Alex Oosterveen was in the middle of building a company when his life changed overnight. A former investment banker turned founder, Alex was diagnosed with Multiple Sclerosis at the very start of building Caribou - a moment that forced him to confront his health and the choices that led to this moment. In this conversation, we unpack what it really takes to scale a company while navigating uncertainty, chronic illness, and building a family.

Alex is the Co-Founder and CEO of Caribou, a Canadian healthtech startup tackling one of the most overlooked challenges in healthcare: the caregiver shortage. Caribou is a caregiver engagement platform that helps home care companies better support and retain caregivers.

He discusses:

• Being diagnosed with MS while building his company and how it reshaped his relationship with work, health, and ambition

• The lifestyle and environmental changes that transformed his health (spoiler alert: it wasn’t a drug)

• The deliberate path he took to gain the insight, experience, and credibility needed before entering the caregiver industry

• The pivotal decisions that accelerated Caribou’s growth

• Building a company with his wife, and how that choice strengthened both their partnership and the business

• How he thinks about work-life integration while raising their young boy

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Chapters

• 00:00:51 The MS Diagnosis: A Life-Changing Moment
• 00:03:27 Taking Control: Treatment and Lifestyle Changes
• 00:11:15 The Origin Story: From Investment Banking to Caregiving
• 00:19:22 The Labor Shortage Crisis in Home Care
• 00:22:58 Building Caribou
• 00:55:07 The COVID Pivot: Adapting to Survive
• 00:31:42 Bringing on a Co-Founder
• 00:38:10 Working with Your Spouse
• 00:44:19 Becoming a Father
• 00:45:56 Defining Success and Future Vision
• 01:00:22 Closing Wisdom: Advice for Parents and Founders

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Between Two Brunettes

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Samantha Miller

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Germana Kazazi

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Tiktok:https://www.tiktok.com/@germanakazazi

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Alex Oosterveen

LinkedIn: https://www.linkedin.com/in/alex-oosterveen/

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Produced by Thirty Two Media Inc.