Best Story Wins

Column Five
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Jan 8, 2026 • 47min

Taste as a Secret Weapon with Jeff Stark of Suki AI

Your brand isn’t losing to “faster” AI teams. It’s losing to the ones protecting their humanity. As generative tools flood feeds with beige, lookalike creative, the real threat isn’t robots—it’s your team quietly lowering the bar. Are you using AI to unlock better ideas…or to justify shipping forgettable work faster?In this episode, Jeff Stark, Head of Creative at Suki AI, gets brutally honest about what AI can’t do: develop taste, earn trust, or build a point of view. He shares how Suki—an AI healthcare company—thinks about ambient clinical intelligence and why their creative approach starts with real clinicians, real stories, and craft that doesn’t feel like it came out of a content vending machine. We also get into:Rebrands as high-stakes bets: the real variable isn’t color—it’s courage.Art vs. design: why “beautiful but useless” is the most expensive mistake in B2B.Jazz-room leadership: running creative teams like improv, not assembly lines.AI as assist, not author: a “bookend” model that keeps humans in the creative core.Living an integrated life and how one’s faith and beliefs should show up in every aspect of their lives. And much more. 
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Jan 2, 2026 • 57min

How to Increase Brand ROI Through Scale, Speed, and Quality” with Dan Schwer of Rippling

Your brand isn’t losing to competitors, it’s getting flattened by “good enough.”In a world where AI can generate passable B2B content in seconds, bland isn’t safe. It’s fatal.In this episode, Dan Schwer of Rippling breaks down what brand actually looks like inside a 6.000-person SaaS company with a creative team of 15. We go straight at the uncomfortable stuff: why “brand vs. demand” is a lazy (and expensive) debate, how a brand refresh becomes a business lever (not a design hobby), and what it takes to keep quality high when the org is moving at startup speed and the pipeline still wants receipts.If you’re still treating brand as the “pretty layer” on top of performance, this one’s going to sting — in a useful way.We also cover:Brand ROI without the fantasy math: Measuring impact through speed, scale, and craft.The “brand vs. demand” trap: Why the fight is fake — and what actually drives pipeline.Video as the new moat: Product launches, customer stories, and earning attention in B2B.AI won’t fix bad taste: Where AI helps, where it slows you down, and why judgment still wins.
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Dec 18, 2025 • 40min

The Bold Bet Smart CMOs Are Making in 2026 with Sylvia LePoidevin

Your brand isn’t losing to competitors, it’s drowning in “helpful” content no one remembers. In an AI-everywhere world, bland is broken and volume is just a faster way to disappear.If LLMs can write what you ship in 10 seconds, why would a buyer choose you?This week, Sylvia LePoidevin delivers the reality check B2B marketers have been dodging: content volume is a commodity, brand is the moat. We dig into how AI-native teams actually work (tastemakers and operators), why “helpful” guides are table stakes, and how human stories, conviction, and point of view become the only defensible edge in a world where production is free. We also get into:Content brands > corporate blogs: Building something people follow, not just something you publish.Helpful is dead: Why every piece needs a person, a story, and a spine—or it’s AI fodder.Anchors and distribution: Human-made “anchor” content, AI-powered repurposing, zero soul lost.Manifestos, not messaging decks: Founder-fueled conviction as the real brand operating system.Brand as last moat: Community, ecosystem marketing, and taste as the next-gen B2B unfair advantage.
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Dec 11, 2025 • 51min

SEO, AEO, and the Return of Good Marketing with Jenna Hannon of Hatter

Your brand isn’t losing to competitors, it’s getting ghosted by the algorithm. As AI eats search, the “spray and pray” content playbook turns invisible. Are you training the models…or training your team to burn cash?This week, Jenna Hannon, Founder & CEO of Hatter, drops a State of the Union that B2B marketers need to hear: SEO isn’t dead, AEO (AI Engine Optimization) is here and lazy tactics are DOA. We unpack why LLMs reward actual marketing (crisp messaging, specific content, real PR) and punish AI-slop; how to merge SEO, AEO, and content into one motion instead of siloed teams; and why product marketing is the new growth core powering every channel.We also get into:SEO → AEO: Same inputs, new outputs and the extra layers that matter now.Quality > quantity: Why “programmatic, no-human” content craters (and how Google/LLMs sniff it out).Metrics that matter: Beyond traffic to AI visibility, context, and link-back citations that convert.Org design for 2026: Product marketing as the engine; experts in the loop; PR that teaches LLMs.
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Dec 4, 2025 • 52min

Ditching Best Practices: How Courageous Brands Get Remembered with Udi Ledergor of Gong

Your funnel isn’t broken, but your nerve is. “Best practices” are just average practices with better PR. If every headline, homepage, and hot take sounds the same… what’s the one bold move that makes you unforgettable?In this episode, Udi Ledergor, Chief Evangelist at Gong and author of Courageous Marketing, torches the safe playbook and helps us build a braver one: a sharp, differentiated POV that slices through “sea of sameness” B2B. We get brutally practical on how to stop shipping beige content, why the CEO (not marketing) owns the brand, and how psychological safety unlocks the kind of creative risks that actually move pipeline. We also cover:Why “best practices” guarantee mediocrity and how to replace them with courageous bets.How to punch above your weight at tentpole events without buying the $500K booth.The 3-part brand promise test (and how most orgs break it in customer support).How to interview your CEO and Sales for risk tolerance before you take the job.Using AI to kill drudgery, not taste so your POV stays unmistakably human.
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Nov 20, 2025 • 1h 3min

Tomato Sauce and the Stories Behind What We Buy with Andrew Lee of Microsoft

Marketing is drowning in AI sludge, vanity dashboards, and “spray and pray” content. Your brand is getting lost, not because your product is weak, but because your taste is.In this episode, we sit down with Andrew Lee, Partner Marketing Leader at Microsoft, to torch the illusion that more content equals more impact. Together, we unpack why “brand vs. performance” is a fake fight, why taste is the last unfair advantage, and how to build owned distribution that survives algorithm mood swings. Your CMO will either thank you or feel attacked.We also cover:Annual planning as a power move: kill random acts of marketing.Turning founder POV into a scalable channel (without turning them into a dancing bear).How to benchmark “taste” (with simple, brutal quality bars your team can actually use).Converting narrative into numbers: story→search→sales enablement→SQLs.The “No Rented Moats” playbook: email + podcast + events > social roulette.
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Nov 13, 2025 • 51min

The Feeling of Knowing: Brand in the Age of LLMs, with Ari Yablok of Island

LLMs are already “deciding” your brand for buyers. Are you shaping that story or letting the machine write it? If your marketing still sounds like everybody else’s, congratulations: you’ve trained the models to ignore you.This week we rip into the hottest B2B reality: AI Engine Optimization (AEO) meets human-only brand. Ari Yablok, head of brand at Island, shows how to beat sameness by sending clear “this is new” signals, building experiential brands that people feel (not just read), and using unreasonable hospitality to make products and events feel theirs, not “yours.”We also cover:AEO is the new SEO: how to show up inside LLM answers and make people prefer you before they ever ask a bot.Signals over slogans: designing booths, visuals, and copy that telegraph “category shift” without a single bullet point.Unreasonable hospitality in B2B: turning product nuance and in-person moments into retention (and reputation) machines.The “feeling of knowing”: why brand confidence shortens deals—even when buyers can’t explain why.Human as the counter-trend: embracing curated flaws and analog touchpoints to stand out as AI perfects the average.
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Nov 6, 2025 • 54min

Everything’s Changing: How Smart CMOs Stay Ahead with Drew Neisser of CMO Huddles

Budgets are shrinking, patience is thinner and the CMO seat is a revolving door. Keep playing the old playbook and you’re next.What if the path forward isn’t “more content, faster”, but a hard reset on power, process and what we even call “brand”?In this episode, Drew Neisser, Founder of CMO Huddles, drops a reality check on B2B: CMOs are operating in Antarctica—hostile, short-term, and PE-pressured and it’s still the most exciting moment in marketing. We get blunt about the “do more with less” lie, why “brand” is a budget-killing word (start saying “reputation”), and how AI should first nuke your workflows and org chart before you let it ghostwrite your strategy.). This is the insider’s guide to surviving the freeze and shipping work that closes.We also cover:CMO power plays: why owning Partnerships/Rev levers earns a real seat at the table.Short-termism judo: aligning with CFOs on “metrics that matter” and fixing attribution theater.What actually converts now: late-stage, face-to-face moments (small dinners > giant trade shows).Direct mail’s comeback: high-impact, targeted sends that unblock stalled deals.
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Oct 30, 2025 • 44min

Story Is the Moat: How to Build One at Scale with Julien Palliere of Column Five

Everyone’s racing to “do more with less,” then wondering why everything sounds the same. Budgets shrink, headcount drops, and the AI mandate lands like a memo from Mount Olympus: use it, ship faster, cut costs. Here’s the plot twist: AI isn’t your edge but your point of view is. If your story’s bland, the tech just scales blandness.In this episode, Julien Palliere, AI Strategist at Column Five joins Jason and Josh to deliver a necessary reality check.We unpack why “just add AI” is a lazy brief, how AEO is quietly disintermediating brands, and why volume is the enemy of results. The verdict: bad marketing makes you generic, not AI. We also cover:The Wedge System: Turning a sharp POV into a repeatable AI-powered content engine.Personalization That Actually Personalizes: Using CRM, 6sense, and LinkedIn signals to change copy by persona in real time.Where AI Belongs (and Doesn’t): Map the workflow, target structured/repeatable steps, avoid breaking fragile creative processes.
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Oct 23, 2025 • 48min

Building a Growth Engine That Converts with Nicole Gates of Varonis

Marketers are hooked on attribution perfection. Meanwhile, your buyers are ghosting and your “AI-powered” campaigns sound like everyone else’s. What if the edge isn’t more dashboards but it’s better judgment?In this episode, Nicole Gates, VP Growth Marketing at Varonis tears up the playbook B2B keeps clinging to. She shows how a “process person” builds a launch machine that actually ships, why tiering by customer impact (not internal hype) changes everything, and how moving SDRs under marketing with real SLAs turns MQL theater into pipeline. We dig into the noisy AI arms race (robots fighting robots), shifting budget from paid-to-play to earned trust via thought leadership, and using AI where it improves outcomes (routing, enrichment, speed-to-lead), not where it creates slop.We also cover:How to tier your launches by what matters to customers, not your org chart.Why the best growth marketers think more like editors than analysts.What happens when you replace data obsession with decision confidence.

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