Parents are SCREAMING.

Tiny fingers clench the dugout fence like it’s the only thing holding them to Earth.

Bottom of the last inning. Bases loaded. Only one out.

I can’t look.

But I still do…

I look up from my coaches clipboard just in time to see our best hitter strike out.

I thought the game was in the bag.

Sobbing, the kid walked into the dugout.

I walk over and say:

“You know I don’t care if you strike out. Hitters hit. And to hit we have to….”

“Swing,” he says.

“And when we swing?”

He already knows because I’ve gone through this mantra ALL season.

“The other kids swing.”

“And?”

“We get hits.”

And sure enough, the next kid went up and swung the bat.

*Crack*

I’ve coached 500+ games for my kids and I can tell you the only way to guarantee you lose is not to swing.

To hesitate.

Same goes for your brand.

Most teams try to protect themselves by playing it safe:

Safe messaging. Safe positioning. Safe design.

But in saturated markets, safe doesn’t protect you.

If your brand sounds like everybody else,

You’ve already struck out.

Ambiguity aversion is real. People would rather choose something polarizing that feels real than something that feels safe but generic.

If I take your logo off your brand's tagline, does anybody know it's you?

Let's fix that.

The “Invisibility Trap”

Here’s the trap I see all the time in my discovery calls for Growth Sprints:

• Messaging that was committee'd to death
• Design that looks “enterprise-ready” (read: boring)
• Positioning that checks all the right boxes (and sparks zero emotion)

I once met with a team who spent a full year copying the category leader.

Their site, their ads, their features page. It all felt… familiar.

That was the problem.

They blended in so hard they almost vanished entirely.

They'd just learned weren’t just losing deals... they weren’t even being considered.

Safe = invisible.

Invisible = disqualified.

The campaign that should’ve bombed

Remember Dollar Shave Club and their debut YouTube video?

They weren’t selling razors.

They were selling a punch in the face to razor-industry fluff.

Opening line:

And then it got hilarious - talking about “f*cking great blades,” belly laughs, zero polish STRAIGHT AT THE THROAT of giant razor brands.

It cost just $4,500 to make.

Within 48 hours... they had 12,000 sign‑ups.

Today it’s 28+ million views and still iconic.

Can you think of a B2B brand doing something truly BOLD? Yes No

3 “Boldness Triggers” (that actually close deals)

1. Say the quiet part out loud

My kids always know when I’m sugarcoating something.

So do your prospects.

Buyers don’t trust perfect messaging. They trust honest, slightly uncomfortable truth.

Try this:

1. Dig up your last 5 emails, blog posts, or sales slides.
2. Highlight the polished, fluffy stuff.
3. Now rewrite one like you’re explaining it to me over coffee.

2. Push an enemy into the light

When I was a teacher, we used to say: “If you name it, you can tame it.”

Same in marketing.

The best brands don’t just raise awareness. They name the villain.

Try this:

1. What’s the invisible cost your buyers are ignoring?
2. Give it a name (Content IP). Make it a threat.
3. Then show how you neutralize it.

3. Be someone’s “hell yes” or “hell no”

I know I'm not for everybody.

The unsubscribes from this email alone are enough to let me know that's true.

But that's GOOD.

It doesn't give me permission to be an a-hole (and call it "marketing"), but if my work gets nods from everybody, nobody has the conviction to hire me, either.

Try this:

1. Pick one thing you do that breaks the “rules” in your industry.
2. Now highlight it.
3. Put it in a subject line. A homepage headline. A sales deck title. Make it your email signature.

Mini Framework: Boldness = Relevance × Risk

If your message isn’t rooted in something real, then yeah, boldness is just noise.

But if it’s relevant? if it speaks to the things your buyer is whispering to themselves?

Then boldness creates resonance.

It doesn’t push people away. It pulls them in.

Sprint I'm running week: The Boldness Sprint

This is what I’d do if we were in a Sprint together:

Day 1–2:

• Audit your homepage and top 3 sales assets.
• Highlight every line that feels “safe” or interchangeable.

Day 3–4:

• Rewrite one using a boldness trigger.
• Doesn’t have to be perfect. Just send it. Ship it. Post it.

Day 5:

• Ask your sales team if anyone noticed.
• If you hear, “That’s exactly what I was thinking” - you NAILED it.

Want to do this sprint along with me?

Here’s the truth:

I’ve got 4 kids, a business, a mountain of Warhammer models in my basement, and maybe five hours of sleep on a good night.

I don’t have time for brands that sound like everyone else.

And neither do your customers.

Stop trying to sound “right.”

Be the one they can’t ignore.

Make your brand the easiest to say “hell yes” to…or the easiest to say “hell no” to.

Either way, you win.

Because safe doesn’t scale.

Bold gets bought.

👆 seriously if you only take away one thing from this whole thing, make it be those 3 words.

If this hit home, here are 2 ways to make it real this week:

DM your teammate:

“I know we can’t go full-unhinged Duolingo or Wendy's overnight, but don't you wish we stopped trying to sound ‘professional’ and just said what everyone’s actually thinking?”

Before your next 1-on-1 with your manager:

“Can I show you one idea I think is risky… but could actually change the game for us?”

Then forward them this newsletter.

- Brendan
PS - Next up? The chapter I wanted to write about 100 challenger brands (brands doing creative work and punching above their weight) but could barely find five. 😢

That's why all this is soooooo needed!

• ​Navattic - Double trials/leads *and* cut sales cycles in half
• ​Dreamdata - FINALLY know the ROI of your content (free)
• ​Surfer - Boost content visibility in Google & ChatGPT.
• ​Sendoso - Double win rates, 6x second call rates, and close deals 29% faster
• ​Videodeck - Scale video marketing by turning boring video assets into customers
• ​SparkToro - find out who your customers really listen to (& what they Google!)
• ​Growclass - Our community’s most highly recommended marketing training

Have a great week!

Lindsay & Brendan