[reply worthy | day 1] she knew by the appetizers
(the 5 words that decide whether your prospect reads your DM)
She knew by the appetizers.
8 minutes in. Burrata between them, untouched on her side.
He was telling her about the company he almost sold in 2021.
The deal had been at $14M. Then it fell apart in due diligence.
Something about the cap table. He talked her through the cap table.
All this because she had asked one question. “What do you do for work?”
That was 12 minutes ago.
By the entrees, he’d covered his gym routine.
The trainer who changed his life. The deload weeks.
His standing 7am Saturday at Equinox.
She mentioned she ran sometimes. He said running was hard on the knees and he’d send her a podcast about it.
By the second cocktail, he was on his five-year plan.
Real estate. A second business. A boat, eventually, if the timing worked out.
By dessert, which she declined, he’d told her about the CEO he’d met at a conference last spring.
She asked if she could get the check split. He said don’t worry about it. He insisted. She let him pay because arguing would have meant staying longer.
He hugged her at the curb. Asked if she’d had fun. She said yes.
She gave him the kind of smile women give when they’re already in the Uber in their head.
The next morning he texted her.
“Had a great time last night. Would love to take you out again. You free Friday?”
3 blue dots appeared. Disappeared. Appeared again.
She put her phone face down on the counter and went to make coffee.
He never heard from her again.
When my friend Reid sent me the DM outreach sequence he’d been using the other day, this exact date scenario instantly popped in my head.
He’d asked me to be honest. Was it any good?
He’d paid an agency two grand to write it.
He’s been sending the same 7-message sequence for three months.
It’s getting some replies. Mostly silence.
The few replies he gets die on the booking link.
Today, I’m talking about the first mistake that’s killing your DM reply rate before message two:
→ The 5 words that decide whether your prospect reads sentence two
→ Why “hyper-personalized” templates still feel templated
→ The 60-second test to know if your opener is fixable or scrap-and-rebuild
Let’s start with the first message...
Here’s the first message of Reid’s sequence:
“I’m talking with B2B SaaS founders who know they should be running more outbound but aren’t sure where to start. At a high level, we help SaaS companies generate 30% of pipeline from outbound by handling the campaign planning and execution. Would it be alright if I shared a few ideas for how you can generate more pipeline from outbound?”
Read it twice.
3 sentences. Every single one is about Reid.
Who he’s talking to.
What his company does.
What he wants to share.
The prospect is a placeholder for the words “you” and “your.”
Nothing in this message proves Reid noticed anything specific about the human on the other side of the screen.
Reid is the guy at the dinner.
And right now, three months of prospects have hugged him at the curb and gone home and put their phones face down on the counter.
The first DM mistake… you’re the spotlight.
You’re drafting your opener. You want to sound credible, so you lead with what you do.
You name your company. You name the result you get for clients. You ask if they’d be open to a quick conversation.
Reading it back, it sounds professional. It sounds polished. You hit send to 50 prospects and go to bed.
48 hours later, 2 replies. Both polite passes.
Most DM outreach puts the sender at the center of the frame.
“I help.” “We specialize in.” “My team.” “Our clients.”
The first 5 words of any DM either make the reader feel seen, or make them feel like one of 500.
Sender-first openers always feel like one of 500.
❌ Before: “I’m talking with B2B SaaS founders who know they should be running more outbound...”
✅ After: “Saw your post about hiring an SDR before product-market fit, fully agreed...”
Here’s how to change the spotlight:
1️⃣ Read your first 5 words out loud. If those 5 words could be sent to anyone in your prospect list, they’re too generic.
Specific openers can’t be copy-pasted. “Hey [NAME], I’m talking with people in your industry who...” works for everyone, which means it lands on no one.
2️⃣ Find one detail only this prospect would recognize. Their company name doesn’t count, that’s a placeholder.
Their job title doesn’t count, that’s a category.
What counts: a podcast they were on, a post they wrote, a product detail on their site, a hire they just made.
Something that proves you read past the headline.
3️⃣ Run the stranger test. If a stranger read your first 5 words with no other context, could they guess who the message was sent to?
If yes, you’re writing a real message. If no, you’re writing a template with the prospect’s name pasted on top.
Instead of treating the prospect like “another SaaS founder,” you speak to them like a human reality.
That’s it.
Here’s what you learned today:
→ Sender-first openers always feel like one of 500
→ Specific openers can’t be copy-pasted. That’s the whole point
→ If a stranger can’t guess your recipient from the first 5 words, neither can your prospect feel singled out
Your prospects aren’t looking for another agency pitch. They’re looking for proof that someone actually read their stuff before sliding into their DMs.
Open the last DM sequence you sent. Read just the first 5 words out loud. If you could send those exact 5 words to anyone in your prospect list, you have your first rewrite.
Want this test as a permanent operator tool?
I packaged The 5-Word Test as a standalone guide.
→ The mega-prompt that runs the diagnostic
→ A Claude skill that installs once and runs in 3 seconds
→ The project setup that personalizes it to your offer
→ The Claude Cowork workflow that audits an entire sequence at once
→ 3 worked examples, and a swipe library of 10 pre-tested openers across 3 angles
So you can stop pasting the prompt every time. Skill installs in 60 seconds.
This guide shows you how to build a system that auto-loads your offer, ICP, and past wins, so rewrites are tuned to YOUR business.
Once installed, you can run it on one opener or 100 in the same workflow.
Paid 8am In Atlanta subscribers: use code included with today’s mega-prompt at checkout for $20 off → $27.
Not a paid subscriber yet? Upgrade your subscription to get $20 off this guide (and every paid guide I drop in the May Series).
Over the next 31 days, I’m walking you through:
→ The 11 mistakes hiding in Reid’s 7-message sequence (one per day, message by message)
→ The “Thoughts, [name]?” follow-up everyone sends and why it’s the laziest move in DM outreach
→ The fake-urgent breakup line that’s in 90% of DM sequences right now
→ Why the case study name-drop kills more deals than it closes
→ The booking reply that loses 60% of warm leads between “yes” and butt-in-chair
→ The “did the link work?” follow-up that’s the passive-aggressive cousin of “any thoughts?”
→ The 60-second Loom move that closes more prospects than any other follow-up
→ The full rebuild, opener through real goodbye, plus the booking flow that doesn’t fumble warm leads
→ The swipe library of 50+ pre-written quick wins you can drop into message two
→ The 5 master assets you can personalize for message three without melting your week
→ The reply-rate diagnostic that tells you whether to fix the observation, fix the thread, or scrap and rebuild
Ready to fix your opener without rewriting your whole sequence?
When the first 5 words of your DM put you at the center, prospects pattern-match it to every other agency pitch and bounce.
Today’s paid member mega-prompt runs the 5-word test on any DM opener you’ve ever sent...and rewrites it 3 different ways.
Paid members get:
✔ The 5-Word Test Diagnostic
→ Paste any DM opener, get a PASS/FAIL score on 3 specificity questions
→ Plain-language breakdown of exactly what’s broken in your first 5 words
✔ 3 rewrites of your opener, each scored against the diagnostic so you can see why they pass
✔ A prospect-specific question the prompt asks before rewriting (so you can’t fake it)
