Marketing That Stands Out: Peter Freedman’s Guerrilla Strategy Behind Calm’s Rise

Launching or scaling a brand in today’s saturated media landscape requires more than just ad spend or slick creative—it demands emotional resonance, bold storytelling, and a fearless embrace of the unconventional.

Few marketing folks embody this mindset better than Peter Freedman, founder of the creative PR agency Thinking of Think. But his path wasn’t always viral hits and media buzz. Like many founders in the creative space, Peter wrestled early on with the tension between unconventional ideas and commercial viability. Would clients trust weird? Would the media take it seriously? Could “funny” and “effective” coexist?

The answer came through persistence—and proof. His work with Calm, the now-iconic wellness app, turned the tide. With little budget and a lot of creative license, Peter helped the then-unknown brand grab global attention through quirky, emotion-driven campaigns. From an AI-generated fairy tale to an 8-hour film of sheep, Calm didn’t play it safe—and it paid off.

In a recent episode of the Marketing Umbrella Podcast, Freedman revealed the strategies behind Calm’s early viral hits—and why playing it safe is no longer a safe strategy.

Let’s dive into the key lessons and how you can apply them to grow your brand with creativity, courage, and heart.

1. Why Marketing Weird Wins: Quirky Ideas Create Unforgettable Attention

In a world overflowing with content, quirky and unexpected ideas aren’t just amusing—they’re essential.

Freedman helped Calm stand out with offbeat campaigns like an AI-generated Brothers Grimm fairy tale and an eight-hour video of sheep peacefully grazing in a field. These were more than gimmicks—they were brand-aligned, emotion-driven moments of delight that begged to be shared.

For marketers, the takeaway is simple:

  • Safe blends in; weird breaks through.

  • Audiences remember how you make them feel.

  • Surprise and humor are your secret weapons.

Supporting Stats:

  • 70% of viral content triggers an emotional response, particularly amusement and awe (NYT).

  • 58% of consumers say humor makes brands more relatable (Oracle).

Actionable Tip: Run a “Weirdness Workshop” with your team. Brainstorm 10 campaign ideas that would make your competitors nervous—but your audience delighted.

2. From Flash to Flow: Why “Rolling Thunder” Beats Big-Bang Markting Campaigns

Freedman’s philosophy is clear: one viral moment is good—ongoing creativity is better.

Rather than relying on a single big launch, Calm embraced a steady drumbeat of unusual, emotion-forward content that kept them in the public eye long after product announcements had faded.

This “Rolling Thunder” model favors consistency, evolution, and experimentation.

Key Practices:

  • Build momentum with a series of campaign “beats” rather than one massive push.

  • Use humor and surprise to keep audiences engaged over time.

  • Make every campaign part of a broader brand narrative.

Supporting Stats:

  • Brands with consistent messaging see 3-4x greater brand visibility (Lucidpress).

  • 45% of people are more likely to engage with campaigns that evolve over time (Google).

Actionable Tip: Plan campaigns as episodic arcs—think seasons, not episodes. Keep curiosity alive and evolving.

3. The Two Types of PR—and Why One Builds Real Buzz

Freedman breaks PR into two buckets:

  • Traditional PR: Product launches, founder bios, feature stories.

  • Guerrilla/Quirky PR: Weird ideas, viral content, emotional resonance.

While traditional PR plays a key role in launches, Freedman argues it’s guerrilla PR that keeps brands top-of-mind and culturally relevant. It’s cheaper, more memorable, and infinitely scalable.

Supporting Stats:

  • Quirky campaigns outperform standard PR by 2x in shareability and earned media (Nielsen).

  • 62% of consumers discover new brands via non-traditional media (Edelman Trust Barometer).

Actionable Tip: For every traditional press pitch, pair it with a left-field creative concept designed for social media, community sharing, or guerrilla exposure.

4. Markting Humor = Trust: Why Laughter Builds Brands Faster

Freedman believes humor does more than entertain—it builds emotional trust.

In Calm’s early days, campaigns used gentle humor to disarm skeptics and connect with stressed audiences. The result? A wellness brand that didn’t preach—it played.

Why Humor Matters:

  • It humanizes the brand.

  • It lowers defenses and increases engagement.

  • It transforms passive viewers into active sharers.

Supporting Stats:

  • Humor increases ad recall by 47% (Clutch).

  • 90% of people are more likely to remember a funny ad (Ipsos).

Actionable Tip: Test humor in your next campaign—even a small twist of irony or absurdity can spark deeper connection and memorability.

5. Playing It Safe Is the New Marketing Risk

Freedman’s most powerful insight might be this: Inattention is the real danger.

Many brands default to “professional” messaging to avoid risk, but in doing so, they vanish into the background. Freedman argues that taking smart creative risks is what drives real results—and builds the kind of brand loyalty that lasts.

Supporting Stats:

  • Brands seen as “bold” are 3x more likely to win Gen Z loyalty (McKinsey).

  • 80% of viral brand campaigns had some element of calculated risk (Wired).

Actionable Tip: Review your last five marketing pieces. Ask: “Would anyone share this with a friend?” If not, it’s time to push creative boundaries.

Apply These Lessons to Your Own Brand with Umbrella

Peter Freedman’s success with Calm isn’t about luck or big budgets—it’s about bravery, creativity, and a deep understanding of how emotion drives attention.

Here’s what you can steal and scale:

  • Embrace weirdness—it’s cheaper and more effective than celebrity.

  • Roll out campaigns over time, not just in one shot.

  • Use humor to build trust and humanize your message.

  • Dare to break the mold—risk is the new safe.

Want to create campaigns that actually get noticed? Umbrella offers white-label solutions and AI-powered tools to help your agency deliver creative work that scales—and sells. Learn more at https://umbrellaus.com!

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