Stop being boring, Start being bold

B2B is rapidly becoming Boring to Boring 😴

Every corporations, from startups to enterprises is the #1 solution in their category, the best product providing the best results and shipping the most features.

But we’re not dumb, we know most of it is fake, hiding behind a corporate tone and brand.

And with everyone out there following the old playbook, it just feel bland and full. There’s a solution, but it’s definitely not for all.

I’m talking about being “bold”, instead of boring.

That was a big reason why We’re Not Marketers 💀 grew so much quickly. We started saying that we would take down Salesforce, started blasting egotistical founders and said that product marketers are not marketers.

In B2B SaaS, everyone in your industry talk about the same two things:

1. Save costs

2. Increase revenue

They act as if this isn’t the two lungs of any businesses out there 🫁

→ Martech alone has 10K+ solutions.

When there’s too many actors in a market, it’s creating a fog of war for the prospects—they are only going with clear and visible market leaders.

Your unknown startup will stay in the obscurity, because there’s no reason for people to give you attention.

But there’s a limit to “boldness”, and too much of it make you “unhinged”

“unhinged” = exhibiting unstable, erratic, or irrational behaviour.

It’s not necessarily a bad thing, you don’t want to be the brand that goes “overboard” but you want prospects to give you attention. You have to find the right balance ⚖️

TLDR; Be bold enough to stand out from the B2B (Boring to boring) but not too far left so people freak out because they are associated to your brand

When we’ve interviewed Devin Reed, he told us that the most free marketers are the ones that have creativity liberty. This is scary, especially if you’ve been living in boringville for a while.

But bloody markets required bloody positioning 🩸

Today, I’ll show you examples of unhinged positioning, how much is too much, and how you can apply being bold at your startup.

Let’s go 🫡

How much is too much?

That’s the first question I ask when I get offered free samples at Costco

“Speak well of me, speak ill of me, but speak of me” is a French adage capturing the idea that any publicity is better than no publicity.

It’s the equivalent of: “All press is good press.”

I disagree with this statement, you can’t please everyone. Hot and spicy takes get the attention of people, but usually needs to be researched.

But in crowded markets, attention is the ultimate currency. Here’s some example of different “unhingedness”.

1. Ken Cheng and his crazy LinkedIn posts

If you don’t know Ken, your LinkedIn feed is about to get a whole lot spicier 🌶️

One of the worse debate I’m seeing on LinkedIn is instructions on spotting AI content (and don’t get me started on em dashes)

Ken found the perfect way to come up with unhinged take + making sure AI can’t copy him.

This is peak comedy ✨ 

While the reactions are massive, not everyone like this and I can’t really see this content helping him drive business or get a job, but that’s entertaining ✨

I would not suggest taking this road because even if Ken was selling something or pushing his business, it would be way too far from his extreme style

At the end of the day, you do you but this really isn’t for everyone.

2. Air, the startup that hired a pornstar

This one is the definitely up there.

Air is a Dropbox competitor, and they are targeting teams of creative, it’s a digital asset management tool (DAM).

They hired Bonnie Blue, the woman who broke the world record by sleeping with 1000 men, paid her 5 figures and calls Dropbox directly (they are hiding it but it’s not subtle)

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You can search Bonnie Blue and Air for yourself if you want to see the ads. I think that’s an unique angle but to me it’s too much.

I’m sure Air got a lot of foot traffic from this, but there’s a lot of their customers that might have got mad at this as well.

“How would you feel if the app you were a subscriber or investor on, was encouraging or supporting a pornstar?”

If your angle doesn’t reflect your values, it might be a good idea to think twice about it. But they are targeting creatives, so I don’t know, maybe it worked well for them.

Did it create a lot of attention on them? Sure

Will it translate into the right type of customers? I don’t really know

That’s bold and this is definitely far from boring (lol), but there’s better ways to spend a 5 figure budget IMO. 🙃

3. Duolingo killing their mascot

When I think unhinged, I think Duolingo.

The app threaten you if you don’t do your lessons (exhibit A: Spanish or Vanish 🥲)

They announced that Duo the Owl (and his friends) all died, only to be revived a few weeks later.

This one actually made me redownload the app and practice back my “espagnol”. Until I stop doing my lessons again out of boredom.

Some people didn’t like it because they took the suggestion from a user without giving the credit, and others are saying that you can’t joke about death, but that’s the thing. You can’t please everyone, and it’s better than being boring.

Plus, it suits their brand, they did a Christmas video about kidnapping the parents from a kid not doing his lessons.

4. Liquid Death partnering in creating a special golf club

If you ever play golf, you know that finding the bathroom can be “challenging”.

It’s either that or you “fake” looking for your ball in the woods to release yourself.

Well, Liquid Death create a golf club that opens so you can, well, do what you need in it!

This is such an awesome collab too because what is the final stage of water or ice tea?

Bad birdie is a premium golf brand so that’s an unhinged partnership that just works.

→ You get a golf club you can urinate with, and doesn’t stress in finding the right spots in the wood, or the only bathroom on the 18 holes course.

This might seems weird, but whether you’re drinking water or adult bevies on the green, it’s only natural for it to go out.

5. Torq Lasers and Skeletons

Torq is my favorite B2B brand in the security space, and not just because they use skeletons.

Having worked in cybersecurity, it can get dull pretty quick. But you know what’s not dull?

→ Lasers and skeletons. 💀

They keeps coming back and is nailing their positioning with the statement that SOAR is dead. (They even wrote a manifesto on it)

And this year, they got the award of the best booth (which they always shoot for) by putting a real monster truck with a skelly on board.

What a fantastic way to get attention in a boring field. Torq CMO, Don Jeter is embracing it completely.

Develop your bold positioning

Ok but Gab? How do I start being bolder with our brand?

I got you, here’s how you should start.

1. Start with your POV

What is something that you believe in, and are talking about behind closed doors that can feel controversial, about your industry?

Once you have it, test how insightful it is by:

“Telling it to a friend, and watch if their eyebrow move”

• If they are raising their eyebrows up, they find it insightful

• If they are furrowing their brow or moving their head, it’s thought-provoking

Both are okay, it means that you’re trying to shift the way they are thinking, and that make your POV clearer instead of just being opinions.

2. Craft the story

To make your bold POV resonate, wrap it in a story that shows what’s at stake and who it’s for. A compelling story often hinges on a core angle, a narrative frame that gives your message meaning and urgency.

Here are five you can use:

The Enemy of Progress

Inspired by Andy Raskin's "Enemy" principle

Identify a belief, practice, or trend that’s holding your industry back, and position your product or idea as the antidote.

Example: “Legacy software is killing creativity. We’re building tools that unleash it.”

A New Game

From Raskin’s “Change in the world”

Frame your POV as a shift in the landscape — the rules have changed, and those who adapt will win.

Example: “It’s no longer about owning data — it’s about using it in real time. The old model is dead.”

The Underdog vs. the Giant

Classic narrative tension: David vs. Goliath

You’re the challenger brand taking on the status quo. People love rooting for the underdog, especially when the giant is clumsy, arrogant, or slow.

Example: “Salesforce has overpromised and underdelivered for a decade. We’re here to do it right.”

The Missed Insight

Borrowed from April Dunford’s “Insight Selling” approach

Highlight something everyone’s overlooked, a truth hidden in plain sight. Your POV becomes a lens to help others see more clearly.

Example: “Everyone’s optimizing conversion rates, but no one’s talking about trust. That’s the real bottleneck.”

The Movement

A blend of Raskin + category creation playbooks (e.g., Play Bigger)

Cast your POV as the foundation for a bigger shift, something people can join, not just buy.

Example: “This isn’t just software. It’s a new way to work. Join 10,000 teams already leading the change.”

3. Test it with distribution

Now that you have your POV and your story, you need to distribute it.

This is a uncomfortable exercise. I did it almost 2 years ago when I posted that product marketers were not marketers.

When people disagree and start calling you on your opinion and POV, you know that you’re taking the right direction.

Saying “the sky is blue” isn’t debatable, but this take is and many people were agreeing with us, even if the majority was against it.

It was called the worse take on LinkedIn, but it also helped us grow to 1000+ monthly listeners in less than a year and getting $15K in sponsorship so far.

Hot takes actually do pay off. All you need is to post about it and see the reactions.

How being bold helped Chameleon

We did a LinkedIn campaign with our season 4 sponsor: Chameleon

The angle? Product tours are dead

They worked on a benchmark report dissecting in-app report, trends, product our myths, and analysed 550 millions user interaction.

That’s a reminder that it’s all about the offer, because they delivered on an amazing report. Even if your copy is good, it’s all about what’s in it for them at the end of the day.

The results? 60+ unique relevant clicks from product marketers

They wanted a voice that was different from their brand, and that could reach PMM directly. So that partnership was a no brainer.

That’s about it folks 👋

You don’t need to be unhinged, but please, don’t be boring.

Let's work together 👋

There are two ways I can help your messaging resonates with your ICP:

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"After working on our messaging and ICP, Gab started owning our social content strategy. Within 2 weeks, I've got a 10x impressions boost and my first inbound lead from LinkedIn. Gab's the GOAT!"
-Warren Sadler, CEO, Therify

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