In this episode, we’re joined by Amy Stein, Chief Impact Officer at Generations Trusted Family Business Advisors. With over 20 years in her family’s fourth-generation business, Henry’s, and experience launching its mental health foundation, Amy brings a rare perspective on legacy, leadership, and impact. Our conversation focuses on what transition really feels like, how identity shifts, how clarity emerges through change, and how purpose can take on new meaning when familiar roles evolve. It’s a personal, layered look at the emotional side of stepping into what’s next.
Amy shares reflections shaped by lived experience and thoughtful observation. We talk about resilience, voice, and the quiet work of preparing for change even when you don’t yet know what the next chapter will hold.
About Amy Stein
Amy Stein is the Chief Impact Officer at Generations Trusted Family Business Advisors, where she helps family enterprises and their family offices develop values-aligned philanthropic strategies that engage rising generations and create measurable impact. With a strategic, people-centred approach, she supports families in looking beyond financial metrics to integrate business, employees, customers, and community in meaningful ways. Her work focuses on designing initiatives that scale with intention, reflect legacy, and build lasting social capital.
For over two decades, Amy was a key leader in her family’s fourth-generation business, Henry’s, Canada’s largest independent imaging retailer. She later spearheaded the launch of the Foundation for Henry’s, a creative mental health initiative rooted in community impact. Drawing on deep experience in governance, strategy, and operations as a family member, executive, board member, and shareholder, Amy brings insight into the complex dynamics of family enterprise. She is especially skilled at bridging generational perspectives and helping families align purpose with action.
Resources discussed in this episode:
- Rotman School
- Pixel Foundation
- David Bentall
- Family Enterprise Canada
Contact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.
- Website: BeaconFamilyOffice.com
- LinkedIn: Cory Gagnon
- LinkedIn: Beacon Family Office
- Email: beaconfamilyoffice@assante.com
Contact Amy Stein | Generations Trusted Family Business Advisors:
- Website: gtfba.com/ | pixelfoundation.org
- LinkedIn: Amy Stein
- Email: amystein24@gmail.com
We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises.
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