In this episode, we sit down with Quinn Underwood — serial entrepreneur, University of Toronto grad, and founder of Autumn, a groundbreaking mental health startup acquired by Qualtrics. Quinn shares his journey from growing up around small business owners to becoming a tech founder. Today, he's helping organizations rethink how they measure mental health, detect early signs of burnout, and proactively strengthen team dynamics.

We explore how he pivoted from early interests in medicine and law to launching Autumn, and how he and his team built proprietary AI models that redefined employee wellness — shifting the focus from outdated surveys to behavioral and communication-based insights. Quinn also shares what it was like transitioning from running a tight-knit startup to joining a 6,000+ person company at Qualtrics, and the key differences in strategy, execution, and leadership.

As both an entrepreneur and angel investor, Quinn dives into what makes a great founder, the anatomy of high-performing teams, and the critical role of autonomy, trust, and psychological safety in preventing burnout and unlocking peak performance.

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