

Best Story Wins
Column Five
Welcome to “Best Story Wins,” a podcast for marketing and branding professionals looking to unlock their growth potential. Hosted by Column Five—a B2B marketing agency that specializes in brand and content marketing for SaaS companies—each episode features insightful conversations with industry leaders who are winning customers’ hearts and minds by building world-class brands. Tune in to hear expert insights, hard-won lessons, and key strategies to take your own marketing efforts to the next level.
Episodes
Mentioned books

May 29, 2025 • 37min
What Smart Brands Do Differently with Harrison Iuliano Moving you to BCC
The old agency model is broken, and smart brands aren’t waiting around to fix it. Instead, they’re building lean, strategic ecosystems where storytelling, rather than scale, is the engine that propels growth.In this episode, Harrison Iuliano, cofounder of Moving You to BCC, breaks down why the classic agency-client model is officially dead and what smart brands are doing to replace it. He shares how high-performing brands are creating modern marketing machines by blending fractional talent, curated creative partnerships, and brand-first thinking. We dive into:Why brand, not performance, is your most defensible assetHow to structure your team for speed, quality, and creative outputWhat most companies get wrong about agency selectionWhy great products don’t save bad brands—and vice versa

May 22, 2025 • 34min
How to Build Micro-Communities That Last with Allison Stadd of Shipt
The brands that move first on human connection build an edge no algorithm can touch. The question is: Will you move fast enough to matter?In this episode, Allison Stadd of Shipt lays out why brands that lead with care, and not only convenience, are the ones winning now and leading the human-centric revolution in marketing. She breaks down how human connection is becoming the real growth engine, how collapsing old brand and performance silos is unlocking smarter strategies, and why micro-communities are the future of loyalty.We also discuss:Why cultural activation is the new brand foundation.How customer anecdotes can turn into an untapped growth channel.Why every brand needs a drummer mindset to lead from the back and still own the stage.

May 15, 2025 • 40min
B2B is Broken, here's how to fix it with Victoria Gamlen CMO of Boundary Analytics
Most B2B marketers are stuck proving short-term wins. Not because it drives the best results, but because it’s the only story the numbers can tell. Could this be why long-term growth, brand equity, and strategic influence keep slipping through the cracks?In this episode, Victoria Gamlen, CMO of Boundary Analytics, unpacks the disconnect between brand investment and how we measure success. She explains why traditional attribution models fall short in B2B, how correlation and time lag analysis offer a clearer view of pipeline impact, and what marketing leaders need to rethink to align with how buyers make decisions today.We also discuss:Why “brand vs. demand” is a false choice—and what to focus on insteadHow to use high-intent inbound as a bridge between brand activity and business outcomesWhat’s behind the recent shift in how leading companies approach brand marketingHow to advocate for brand investment with data that resonates with the C-suiteThe biggest gaps in B2B marketing measurement—and how to fix them

17 snips
May 8, 2025 • 42min
The CMO Comeback Story with Michael Duda of Bullish
Michael Duda, a partner at Bullish and former agency leader, tackles the pressing challenges CMOs face in today’s market. He argues for marketing as an investment rather than a cost, emphasizing the need for a creative and financial strategy blend. Duda explores how to reclaim marketing power, the ROI of early storytelling, and the importance of customer-centric branding. He also discusses navigating market conditions, the dangers of 'safe' content, and how to build brands that withstand tough economic climates.

May 1, 2025 • 37min
How InfoTrust Builds Brands People Actually Believe In with Chase Howell of InfoTrust
Marketers are pumping out more content than ever, yet consumers somehow trust it less than their own data. Impressions are meaningless if you’re not driving impact. In this episode, Chase Howell, VP of Marketing at InfoTrust, shares the formula of B2B marketing that builds trust, converts, and scales without losing its human touch. From launching bestselling books to ditching digital-only in favor of in-person events, Chase shares what it takes to make your brand unforgettable in a landscape obsessed with efficiency and drowning in AI-generated content.We also discuss:Why most "free reports" get ghosted (and what to do instead).How to turn your internal experts into legit thought leaders.Why authenticity will be the new conversion rate in the AI era.How philanthropy and brand are merging into one powerful differentiator.

Apr 24, 2025 • 53min
Startup Storytelling in the AI Age with Ben Parr of Octane AI
Today, anyone can build an AI product on a weekend. To stand out in the market, you must rely on your story. In this episode, we are joined by Ben Parr, co-founder of Octane AI and Theory Forge Ventures to talk about what separates good companies from great ones: story and speed. Drawing from past experiences building AI products (before LLMs existed), Ben shares insights on how startup founders should think about brand, content, competition, fundraising, and the marketing industry post-ChatGPT. We also dive into:How AI is transforming marketing (and which jobs are disappearing first).The difference between pitching VCs vs. customers.How Octane AI built a loyal customer community.

Apr 17, 2025 • 57min
Why AI Can’t Replace Intuition with Hiten Shah of Dropbox
Today, thinking about AI completely replacing humans is impossible. Why? Because it means replacing creativity, context, and more importantly, intuition. Hiten Shah, serial entrepreneur, investor, and now working on AI at Dropbox, joins Josh and Jason to discuss how smart marketers and builders are using AI as a thought partner rather than a content machine. Hiten also drops hard-earned wisdom on what marketing still gets wrong, why engineers still (and will likely always) lead the startup ecosystem , and the explanation of why “the best story wins” is more than just a nice phrase.We discuss:Why getting the best from AI starts with better prompting and pre-prompting conversations. Why the road to content quality often starts with content quantity. Augmenting vs replacing human task management with AI.The biggest myths about AI-generated content, and why it’s dangerous for your brand.

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.

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.

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.


