Messaging Fundamentals

💡 Key Idea: Everyone's read the same cold email blogs. Everyone's using the same templates. That's why your prospects' pattern recognition is so finely tuned - they can smell a sales email from the subject line alone. You need to pattern-disrupt, not pattern-match.

✋ Permission Slip: You have permission to get creative. Break the rules. Send weird emails. Use sentence fragments. Include typos on purpose. The weirder you are (while still being relevant), the more likely you are to get a response.

📊 Outcome

By the end of this section, you'll have:

• Pattern-disrupting techniques that nobody else is using
• Messages that fight through the noise of being ignored
• Creative approaches that make prospects stop and actually read
• The ability to sound like an insider, not a vendor

Fighting the Curse of Being Ignored

Your enemy isn't spam filters. It's invisibility. Your prospect gets 147 emails a day. They actually read maybe 12. Your job is to be one of those 12.

The 5 Pillars of Messages That Get Responses

Here's what we're covering:

‼️ Real Personalization: I think it goes without being said, but ALL OF THE ABOVE, is enhanced if you can truly personalize to the prospect. This proves you're a real person who's taken time to assess whether the prospect might actually benefit from using your product/service.

In the examples below, you'll notice that often times we are personalizing the individual pillars i.e. something can be a "pattern disrupt" because it's personalized, "insider knowledge" is inherently personalized if done correctly, to be effective "unexpected questions" ALSO have to be personalized.

Pillar 1: Ultra-Short

If it requires scrolling on mobile, it's too long. Period.

Example Evolution:

Too Long (120 words):

Hi Sarah,

I hope this email finds you well. I wanted to reach out because I noticed that TechCo recently raised Series B funding, which is really exciting news for your company.

As companies scale at your stage, I’ve observed that customer onboarding often becomes a bottleneck that can limit growth potential. Many fast-growing SaaS companies struggle with this.

We’ve developed a solution that helps companies like yours reduce onboarding time by up to 60% while maintaining quality. Our platform has helped similar companies achieve impressive results.

I’d love to schedule a brief 30 minute call to discuss how we might be able to help TechCo with these challenges.

Would you be available for a call next week?

Best regards,
Mike

Just Right (52 words):

Hi Sarah,

Saw TechCo’s Series B announcement, congrats!

When we helped CloudCo through their similar growth phase, their biggest bottleneck was customer onboarding taking 14+ days.

We got them down to 5 days. Worth exploring if TechCo faces similar challenges?

Best,
Mike

P.S. Your post about scaling challenges really resonated.

Pillar 2: Pattern-Disrupting

Everyone's emails look the same. Time to be different.

Simple Ways to Pattern-Disrupt:

• all lowercase subject lines (no caps at all)
• Intentional typos that feel human ("just saw your psot about...")
• The BTW follow-up: Send main email, wait 47 seconds, send "btw forgot to mention..."
• Text message style (no punctuation, line breaks instead of paragraphs)
• Start mid-thought ("...so that's why I'm reaching out")

Example:

Subject: quick q about your CAC

Noticed you're running fb ads to a Calendly.

Any reason why?

I'd bet that's causing 70%+ dropoff.

Pillar 3: Insider Knowledge

Talk like you actually work in their industry. Use their abbreviations. Know their specific pain.

If you're selling to SaaS companies, you better know:

• CAC, LTV, MRR, ARR, churn
• Why everyone hates their attribution model
• Etc.

Don't say: "customer acquisition costs" Say: "your CAC is probably 3x what you're telling the board"

Pillar 4: Unexpected Questions

Stop asking "Is this a priority?" Start asking questions that make them think.

Some intriguing questions:

The Counterintuitive:

Why haven't you solved this yet?

What's stopping you from just building this internally?

Who internally is fighting against fixing this?

The Peer Comparison:

Your competitors all do X - why don't you?

Everyone else in your space uses Y - what's your secret?

3 of your customers asked us about this - they talking to you?

Pillar 5: Strategic P.S.

The P.S. gets read more than your body copy. Use it wisely.

A Few P.S. Templates:

P.S. [Competitor] just started doing [specific thing]. Thought you should know.

P.S. Line 47 of your pricing.js file - clever approach to tiering.

P.S. 3rd fastest-growing company I've seen make this exact mistake.

P.S. Loved your LI post on [relevant topic].

P.S. I was just in Berlin w/ my wife, late night Kater Blau was a highlight. 🪩

LinkedIn: Keep It Stupid Simple

LinkedIn messages should feel like texts, not emails.

Connection request? Start by sending them blank without a connection request message. Why? You'll often times get less accepted requests if you include a note. The folksfrom Lavender AI hypothesise thisis because you're more likely to give them a reason not to accept.

Example First Message:

Solid $30M round, congrats! Just signed up for Juicebox, pretty badass product so far. Curious, is there a version for people LOOKING for jobs?

Saw your comment on [person]'s post about [thing]. I'm dealing with the exact same thing. Mind if I ask how you've solved this in the past?

Remember, you're main goal at this point is to get a response and start a conversation. Meaning it's okay (and even encouraged) to not even pitch your product in your first message or two. Once your prospect responds, your goal is to respond as quickly as possible, have a real conversation, and subtly steer the conversation in a direction to naturally introduce your product. Often times, the best way to do this is to ask genuine, nuanced questions around the problem space your product solves.

The Rapid-Fire Checklist

Your emails also need:

• Active voice over passive ("we help companies" not "companies are helped by")
• "You" more than "I/we" (2:1 ratio minimum)
• Grade 5 reading level (shorter words, simpler sentences)
• Questions to end paragraphs (drives responses)
• No spam triggers (avoid "free," "guarantee," "limited time")
• Mobile-optimized (50-125 words total)
• One link max (more = spam filters)
• Positive sentiment (solution-focused, not problem-dwelling)

✏️ Assignment

1. Review your last cold emails or LI messages you've sent.
2. Audit them, do they adhere to the lessons above?
3. If not, create 1-3 new cold outreach messages optimized for response rate.

🚀 What's Next

Now that you can write messages that break through the noise, let's talk about managing the chaos when they actually start responding.