Can the skills that make an Olympic champion, the obsession, the resilience, the ability to surrender under pressure, be transferred to the real world? What happens when the cheering stops, the medal tarnishes, and you have to build an entirely new identity from scratch? And can a mission bigger than yourself actually pull you out of the darkest chapter of your life?

In this powerful episode of Giants, host Nejeed Kassam sits down with Jennifer Heil at the beautiful Cypress Mountain, the very site where she won Canada's first medal of the 2010 Vancouver Olympics. Jennifer is one of Canada's most decorated athletes, an Olympic gold and silver medalist, a four time world champion, and most recently the chef de mission for Team Canada at the 2026 Milano Cortina Olympics. But she is also so much more: a relentless entrepreneur, an advocate for safe sport and women's health, a Stanford GSB graduate, and a mother of three.

She opens up about her small town Alberta childhood, where she was raised with a "no gender norms" philosophy and learned to meditate before it was cool. We hear about the intense pressure of competing at home in 2010, the personal challenges she faced behind the scenes, including a friend's tragic accident that made her hate her sport, and the crushing disappointment of winning silver when gold was the only acceptable outcome. She talks about the physiological and emotional toll of retiring from sport, the "obsession to build" that led her to co-found B2Ten, and the difficult decision to close her first startup, Raya Health. She explains the mission behind her new venture, Revvel, which uses AI to scale the expertise of world class practitioners to support women's injury recovery.

It's a raw, honest, and insightful conversation about grief, identity, the burden of being an expert, and the realization that success isn't about the color of a medal. It's about the systems you build and the people you empower along the way. Let's dive in!

In This Episode:

• [01:09] Welcome & Framing: The Human Behind the Athlete
• [03:43] Small-Town Alberta, Family Toughness, & Choosing the Olympics at 9
• [08:05] Inner Competitiveness & Believing Before Anyone Else
• [10:43] Highs, Sacrifices, & Control in Elite Sport
• [16:27] Mental Training, Managing Expectations, & the Road to 2010
• [18:52] 2010 Vancouver Olympics: Competing at Home, Silver Medal, & Retirement
• [22:07] Post-Sport Realities: Physiological Toll & Canadian Athlete Funding
• [25:56] Transition to Entrepreneurship: Early Startups & Founding B2Ten
• [31:08] SafeSport Advocacy & Abuse Safeguards
• [36:09] Athlete-to-Founder Evolution & Stanford
• [37:35] Raya Health & Gaps in Women’s Health
• [45:12] Closing Raya & Pivot to Revvel (AI-Powered Reconditioning)
• [49:25] Redefining Success
• [51:51] Rapid Fire Questions

Our Guest

Jennifer Heil is an Olympic gold and silver medalist in freestyle skiing, four-time World Champion, and chef de mission for Team Canada at the 2026 Milano Cortina Olympics. While competing, she co-founded B2Ten, transforming how Canadian athletes are supported. After retiring, she earned an MBA from Stanford GSB and co-founded Raya Health. She now leads Revvel, using AI to scale elite injury reconditioning for women.

Giants

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Jennifer Heil

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• This Is Victory Podcast

• Revvel

• B2Ten

Nejeed Kassam

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