The Cherry Kicks Show

Alexis Santacruz grew his Colombian company from 100 to 600 people off one conversation. Then the government changed the rules and it all came apart. Jude and Tom sit down with the founder of OpenWorks to dig into the weirdest sales data he ever found (the best phone salesperson wasn't the hungry 25 year old techie, it was a woman with one kid), what it actually takes to restart from zero in a new...

What if the patterns quietly running your life were never actually yours to begin with? Trina Parnell (TP Coaching) is an Alignment Strategist who became obsessed with that question after her own long mental health battle — and built a coaching practice around helping people see what's really going on beneath the noise. Jude and Tom dig into why fear is a signal not a direction, why micromanagemen...

What happens when a bunch of school bus-sized humpback whales break the surface together, mouths wide open, herring jumping everywhere — and you forget to press the shutter button? Kevin Smith (Maple Leaf Adventures) has spent 25 years captaining expedition cruises through BC's Great Bear Rainforest, and his stories of "charismatic megafauna," COVID-era coastal cleanups, and why 40 million Canadia...

She called a bald eagle from three-quarters of a kilometer away—and it landed on her arm. Robin Radcliffe, Director of Pacific Northwest Raptors, joins Jude and Tom (with a spectacled owl named Elton in tow) to talk about the "landscape of fear," why your cat is the number one threat to songbirds, and what it's like to buy a family business your mom funded for a decade. We also hear...

Why is it getting harder to convince top talent to switch jobs in 2026? According to recruitment expert Kael Campbell (Red Seal Recruiting) , it isn’t just about the money—it’s about the "Best Friend" factor and a shifting sense of economic risk. In this episode, Jude and Tom dive deep with Kael into the "micro-markets" of the Canadian labor force, the "epidemic of lonelin...

In this episode, Jude and Tom sit down with Stewart Story . We talk about his experience growing up in the family business, his experience as a relatively new member to EO and how he feels very positive about the future of Victoria.

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...

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 rea...

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’...

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 per...

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 th...

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 http...

Co-founder of Berlin Eaton and Associates, Shelly has been a fixture of the BC management consulting community for three decades. Listen to how she has changed the industry and weathered the storms over 29 years at the helm. 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://e...

Founder of Full On Lighting, First Light and CEO at Xlynx Materials. Find out how this Esquimalt native specializes in imbedded logic to pioneer world-class products and the mental resilience he has unlocked along the way. 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://eov...

Our EO Vancouver Island Board President, Rich Van Leeuwen shares his plan and insights with us today and helps us to catch up on events local and far flung. 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/

In our inaugural podcast, we are joined by the straighttalking co-owner of Yeshi Foods Paul Kleinschmidt. Enjoy and keep your dumb feedback to yourself. Sheesh! The Entrepreneurs Organization is a globalcommunity of 20,000 business owners dedicated to peer-to-peer learning. Learn more about the Vancouver Island chapter here https://eovancouverisland.com/