In the Ring with Rob: From Corporate Finance to Entrepreneurship with David Rogers

In this episode, host Robert Olson sits down with veteran finance leader and entrepreneur David Rogers, who shares his remarkable journey from corporate roles at Cooper's and Lybrand and TD Bank to creating Caledon Capital, which grew to manage $10 billion in assets under management. David offers candid insights into his career transitions, from joining FirstService in its infancy as Vice President and CFO to building OMERS' private equity program and ultimately launching his own successful investment firm. Throughout the conversation, he emphasizes how his people-first leadership philosophy shaped his success, the importance of trusted mentors, and finding the right strategic partners for business growth. Now semi-retired and serving on Nicola Wealth's private capital investment committee, David reflects on balancing professional accomplishments with personal fulfillment. Highlights 3:40 - Early career beginnings 10:45 - Creating OMERS' private equity program and investment approach 14:40 - Lessons in leadership and building a people-first culture 16:00 - Identifying market gaps and launching a business 22:15 - Strategic partnerships and business evolution 24:50 - Balancing advisory roles and achieving work-life balance 29:00 - Career reflections Sign Up for our Newsletter