Best Story Wins

Hosted by Column Five

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137

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Aug 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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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

June 11, 2026Episode 13049 min

Stop Measuring Brand Like a Performance Channel with Bill Kenney from Focus Lab

Every quarter, someone asks you to prove the rebrand paid for itself in dollars. Bill Kenney's answer after 16 years: you're measuring the wrong thing, and the spreadsheet was never going to save you anyway. Bill built Focus Lab into one of B2B's sharpest branding shops by owning a single vertical back when everyone warned him that niching down would scare off clients. He makes the case that brand ROI behaves like going to the gym — you don't step on the scale the morning after — and that the real opportunity for agencies isn't using AI to ship work faster, it's handing clients the tooling to run their own brand without you in the room. He also says the quiet part out loud about why a weekend in an AI tool will never replace what actually happens inside a 16-week rebrand: the second-guessing, the cold feet, the "can we sit on this another week." We also cover: The Apple test for why feature parity just turned product differentiation into a branding problem, not an engineering one Why he shut down his own sub-agency after realizing clients "don't give a shit" how big or small your other clients are The one belief he died on for years — that a brand has to launch in a single perfect moment — and why he now thinks a slow, slightly messy rollout works fine The first-meeting question he asks every CEO that quietly decides whether the whole project survives

June 4, 2026Episode 12737 min

Why Nobody Trusts a Brand They Just Met with Amit Singh

You're being outshouted. The average person now absorbs 5,000+ messages a day and reaches for their phone 205 times — and the industry's big answer was to staple "AI-powered" onto the homepage and call it a repositioning. That's not building a brand. It's a withdrawal from the one account you can't overdraw. Amit Singh has spent three decades building brands at Adobe, American Express, Starbucks, and Nintendo — long enough to watch "dot-com" go from billboard flex to embarrassing relic, and he's convinced AI is headed the exact same way. His argument: the companies sprinting to rebrand as AI companies are mortgaging years of earned trust, while the question that actually decides whether you survive — why should you exist? — goes unanswered in most boardrooms. He maps where AI earns its seat at the table, where it quietly wrecks your creative without anyone noticing, and why the people declaring storytelling dead are reading the wrong scoreboard. We also cover: A Meta study found AI-generated copy matches or beats humans on sub-$100 products — and consistently *loses* on anything pricier, where emotion does the selling. Most teams are pointing it at exactly the wrong work. Nintendo doesn't make video games. It makes smiles. Why your reason to exist is the North Star you build against — and the one thing you'll never put in an ad. 88% of marketers have adopted AI. Adoption was never trust — and Amit thinks the gap between the two is where the real risk is hiding. Long-form is quietly back: why a five-minute Adidas film outperforms your six-second TikTok precisely *because* attention has never been scarcer.

May 28, 2026Episode 12643 min

The Irreducible Part: Taste, Judgment, and the Stories Machines Can't Tell — with Julianne DeVincenzo & Dan Reid from Optimizely

Most marketing teams are drowning in output and starving for meaning. The more they feed the machine, the more the machine becomes the creative director — and somewhere in the noise, the person on the other end of the content stopped mattering. In this episode, Josh and Ross are joined by Julianne DeVincenzo , Head of Content Strategy, and Dan Reid , Creative Director — both at Optimizely — two people deep inside one of the most interesting rebrands happening in B2B right now. They make the case that the real threat of AI isn't job replacement — it's the slow erosion of judgment, taste, and the willingness to make someone uncomfortable. Julianne and Dan talk about how they're rebuilding Optimizely's content engine from the ground up, why they're turning their own marketers into subject matter experts and journalists, and where they're drawing the line between what AI can own and what stays irreducibly human. We also cover: • Why the volume-as-strategy era is producing content that 'passes through people like water through a screen' — and how Optimizely is deliberately building against that. • How Dan is working directly with engineers to teach their own AI to honor brand — including the surprisingly simple feedback that blew a senior engineer's mind. • What happens when you empower employees to use AI and wake up to find your unreleased brand assets have already been fed into someone's personal workflow.