How I Learned to Stop Sending Spam and Start Having Conversations

I used to think my Instagram DM game was just a math problem. Send 100 messages, get a few replies, land one sale. Rinse, repeat. I’d fire off DMs like a digital t-shirt cannon, leaving a trail of “seen” receipts and crushing silence in my wake.

I was playing the numbers game. Then I realized something: the game was rigged, and I was the one rigging it against myself.

We were all doing it wrong.

The Problem with "DM Outreach"

Most advice about DM outreach sounds like it was written by a sales robot that just discovered caffeine. “Automate your funnel!” “Use this killer script!” “Convert leads in the DMs!” It’s no wonder our messages sound like a hostage negotiation.

The real issue isn’t that people hate getting DMs—it’s that they can smell a sales pitch from across the internet. And when your “genuine” message is just a template you copied from a marketing guru, people know. They can feel it.

What Actually Works: Three Approaches That Don't Suck

A founder recently shared their story. They sent 142 DMs and got a 5% reply rate. Total garbage. Then they changed their approach. Two weeks later, their reply rate was over 35%. That’s a 7x jump.

They didn’t use a new hack. They just stopped acting like a marketer and started acting like a human.

1. Start a Real Conversation (Not a "Sequence")

Instead of launching into a pitch, just find a reason to talk. A real reason. Spend 60 seconds on their profile. Look at their last post, their bio, a story. Anchor your message to something that shows you actually paid attention.

I've seen this work wonders:

“Saw your post about content burnout. Is finding new angles the hardest part for you right now?”
“Noticed you’re a product leader in SaaS. Is user onboarding something that’s on your radar at all?”
“Congrats on the launch! How’s the feedback from early users been?”

These work because they’re not about you. They’re low-effort questions that open a loop. You’re not asking for their time or money; you’re just showing curiosity.

The key: Your opener has one job: to make them think, "Oh, this person isn't a bot."

2. Ask for Permission (Instead of Forcing the Pitch)

If they reply, you’ve made it. Now, for the love of god, don’t immediately pivot to your sales page. Just have a normal conversation. Respond to what they said. Show you’re listening.

After a back-and-forth, you can make your move. But you’re not going to pitch. You’re going to ask for permission to share something useful.

Good examples:

“I actually wrote a short guide on that. It’s not a sales thing. Mind if I share it?”
“This reminds me of a tool I found that helps with that process. Happy to send the link if you’re interested.”
“Would it be helpful if I sent over a one-page doc that breaks down how we solved that? No pressure at all.”

This works because it gives them control. By giving them an easy “no,” you make their “yes” mean something. You’re not a pushy salesperson; you’re a helpful resource.

The key: Stop pushing your solution and start asking if they’d like to see it.

3. Deliver Value (Not Just a Link)

When they say yes, you have one last chance to mess it up. Don’t just drop a raw, mysterious link. Frame it. Tell them what it is and why it’s useful.

Bad: Here you go: mywebsite.com/buy-my-thing

Good:

“Awesome. Here it is. It’s just a Google Doc with a few bullet points. The second one was a game-changer for me. Hope it helps!”
“Great, here’s that tool. The free version is super powerful and is what I used to get started. Let me know what you think!”

You’re managing expectations and highlighting value. You’re guiding them, not selling to them. And for the link itself? Send them to a blog post, a template, or a case study. Something that actually helps.

The key: The thing you send should be as generous as the conversation that led to it.

The Real Rules of DMing

The line between helpful outreach and clever spam is thin. It all comes down to one thing: your intent. Are you actually trying to help, or are you just running a better script? People can tell.

Here’s what actually matters:

Talk to the right people. This only works if you’re reaching out to people who genuinely have the problem you solve. Spraying and praying is still spam, even if the message is polite.
Be willing to get nothing. Your goal should be to help, full stop. Be prepared to have a great chat that goes nowhere. If your only goal is a sale, that desperation will leak out.
Let the conversation wander. A real conversation isn’t a straight line. If they go on a tangent, go with them. Be curious.

What This Actually Looks Like

Here's an example from my own DMs last month:

I saw a founder post about their anxiety over an upcoming product launch. I sent a message: "Launch anxiety is the worst. Is it the tech side or the marketing side that's stressing you out?" They replied that it was the marketing.

We chatted for a bit about how hard it is to build buzz. I mentioned a simple pre-launch checklist I’d made for myself to stay sane. I asked, "Happy to share it if you think it'd be useful. No worries if not." They said sure. I sent them a link to the Google Doc.

Result: They didn’t buy anything. But they followed me, and a week later, they recommended me to someone in another group who was looking for exactly what I do.

The Long Game

This isn’t about instant conversions or hacking your way into someone’s wallet. It’s about becoming a known, trusted resource for the people you want to serve.

This takes time. Months, not days. But the payoff is that you stop chasing customers. Instead, you build a small army of people who trust you. When they—or someone they know—have a problem you can solve, you’re the first person they think of.

Getting Started (Without the Scripts)

Pick 5 people in your target audience on Instagram.
Spend a week just looking at what they post and talk about.
Start by just replying to their Stories with a genuine comment or question. No pitch.
Send one DM this week based on something specific they shared. Ask a simple, curious question.
Be patient and consistent.

That’s it. No "funnels." No "scripts." Just showing up and starting conversations.

The Bottom Line

DM outreach works when it doesn't feel like outreach. When you’re genuinely trying to connect with another human, people want to know what you’re working on. When you’re just trying to run them through a sales process, they can tell.

The best DM strategy doesn't feel like a strategy at all. It feels like making a new, interesting friend who happens to be building something cool.

And you can’t fake that—you just have to be human.