Lil Nas X’s “Old Town Road” topped the charts for nineteen straight weeks, breaking a 60-year record for the longest-held No.1 spot on Billboard’s Hot 100.

What can leadership teams take away from his meteoric rise?

Earlier this year, Montero Lamar Hill — now widely known as Lil Nas X — was just another 19-year old kid living with his parents in his childhood home outside of Atlanta, Georgia.

He dedicated a lot of time to building his online presence, creating music from his laptop, and trying to defend his ambitions to people who wanted him to get a “stable job” with “stable income.” In fact, the lyrics of the song “ain’t nobody tell me nothin’” are about just that.

Like Lil Nas X, most creative entrepreneurs or freelancers feel similarly. Frustrated with a world that continues to dub them disposable or illegitimate in some way, many have begun unionizing and rightfully laying claim to so much of the content that is created and shared online today. What people don’t know about the most recent smash hit is that wasn’t released with the backing of a large record label, or engineered with the best and most expensive equipment, or marketed and branded by some top-tier industry giant.

“Old Town Road” was produced, released, and marketed entirely remotely, by three strangers in different parts of the world, using tools of their own finding. The power of people collaborating remotely while being enabled through technology represents a larger shift in how and why people do work together today.

As of 2019, there are 17M members of GenZ entering the U.S. workforce. And they’re the most entrepreneurial generation yet — 46% of them already freelance.

Companies like Ruby Tuesday are already reporting on new tactics they’re testing to engage this new workforce — a mobile-first cohort that craves the worker-driven schedules that companies like Lyft and Uber provide, and most of all, the simple desire for a safe and comfortable environment to work in. 

The most diverse generation yet, this group of digital natives has grown up in an era where information has always been at their fingertips, where everyday communication tools like TikTok and Snapchat are creative in and of themselves, and where the people have more power than ever over who is deemed relevant. Social media has democratized creators, and for all of its flaws, it has also empowered the young generation to redefine who the gatekeepers are and who gets through.

Lil Nas X, like most brilliant digital-native marketers, will tell you that the virality of Old Town Road was no random act.

His carefully-seeded grassroots strategy kicked off months before the release of the actual track. From his sister’s basement, Lil Nas spent all of his time savagely dedicated to creating content and building as much momentum as possible.

While there are many recent pieces that talk about the brilliance of Lil Nas X’s marketing strategy, no one has given much analysis on the powerful way the song came to life to begin with.

As Lil Nas X worked to build his fanbase from small-town Georgia, YoungKio sat on the other side of the world. Another 19-year-old creative in the Netherlands, YoungKio was recording and producing 10–12 beats a day and selling them online through Beatstars, the very same marketplace where Lil Nas X decided to spend $30 on the raw materials to make a new song.

Pulling in Cinco, a recording engineer living in Toronto, Lil Nas X jumped into his sisters closet to lay a vocal track on top of YoungKio’s beats and record the first version of “Old Town Road” that would eventually go viral on TikTok, and subsequently Twitter.

NYT Reporter: Were you working during this time or just living with your parents?

Lil Nas X: No, no I wasn’t working. I mean, I was working full time on pushing as much content out on the internet as I possibly could. So I was fully focused on that."

Do I even need to mention that this entire New York Times interview was conducted remotely and posted to YouTube?

Remote collaboration is already here. Whether we’re ready for it or not, GenZ is actively redefining what it means to collaborate online.

1. Mobile-first work apps

While there are tools like Slack and Zoom to help facilitate traditional means of work communication (messaging and video), mobile-first work apps will look a lot more like Instagram Stories and social media platforms. A digitally native generation, GenZ lives and connects through mobile-first content-creation. Professional tools developed with this in mind would optimize for the emerging workforce, rather than forcing them into a legacy operating system that requires a more formal desk setup.

2. Work/life integration

We use the term work/life balance a lot, but let’s call it what it really is: work/life integration. When you have the freedom and flexibility to choose what you work on and who you work with, it results in a sense of purpose and creativity. Every generation, not just GenZ, is increasingly frustrated that they can’t have dinner with their kids at 5pm, or go for a run in the middle of the afternoon. Most employees care more about being compensated fairly, feeling safe in their environments, and doing meaningful work than they do about sitting in an AC-blasting freezer disguised as an office.

3. Virtual presence over physical presence

In a world where location has always dictated opportunity, the remote workforce is opening doors to underestimated talent in every corner of the country. Apps like Sococo and High Fidelity have become the “Fortnite for work” as strong human connections are built and exist online more than ever. Twitter, Snap, Tinder, Insta — a vast majority of young people have really good friends they’ve never met in person and work is extending to this reality as well.

The truth is, Lil Nas X wasn’t the first one to facilitate his own rise to fame. The vast world of influencers, creators, and makers are already deconstructing the conventional “company.”

Success today is not completely reliant on name recognition or the heavy infrastructure of a legacy record label or ad agency. In fact, our technology has gotten so good that you can shoot, record, and distribute entire music videos or marketing materials with a few apps on your phone. Counter to what many companies may have you believe, the traditional operating infrastructure is becoming more and more obsolete as our technology gets better and better.

The trap-country “Old Town Road” mashup that broke the charts was entirely self-released.

Posted to the country sections on iTunes and Soundcloud by Lil Nas X himself, the song went straight from upload to Billboard’s Hot 100 list in just 4 months, leaping right over tracks by top pop acts like Ariana Grande and Post Malone.

According to Rolling Stone, what Lil Nas X accomplished would have been “unimaginable” just 20 years ago —

“Since artists needed those institutions (record labels and radio stations) to become popular, it was easy to dictate certain paths to success — a country hit came from a country label and earned support from country radio. But now the music industry often scrambles to sign and endorse tracks like “Old Town Road,” which have already erupted online. Hits are not initially dependent on industry support, which means that for a brief, giddy moment, some songs exist entirely outside of traditional commercial categorization.”

What they don’t realize is that this is not a “brief and giddy moment”, it’s an entire shift in how and why we do work together.

Finding one another, collaborating, building momentum, and making world-changing music or telling world-changing stories, we’ve redefined what it means to start and run micro-companies.

All of our industries are not ready for the pace in which we are moving today, and while they fall behind with their legacy operating models and a “work-from-home Friday” bandaid over the “spend-5-hours-of-your-week-commuting” bullet hole, GenZ will transform the way we work before we know it. With a rapidly-evolving digital landscape, and the brightest minds choosing an independent path, the desire to accelerate progress will require responsive teams to come together at 100x the speed they do today.

Within 10 years, the new, deconstructed company may be the rule, not the exception.

And we’ll need the tools to make it happen.