In this episode, Cole Heilborn sits down with Massimo Alpian, the Global Director of Communications at Tracksmith, to explore the evolving challenges of brand storytelling in today’s fast-paced digital landscape. They dive into the creative philosophy behind Tracksmith’s most successful campaigns, including the "Year of the Amateur" and "Church of the Long Run," and discuss the brand’s unique approach to fostering emotional connections with runners.

Massimo shares insights into why authenticity is key in content creation, how Tracksmith balances long-form and short-form storytelling, and the complexities of measuring ROI in brand marketing. They also unpack the impact of shifting social media trends and how brands can adapt their creative strategies to maintain audience engagement.

Referenced Topics:

• Tracksmith’s "Year of the Amateur" campaign: Watch here

• "Church of the Long Run" project: Explore here

This podcast is produced by Port Side, a creative studio powered by the Backcountry Marketing Filter™, our methodology shaped by 200+ conversations with marketing leaders to turn insight into emotionally-driven video strategy.

Enjoy this episode and discover other resources below:

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

Patreon | Want to support us financially? 

Every person who watches your content is silently asking the same question: “Why should I care?” And if your brand doesn’t answer that clearly and quickly, the message won’t land, no matter how beautiful the visuals are.

In this solo episode, Cole unpacks why this question is the real test of whether content works. Drawing from hundreds of interviews with outdoor marketing leaders, he shares common pitfalls brands fall into, how to avoid them, and why answering why it matters is the creative north star for any campaign.

Whether you're planning a brand film, campaign, or product launch, this episode will challenge how you approach content and give you a framework to make sure your story sticks.

This podcast is produced by Port Side. We're a creative studio that blends the best of a creative agency with the executional power of a production company backed by a methodology crafted from 200 marketing leaders that produces emotional and strategic video content.

Enjoy this episode and discover other resources below:

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

Patreon | Want to support us financially? 

If you’re a creative, marketer, or brand strategist, you’ve probably felt the frustration of working on campaigns that lack clear direction. Maybe you’ve been handed a brief and thought, This doesn’t feel right, but you weren’t given the space to challenge it. Or maybe you’ve seen brands struggle to stand out because they’re stuck following trends instead of creating something original.

In this episode, Cole sits down with Matt Trappe—photographer, director, and brand strategist in the running world—to help you understand how creatives can play a bigger role in shaping brand strategy, rather than just executing it. Matt and Cole break down why integrating creative thinking into brand strategy leads to stronger, more authentic storytelling—and ultimately, better results.

Key Topics: 

• The tension between marketing and creativity—why brands need both but often default to marketing-led approaches.

• How brands can empower creatives to contribute beyond execution and influence strategy.

• The importance of knowing your audience deeply rather than relying solely on data-driven decisions.

• Why originality and authenticity matter more than ever in an era of mass content production.

• The viral success of the Strava x Chipotle challenge and how great storytelling drives engagement.

This podcast is produced by Port Side. We're a creative studio that blends the best of a creative agency with the executional power of a production company backed by a methodology crafted from 200 marketing leaders that produces emotional and strategic video content.

Enjoy this episode and discover other resources below:

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

Patreon | Want to support us financially?

In today’s episode, Cole pulls back the curtain on Port Side’s next evolution and reveals a powerful new tool for outdoor marketers. The Backcountry Marketing Filter is a living database built from over 250 insights shared by the brightest minds in the outdoor industry—leaders who’ve mastered the art of creating strategic, emotional, and effective video content.

This isn’t just a resource. It’s the foundation of a new approach.

Port Side is no longer just a production company. We’ve become a creative studio that blends the best of a creative studio with the execution power of a production company.

Curious how it works? Tune in to learn how the Backcountry Marketing Filter can help you identify blind spots, avoid common pitfalls, and pressure-test your brand films, product launches, and campaigns—before they go live

This podcast is produced by Port Side. We're a creative studio that blends the best of a creative agency with the executional power of a production company backed by a methodology crafted from 200 marketing leaders that produces emotional and strategic video content.

Enjoy this episode and discover other resources below:

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

Patreon | Want to support us financially? 

In this episode, Cole Heilborn sits down with Charlie Grinnell, the co-founder and CEO of RightMetric, to unpack the changing landscape of audience behavior, content strategy, and digital marketing.

Charlie shares why outdoor brands aren’t just competing with each other—they’re competing with Netflix, TikTok, and everything else that demands attention. He explains why understanding audience behavior is more critical than ever, how brands should rethink content effectiveness, and why data-driven insights should fuel creative decisions.

They also discuss how brands can avoid making content for a destination that doesn’t exist, the pitfalls of the one-size-fits-all approach to audience personas, and the power of using insights to unlock creative potential.

• You’re competing for attention, not just with your industry. Outdoor brands need to recognize that consumers are bombarded with content from all directions.

• Audience understanding is no longer optional. If you don’t know exactly who your audience is, where they spend time, and what they engage with, your content won’t perform.

• Data and creativity must work together. The best marketing decisions combine strategic insights with bold creative ideas.

This podcast is produced by Port Side. We're a creative studio that blends the best of a creative agency with the executional power of a production company backed by a methodology crafted from 200 marketing leaders that produces emotional and strategic video content.

Enjoy this episode and discover other resources below:

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

Patreon | Want to support us financially? 

In this episode, we sit down with Myles McCutcheon, Director of Content for the Vancouver Canucks, to explore the fascinating parallels between professional sports and the outdoor industry. Myles shares insights on audience engagement, the importance of authenticity, and how sports teams operate like content powerhouses. We discuss the differences in content strategy, the role of athletes versus creators, and what the outdoor world can learn from sports teams' storytelling approaches. If you're looking to refine your brand’s content strategy, this episode is packed with valuable takeaways.

Key Topics:

• Real-time storytelling during live sports games vs. content creation timelines in the outdoor world.
• Balancing evergreen vs. timely content and understanding where each adds value.
• The evolving roles of athletes and creators as key storytellers and ambassadors.
• How budget allocation and social impact initiatives differ between industries.
• The power of emotional storytelling to build human connections and drive audience loyalty

This podcast is produced by Port Side Productions. We are a production company that works with outdoor brands to create effective and emotional videos. To date, we’ve made feature documentaries, video podcasts, product videos, and commercials. The thing that unifies us is our unwavering goal to help brands make effective videos driven by emotion and backed by strategy.

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

Find Out Why | Curious why a video production company would produce a marketing podcast?

In this episode, Myles McCutcheon, the Director of Content at the Vancouver Canucks joins Cole to dive into the world of content creation, drawing fascinating parallels and distinctions between the sports and outdoor industries. Myles shares insights on audience engagement, the importance of authenticity, and the unique challenges of crafting content for highly knowledgeable markets.

Key Topics:

• Real-time storytelling during live sports games vs. content creation timelines in the outdoor world.

• Balancing evergreen vs. timely content and understanding where each adds value.

• The evolving roles of athletes and creators as key storytellers and ambassadors.

• How budget allocation and social impact initiatives differ between industries.

• The power of emotional storytelling to build human connections and drive audience loyalty

This podcast is produced by Port Side Productions. After nine years of production work and 190 episodes on this podcast (and counting), we’ve learned there’s no magic formula for brands to break through the noise of the world.  Instead, we work with brands to ask hard questions, rethink assumptions, and create work that demands attention.

At Port Side, we’re more than a production company. We’re your partner in charting a unique path to stand out—and staying true to who you are. Need help standing out? Say hi.

Enjoy this episode and discover other resources below:

‍

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

Find Out Why | Curious why a video production company would produce a marketing podcast? 

In this episode, Cole sits down with Chris Pew, the CEO and co-founder of TREW, to explore the pressing challenges brands face in standing out in 2024. They dive into the creative heartbeat of the outdoor industry, discussing TREW’s “TREW To You Film” contest—a celebration of community-driven storytelling, self-expression, and creativity.

Chris shares how TREW is fostering deeper connections with its core audience through storytelling and innovative community engagement strategies. The conversation spans the evolution of ski film culture, the role of social media in building authentic communities, and how small brands can leverage creativity to make a big impact.

They also unpack the importance of measuring ROI in creative projects while maintaining the balance between marketing goals and authentic storytelling. With a sneak peek at what’s ahead for the TREW To You, Chris reveals how TREW continues to push boundaries with fresh innovations and a renewed focus on community connection.

Key Takeaways

• Standing out as a brand in 2025 is increasingly challenging.

• Brand storytelling should reflect the values and experiences of the community.

• Community engagement is key to building brand awareness.

• TREW’s approach contrasts with traditional brand films that often promote self-interest.

• With a little creativity, there are ways to carve out a niche in your market

This podcast is produced by Port Side Productions. We are a production company that works with outdoor brands to create effective and emotional videos. To date, we’ve made feature documentaries, video podcasts, product videos, and commercials. The thing that unifies us is our unwavering goal to help brands make effective videos driven by emotion backed by strategy.

‍

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

This past year has been a year of reflection.  

In this solo episode, I share an update about the future of the podcast. As Port Side approaches its 10-year milestone, I reflect on key lessons learned and announce a new, more focused direction for the show. After nearly 200 episodes and years of conversations with marketing leaders, I’ve come to realize that both Port Side Productions and this podcast’s true value lie in helping brands create content that is both emotionally compelling and strategically effective. Moving forward, the show will double down on exploring how to make creative work that truly resonates and delivers results.

This podcast is produced by Port Side Productions. We craft effective, emotionally-powered videos for outdoor brands.  

Enjoy this episode and discover other resources below:

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

In this episode, Cole sits down with Robin Thurston, CEO and founder of Outside Interactive, to discuss the importance of inspiring people to engage with the outdoors. They explore the cycle of inspiration, activation, and celebration, emphasizing the role of storytelling and user-generated content in motivating outdoor activities. Robin shares insights on the challenges posed by content overload and the evolving landscape of advertising, while also highlighting the need for brands to adapt to change in the outdoor industry. The discussion also touches on the role of social media in promoting outdoor activities, the necessity of original content for storytelling, and the evolving landscape where brands must act as media companies. 

Key Takeaways

• Inspiration is the first step in getting people outdoors.

• The outdoor industry faces competition from technology and indoor entertainment.

• Storytelling remains vital, but the quality of content is declining due to AI.

• Change is constant, and adaptability is key in the outdoor industry.

• Authenticity in storytelling will attract audiences in a content-saturated world

• The outdoor industry must support each other to grow.

If you like what you’re hearing, feel free to leave us a review on Apple or Spotify. It helps more people like you find the show. Let’s help everyone learn together.

This podcast is produced by Port Side Productions. We craft effective, emotionally-powered videos for outdoor brands.  

Enjoy this episode and discover other resources below:

Booklist | Here's our curated list of recommended books over the years.

LinkedIn | Join the conversation and share ideas with other industry peers.

Apple Podcast | Want to help us out? Leave us a review on Apple.

Guest List | Have a Guest in Mind?  Share them with us here.

Find Out Why | Curious why a video production company would produce a marketing podcast?