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Episode 36

Bootstrapping a Billion-Dollar Underdog with Mike Wessinger

In this episode, Fahd sits down with Mike Wessinger, founder and Executive Chairman of PointClickCare, to explore his journey from installing desktop computers in nursing homes to building one of Canada's most valuable tech companies. Mike shares how a firsthand look at an industry still running on paper charts and binders led him and his brothers to bet on cloud-based software before "cloud" was even a word, taking on Goliaths in one of the most regulated industries in tech.From bootstrapping through the early days of hand-to-hand sales to de-risking adoption for an industry that couldn't afford to gamble, Mike discusses what it really takes for a David to survive long enough to win over an entire sector. He also shares insights on leadership, resetting culture through hypergrowth, and how PointClickCare has stayed nimble and innovative even after becoming the Goliath itself.

Guest Bio

Mike Wessinger

Mike Wessinger is PointClickCare’s Co-Founder and Executive Chair of the Board. Prior to taking on the role of Executive Chair, Mike served as PointClickCare’s Chief Executive Officer from 1995 to 2021. Mike’s vision and leadership established PointClickCare as the first cloud-based health information system for the senior care industry. Relentless in his pursuit to disrupt the healthcare status quo, Mike’s forward-thinking vision drove the organization to break silos across the healthcare ecosystem, creating North America’s largest care collaboration network. In his role as Executive Chair, Mike continues to champion corporate culture, enhance governance, recruit diverse talent, and partner both internally and externally to solve critical healthcare challenges and propel PointClickCare forward as a world-class organization. Outside of PointClickCare, Mike serves on the Ontario Health Data Council and is also Co-Chair of the C100 board of directors, where he actively leverages his years of experience to coach and mentor leaders at the helm of rapidly scaling tech companies.