You are probably reading this because I DM’d it you…

Today, I want to highlight the story of how I learned to turn connection into collaboration. My greatest teacher in this lesson isn’t just a friend—he’s my brother and creative partner, Juan “Papo” Santiago.

A true bridge builder and a guiding light for writers looking to share their stories, he continues to be major inspiration for the work I do today.

Once upon a time, DMs were considered a red flag. A man sliding in uninvited? Blocked. A stranger hitting you with a “Hey ma” or “U up?” at 2 AM? Disrespectful.

Basically, DMs had the same energy as an unmarked white van offering candy— naaah, I’m good.

Fast forward to now, and DMs are the ultimate power move. Friendships? Started in the DMs. Business deals? Closed in the DMs. Speaking gigs, brand collabs, podcast invites? All birthed in the DMs. Somehow, what used to be cringe is now the fastest way to build real relationships—if you do it right.

But let’s be clear: sliding into DMs can still be creepy if you have no reason to connect, you can’t just be throwing yourself into someone’s inbox with no context like a LinkedIn bro trying to sell you crypto. It’s an art. A vibe. A strategy.

Nobody did it better than PapoSwiggity.

I learned this way back in the early 2000s, before DMs were even called DMs. It all started on MiGente, an online community for Latinos that existed long before MySpace took over and social media became what we know today.

MiGente wasn’t just a platform—it was a movement. And one of the most viral people on it was Juan Santiago, aka PapoSwiggity. If you were part of the NYC nightlife scene back then, you knew his name. But how did he get so popular?

He simply said hello in his own special way…

See, MiGente had this alert feed that let you know when a new member joined. Every time Juan logged in, he’d send a personal message welcoming them to the “family.” No pitch, no agenda—just genuine connection. Over time, his mailing list grew exponentially, and so did his influence.

Within two years, he wasn’t just a digital name—he was bringing hundreds of Latinos together for culturally relevant after-work events every single week. And not just showing up—really getting to know them.

And that is exactly how we met. We built a friendship, started collaborating, and eventually co-founded Capicu Cultural Showcase, which became a staple in the NYC arts scene—the official home of poetry in Brooklyn. The very community he cultivated became the foundation of what we built, as his audience naturally transitioned from clubbing to exploring the arts

A few years later, Tom from MySpace would use the same strategy—adding every new user as a friend—but let’s be real, Tom wasn’t actually pulling up to NYC’s trendiest clubs like PapoSwiggity was.

The lesson? The best connections start with a simple hello.

So Papo laid the foundation, Now I am going to show you how to scale this today with some creative direction.

So, if you’re ready to stop leaving money, opportunities, and meaningful connections on “seen,” here’s your Siembra-style guide to turning DMs into deeper relationships.

Before we dive in, let’s be clear—this is the real, organic approach. No automation hacks, no canned responses triggered by a keyword. This isn’t about quick tricks; it’s about building real connections. It takes time and effort, but if you do it right, you won’t just be growing followers—you’ll be cultivating a true community in these timelines.

I am just not opening gates for you, I am gonna tell you where the most beautiful flowers are in the garden.

Ohhhhh and just in case, I am not selling anything. My gift to you…

Sliding into DMs is easy, but making it meaningful? That’s an art. Before you hit send, ask yourself:

✅ Am I starting a conversation or just taking?
✅ Have I engaged with their content before this?
✅ Do I have a real reason to connect, or am I just networking for networking’s sake?

Best Practice: Engage with their posts first—comment, share, and react before you pop up in their inbox. It makes your DM feel natural, not random. reference the piece of content that made you want to connect. Be brief… no need for long intros. If they are interested in learning more, they will scan your profile page (hope it’s optimized as per last week’s lesson)

Here is how you do it…

A lazy “Hey 👋” or “Love your content!” won’t cut it. Instead, personalize your message:

💡 Mention a specific post that resonated with you.
💡 Share a quick thought or question that adds to the conversation.
💡 If you have a mutual connection, reference them (but naturally).

🚫 Avoid: Asking for favors in your first message. Nobody wants to be used.

📝 Example DM:
"Hey [Name], I loved your post about [specific topic]. That part about [mention something specific] really hit home for me. Curious—how did you [ask a thoughtful question]? I would love to learn more!"

The goal? Deeper connections—not an eternal chat thread. If the convo is flowing, take it to:

🔹 A quick Zoom or coffee chat.
🔹 A collaborative opportunity (IG Live, Podcast, Newsletter Feature).
🔹 A community they’re part of (Slack, Discord, LinkedIn Group).

👀 Look for cues that they’re open to moving beyond DMs. If they reply with depth and engagement, that’s a green light!

🚫 Avoid: Forcing a phone call too soon—let the connection breathe first.

Stay on their radar without being annoying by:

📌 Sharing a resource relevant to them.
📌 Connecting them with someone valuable.
📌 Supporting their work (comment, share, buy, or shout them out).

The Rule: Give before you ask. Relationships should be mutual, not transactional.

A strong DM relationship can become:

🔥 A podcast guest
🔥 A business partner
🔥 A friend you vibe with in real life (this is so real to me)

🌟 Keep it real, show up authentically, and treat connections like collaborations, not transactions. This works on any platform, just know your audience and connect accordingly.

Do you have a tactic that works for you that you want to share with the community… leave it in the comment section. Would love to read how you use DMs to build community.

If you’re all about authentic connections, impactful collaborations, and making moves that matter, let’s connect! Whether it’s storytelling, community-building, or creative strategy—I’m here to cultivate ideas that grow.

💬 Slide into my DMs or book a call, and let’s see how we can make beautiful grow.

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