Best Story Wins

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.

Best Story Wins is a business podcast hosted by Unknown Host, with 137 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Best Story Wins, a business show with 137 episodes published.

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  Best Story Wins

  Taste beats Trends with Nick Sickleton

  Aug 6, 202644 min

  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

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  Best Story Wins

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

  Jul 23, 202633 min

  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

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  Best Story Wins

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

  Jul 9, 202633 min

  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

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  Best Story Wins

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

  Jul 2, 202648 min

  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

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  Best Story Wins

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

  Jun 25, 202649 min

  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

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