Best Story Wins

Hosted by Column Five

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Episodes

141

Latest episode

Oct 2026

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About the show

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.

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60 recent

October 15, 202644 min

Build a Personality Before an Agent Picks Your Competitor with Dave Breckon of Carta

Your CFO just found out AI agents can do the buying, and now they want to know why you still need a creative team. If the brand's only job is getting picked by an algorithm, what's left for you to build? Dave Breckon has done this work from almost every seat: rave-era record covers, a branding studio in Madrid, a startup design team built from scratch, and now Head of Brand Design at Carta. His case is that the marketers racing to optimize for AI agents are walking into a trap. When everyone can produce work instantly, the only edge left is being different, and that comes from personality, which comes from people, not from systems, org charts or a 30-slide brand deck. We discuss: Brand archetypes are "kind of fun, but ultimately pretty useless." Personality can't be planned in a workshop. It shows up in the small corners of a company where good people are working on good problems. Why a furry owl is a better strategy than a world-changing mission. Duolingo's personality gets to new markets before its business plan does, which is why it can move into new categories without rebranding. Leaning hard into "brand to agent" puts you back in a price war. A brand with charisma never gets compared by an LLM in the first place. People just go straight to its site. "Buying moments" may be on the way out. Dave expects people to sign up for a lifestyle through an agent instead of picking products, so B2B has to become a personality buyers want to spend time with, not a store they shop at.

September 24, 2026Episode 13946 min

Momentum Beats a Big Launch, Every Single Time with Nick Farrar of Shaped By

A CEO shows up ten minutes late to his own rebrand kickoff, announces he doesn't have time for it, and hands the whole thing to a marketing manager. Nick Farrar has watched that exact meeting kill more good creative work than any recession ever could. Nick runs Shaped By, the Bristol-based agency that spent fifteen years operating under a name its own founder couldn't stand before he torched it and rebuilt from scratch. He's since built a specialty in B2B tech brands and learned, the hard way, where most companies get branding wrong: they treat the launch as the finish line, reach for AI to shortcut the thinking that actually makes them different, and let anyone but the real decision-maker sit in the room. This is a working postmortem on what separates brands that compound from brands that quietly fade. Why Nick killed a name with fifteen years of built-up equity behind it, and what it cost him to start over The exact meeting-room moment that predicts a rebrand is doomed before a single concept gets shown Where he draws the line on using AI in the creative process, and why using it too early guarantees a race to the bottom What actually needs to happen the day after a brand launches, and why most agencies treat that day as "done"

September 3, 202629 min

B2B Branding Was Never Supposed to Be Boring with Wesley Bancroft of Lunour

Your logo hasn't changed in three years and your brand still feels broken. That's not a design problem, it's everywhere else you stopped paying attention. Wesley Bancroft co-founded Lunour, a small B2B creative agency, and he's watched AI compress a year of brand production into a season without compressing anyone's hours, he's busier now, not less. His argument cuts against how most companies actually treat brand: not a guidelines deck someone polices, but every touchpoint the company has. A buddy of his at a Fortune 500 company diagnosed his org's broken cross-department communication as a brand problem, not an ops one, and Wes thinks he's right. He gets specific about what Lunour builds instead of mood boards, why B2B branding beats consumer work, and the mindset shift that changed how he works entirely. • Why Wes calls B2B "blue ocean" next to consumer brand work and admits it makes his agency look cooler than it actually is • The Fortune 500 sales exec who diagnosed his company's broken cross-department communication as a brand problem, not an ops one • Why Lunour refuses to build moody, vibey mood boards for clients and what it hands them on day one instead • The unlikely, fourth-grade-level book that convinced Wes the output never mattered, only the process did

August 20, 20261 hr 5 min

Publishing More Is Making You Less Credible with Ben Hasskamp

You've published four posts a week for a year, and your buyers still can't tell anyone what your company believes. Somewhere in all that output there should be one sentence you could be wrong about. There isn't. Ben Hasskamp spent years running thought leadership inside a company where the executive bench included some of the sharpest people in security and watched most of what shipped turn into product brochures wearing a byline. His argument: thought leadership is a point of view you could be wrong about, and everything else is volume cosplaying as authority. He gets specific about the formats that fake it best, including the one your team is probably scoping right now.We also cover: Why every "State of the Industry" report reaches the same conclusion — and the tell that gives it away The exact reason polished SEO writing now reads as noise to the models people actually search with How Ben cut executive review cycles from 14 days to 3 by feeding AI everything an exec had ever said on record and what happened when one of them insisted he'd never say that The film-school question that works on a CISO as well as it works on a protagonist

August 6, 202643 min

Taste beats Trends with Nick Sickleton

Everyone with a prompt window now calls themselves a creative, and the feed shows it: the same look, the same motion, the same instantly forgettable output on repeat. The teams still cutting through aren't generating more than everyone else. They're the ones who figured out what a machine can't fake. Nick Sickleton has directed creative across software, consumer tech, and even defense, an industry where the people paying for the product never actually see it. His argument for this moment is blunt: AI isn't here to replace your taste, it's here to expose whether you have any. The winning brands build the picture frame before they ever touch the picture, and the creatives who lean hardest into trends are the first ones getting cut.We also cover: Why AI-generated design already has a visible "tell," and the one discipline that still can't be automated away The "picture frame vs. the picture" rule that keeps Apple, Netflix, and Airbnb cohesive no matter how wild the artwork gets What directing creative in defense (where the buyer is never the user) quietly teaches you about every consumer brand The counterintuitive reason junior creatives who chase AI trends are getting cut, while the ones forced to explain why are accelerating their careers by five years

July 23, 202632 min

Why Content Systems are the Future with Ross Crooks of Column Five

Everyone on your team can suddenly make content. That's not the win it sounds like, it's how a brand starts dissolving, one "good enough" post at a time. Ross Crooks, co-founder of Column Five, has a fix that flips the whole production model: stop treating your brand team as the last line of defense and start treating the brand itself as the first input every tool reads. He argues the old system (brief, create, brand-team-approves, ship) is exactly what buckles under AI's volume, and that the brands pulling ahead aren't the ones making the most content. They're the ones encoding something their guidelines deck never captured.We also cover: Why moving your brand team from the end of the process to the beginning is the actual unlock The difference between "correct" content and "good" content and why AI only produces the first Taste and intelligence: the two things your brand guidelines never had, and how to encode them "Brand drift": how fine-looking content slowly pulls you off what made you distinct

July 9, 202632 min

The Small Team Advantage: Turning Size into a Superpower, with Maria Irie of Chili Piper

Every designer you know is quietly panicking about the same thing: their Figma hours dropped from 90% of the week to 30%, and nobody told them what to do with the other 60%. Is that a crisis or a promotion? Maria Irie runs brand at Chili Piper with a team of two — and she's spent the last year rebuilding her entire job around AI without losing what makes the brand feel human. She's mid-migration from Webflow to Claude, she's turned herself into a systems-builder instead of a one-pager machine, and she's got a theory about why the scrappiest, least "scalable" parts of marketing — the Ibiza offsites, the events, the stuff that doesn't show up in a report — are exactly what AI can't touch. This isn't a "prompt better" conversation. It's what happens when a whole discipline gets rewritten mid-career. We also cover: Why Maria cut her Figma time from 90% to 30% — and what she's building instead The "too many windows" problem: what it actually costs your brain to run five AI tools at once Why a two-person brand team deliberately protects the stuff that doesn't scale — and bets the whole brand on it

July 2, 202648 min

Beige Is What Happens When Nobody's Brave Enough to Be Wrong with Sonja Silveira of Cisco

Every AI tool you use was built to keep you happy, not to make you right. That's a problem when "happy" is also the fastest route to content nobody remembers. Sonja Silveira has run content teams at Meta, athenahealth, and now Cisco , and she's done with the idea that AI is either a job-killer or a magic answer box. Her real argument: these tools are optimized for engagement, not accuracy, which means the marketers using them need more suspicion, not less. She also names the thing most B2B brands won't say out loud — they all sound the same now, AI just sped up the slide into sameness, and the fix has nothing to do with the tools.We also cover: Why treating AI like "an answer machine" is the fastest way to lose your edge — and what to check before you trust a single stat it gives you The real reason beigefication isn't new, why it's "safe," and why safe is exactly what's killing your content Why almost every B2B brand that tries to become a media company hits the same wall — and what Cisco's Story Lab is doing differently

June 25, 202648 min

AI Made Brand the Only Thing Left That Matters with Adam Morgan of Twilio

Twilio used to read like a company built for developers and nobody else. Then it found one word that made every audience feel like they belonged to the same tribe. Adam Morgan , VP of Brand and Creative at Twilio , spent three months finding that word "builder" and watched it turn a stalled rebrand into what he calls lightning in a bottle. He explains why most companies chase logos and color palettes before they've earned the right to, and why brand resurgence isn't a reaction to AI fear — it's AI's actual byproduct. When everyone can generate a slick landing page for free, the thing AI can't fake becomes the whole game.We also cover: Why Adam built Twilio's entire rebrand around a single emotional truth he found at Hearst Castle — not a brand workshop The real reason AI is making brand storytelling more valuable, not less, and why "AI-resistant content" is the new differentiator Why locking creatives into rigid brand guidelines backfires, and what a "systems approach" looks like instead

June 18, 202638 min

Taste Is the Only Thing AI Can't Generate (Yet) with Matt Scribner of Atlassian

Every brand team is being handed AI tools and told to do more with less. What they're not being told is that without taste and a real idea, the output is just sophisticated noise at scale. Matt Scribner is a growth designer at Atlassian — a company whose brand touches tens of thousands of visitors a week — and he's been inside the AI-enabled design workflow longer than most. His take isn't a sales pitch for the tools or a doomsday headline about job loss. It's something more useful: an honest account of where AI actually helps, where it quietly fails, and why the designers who thrive won't be the ones who prompt the best. We also cover: AI can get you to 60% — but if you couldn't get past 60% without it, you're not getting past it with it either We're heading toward a "singularity of design" where everything starts looking the same, and the only antidote is taste you built before the tools existed The Arts and Crafts movement followed the Industrial Revolution for a reason — and the same correction is coming for brand

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