Founders, Fix Your First Line

A few weeks ago, a founder asked me this:

“Hey AJ, should I personalize the subject line or the first line of my cold emails or DMs?”

It stuck with me.

Not because it was a bad question—it’s a great one.

But because it made me realize just how many people are wildly underestimating the power of that first line.

Just like how people wildly underestimated the success of Baby Yoda.

But he came in silent, left with Disney+ on his back.

I digress…

This newsletter is not about subject lines.

It’s about first lines that actually get replies.

Ready to stop being ignored?

Why First-Line Personalization is Non-Negotiable

Here’s what most founders are doing right now:

“Hi AJ, I help B2B brands scale with an AI-enhanced 360° solution that leverages synergy across content ecosystems.”

Or worse…this.

 

His first line is asking me to meet without an agenda?!

What the FU*K are we meeting about?

Hard pass.

You don’t need to sound like ChatGPT after three Red Bulls.

You just need to sound like a real person who did their homework

When you nail the first line, you earn permission to be in their inbox.

When you don’t?

You end up in Trash faster than my guy Michael here.

RIP Michael.

How to Write a First Line That Works (Like, Actually Works)

This isn’t about flattery. It’s about context and relevance.

A) Every First Line Should Answer Two Questions:

• Why? Why are you reaching out to this person?
• Why Now? Why are you reaching out NOW?

B) Top Down Ways I Like to Personalize First Lines

Their LinkedIn Post (within 7–10 days)

Where to Look:

• Go to their LinkedIn profile → Click “Activity” → Filter by “Posts”
• Bonus: Use tools like Taplio or Clay to surface their top recent posts faster
• Pro Tip: Search their name + “LinkedIn” in Google for public posts if you’re not connected

A Role Change or Title Update

Where to Look:

• Scroll through their LinkedIn “Experience” section
• Look for the little blue “New position” notification badge
• Use Apollo.io or Clay to automatically detect role changes

Pro Tip: New roles = new priorities = great timing to offer help

A Company Milestone or News Update

Where to Look:

• Google News search: “Company Name” + funding / product launch / partnership
• Company blog or press page
• Crunchbase or TechCrunch for funding announcements

Pro Tip: Search by “past month” in Google News to stay timely

Recent Podcast Interviews

Where to Look:

• Google: “First Name Last Name” + podcast interview
• Use tools like Podchaser.com or ListenNotes.com
• Check their LinkedIn/Twitter—they often promote appearances

Pro Tip: Listen to the first 2 minutes—intro banter = easy personalization material

Recent Articles They Were Featured In

Where to Look:

• Google: “First Name Last Name” + Forbes / TechCrunch / Business Insider / etc.
• Check the “News” tab in search results
• If they’ve published on Medium, Substack, or company blog, grab a quote or insight

Pro Tip: Quote them directly—it shows you actually read the piece

Events You Saw Them Speak At

Where to Look:

• Search their name + “conference” or “panel”
• Check LinkedIn posts or comments—people often tag themselves in event recaps
• Browse YouTube for event recordings (especially for niche industry events)

Pro Tip: Mention the talk title or one line from their presentation

The Formula (So You Never Have to Guess Again)

Here’s your no-fluff structure:

“Saw [specific, recent signal]—[insight or empathy].”

Example: “I saw your recent post on startup funding. I 100% agree with your thoughts on waiting to do a raise until you have product market fit.”

Your Homework This Week

Audit 5 of your last cold emails or DMs.

1. Did the first line prove you know the person?
2. Did it make the timing feel relevant?
3. Would you reply to it?