The B2B Playbook #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 credibility
If you’re a B2B marketer trying to stand out, build trust, and stop blending in, this episode is essential.
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00:00 Why Humour Is a Smart B2B Brand Strategy
01:10 Why B2B Comedy Is Untapped
02:00 AI vs Memorability
03:20 Why Corporate Videos Fail
04:10 The Video That Changed Everything
06:00 From 234 Views to $300K
07:00 The Showmanship Era
08:10 Why B2B Content Gets Ignored
09:10 Showmanship vs Salesmanship
10:00 Turning Pain into Comedy
11:30 The Data Behind Funny Ads
13:00 Why Humour Isn’t Risky
15:00 The Customer Is the Hero
16:40 Comedy Frameworks
20:20 Comedic Displacement
23:20 Opposites in Comedy
26:00 Metaphors That Work
28:00 Parody and Associations
31:40 Testing with Memes
34:30 Sitcom-Style B2B Content
36:50 Getting CEO Buy-In
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S08 E218 - The B2B Playbook
#b2b #b2bmarketing #brandstrategy #humourinmarketing #demandgeneration