The Cherry Kicks Show

In this episode, Jude and Tom sit down with ⁠Jason Henneberry. They talk about growing up in a family of entrepreneurs, learning how to pivot from his parents and what it's like to face failure and dig your way out.

The latest edition is brought to us by Fischer Financial Services and Green Label Creative.

In this episode, Jude and Tom sit down with Robin Kelley. They talk about growing up, crashing motorcycles, friendship and why Robin joined EO.

This episode is brought to you by Adam McLean and the team at BMO — dedicated partners helping business owners and entrepreneurs navigate growth with financial expertise and strategic support. If you’re looking for a banking relationship built on local insight and global reach, connect with Adam on LinkedIn here.

Today, we sit down with Tom Benson, Co-Founder and CEO of WildPlay. Tom’s story is a masterclass in turning a passion for adventure into a global business.

We trace his journey from:

• The Early Years: His first formative adventures as a young man that sparked a lifelong love for the outdoors.

• The Guiding Days: Learning the ropes of leadership and risk management while running his own guiding business.

• The WildPlay Era: Scaling a vision of "active play" into a world-renowned brand and his evolution into a Chief Experience Officer focused on pushing human boundaries.

It’s a wide-ranging conversation about the mechanics of adventure, the transition from guide to CEO, and why we all need a little more "edge-of-your-seat" experience in our lives.

This episode is brought to you by Sang Ly and the team at KPMG. As the leader of KPMG’s Enterprise and Technology Practices in Victoria, Sang brings over 17 years of global experience—from London to Silicon Valley—to help private companies and non-profits thrive. Whether you are navigating complex audits or scaling a multinational enterprise, Sang and KPMG provide the local insight and global reach necessary for long-term success. Connect with Sang on LinkedIn or visit KPMG Canada.

Why do some high-performing leadership teams stall while others thrive? Today, we’re sitting down with Greg Nuk, a specialist in unlocking "execution velocity." Greg is the creator of the Total Team Effectiveness (TTE) metric and an AI Team Coach designed to help leaders see the "invisible" dynamics that hold their organizations back.

In this conversation, Greg breaks down how team alignment is the ultimate, often overlooked, competitive advantage. We explore:

• The TTE Metric: How to turn "soft" team dynamics into hard data that predicts EBITDA performance.

• Rapid Alignment: How to spot misalignment early and guide dysfunctional teams toward exceptional results.

• AI in the Boardroom: Using technology to visualize what is really holding a team back before it leads to burnout or attrition.

• The 15% Lever: Why only a fraction of executives are pulling the strategic lever of team effectiveness—and how you can join them.

Whether you are leading a $600M AUM firm or a growing regional team, Greg’s systematic approach offers a roadmap to executing faster, with more precision and more joy.

The Human Side of Execution

This episode is brought to you by Gabe Dhahan and the team at Bellrock. If you are a leader looking to unleash your organization's potential, Bellrock brings the strategy, change management, and hands-on support you need to overcome your biggest challenges. To find those "Aha!" moments that lead to lasting results, connect with Gabe on Linkedin or at their website: https://bellrock.ca.

Today we’re sitting down with Holly Dickinson, the founder of StrideHer Run Coaching. Holly is redefining how women train by blending running, strength, and mobility into routines that fit real life—not the other way around. She digs into how she helps women discover what their bodies are capable of through every stage of life, from pregnancy to menopause. It’s an empowering conversation about building confidence, coaching the "whole human," and creating a global community.

This episode is brought to you by Vern and the team at Fischer Financial — trusted advisors who help founders build financial clarity and confidence. If you’re looking for expert guidance delivered with real integrity, connect with them at fischerfinancial.ca.

Today we’re sitting down with Nick Banks — a leadership coach and culture strategist who helps organizations align people, purpose, and performance. Nick digs into what he’s learned from real comeback stories, why setbacks can sharpen your focus, and how teams rebuild with intention. It’s a sharp, grounded conversation about resilience, culture, and designing your next chapter.

Today’s guest is Karen Fishwick, founder and head of Atlassian operations at Highway Three Solutions. With over 25 years in the IT industry, Karen has become a go-to expert in helping organizations modernize their systems of work, from complex Jira migrations to large-scale digital platforms. She’s known for her technical depth, steady leadership, and a long track record of delivering solutions that actually move businesses forward. Excited to have her with us today.

Jude and Tom spend time chatting to Paul Nursey who is the Chief Executive Officer of Destination Greater Victoria, where he leads tourism marketing, strategy, and branding efforts for the region.

The Entrepreneurs Organization is a global community of 20,000 business owners dedicated to peer-to-peer learning. Learn more about the Vancouver Island chapter here https://eovancouverisland.com/

Jude and Tom have a chat with Tessa Mcloughlin the CEO and founder of Club Kwench Co working space in Victoria. Learn about how she fosters the ideas of community and inclusiveness in her unique space.

The Entrepreneurs Organization is a global community of 20,000 business owners dedicated to peer-to-peer learning. Learn more about the Vancouver Island chapter here https://eovancouverisland.com/

The owner of Gladiator Drywall Blue Vasseur is EOVI's newest member. Blue tells us about the discipline he learned in the Alberta oil patch and how that has lead to his success in the construction industry and in his family life.The Entrepreneurs Organization is a global community of 20,000 business owners dedicated to peer-to-peer learning. Learn more about the Vancouver Island chapter here https://eovancouverisland.com/