The best lesson I never asked for

_{Day 236/100}

Hey—It's Tim. 

I still remember the first time someone told me to fuck off over email.

I wasn't a marketer - not really. I was a structural drafter with a half-broken laptop, a Gmail account, and zero clients.

But I'd decided SEO was my ticket out. So I made a list of 300 local businesses. Then I wrote one email template - something painfully average like "Need help ranking on Google?" - and copy-pasted it 300 times.

I hit send. Went to bed. Woke up to… nothing.

No replies. Not even a bounce. Just silence.

For two weeks straight, that's all I got. Crickets in email form.

Until Colin.

Colin's reply came in at 9:47am on a Monday.

Subject line: "Re: Need help ranking on Google?"
Body: "Fuck off."

That was it. Two words. All lowercase. Not even a signature.

And you know what? I was thrilled. Someone actually opened it. Someone felt something enough to hit reply.

So, as the spunky twenty-something year old I was, I wrote back:

"Wow, is Monday really that bad? I'm here for you Colin. Let it all out. I'll be your email punching bag for the afternoon."

I genuinely meant it. The man was clearly having a day. I'd been there.

What happened next was... instructive.

Colin didn't hold back. I got called every name under the sun. Some creative ones, honestly. The guy had range.

He spent three paragraphs explaining exactly why cold emailers were ruining the internet, why SEO was a scam, and why I specifically should reconsider my entire career trajectory.

And multiple sentences about what he would do to me should he ever meet me in real life…

Then, when he was done, I replied again:

"Feel better? Seriously though - want to jump on a call? No pitch. Just curious what pissed you off this badly. Might help me stop annoying people like you."

Radio silence for 12 hours.

Then: "Fine. Tuesday at 2pm. Don't make me regret this."

I took the call on my lunch break from my real job.

Colin showed apologetic. Embarrassed, even. Turned out his site had tanked after hiring some "SEO expert" who'd destroyed six months of rankings overnight.

He was gun-shy. Angry. Burned.

We talked for an hour. I did some small design work for him. Not much. But I stuck it through, earned his trust back bit by bit.

And Colin became one of my best referral sources for two years.

Here's what I learned: my favourite emails are actually when people speak their mind. Some people have nowhere else to vent, and that cold email gets every last bit of it.

Most marketers see hostility as rejection.

I started seeing it as an opening.

Someone who replies with rage still replied. They're engaged. They're human. They care enough to be angry.

And if you can match their energy - not mock it, not dismiss it, but match it with honesty and a bit of snark - you'd be surprised how often they soften.

Not every angry reply turns into a client. Most don't.

But every single one teaches you something about what people are actually feeling when your email lands in their inbox.

And that data? Worth more than 298 non-responses.

✌️ Tim "Colin’s Punching Bag" Hanson
CMO @Penfriend.ai

Same brain, different platforms: X, Threads, LinkedIn.

P.S. I regret losing Colin’s emails when I changed jobs. I didn’t pay for the upkeep of the domain, and never saved them elsewhere. But I would look at them often.

A reminder that I’m sending these to other people.
People who are busy. Have entire other lives. And I have to earn that tiny slice of attention they might give me. Regardless of what that looks like.

All replies are good replies.

Penfriend.ai
Made by content marketers. Used by better ones.