In partnership with

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.

Cultivating Connection: How DMs Became the Vibe

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.

The OG DM King: How a Stranger on MiGente Taught Me the Power of Connection

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…

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