What does it take to redefine an industry, navigate the highs and lows of entrepreneurship, and still emerge with a relentless drive for impact? In this episode of Leadership Odysseys, we sit down with Arvin Singh—a visionary fintech leader whose journey from the rice fields of Guyana to co-founding hoolah, and driving its acquisition by ShopBack, is nothing short of extraordinary.

Arvin’s story is one of bold decisions, unwavering resilience, and the art of embracing the journey, both professionally and personally. From his early days at Visa and Worldpay to shaping fintech ecosystems across Asia, Arvin shares not just milestones but the lessons learned in the messy, beautiful middle of leadership.

~ The Power of Starting Small: Arvin reflects on his humble beginnings in Guyana, the pivotal move to Canada, and how these early experiences shaped his worldview and leadership philosophy. ~ Entrepreneurship with Purpose: Discover how Arvin transitioned from corporate roles to co-founding hoolah, tackling self-doubt, and embracing the chaos of startups with conviction. ~ Navigating the M&A Rollercoaster: He offers an honest look at what it really feels like to sell the business you’ve built from scratch—the excitement, the grief, and the lessons in letting go. ~ Building Resilience Through People: Arvin emphasises the importance of surrounding yourself with the right people—mentors, co-founders, and advisors—and how these connections became his anchor during tough times. ~ Leadership Beyond Titles: As a current advisor and Board Member at Fly Fairly, Arvin shares insights on leading without authority, influencing change, and staying true to one’s values in evolving roles.

Arvin’s journey isn’t just about fintech success; it’s about growth, grit, and gratitude. His story reminds us that leadership isn’t a destination—it’s an odyssey, filled with unexpected detours, transformative experiences, and the courage to keep going even when the path isn’t clear.

If you’re a leader navigating change, an entrepreneur chasing your next big idea, or someone curious about what happens after the “big win,” this episode will resonate deeply.

Connect with Arvin Singh : LinkedIn

Connect with Kirsty Gee: LinkedIn | Instagram

Sponsorship: Flagship | Naturally Glutenfree