This is the Leadership Journey series on the Choosing Leadership Podcast.

I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name.

In this candid conversation, James Jackson, CEO and co-founder of Bumper, shares the behind-the-scenes of building a high-growth fintech—while staying humble, hiring intentionally, and protecting company culture across borders.

From fixing tractors on his farm to navigating billion-dollar payments, James proves that great leadership isn’t about titles—it’s about ownership, balance, and grit.

If you’re leading a team through rapid change or wrestling with how to grow without losing your soul, this episode is your playbook.

Tune in to discover how humility, vision, and discipline come together to create lasting impact.

You can find James Jackson at the below links

• https://www.linkedin.com/in/james-jackson-103ba412/    

In the interview, James shares

• "Our culture is rooted in humility—no egos, just people making things happen together." 
• "Leadership means being willing to do the dirty work and the strategy—sometimes in the same hour."
• "We built Bumper by seeing a financial gap no one was solving for—and then obsessively solving it."
• "Hypergrowth doesn't happen by accident. It takes bold moves, strong talent, and a culture of ownership."
• "Hiring the right people isn’t about speed—it’s about patience and finding those who truly fit."
• "Leadership is about creating a place where people want to take ownership, not where they’re told to."
• "We’ve evolved from a buy-now-pay-later tool into a full payment orchestration platform. That’s scale with intention."
• "Farming keeps me grounded. Fixing a tractor gives me clarity a boardroom sometimes can’t."
• "Daily high-intensity workouts are my mental reset—they make me a sharper leader."
• "Great leadership isn’t about being in charge. It’s about being in service—to your team, your customers, and your mission."