111428
• Spotify: https://open.spotify.com/show/4CoiR10nazd9zVIStLkcjk

 

Connect with Peter:

• LinkedIn: https://www.linkedin.com/in/peterfreedman1/ 
• Website: https://www.think-inc.co.uk/ 

 

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To learn more about Umbrella and to connect with CEO Itamar Shafir, go to ⁠https://umbrellaus.com