
Wednesday, June 10, 2026

A tale from my freelancing days:
I once worked with a client who told me he hired the great Dan Kennedy to write him a sales letter.
The cost?
$50,000.
The result?
Complete bomb.
Literally zero ROI on a $50k investment.
And I remember sitting there just... stunned.
Because at the time, Dan Kennedy was basically a god to me.
I'd read his books.
I'd studied his sales letters like scripture.
The guy was untouchable in my mind.
So when my client dropped that little nugget on a Zoom call, my brain genuinely couldn't process it.
The world's greatest copywriter... wrote something that flopped?
That wasn't supposed to be possible.
But here's what I discovered after that conversation...
This happens all the time.
Not just Kennedy.
Every A-lister you've ever heard of has a graveyard of bombed campaigns behind them.
Carlton. Halbert. Bencivenga.
The best in the world still swing and miss.
Moral of the story is:
Nobody writes a winner every time.
Not the legends.
And not you and me either.
Once I really absorbed that... something shifted.
Because I realized the people making consistent money from email aren't the ones writing perfect emails…
They're the ones sending enough emails that the winners have room to show up.
But if you only step up to the plate once a week because you're terrified of striking out…
You're not giving the winners a chance to land.
That's what's happening to many of the entrepreneurs I talk to.
They’ve got a decent sized list…
But they're sending one carefully crafted email a week (sometimes less)...
Agonizing over every word and waiting until it's "good enough" to send.
While their list is slowly forgetting they exist.
And when they finally do show up with an offer…
It lands like a stranger knocking on the door.
The fix isn't writing better emails.
It's writing MORE of them…with LESS friction… so you can actually find out which ones your audience responds to.
That's the whole reason I built EmailStoryselling.ai.
It's a purpose-built AI writing assistant that learns your voice, remembers your audience, and gets faster and more accurate every time you use it.
Not a generic chatbot that spits out corporate slop with em dashes every third sentence.
So if you've been sitting on emails because they don't feel ready...
Or worse, not sending them at all because you’re too busy to write…
Or can’t figure out what the heck to write about…
Then your list is paying the price for that.
Fix it here:
→ Start writing daily emails that sell with EmailStoryselling.ai
Jim Hamilton
P.S:
The AI doesn't need to be perfect either. It just needs to help you show up consistently. That's where the money is.

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