Best Story Wins

Column Five
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Apr 10, 2025 • 46min

Why You Shouldn’t Publish Without a “So What” with Drew Evans of Notion

If your content doesn’t have a ‘so what,’ you shouldn’t bother hitting publish. Drew Evans, who leads B2B content strategy at Notion, joins the show to talk about why storytelling—not templates, tools, or tired SEO tactics— moves the needle in B2B marketing.Drew makes a strong case for substance over spam by emphasizing the importance of a great writing comeback. He gets candid about what’s broken in B2B and what marketers need to prioritize instead.We also explore:Why traditional blog content is dying and what’s replacing it.The role of community in shaping a brand’s content strategy.How to turn customer stories into compelling narratives (without sounding like a sales pitch).The untapped power of Notion as a storytelling tool.Why storytelling is making a comeback in B2B marketing—and why it’s the best way to stand out in an AI-driven world.
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Apr 3, 2025 • 42min

Brand, Boldness, and the Bottom Line with Gabe Larsen of Kustomer

If your brand only shows up when a customer has a problem, you’ve already lost the game.In this episode, we sit down with Gabe Larsen, CMO of Kustomer, to tear into what most B2B marketers are getting wrong, and why brand isn’t a “nice to have,” function but rather the differentiator. Gabe drops the kind of no-fluff, first-principles manifesto that B2B leaders need to hear right now: customer service starts at hello, not help.We break down:Why “AI-powered” means nothing if your messaging isn't good enough.How to build a prolific, persistent drumbeat that earns attention.Why LinkedIn is the new B2B battleground (and most marketers are whispering).How digital workers, partnerships, and sharp storytelling are redefining GTM in real-time.
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Mar 27, 2025 • 36min

The Power of Scrappy Creativity with Megan Brunner of Adobe

B2B marketing doesn't need to be predictable or stale. As people’s attention span is shrinking, shouldn’t B2B content be as vibrant and creative as consumer-focused storytelling?In this episode, Megan Brunner, B2B Content Strategist at Adobe, reveals how brands can level up their storytelling, infuse genuine creativity into their content, and move beyond traditional corporate imagery by applying the best from B2C content strategies. Megan's unique career path from action sports to working at some of the leading tech companies highlights why a willingness to be hands-on and scrappy combined with working a strategy is often the key to marketing success.You'll learn:How Adobe is setting a new standard for engaging B2B content. Why a lean, creative team can often outperform bigger, better-funded competitors.Practical ways AI is quietly transforming B2B marketing.And much more.
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Mar 20, 2025 • 40min

The Future of B2B Content Is Video-First with Laura Wilkinson of Vidyard

In today’s world, attention spans are shorter than ever. With this in mind, marketers need to let go of outdated content tactics to embrace the future of B2B content, and some of the best ways to do this is through the smart use of video and leveraging original insights.In our latest episode of Best Story Wins, we sat down with Laura Wilkinson, Director of Brand Marketing at Vidyard, to talk about how video is the not-so-secret weapon for cutting through the noise, and what it means to optimize for content quality over quantity. Laura shares why her team has moved away from the traditional blog, the power of AI avatars in sales, and how great storytelling is the key to building better customer relationships.We also discuss:Why video-first brands are leaving traditional content in the dust.The marketing myths that need to die immediately.How to make your brand unforgettable (without annoying your audience).And much, much more. 
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Mar 13, 2025 • 34min

Why Brand Awareness Is the New Revenue Driver with Jenny Thai of Vanta

Most B2B content today feels generic: AI-generated fluff, generic SEO blog posts, and bland corporate jargon no one reads. Meanwhile, the brands that stand out—the ones people want to engage with—are playing a different game. So what’s their secret?In this episode, we sit down with Jenny Thai, Head of Content at Vanta, to dig into how to build a winning brand through content. Drawing from her experience in crafting compelling brand narratives, leading content teams, and leveraging expert-driven content, Jenny unpacks how to create content that captures attention, resonates with people, and drives demand. We’re diving deep into:What it takes to evolve a content strategy to move up-market.Why brand awareness drives revenue.What’s legit in AI-generated content, what’s overblown, and how to use it without losing your brand’s soul.The rising power of expert-led content—and why if you’re not embracing it, you’re already behind.And much more. 
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Mar 6, 2025 • 48min

How AI Is Redefining B2B Marketing Forever with Stewart Hillhouse of storyarb

The marketers who know how to wield AI as a force multiplier are already outpacing everyone else. Are you evolving fast enough to stay relevant?In this episode, we sit down with Stewart Hillhouse, VP of Content at storyarb, to explore the evolving B2B marketing flywheel—where AI, creativity, and strategy must work together to keep brands growing. Stewart explains why the old approach to content marketing is dying and how today’s marketers need to think and work differently in this new AI-powered future.We also discuss:The three high-value roles marketers should be focusing on in 2025.How to build AI-driven workflows without losing the human touch.Why brand trust beats attribution—and what that means for demand gen.The death of massive marketing teams and how to future-proof your career.And much more.
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Feb 27, 2025 • 42min

How to Build Brands That Actually Stand Out with Ross Crooks of Column Five

Every brand creates content, but only a few stand out. AI has made it easier for everyone to produce high-quality content, yet most brands get stuck in a cycle where they're creating good enough content but fail to stand out. What does it actually take to break through?In this episode, we interviewed Ross Crooks of Column Five to explain why the past decade's content playbook is dead.Ross shares why brands that aren't differentiated waste their time and resources, and why you should stop churning out content for content's sake and start creating with intent. We also explore:The biggest mistake brands make when trying to stand out (and how to fix it).How to inject real emotion in B2B content.The importance of using AI as a tool for leverage, not a crutch.How thoughtless scaling leads to generic, ineffective content.And much more. 
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Feb 20, 2025 • 35min

How Mews Builds Emotion Into Every Brand Move with Michael Fitzsimmons of Mews

It can be easy to lose sight of the need for deep emotional connections in a world where everyone seems obsessed with AI, automation, and bottom-funnel conversions. But being able to connect authentically with your customers is the lifeline of every business. In this episode, we sat down with Michael Fitzsimmons, VP of Growth at Mews, who shared how forward-thinking brands reject generic tactics and double down on storytelling, bold positioning, and strategic risk-taking – all with a mind to never rest on one's laurels, but rather to keep setting the bar higher and higher when it comes to quality, connection, and well, growth. He shares how AI fits into the creative process without killing originality, why content needs more taste, and how modern brands must prioritize community-building to stay relevant.We also discuss:Why most B2B brands fail at differentiation—and how to fix it.The importance of owning a category instead of competing in one.Why taste and human creativity are still some of marketing’s biggest competitive advantages.Where AI shouldn’t be used in content marketingAnd much more. 
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Feb 13, 2025 • 47min

The Secret to Un-Ghosting Prospects with Matt Hogan of HG Insights

The biggest challenge in B2B marketing isn’t so much generating demand, but it’s keeping folks from ghosting you, even long before they enter your pipeline.In this episode, Matt Hogan, VP of Marketing at HG Insights, reveals why B2B buying behavior has radically changed, and how most companies struggle to keep up. He breaks down the rise of shadow buying, the increasing role of CFOs and CIOs in decision-making, and why your brand is being judged before you ever get on a call. We also discuss: Why poor positioning is sabotaging your marketing efforts before they even begin.The new golden age of cold calling.Why generative AI is changing the content game—but most brands are using it wrong.How to leverage data to create magnetic, high-impact marketing.And much more.
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Feb 6, 2025 • 35min

How to Stand Out From the 85% with Egan Montgomery of Backstroke

About 85% of competing software companies are pretty much the same.The winning companies focus on staying in the 15% that represents an opportunity to truly differentiate, which is also what the company’s goals should be tied to.In this episode, Egan Montgomery, Co-founder and VP of Marketing at Backstroke, reveals how his generative AI-powered platform is changing how email marketing works, boosting performance by 30% compared to human-written emails. Egan also shares why “doing things that don’t scale” is the future of marketing, and how tailored in-person experiences are becoming the best way to build trust with clients. We also dive into:Why the old B2B marketing models are crumbling and what’s replacing them.How personal branding is no longer optional for founders and executives.Why generative AI’s second wave will change how we work, sell, and connect.Building trust in a world saturated with noise and gimmicks.And much more. 

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