February 8, 2026
#218: Why Being Funny in B2B Marketing is a Serious Brand Strategy (and How To Do It!) - Deadpan's Luke Winter
Most B2B content looks polished. But almost none of it gets remembered.In this episode, we break down why humour isn’t a creative risk in B2B.It’s a strategic advantage.We’re joined by Luke Winter, founder of Deadpan and one of the few people proving that B2B marketing with humour drives memory, brand lift, and real revenue.Luke shares how a single funny B2B video generated over $300K in sales, why AI-generated content is creating sameness, and how brands can use comedy frameworks to stand out without needing a massive budget.We also unpack:+ Why most B2B brands confuse looking professional with being effective+ The science behind entertaining ads and higher conversion rates+ How to turn real customer pain points into memorable content+ Five practical frameworks to generate funny B2B ideas+ How to build a sitcom-style content series for your brand+ How to get CEO buy-in without calling it “comedy”Tune in and learn:+ Why humour works better than features in B2B+ How to create distinctive brand memory in a world of AI slop+ How to apply comedy without damaging credibilityIf you’re a B2B marketer trying to stand out, build trust, and stop blending in, this episode is essential.-----------------------------------------------------🔗 Links + CTAs-----------------------------------------------------🎓 Join our Demand Generation Program: https://theb2bplaybook.com/demand-generation-course🧠 Learn how to drive revenue across your organisation with CRO School: https://theb2bplaybook.com/cro-school💼 Need help running your own LinkedIn Thought Leadership Ads? https://theb2bplaybook.com/linkedin-ads-agency-----------------------------------------------------SUBSCRIBE to our channel: / @theb2bplaybook SUBSCRIBE to our newsletter: https://theb2bplaybook.com/newsletterGET the latest CONTENT: https://theb2bplaybook.com/-----------------------------------------------------00:00 Why Humour Is a Smart B2B Brand Strategy01:10 Why B2B Comedy Is Untapped02:00 AI vs Memorability03:20 Why Corporate Videos Fail04:10 The Video That Changed Everything06:00 From 234 Views to $300K07:00 The Showmanship Era08:10 Why B2B Content Gets Ignored09:10 Showmanship vs Salesmanship10:00 Turning Pain into Comedy11:30 The Data Behind Funny Ads13:00 Why Humour Isn’t Risky15:00 The Customer Is the Hero16:40 Comedy Frameworks20:20 Comedic Displacement23:20 Opposites in Comedy26:00 Metaphors That Work28:00 Parody and Associations31:40 Testing with Memes34:30 Sitcom-Style B2B Content36:50 Getting CEO Buy-In-----------------------------------------------------👥 Are you a B2B marketer in a small team??💰 Need to bring in more revenue for your company (so sales and your boss love you??)Get the:🔹 strategy🔹 templates🔹 toolsSo you have everything you need to drive more revenue for your brand.See why other B2B marketers like you love The B2B IncubatorCheck out: https://theb2bplaybook.com/demand-generation-courseS08 E218 - The B2B Playbook#b2b #b2bmarketing #brandstrategy #humourinmarketing #demandgeneration
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