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 139 episodes on record and a Required Pod Score of 80.

Unknown Host hosts Best Story Wins, a business show with 139 episodes published.

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  Best Story Wins

  B2B Branding Was Never Supposed to Be Boring with Wesley Bancroft

  Sep 3, 202629 min

  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

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  Best Story Wins

  Publishing More Is Making You Less Credible with Ben Hasskamp

  Aug 20, 20261h 5m

  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

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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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