In this episode of The Retail Pilot, host Ken Pilot dives into the future of branding and retail innovation with Emily Heyward & JB Osborne, Co-Founders of Red Antler and a pre-flight discussion with retail futurist Jan Kniffen.

From the transformative role of AI in customer experience to the secret sauce behind some of today’s most iconic brands, this conversation explores how emotional resonance, creativity, and technology intersect in modern retail. Ken, Emily, and JB also discuss brand building from scratch, the challenges of rebranding, and their venture fund Habitat Partners. Plus, they reflect on favorite campaigns, dream brand revivals, and the evolving landscape of consumer expectations.

Show Notes

• Ken Pilot introduces the episode with commentary from retail expert Jan Kniffen on the seismic impact of AI across industries, especially in retail.

• Jan shares why AI will redefine omnichannel experiences and customer expectations, emphasizing the urgency for retailers to invest or fall behind.

• Emily Hayward and JB Osborne join Ken to discuss Red Antler’s approach to branding, which centers on empathy, storytelling, and strategic creativity.

• Insights into how Red Antler partners with early-stage founders and legacy businesses, building emotional connections through meaningful brand positioning.

• Reflections on helping launch brands like Allbirds, Casper, Burrow, and Hinge, including the challenges and rewards of naming and storytelling.

• Candid thoughts on the rise and stumbles of DTC pioneers and how capital structure, not branding, often drives downfall.

• A look at Habitat Partners, their investment arm, and why equity plays helped foster long-term alignment with founders.

• Exploration of how AI is impacting creative workflows, campaign ideation, and brand communication.

• Rapid fire favorites, from travel destinations to go-to coffee brands, and the dream jobs Emily and JB would pursue outside of Red Antler.

• Plus, JB and Emily name the brands they’d love to reimagine—from OpenTable to LinkedIn—and share their vision for brand leadership in a tech-driven era.

This episode is sponsored by Firework.

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