Kelsey was a world politics major at Hamilton, but hockey was his bedrock. By his junior year, he was in talks with professional agents. Ultimately he extended his playing career, most notably with the Memphis RiverKings. But after more than a decade of being “in it 24/7,” Kelsey tapped into his network of Hamilton friends to find his next step. Encouraged by Kevin Kenyon ’82, brother-in-law of his roommate Matthew Henderson ’93, Kelsey began a career in the mortgage industry.
Then came the unexpected. Kelsey suffered a traumatic brain injury from a fall in 2018, which prompted him to reflect on other areas of his life — notably the anxiety and depression he experienced during his hockey career. “One of the biggest parts of my recovery, starting then, was speaking with other people who had gone through something similar,” Kelsey explained. “That’s how Shareapy was born.”
“We’re re-engaging in relationships that we had 10, 15, 30 years ago ... And at the same time, we’re building a wellness community.”
Close friends, some of whom had also experienced life setbacks, encouraged Kelsey to scale up his passion project into a cross-generational community that’s part of a continuum of care, and he’s only continuing to expand. Hamilton alumni have been with him at every stage, from investing in the business to testing the platform and advising the Shareapy team. “We’re re-engaging in relationships that we had 10, 15, 30 years ago,” Kelsey said. “And at the same time, we’re building a wellness community.”
Shareapy relies on a collaborative model. Members can receive training to become meeting facilitators, through which they acquire problem-solving and communication skills that are also applicable to their daily lives. Facilitators lead weekly 60-minute sessions for other users. As the needs of Shareapy users change, the platform shifts with them. Specialized groups now exist for athletes, military personnel, and corporate employees.
Storytelling and sharing, which Kelsey feels are often underestimated, remain at the platform’s core. “There are times when we don’t give ourselves credit in terms of our experiences,” he said. “A problem shared is a problem halved.”
Kelsey judges the future of Shareapy by its impact. Currently the platform boasts 200+ members, including several Hamilton alumni and current students. “The proof is already there in terms of what we’re doing. The key is getting more people to experience it,” he said. “The Hamilton community is proof.”
Posted February 24, 2026
