From context to conversation

How to Actually DM Someone

You've done the groundwork.

You've joined the community. You've shown up. You've participated. People are starting to recognize your name. Now it's time to start building one-to-one relationships.

This is where most founders go wrong.

They skip straight to pitching — without being thoughtful about who they're reaching out to, why it matters, or how to do it in a way that feels human.

In this lesson, we'll show you how to move with care, precision, and intent.

Why Relationship-Building Is a High-Leverage Growth System

Let's zoom out for a moment.

When founders think about user acquisition, they often default to one-to-many tactics: run ads, create content, launch on Product Hunt. That's fine.

But social DMs live in a different category. They're high-touch, low-scale — but often high-leverage.

They can get you:

• Early users who give great feedback
• Warm intros to other communities
• Mentions in newsletters or podcasts
• Access to someone else's audience
• Connections to investors, talent, or future hires

Social outreach isn't just a way to "sell." It's the beginning of building your own tribe.

And that's why this stage matters so much.

Step 1: Define Your Relationship Goals

Before you start messaging anyone, pause and ask yourself: Why am I reaching out in the first place?

Some common (and valid) goals:

• Get your first 10–20 users
• Start customer discovery conversations
• Get feedback from people who've tried similar tools
• Connect with creators who might promote or collaborate
• Build a network of early evangelists or distribution partners

Each goal comes with different types of targets. That brings us to…

Step 2: Build a Lightweight Prospect List

We're not talking about scraping thousands of contacts or using enrichment tools. You don't need to find emails — you already see these people in the communities you've joined.

But you do want to be intentional.

Create a simple list — a spreadsheet or Notion doc — that includes:

• Name
• Handle or profile link
• Platform/community (e.g. Slack, Reddit, LinkedIn, X)
• Goal of the relationship (potential user, feedback convo, amplifier, etc.)
• Notes (relevant posts, where you're at in the relationship-building process, or specific moments when they might be open to outreach — we'll explain this in Step 4)

This helps you stay focused, track progress, and make sure you're building toward the right outcomes — without treating the process like a mass campaign.

Step 3: Categorize People by Relationship Type

Not every relationship will follow the same playbook. Some people are looking for tools like yours. Others just happen to be visible in your space.

Here's a simple way to categorize who you're talking to:

Direct Prospects

• People who might actually use your product
• These are your highest-confidence conversations
• It's okay to be more direct (if timing and context allow)

Connectors

• People who are plugged in — they know your audience
• Often founders, community hosts, moderators, advisors
• Treat these relationships with care and a longer runway

Amplifiers

• People with reach: newsletters, large followings, podcasts
• The highest potential upside — and highest filter for noise
• Often skeptical of cold outreach unless it's deeply relevant

🧠 Critical Strategy Tip:

Start your outreach journey with direct prospects ONLY.

Here's why: Connectors and amplifiers are rare. If you blow your shot with them, you rarely get a second chance. They also get pitched constantly and have highly-tuned BS detectors.

Begin with direct prospects — build your skill, confidence, and understanding of what resonates. Only approach connectors and amplifiers once your messaging is sharp and you've built a track record of quality conversations.

Think of it like dating: you don't ask the most attractive person at the party to marry you as your opening move.

Step 4: Look for Trigger Moments

This is your moment to shine.

You've been showing up in the community. You're participating. You're visible. Now you're watching for the right time to engage more directly.

What you're looking for are trigger moments — little openings that signal someone might be open to conversation.

New Framework: The Intent × Consent Matrix

Trigger moments aren't all created equal. Some people are signaling that they need help (intent). Others are actively inviting engagement (consent). Your job is to read those signals — and match your message accordingly.

🔄 Use this 2×2 framework to guide your tone and approach:

• Intent = How much they need what you offer. High intent means they have a problem you can solve.
• Consent = How open they are to engagement. High consent means they're inviting conversation or help.

🎯 How to Message Based on the Matrix

✅ High Intent + High Consent

They have a clear need, and they're open to engagement.

You can be direct.

Example DM:

"Hey — just saw your post about struggling with [X]. Totally resonated. We actually built something to solve that exact pain — want me to send over a quick demo or explainer?"

—

🔄 High Intent + Low Consent

They're in pain, but not inviting help (yet).

Be thoughtful. Don't pitch—probe.

Example DM:

"Saw your post about [problem]. Curious — have you tried anything that's actually worked for that? It's been a huge challenge for us too."

—

👋 Low Intent + High Consent

They're engaging in your space, but not expressing a clear need.

Lean into the shared interest.

Example DM:

"Really liked your comment on [thread/topic] — we've been wrestling with that too. What's been your experience with [tool/process] so far?"

—

👀 Low Intent + Low Consent

They're talking about adjacent topics, not problems or help.

Keep it very light — tribe alignment only.

Example DM:

"Saw your post on [Tool]. Been thinking of trying it too. Curious if it's been worth it?"

🎛 Modifier: Adjust Based on Audience Type

Now layer in the person's relationship type (prospect, connector, amplifier):

• Connectors/Amplifiers, even when they show high intent/consent, should generally be treated as if they're low intent and low consent.
• Why? They get tons of outreach and are used to being pitched. Your job is to break through that noise — patiently, authentically.
• We have bigger goals for these individuals than direct prospects. We want to build genuine, long-term relationships

⚠️ How NOT to Approach an Amplifier (Bad Example):

You see a newsletter writer with 50K subscribers post: "Looking for new productivity tools to feature."

Don't do this:

"Hey! I saw you're looking for tools to feature. We just launched [Product] and it would be perfect for your newsletter. We help people save 10 hours per week. Can I send you more info? Would love to get featured!"

Why it fails:

• Too eager and transactional
• Makes it about you, not their audience
• Asks for value without offering any
• Sounds like every other pitch in their inbox

Better approach:

"Hey Sarah — been reading your newsletter for months (the piece on deep work vs. busy work really hit home). Noticed you're exploring productivity tools. What specific angles resonate most with your readers? Always curious how different audiences think about this space."

Start with genuine interest. Build the relationship. The opportunity will emerge naturally if there's real alignment.

Step 5: Start With Shared Context

Your goal in the first message isn't to pitch. It's to make the conversation feel natural — ideally, one they'll actually want to have.

The key is to anchor it in something recent and specific. You're not showing up out of nowhere — you're continuing a thread they already started.

Example DM:

"Hey Tom — just saw your post about [Tool]. We've been eyeing it as well. Curious how it's been holding up. The one thing holding us back is the [X limitation] — have you found a workaround for that?"

That message does a lot of heavy lifting:

• It's specific and timely
• It shows you're paying attention
• It doesn't pitch anything
• It invites a low-pressure reply
• And it makes you feel like a fellow builder — not a salesperson

That's all you need to open the door.

Reminder: Starting a Conversation Is Adding Value

You don't need to offer a resource or give someone advice for the exchange to be worthwhile.

Just showing up as a like-minded founder — someone working on similar problems, in the same space, who speaks their language — is inherently valuable.

Most people enjoy talking about what they're building. They enjoy being seen. They enjoy thoughtful questions. That's what you're offering.

What's Next

In the next lesson, we'll explore how to move a conversation forward:

• How to spot when interest is growing
• When and how to make a "next step" ask
• How to avoid the common traps of friction, over-framing, or sounding apologetic

But for now, focus on:

• Spotting trigger moments
• Understanding consent and intent
• Crafting the right type of first message for each situation

Action Steps

1. Start with your prospect list — Direct Prospects ONLY
   • Save connectors and amplifiers for when you're experienced
   • Aim for 20-30 direct prospects to start
   • Remember: there are many prospects, few amplifiers
2. Identify likely intent × consent signals
   • Review a few recent posts for each person
   • Score them: high/medium/low for intent and consent
3. Write 3 DMs using the framework
   • One for each quadrant (or based on your list)
   • Keep it relevant, light, and based in shared context

When you lead with the right tone and message for the moment, your odds of getting a reply — and building something real — go way up.