play the long game

brought to you by Foster​

Hey! My latest essay, The OutKast Edge, is here. Before we get started, a few quick things:

new Trapital pod: "Call Me If You Get Lost" with Amber Horsburgh

Amber is a music marketing expert who runs Deep Cuts, an online school to help artists with their music rollouts and campaigns. She invited me on her YouTube show to talk about Tyler, The Creator's campaign and rollout for Call Me If You Get Lost: what worked well, what could have been improved and more! This week's pod is the audio from that convo.

Tap in on Apple Podcasts, Spotify, or watch on YouTube.

Also, my guy DJ Semtex invited me on his Hip Hop Raised Me podcast to discuss rappers business moves, Rihanna, the hip-hop heavyweights dropping albums in 2021, and more. Listen here.​

The essay is below. If you like it, please share with someone who should read it!

Was this forwarded to you? Sign up here.

The OutKast Edge

How slept-on trends build a following, become mainstream, and maintain their unique vibe.

​read in browser​

Hip-hop’s late 80s and early 90s “golden age” was dominated by East Coast boom-bap and West Coast G-funk. At the time, people looked down on Southern hip-hop for its booty-shaking music that struggled to be taken seriously. Out of this landscape rose two Atlanta teenagers, known as OutKast. Andre “3000” Benjamin and Antwan “Big Boi” Patton were making music on their own terms, even with the odds stacked against them.

The eclectic duo started with the right co-signs. OutKast was the first rap group signed to LaFace Records. Their debut music video “Players Ball” was directed by Puff Daddy. Still, OutKast’s debut Southernplayalisticadillacmuzik (1994)only peaked at #20 on the Billboard 200. Hip-hop wasn’t ready for a mix of soul, dub, psychedelic rock, and gospel-infused into its Southern rap.

But things changed after the 1995 Source Awards. OutKast was named Best New Artist in front of an audience of haters. The crowd booed Andre as he accepted the award and said, now famously: "The South got something to say."

The statement was prophetic. Andre’s words spoke directly to Southern hip-hop fans that finally had hometown heroes to root for. Each subsequent album reached an even bigger audience. ATLiens (1996) led to Aquemini (1998), which paved the way for Stankonia (2000). There were bigger hip-hop acts at the time, but few had a loyal following like OutKast.

Then in 2003, they went mainstream. OutKast’s #1 hit “Hey Ya!” landed on wedding playlists everywhere. Speakerboxx/The Love Below (2004) was the last rap album to win Album of the Year at the Grammys. It took ten years, but the Atlanta duo reached the industry’s peak. OutKast’s triumph was a catalyst for Atlanta’s lasting dominance in hip-hop.

The group's journey is the namesake for a theory I'm calling The OutKast Edge. It's when an outsider takes longer to succeed but slowly rises to the top by growing a loyal and like-minded audience. OutKast was forced to use grassroots and unique growth tactics, which only added to their longevity. These solid stables of fans give those with the OutKast Edge leverage to call their own shots and stay true to their core mission.

This theory is valuable for artists, entertainers, content creators, startup founders, and more. Today’s available technology has opened the doors for outcasts in all walks of life to reach their audience. It’s still hard as hell, but it’s possible. The OutKast Edge is a framework to understand how slept-on trends become popular and sustain their unique edge after they succeed.

The OutKast Edge 101

1. Create content for like-minded outsiders

In the beginning, OutKast didn’t shy away from making music that was hyper-specific to them. Their narratives didn’t exist in the mainstream media — they had to create their own paths so people like them could be seen. Their music hits different. For the OutKast Edge, the creator's connection to the material must be personal. It invites like-minded fans into a world that builds an even deeper connection.

2. Build an audience on independent platforms

Independently released content is the most common way for true outcasts to grow a community. These types of creators learn where their fans consume content and adapt accordingly. Early on, bigger corporations — record labels, TV networks, publishers — are rarely interested in the outsider’s content because they often underestimate the market. If those companies are interested, they make lowball offers or want to alter the material in ways that feel inauthentic. But those offers get turned down. The OutKast Edge is about honoring yourself and your fans through authenticity.

3. Play the long game: persevere and push through

The OutKast Edge is a long game. In the early days, outcasts will see their peers rise faster. Those artists will get big interviews on The Breakfast Club while the outcasts are still selling mixtapes at gas stations. Times get tough both mentally and financially, but they learn from any constructive feedback and keep pushing.

The OutKast Edge requires all three elements

SPONSORED

Take your writing to the next level with Foster​
One of my best career decisions was to start writing online. I published my first Medium post in 2014 and haven't looked back. But those early posts could have been A LOT better if I work with an editor.

That's why Foster was started. It's a community of writers who share ideas, get feedback, and receive edits from people who have the skills to improve their work. In Foster's first year, its writers published 1,000+ pieces! The best writing is a collaborative process. Foster makes it easier than ever for aspiring and seasoned writers.

Foster has a selective application process, but Trapital readers can bypass the application and join for free! In September, I'll host a special Trapital Room in Foster.

Come through! You'll get a preview of what I'm working on, contribute to ideas, and can use Foster to level up your own writing. Sign up here to join us.​

Who else has the OutKast Edge?

Tyler, The Creator: Built loyalty with other outsiders through Odd Future’s Tumblr page.

When the Odd Future frontman started rapping in the late 2000s, even the indie hip-hop blogs ignored him. But the gatekeepers couldn't stop the group'sTumblr account, which gave fans a glimpse of the vast creativity that was on its way.

Tyler and Odd Future started on Tumblr in 2009. It was their channel to release new music, post random photos, and behind-the-scenes content. Their Tumblr feed was one of the first artist feeds with cryptic-type messages that were unknown to outsiders. It forced fans to be all-in to understand the vibes, which built more loyalty. These tactics are common in the Instagram era, but Tyler was doing this as a teenager before Instagram existed.

When Tyler's "Yonkers" music video dropped in 2011, more people caught on. Other rappers from major groups tried to sign him, but Tyler turned them down. He stayed in his lane, grew as an artist, refined his craft, and served his base.

Tyler put that "creator" name to work. He launched the Camp Flog Gnaw Carnival in 2012, years before artist-curated festivals went mainstream. In 2016 he also hosted his own fashion shows, featuring skateboards and basketball shorts. It was 100% on brand. He was in his bag well before he broke out.

For Tyler, 2019 was the watershed year. His self-produced IGOR album outsold DJ Khaled's Father of Asahd—an album full of features from hip-hop superstars, made by an executive producer who implied that Tyler's music was "mysterious." A few months later, Tyler sold out Madison Square Garden, which he's reminded fans of on several occasions. By the end of 2019, his OutKast Edge was so strong that his fans booed Drake, the most mainstream rapper alive.

Tyler has a lot in common with OutKast's Andre 3000. Both started in hip-hop as lanky teenagers who never fit cultural norms, but they outlasted many who started when they did. In a 2021 Hot 97 interview, Tyler spoke on how other artists who "were the hottest shit in 2012, where the fuck they at right now?" Tyler said that shit with his chest. That's how you talk when you have The OutKast Edge.

Issa Rae: The awkward Black girl found her people through YouTube and Facebook.

Issa's life as a Black student at Stanford was the setting for Dorm Diaries, her first YouTube series. Dorm Diaries led to her award-winning Awkward Black Girl YouTube series. In 2012, she told The Washington Post that she launched the series because "Black people are always portrayed to be cool or overly dramatic, anything but awkward."

Fans felt seen by her vulnerability and willingness to challenge TV's norms. Issa leaned into that through grassroots community-building tactics via YouTube comments and her Facebook page, which now has 250,000+ fans. The big networks called to try and rework her show, start a "franchise" of different ethnicities, and even replace her with lighter-skinned actresses, but she held out for the right opportunity.

She teamed up with HBO to launch Insecure in 2016. Its success has been a launchpad for a career that includes movie roles, her Raedio record label, and more. In 2021, Rae signed an eight-figure overall deal for five years with WarnerMedia.

Tyler Perry: Madea reached an overlooked audience with a powerful email list.

The 90s were a beacon for Black media, but not the kind of media that Tyler Perry made. It took six long years of failed plays, homeless stints, and promotional efforts for audiences to buy into the character we all know today as Madea.

Perry found success when he focused on his customer base — Black women at churches. They were his mavens to spread the word to different communities. He also developed a strong email list, which had over 400,000 subscribers by 2004. And at the end of his plays, Tyler would ask the audience to text 3-5 people they knew in his tour’s next city to get them to buy tickets.

His email list helped his first movie, The Diary of a Mad Black Woman (2005), become the #1 movie in its opening weekend, when box office predictions didn’t expect it to land in the top five. He leveraged its success for the entire Madea film franchise, TV shows from Tyler Perry Studios, and maintained ownership along the way.

In 2019, Perry opened the largest film studio in the US in Atlanta, GA. In 2021, Forbes named Perry a billionaire.

The OutKast Edge lasts longer

When Tyler, The Creator talked about artists who "were the hottest shit in 2012, where the fuck they at right now?" he's talking about that blue line.

The OutKast Edge evolves with technology

OutKast, Tyler The Creator, Issa Rae, and Tyler Perry each represent different phases of a creator’s relationship with technology and platforms. In each phase, they democratized access from the gatekeepers. This lowered the barriers to create content, build a following, and give a voice to a community.

When OutKast started, gatekeepers had much more control in the music industry. OutKast had to maximize its media moments with memorable quotes, iconic music videos, and classic albums.

But by the time Tyler Perry gained traction with Madea in the late 90s and early 2000s, email and texting took his game to the next level. Perry was an early adopter. He didn't have polished email marketing solutions like MailChimp, but that worked to his advantage. He got a head start on others who wouldn't have tried until easier-to-use tools existed. If creators are serious, they will figure things out before the landscape matures.

Similarly, if Issa and Tyler, The Creator only relied on email, they may not have reached the same levels of success. In the late 2000s, they leaned into timely Web 2.0 era tools like Facebook, YouTube, and Tumblr to grow their millennial fanbases. In each case, they met fans where they were at.

Today, creators with the OutKast Edge may be inspired by Issa but they can't replicate her playbook. They need to stay up on the latest ways to use platforms and build a fanbase. Web 3.0 tools like tokens, NFTs, and decentralized platforms will play a role in their strategy soon enough.

Each OutKast Edge phase includes more fans

The pitfalls: you can lose your OutKast Edge

When outcasts become stars, they need to maintain their edge. How do they keep day-ones happy, stay true, but still maximize their potential?

It gets real when outcasts get offered big deals that require some tradeoffs. That emotional connection to the material makes it hard to give up any control and may hurt their reputation with fans.

For instance, OutKast split in 2006 after their Idlewild film due to creative differences. When an outcast's career hits that top level, it's hard to have everyone on the same page consistently.

In 2005, Kanye West checked several of the OutKast Edge boxes. No one took the young producer seriously as a rapper, not even his Roc-a-Fella team. But College Dropout spoke to an audience that didn't feel seen by gangsta rap. Oh, how they loved Kanye!

But by the time he became Stadium Ye, he was interrupting the MTV Video Music Awards and dating the most famous people in the world. The pink polos and backpacks were gone. He lost the OutKast Edge. He's still successful—he's a billionaire thanks to the commercial success of Yeezy—but it's a different type of success.

Who's got next?

The OutKast Edge is brewing with late-night comedians Desus and Mero. In the late 2000s, the former summer school classmates had done some occasional blogging but didn't break out until they became popular on Twitter for their hilarious commentary on pop culture. They turned their Black Twitter fame into several hit shows, most recently with Desus & Mero on Showtime. There's also Donald Glover, the future EGOT. The actor/rapper became a YouTube sensation from his NYU days. He's pivoted that into a multi-hyphenate award-winning career. In 2021, he signed an overall deal with Amazon.

The edge was also strong with the late Nipsey Hussle. It took years for the Mailbox Money rapper to break out. His $100 mixtape tactic was ridiculed by many, then celebrated years later. That’s the narrative arc of the OutKast Edge. Some were surprised by the overwhelming response to this untimely death, but it spoke to what he built and the years it took to get there.

Today, it's easy to look at young creators with hundreds of thousands of followers and assume they all have the OutKast Edge, but that's not how it works. This isn't about randomly catching fire and stumbling into a thriving audience.

This is about the person you don't know today but has a small and loyal following. But when they do pop, get ready. The groundwork will already be set. We'll look back and see that they had the OutKast Edge all along.
​

​
Hope you enjoyed it! If so, please share. Forward this email to someone who should read it. Text it to a friend. Drop the link in the group chat.

Share on Twitter, LinkedIn, Facebook. Or copy and paste the link below:

​https://trapital.co/2021/08/30/the-outkast-edge/​​

Thank you Sarah Grant for editing, Jarrod Dicker for feedback, and everyone else who shared their thoughts before publishing. Appreciate it!

Enjoy Trapital? Share it with a friend

Tell them to sign up. I'll send them next Monday's memo. Copy and paste the link below to share:

​https://trapital.co/share-trapital​

Or share Trapital quick via text, email, or Twitter.​

Coming soon from Trapital

Podcast: audio version of The OutKast Edge + Trapital Mailbag! Any questions about the business of hip-hop? Reply to this email. I'll answer the best questions on the episode!

On the Trapital Podcast, hip-hop's heavy hitters explore their ideas that helped them level up their game. Learn more here.​

Memo: next Monday is a holiday in the US, so the next memo will be sent Tuesday, September 7. I'll most likely write about Kanye West and Drake's new releases.