Million Dollar Moments

Let's dive in!

In 2022, a woman named Anna Brose made what she thought was a routine call to Chewy's customer service.

Her dog Gus had just died, and she needed to return an unopened bag of dog food.

What happened next is a masterclass in creating Million Dollar Moments...

First, Chewy issued a full refund – but told her not to bother sending the food back. "Please donate it to a local shelter instead," the representative said.

Anna was touched by the gesture. But Chewy wasn't done.

Two days later, a delivery arrived at her door – a bouquet of flowers with a handwritten note expressing condolences for her loss of Gus.

When Anna shared this experience on Twitter, it exploded: 44,000 retweets and 650,000 likes within days.

But here's what makes this story relevant to us as entrepreneurs and business builders: This wasn't just a random act of kindness by an empowered employee.

It was a deliberately designed emotional connection – one that's helped Chewy build a $17 billion business competing against giants like Amazon in what should be a pure commodity market.

And it reveals a playbook we can all learn from.

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The Profits Hidden in Experiences

Before we dive into tactics, let's address the skeptics: Does emotional connection actually drive business results?

Some data for you:

• Customers with emotional connections have a 306% higher lifetime value (Motista)
• They stay with brands 5.1 years longer than satisfied customers (Gallup)
• They're 71% less price-sensitive (Capgemini)
• They recommend brands at much higher rates (83% vs. 29%)

Chewy understands this math perfectly. Their emotional connection strategy might seem expensive when viewed through a short-term lens:

• Personalized handwritten cards for new customers
• Surprise birthday gifts for pets
• Custom pet portraits sent to random customers
• Flowers and condolence cards when pets die

But when you calculate the lifetime value of an emotionally connected pet owner (Chewy average: $2,700), along with the exponential reach of their word-of-mouth marketing, these "expenses" reveal themselves as high-ROI investments.

Looking back at 15 years of cohort data across my three businesses, our highest-value customers—the ones who spent 4.3x more and stayed with us 2.7x longer—almost always came from experiences we created to drive word of mouth.

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Deep Dive: The Rise Framework

After a decade of testing emotional connection strategies with both startups and global brands, I've found the RISE framework to be consistently the most effective approach.

Here's how it works:

1. Recognition

Customers want to feel seen and acknowledged as individuals. Chewy accomplishes this by:

• Using the pet's name in all communications
• Remembering pet birthdays
• Having support agents view customer pet profiles before calls

2. Integrity

Emotional connections thrive when brands act with authenticity and consistency.

For Chewy, this means their compassionate returns policy isn't just for viral moments—it's their standard operating procedure, even when no one's watching.

3. Surprise

The unexpected creates emotional spikes that cement brand relationships.

Chewy's pet portraits and condolence flowers work because they're unexpected. There's no form to request these items. They aren't advertised benefits. They appear almost magically at emotional inflection points. The element of surprise evokes a far greater connection than something planned or promised.

4. Empathy

Brands that understand and respond to customer emotions—especially during difficult moments—create unbreakable bonds.

Chewy's response to pet death demonstrates profound empathy. They don't just acknowledge the practical need (returning unused product); they acknowledge the emotional reality of losing a beloved companion.

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3 Brands Crushing Emotional Connection

1. Trader Joe's Silent Magic

While other grocery chains optimize for efficiency, Trader Joe's designs for serendipity and human connection. Their smaller-format stores, constantly rotating products, and no-self-checkout policy seem inefficient on paper but create a treasure-hunt experience that builds emotional attachment.

Key Insight: Sometimes the "inefficient" choice is actually the emotional-connection choice.

2. Liquid Death's Identity Revolution

A canned water company shouldn't be valued at $1.4 billion. But Liquid Death has turned hydration into an identity statement by creating an irreverent, rebellious brand personality that transforms the mundane act of drinking water into a statement of values.

Key Insight: Even the most commodity product can become an identity marker with the right emotional positioning.

3. Spotify's Year in Wrapped Phenomenon

Each December, Spotify transforms dry listening data into a personalized, shareable celebration of identity. Their "Wrapped" campaign generated 60 million shares in 2022 and became a cultural moment. It creates an annual emotional peak that drives retention and acquisition through social sharing.

Key Insight: Converting customer data into identity-affirming narratives creates both emotional connection and viral marketing opportunities.

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Implementation Guide: 5 Steps To Take Now

1. Identify Emotional Inflection Points Map your customer journey from start to finish, and identify 2-3 high-emotion moments where connection opportunities exist.
2. Create One Signature Moment Design a specific, repeatable experience that customers would want to tell others about.
3. Train for Emotional Intelligence Help your team recognize and respond to emotional cues in customer communications (email, SMS, customer support, onboarding).
4. Audit Your Communication Review your automated messages, scripts, and policies for opportunities to inject personality.
5. Measure What Matters Beyond NPS and CSAT, track emotional indicators like unprompted mentions, storytelling, and social sharing