Who Dares Wins
Why the brave brands win and how they do it.
In my last post “The Imitation Trap” I mentioned that marketers understood how to break through category traps “to find pastures new”. Indeed it SHOULD be a basic part of the marketers toolkit. To prove this I’m going to open with an example from the 1960s.
In 1960, Volkswagen called their own car a lemon.
The full-page ad showed a spotless Beetle under a single bold word, then explained that the chrome strip on the glovebox was crooked which meant the whole vehicle failed inspection. At a time when car ads were ubiquitously about power and lifestyle, VW took a huge risk. No puffery, no jargon, no excuses. Just a wink to the reader and a quiet suggestion: if this is what they reject, imagine what they let out the door.
At the time, American car ads were all tailfins, sunsets, and slogans like “The car of tomorrow, today!” VW’s black-and-white honesty didn’t just stand out, it sliced through. Because it tapped into a growing cultural suspicion that the bigger the promise, the bigger the lie.
That’s what creative risk really is: a sharp truth, a point of view, and the courage to say it in public.
Playing safe is expensive
In The Imitation Trap, I wrote about what happens when an entire category optimises itself into oblivion. Everyone chases what’s working. Everyone looks sideways. And soon every brand ends up sounding like the same intern wrote their homepage – because, to be honest, they probably did… by prompting ChatGPT.
Logos converge. Language flattens. “Tone of voice” becomes an exercise in removing tension. Performance marketers squeeze ROI out of a funnel that no one remembers going through in the first place.
Playing it safe feels rational. But that’s only because the risk is invisible. You don’t see the customers you never moved. You don’t hear from the prospects who didn’t notice you. You just quietly fade into the middle of the market, surrounded by other smart people doing exactly the same thing all the while looking at your very rational ROI and patting yourself on the back.
The antidote is risk. Real, creative, calculated risk
But not chaos. Not randomness. Not weirdness for weird’s sake. Not provocation purely for attention. And definitely not chasing “engagement” (shudder).
Good creative risk is grounded. The foundation is deep knowledge of and appreciation for your audiences. It starts with a tension your audience feels but doesn’t hear reflected anywhere else. That’s the insight. Then comes the point of view or positioning, ie. what your brand believes about that truth. And finally, the courage to express it in a way that actually lands.
I keep the maths simple:
Creative Risk = Insight × POV × Daring
Miss out those factors and you get something forgettable, incoherent, or safe-by-committee. If you get a couple of these, you’ll probably produce some pretty good work, but pretty good will lose against optimisation. But if you get all of these right, you can create brands that end up defining entire categories.
Let’s look at some case studies.
Nike & Jordan – turning endorsement into mythology
Nike and Jordan is one of the things that got me into marketing. It wasn’t just about the advertising, it was about doing marketing an entirely different way. Of course I didn’t realise this at the time, I just liked the shoes!
In the 1980s, athlete sponsorships were wallpaper. A logo on a shoe, a quote in a print ad, maybe a handshake on camera. Then Nike saw something different: Michael Jordan was culture not just a player (Sidenote: This predated Adidas signing RunDMC). Not just exceptional, but magnetic.
They didn’t just sign him. They built Air Jordan as its own brand. They shaped the narrative. They leaned into his defiance, his gravity. When the NBA banned the original Air Jordans, Nike paid the fines and turned it into an ad. “Banned” wasn’t a scandal, it was a badge of honour.
Insight: Jordan could be bigger than basketball.
POV: Sport isn’t just performance, it’s expression.
Daring: Bet the farm on a single player, and stoke controversy to build brand myth.
Today every athlete-as-brand traces back to that moment. It was bold then. It’s expected now.
TransferWise – naming names in fintech
I’ll always be a fan of the work Wise did because they proved the power of a brand idea at a time when tech believed that marketing was unnecessary.
Consumer Forex is the least sexy corner of finance. It’s all margin tables, hidden fees, and forgettable UX. But TransferWise (now Wise) spotted the real emotion lurking underneath: rage. Customers didn’t just want a cheaper option, they wanted justice.
So Transferwise named names. They broke and unwritten rule in marketing that you shouldn’t name your competitors. But they went further and said “Your bank is hiding something.” Billboards with FX markups. They ran stunts with sandwich boards and staged demonstrations, they took their campaign to parliament and pushed for changes to policy. Their tone wasn’t reassuring. It was insurgent.
Insight: People felt ripped off, and alone.
POV: Transparency is a weapon.
Daring: Go to war with the incumbents, in public.
That kind of campaign doesn’t happen by accident. It comes from knowing exactly what your customers wish someone would say, and saying it louder than anyone else. Importantly, Wise had some of the smartest and best growth and performance marketers in the business, but their work was so much more effective because it functioned in the service of a powerful brand idea.
Australian beer ads – the golden age of weird
This one is close to my heart because it’s where I cut my teeth early in my career.
By the late 1990s, Aussie beer advertising had become one long dad joke. Every brand peddled the same matey clichés: BBQs, eskies, banter. But then something shifted. Breweries started getting weird. Carlton Draught dropped “It’s a big ad”, a knowingly bombastic epic that parodied Lord of the Rings and British Airways AND beer ads themselves. Tooheys told twisted stories with dark humour and strange logic. James Boags went eccentric and Hahn Premium Light went slapstick (this was my ad).
The creative bar rose, but not by playing it safe. The brands embraced entertainment over tropes. Each brand was forced to be smarter, better and more creative just to compete. And in doing so, made themselves impossible to ignore.
Insight: Beer drinkers weren’t stupid, they were bored.
POV: Don’t sell beer, earn attention.
Daring: Commit to the gag. Let the product take a back seat.
It worked because it made people feel something. Even if they didn’t drink that brand, they remembered it and quoted it at the pub.
Apple’s “Think Different” – return to first principles
I’m not a huge “Apple guy” but their Think Different campaign is, in my opinion, possibly the greatest marketing campaign ever. It is perfection in marketing. This is a big claim because some of the other greatest ads are also Apple ads. Because ultimately (and this is controversial) I believe Apple is a marketing company rather than a product company, and this ad is cemented Apple for decades that followed. If you want to understand how far Apple has drifted in recent years, read my post “Thick and Thin”.
When Steve Jobs returned to Apple in 1997, the brand was drifting. Beige boxes. Mediocre specs. No narrative.
So instead of selling features, they sold philosophy. “Think Different” wasn’t a campaign, it was a mission statement. It was a direct line back to the people Apple was for: the creatives, the misfits, the ones who saw the world differently. Apple was the tool with which people could change the world.
The ad showed black-and-white portraits of rebels, geniuses, artists. No product shots. Just belief. The voiceover, narrated by Richard Dreyfus is a call to action and poetry at the same time. This ad is the marketing version of Mohammed Ali holding a punch as George Foreman fell in 1974.
Insight: Creative people felt abandoned by tech (and everyone wants to feel creative)
POV: Tools for rebels and misfits.
Daring: Use Einstein and Gandhi to sell computers, and mean it.
It didn’t just rescue the brand. It set the tone for the next two decades.
Anduril – anime meets autonomy
I realise this is not the first time I’ve written about this! But it’s hard to understate how this ad effectively refined a category and pioneered a totally new direction for marketers in Defence. So much so, it’s an area that I’m increasingly focused on professionally (but more of that another time).
There’s a long-standing rule in defence: don’t make weapons look fun.
And then Anduril dropped a 90-second anime trailer for its autonomous cruise missile system vehicle, Barracuda.
Not a dry explainer. Not a grainy demo. A hyped-up, stylised, cyberpunk mini-epic, complete with an operatic soundtrack and visual nods to Ghost in the Shell and Evangelion. It looked like the teaser for a new Netflix series or classic Daft Punk. But it was a weapons system launch and a statement of intent.
Anduril didn’t just ignore defence marketing norms, they detonated them. But this wasn’t edginess for edginess’ sake. It was a deliberate move to signal to a new generation of engineers, technologists, policy thinkers, and people who worry about a dangerous world that the future of defence isn’t grey. It’s cinematic. It’s software-defined. It’s a battlefield built as much in Blender as in Bethesda. And if you’re our adversaries, don’t even try it on because we’ll take you down and then laugh about you at Comicon.
Insight: The next cohort of defence talent grew up on anime, not Lockheed demos.
POV: Defence tech should be culturally fluent, not sterile.
Daring: Use the language of fandom to introduce cruise missile abundance.
It worked because it respected the audience’s aesthetic IQ. It didn’t dilute the message, it reframed it. You’re not buying a legacy defence contractor. You’re joining the cast of the future.
It’s not about provocation. It’s about truth
This is important: creative risk isn’t about being edgy, and it isn’t about chasing engagement for the sake of it. It’s about being honest.
Bad risk says: “Let’s shock people.”
Good risk says: “Let’s say the thing everyone knows, but no one dares to admit.”
Audiences aren’t fragile. They’re bored. They want to be spoken to like adults. They want brands that take a stance, not ones that say, “We’re just like everyone else, but slightly faster.”
So how do you do it?
You don’t start with colour palettes or your influencer outreach.
You start by asking: Who are we?
Then: What’s the uncomfortable truth in our category?
Then: What do we believe about it?
Then: What would it look like to actually say that out loud?
The answer might be polarising. Good. Great brands aren’t for everyone. If it unnerves the legal team, you’re probably on to something. If your CEO gets a slightly wild, “can we even do that?” look, even better.
You want to provoke a reaction internally, and that reaction should be an enunciation of something felt but not spoken. Because if your colleagues feel that way, chances are your customers do too.
Risk is the cost of relevance
Marketing doesn’t get interesting until someone takes a risk. A real one. Not a novelty, not a TikTok gimmick, not a slight tone shift in a Q4 campaign. I mean an actual act of creative bravery, anchored in audience insight and lit up by point of view.
It’s how you signal in a world full of camouflage. It’s how you build preference, not just presence. And it’s how you stay remembered when the rest of the deck is forgotten.
In other words:
Creative Risk = Insight × POV × Daring
Because what’s safe today is invisible tomorrow. And what’s brave, done right, is what changes categories or creates entirely new ones.
To dare is to do.