Backcountry Marketing

In this solo episode, Cole Heilborn unpacks the reality of digital fatigue and what it means for marketers. With endless competition for attention, from Netflix to Reddit to YouTube, your audience is already exhausted. They don't want to be disrupted. They want content that feels valuable, entertaining, and emotionally resonant. Cole challenges brands to stop creating just to "show up" and start designing campaigns that genuinely add something to people's lives. About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

Insight Deck | Want 20 of our favorite insights shared on the show?

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

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In this episode, I'm joined by Dillon Snyder, Creative Director at Vail Resorts. Dillon makes the case that much of today's marketing output has become the equivalent of "yellow page ads."

We unpack why so much creative feels homogenized, how overemphasis on bottom-funnel tactics hurts long-term brand health, and why simplicity is often harder than complexity. Dillon also shares his vision for a "reset button" on creative: more collaboration between creatives and marketers, less energy on commoditized tactics, and a greater willingness to take risks that actually give audiences a reason to care.

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns.

Enjoy this episode and discover other resources below:

Insight Deck | Want 20 of our favorite insights shared on the show?

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?

What happens when a legacy brand decides to go back to its roots while completely reimagining what it stands for? Mike Donnelly, VP of Marketing, at Superfeet shares the behind-the-scenes process of repositioning Superfeet from a product people don't see to a brand people feel.

We talk about why "Performance Amplified" became the rallying cry, how to build emotional resonance around an invisible product, and the surprising lessons they learned when media and consumers didn't react the way they expected.

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

Insight Deck | Want 20 of our favorite insights shared on the show?

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?

Is there a simple question to understand the ROI of branded content? Cole reflects on his takeaways from a panel discussion he hosted, the value of brand investments, knowing your audience, long form vs short form, and an update to the rebrand of Port Side

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

Insight Deck | Want 20 of our favorite insights shared on the show?

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, I'm joined by Michael Minter, VP of Brand at Sorel, who shares a candid, behind-the-scenes look at the brand's reawakening. Sorel has been everything from a Canadian work boot to a fashion-forward winter staple, and now it's entering a bold new chapter.

We discuss what it takes to bring a heritage brand into the future, how to balance instinct and insight in a data-driven world, and why most outdoor content lacks real emotional impact. Michael also breaks down the creative strategy behind their upcoming campaign, "For Bold Steps," and how brands can avoid the trap of mediocrity by having the courage to be polarizing.

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

• Insight Deck | Want 20 of our favorite insights shared on the show?

• 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, MJ Carroll, Brand Director at HEST, unpacks the tension every marketer faces: How much control do you keep, and how much do you let your community shape your brand? We dive into what happens when you hand over creative control, why tension between brand and performance is healthy, and how HEST has built a passionate community by focusing on comfort, connection, and consistency. MJ also shares what she's learned about content, team dynamics, and why she believes experiential events still have a powerful role in brand building.

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

Insight Deck | Want 20 of our favorite insights shared on the show?

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 follow-up conversation with Chris Burkard, we dive deep into what it really means to take creative risks. Chris shares why physical danger is easier to stomach than financial risk and why most outdoor marketing content falls flat emotionally. We also field audience questions from part one, covering pitching branded projects, giving feedback, the role of feeling in advertising, and the evolving function of creative agencies.

Chris doesn't hold back; this episode is a masterclass on the emotional and strategic layers of doing creative work that actually connects.

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

Insight Deck | Want 20 of our favorite insights shared on the show?

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?

Cole shares a personal reflection on the state of brand content today and why so much of it is falling short. This episode challenges brands, especially mid-size outdoor companies, to rethink how they approach content creation. Why bother doing it if it's not driving results? Cole makes the case for content that's built to solve problems, drive value, and show up creatively in a noisy world. He also includes a litmus test you can use to determine if your content is working as hard as it could.

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

• Insight Deck | Want 20 of our favorite insights shared on the show?

• 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 building a brand from the ground up, where should you actually spend your time and money?

Nic De Castro, founder and CEO of LandTrust, joins us to explore this question through the lens of an outdoor startup that's grown by leading with trust, storytelling, and real-world value.

We dive into why early-stage brands often misplace their marketing bets, how to approach content when budgets are limited, and what it really means to think like a media company even if your intention isn't to become one. Nic shares the strategies LandTrust used to build brand awareness without paid ads and we discuss when it is appropriate for a startup to invest in branded film content.

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

• Insight Deck | Want 20 of our favorite insights shared on the show?

• 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, Bronwen Foster-Butler, CMO at Finisterre, breaks down how the brand is growing without compromising its identity. We talk about their North American expansion, the tension between polished production and platform-native content, and why user-generated stories often outperform high-budget ads. Bronwen also shares how Finisterre uses a fictional "brand muse" to guide creative decisions, what they've learned about emotional storytelling in a data-driven world, and where she thinks AI fits (and doesn't) in outdoor marketing.

About:

This podcast is produced by Port Side, a creative production studio. We help brands that move, create strategy-led, emotionally charged video campaigns

Enjoy this episode and discover other resources below:

• Insight Deck | Want 20 of our favorite insights shared on the show?

• 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?