Sisters in Style: How the Barber Sisters Built Poppy Barley

November 15, 2025

How can two sisters with different career paths create a successful luxury fashion brand while maintaining strong family bonds? In a revealing episode of Table Talk with ABFI, Justine and Kendall Barber share how they transformed a custom footwear idea into Poppy Barley, a thriving, sustainable fashion enterprise. Their journey offers valuable insights for business families navigating entrepreneurship, sibling partnerships, and work-life balance.

From Vacation to Company Visioning: The Birth of a Family Enterprise

The Barber sisters' path to entrepreneurship wasn't planned. "I always thought I wanted to save the world," Justine reflects, while Kendall had always dreamed of being an entrepreneur. Their different perspectives would eventually create the perfect blend of purpose and business acumen.

A pivotal moment came during Justine's trip to Bali, where a custom boot experience sparked an idea. Her subsequent email to Kendall wasn't just a business proposition – it was the beginning of a transformative family journey.

Building a Foundation of Complementary Leadership

The sisters' success stems from their ability to leverage their differences:

  • Clear Division of Responsibilities

"We divided the company very early on," Kendall explains. "We really wanted there to be clear decision making with one person." Today, Justine leads product operations and retail, while Kendall manages e-commerce, marketing, brand, and customer experience.

  • Trust-Based Decision Making 

Their approach to leadership transitions demonstrates remarkable maturity: "We have deep trust for each other," Kendall notes. "We really value each other's skill sets." This trust allows them to regularly reassess and adjust their roles based on the business's changing needs.

Navigating Family Dynamics in Business

The sisters' experience reveals key insights for family business success:

  1. Balance Family and Business

"Work doesn't work unless life's working," Kendall emphasizes. This philosophy shapes not only their relationship but also their company culture, extending flexibility to employees managing family responsibilities.

  1. Create Support Systems

The sisters acknowledge a unique challenge of family business: "Being in a family business is both less lonely and more lonely," Kendall reflects. They recommend engaging coaches and joining peer groups to navigate complex family dynamics.

Learning from Childhood Lessons

The Barbers' business approach was shaped by their upbringing:

  • Financial Literacy

Family budget meetings and early exposure to financial decision-making helped develop their business acumen. "The amount of flip-charting we did as a family was not normal," Kendall laughs, recalling childhood family discussions.

  • Adaptability

Frequent moves taught them to navigate new situations together – a skill that proved invaluable in entrepreneurship.

  • Building for the Future

The sisters maintain a pragmatic approach to their company's future:

  • Focus on sustainable growth
  • Balance personal and professional goals
  • Consider eventual sale to aligned buyers
  • Maintain strong family relationships throughout transitions

Practical Insights for Business Families

For families considering business partnerships, the Barbers offer valuable advice:

  1. Establish Clear Boundaries
  • Define decision-making responsibilities
  • Respect personal and professional space
  • Create systems for conflict resolution
  1. Seek Outside Support
  • Engage business coaches
  • Join peer groups
  •  Build professional networks outside family
  1. Maintain Work-Life Balance
  • Set clear working hours
  • Prioritize family relationships
  • Create space for personal growth

Moving Forward

The Poppy Barley story demonstrates that family business success isn't just about profit – it's about building something meaningful while preserving family bonds. As Kendall notes, "I ultimately cared way more about Justine as a person than I do about the business." This foundation of family-first values, combined with clear business strategies, creates a platform for sustainable growth and positive impact.

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Connect with the Alberta Business Family Institute for more insights into family business dynamics and sibling partnerships. Our community brings together business families, advisors, and researchers to share experiences and best practices. 

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