enny Dop

Hey, can we talk about something?

The content marketing world has gone completely off the rails, and we all know it.

You've seen it too, right? The LinkedIn "thought leaders" who haven't written their own posts since 2019.

The "AI revolutionaries" who were mediocre copywriters last year but are now charging $500/hour for consulting.

The endless parade of morning routine posts that somehow always end with "and that's why you should buy my course."

I'm Tim, and The Penny Drop is my daily reality check for content marketers who are too smart to buy into the hype, but too busy to figure everything out from scratch.

Think of it as your experienced friend who's seen it all and will tell you the truth - but make you laugh while doing it. (Professionally Irreverent™, if you will.)

Every day, I share what's actually working in content marketing - no BS, no guru-speak, just practical advice from someone who's been in your shoes and still has the blisters to prove it.

Because after a decade of going from broke freelancer to agency owner to CMO, I've learned that the best marketing advice usually doesn't come with perfect lighting and a 'link in bio.'

What Nobody Else Will Tell You

Most content marketers in 2025 are trapped in a game they didn't sign up for.

They're:

- Pretending they love writing "hot takes"

- Quietly wondering if their AI tools are just expensive Magic 8 Balls

- Nodding along in meetings while everyone discusses "synergistic content strategies" (which is not a real thing, by the way)

After 10 years of spectacular failures, unexpected wins, and everything in between, I've realized something: The best content marketers aren't the ones with the biggest followings - they're the ones who've figured out how to stay human in an industry that's trying really hard not to be.

And I say this as someone who Co-Founded an AI writing SaaS.

What You'll Actually Get:

Every day, I send one email that's like getting coffee with that friend who always tells you what you need to hear, not what you want to hear.

We're talking:

- Real talk about AI (including which tools are actually worth your time and which ones are just expensive ways to generate mediocre blog posts)
- Strategy shortcuts that actually work (because you have better things to do than A/B test your email signature)
- War stories and lessons learned, so you don't have to make the same expensive mistakes I did

Each issue is written to be both laugh-out-loud honest AND something you can forward to your boss with confidence. (I call it "professionally unprofessional" - feel free to steal that.)

I cover everything from:
- "How to handle your CEO discovering ChatGPT at 11 PM"
- "Why your content calendar is a wish list in a trench coat"
- "The real reason your blog posts aren't working (hint: it's not your H2s)"

Every day, I send one email that's like getting coffee with that friend who always tells you what you need to hear, not what you want to hear.

Monday - Movers.
The last weeks news. None of the boring shit.

Tuesday - Traffic.
How to get more. How to do more with what you got.

Wednesday - Writing.
We're all writers, even if you don't call yourself a writer.

Thursday - Tech.
New tools and tech we're using. Also free tools we make for you.

Friday - Front End.
All the design behind how you present you content. The visuals are half the battle.

Saturday - Strategy.
Straturday. All the strats we're testing. And experiments you can try.

Sunday - Storytelling.
How to tell great stories. And stories of my 10 years doing this shit...

My Promise To You

Every issue will be three things:
1. Actually useful
2. Genuinely entertaining
3. Safe to forward to your CMO (I can't promise this)

Because at the end of the day, we're all just trying to create content that matters while keeping our sanity intact.