Hey! Here's the long-awaited essay on Will and Jada Pinkett Smith. I know, it's about damn time! But hey, gotta get it right. At nearly 2,400 words and two hand-drawn visuals, it's Trapital's longest essay yet.

The model that the Smiths have built is similar to what I've seen from record labels, indie artists, digital media companies, Spotify, Netflix, creators on Patreon, and more. When people say "every company is a media company" this is what they mean.

Before you start reading, two quick things:

1. Check out my latest Trapital Podcast episode is with Brian "Z" Zisook, Audiomack's VP of Content Operations and Artist Services! We talk about the 18th anniversary of DJBooth, where Z is editor-in-chief. We then discuss major record labels, indie artists, TikTok's influence, classic rap albums, and more.
   Tap in on Spotify, Apple Podcast, Audiomack, or watch on YouTube.
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2. Here's a 5-min live TV interview I did on Cheddar. I talk about why I started Trapital, the audience, topics covered, and hip-hop investors. After me, they interviewed Paris Hilton, who started selling NFTs well before they blew up. I keep saying, we're still in the early days for NFTs!

The essay is below. If you enjoy it, share it with someone who should read it.

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How Will and Jada Pinkett Smith Built a Content and Commerce Powerhouse

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In 2013, the Smith family was going through it. Will Smith and his son Jaden Smith's movie After Earth was a box office failure. Jada Pinkett Smith seemed more interested in her heavy metal rock band than Hollywood. And their daughter Willow Smith had backed away from the spotlight after her hit single "Whip My Hair."

The timing couldn't be worse. The entertainment industry was changing fast. Social media became a force multiplier for actors who knew how to use it. But the Smiths, a couple once known for their privacy, were getting left behind.

Hollywood success is hard to maintain, especially for a middle-aged Black couple who rose to power on a 1990s playbook. Many assumed Mr. and Mrs. Smith's best years were behind them. If anything, Jaden and Willow were the ones to watch.

But Will and Jada went back to the drawing board. In a few years, they bounced back like a Cash Money rapper that just got out of a horrible contract. Will can now drive box office results from his Instagram account. Jada's Red Table Talk can dominate social media with ease. Their businesses run in lockstep under Westbrook Inc., a cross-platform holding company that runs the family's content and commerce. Their career resurgence is a lesson on how legacy talent can adapt to the times.

A plan that was ripe for disruption

In the early 90s, Will had it figured out. The Fresh Prince of Bel-Air star told his manager James Lassiter that he wanted to be the biggest movie star in the world. Lassiter and Smith looked at the ten highest-grossing movies of all time and identified three common themes: special effects, creatures, and love stories. That focus led to films like Independence Day, Men in Black, and many more.

For each film, the actor-manager duo targeted a different country to maximize international ticket sales. For instance, Bad Boys outperformed its overseas expectations by 15x thanks to a targeted campaign at the Cannes Film Festival. In the 2000s, Will Smith had eight straight movies gross $100 million domestically. He was a box office cheat code who topped the Billboard charts in his spare time. Hollywood may never see a run like that again.

Jada ran her own game and checked the boxes. She starred in Black cinema classics like Menace II Society, Jason's Lyric, and Set It Off. She did comedy blockbusters like The Nutty Professor. Jada even joined the horror flick wave with Scream 2 (but only for the first 10 minutes because... well, you know). And even though Will turned down the lead role in The Matrix, Jada got a role in its sequels.

But the Smiths' plan was ripe for disruption. They thrived when an actor's name alone could sell movies. Back then, original screenplays like The Matrix could become tentpole franchises. Film studios took more risks. Even if a film had mediocre ticket sales, it could become a cult classic on VHS, DVD, or get syndicated on cable TV. But the rise of the internet, video streaming, and cord-cutting ate into that backend revenue. It became harder to greenlight the same movies.

Today's entertainment landscape has led to a bifurcation of content. Most movies fall into two groups: big-budget franchise films derived from proven intellectual property with worldwide popularity, or arthouse projects from indie studios like A24. Original concept blockbusters, like the ones Will Smith starred in, are now few and far between.

When Will and Jada first rose to power, attention was easier to command. The biggest online distractions were Napster and AOL Instant Messenger. But it soon became hard for the private couple to keep up. The modern era favored social media influencers, reality TV stars, and actors who brought fans behind the scenes.

That wasn't Will and Jada, and the results started to show. Movies like Seven Pounds, Concussion, and Collateral Beauty could no longer rely on Will Smith's name to sell tickets. Meanwhile, Jada's movie star career soon became a TV career in the early 2010s with roles in both Hawthorne and Gotham.

If the Smiths wanted to reclaim that glory, the model had to change.

The shift from private to prolific

For years, Will avoided social media because movie stars "needed mystery and separation." In 2015, one of Will's only social posts was to confirm that he and Jada Pinkett Smith were still together! But eventually, he studied how Dwayne "The Rock" Johnson used social media to become a modern-day box office draw.

The former WWE wrestler has a team who helps him post inspirational videos and entertaining content to engage followers. When it's time to sell his movies, the Fast & Furious franchise star has a ready customer base. The studios pay him to spread the word too.

From Forbes:

"In addition to hefty $20 million up-front paychecks and cuts of back-end studio profits—starting with July's Skyscraper, in which he plays a former FBI hostage-rescue leader—[Johnson will] insist on a separate seven-figure social media fee with every movie in which he appears, according to people familiar with his deals. In other words, rather than have studios dump money into TV ads or billboards, their new paid-marketing channel doubles as their marquee star."

That seven-figure social media fee is a drop in the bucket. Studios spend nine figures to market the blockbusters that Johnson stars in. But The Rock's social media likely drives more revenue per dollar spent than other distribution channels. It's a page right out of Tyler Perry's playbook. The Madea creator's email list was once his primary source to sell tickets to both plays and movies.

In 2017, Will Smith adapted these rules for his career. He signed with Netflix to star in Bright, the entertainment company's first big-budget film. It was the perfect opportunity to establish his online presence. Smith got help from CAA to assemble a social media team. When Bright debuted in December 2017, Will's social media came out the gates hot. He appeared on The Ellen Show to announce that he joined Instagram. His Instagram debut felt even bigger than Bright's debut. Two months later, Smith became the top actor on social media according to The Hollywood Reporter.

When Will Smith's Aladdin movie was announced in 2019, box office expectations were tepid. Disney's past live-action remakes had mixed reviews, and Aladdin's trailer got dragged for how wild Will Smith's Genie looked. But the Aladdin team prevailed. Smith used his socials to propel the movie to beat analyst predictions by over 50% at the domestic box office. Aladdin grossed over $1 billion worldwide.

Analysts estimate that 12-20% of all Aladdin trailer views came from @willsmith. And since trailer views are a proxy for box office sales, Smith proved his impact. The connection between social media and viewership is even stronger now. The COVID-19 pandemic has accelerated the push for on-demand access to movies that are still in their theatrical run.

Will Smith's social media impact is a signal of the power shift from institutions to individuals. A similar shift happened in Silicon Valley. Amazon Web Services cut the cost for startups to get off the ground, which made it easier for founders to operate without the same reliance on venture capital. VC firms like Andreessen Horowitz leaned into this by elevating founders and getting them the best terms possible. The firm's strategy was inspired by CAA founder Michael Ovitz, whose talent agency led Hollywood's power shift from film studios to actors. Today's social media influence, for both actors and founders, is a natural evolution of that dynamic.

Transparent content builds audience trust

In 2017, Jada Pinkett Smith had a year of healing. The #MeToo and Time's Up movements were catalysts for her vulnerability and openness. The following year she launched Red Table Talk, an unfiltered conversation series with herself, Willow, Jada's mother Adrienne Banfield-Norris (aka Gammy), and celebrity guests. Jada chose to host it on Facebook Watch because the social media platform is built to get people talking and commenting, which is the goal of her show. Red Table Talk started as a hobby, but soon became a force in media.

In early episodes, Jada addressed a few never-ending rumors about her and her husband. Were Jada and Will swingers? Was it an open marriage? Were they Scientologists? Do Jada and Gabrielle Union still got a little feud going? It was all on the table, literally. Jada put herself out there, which created content that got covered by all the aggregators, media publications, and social media pundits. It all drove traffic back to her show.

Jada's transparency is the key ingredient. It's a shift from her once-reserved public persona. The Smiths still might not share all their entanglements unless they're forced to. But Jada's openness led other celebrities to join her at the table, including Jordyn Woods and Kid Cudi.

Red Table Talk's average viewership is now 14 million per show. Jada boosts Facebook Watch ratings like Serena Williams in a Grand Slam tennis match. Jada's deal with Facebook was signed in January 2020 and extends until the end of 2022. The series now includes a spinoff series with Gloria Estefan and plans for international expansion. The show's success has been a launchpad for a line of e-commerce products, Jada's Hey Humans personal care beauty company, and more.

From iP to IP

When good content can be produced fast, it's easy to capitalize on its potential if it takes off. Westbrook Media calls this fastlane intelectual property or "FLiP." For instance, Will Smith's Bucket List was a popular Instagram account that led to a deal with the Discovery Channel for its annual Shark Week. Jada's role as a healer in Red Table Talk led to a starring role in REDD ZONE, an upcoming Netflix film.

"iP" (lower case i) is content that is fast, cheap, and easy to produce. The most successful "iP" becomes big-budget "IP," which is often sold to major distributors to maximize its reach.

Here's the flywheel I drew. The more content created, both iP and IP, the more commerce for Westbrook.

For instance, in 2020 Will started Will From Home, a Snapchat series on Will's life in the early days of quarantine. It soon became a testing ground for bigger projects.

From The Hollywood Reporter:

"After Will Smith hosted a virtual Fresh Prince reunion during an episode of Will From Home, the Westbrook Media team realized they could turn that concept into something even bigger. They pitched a 90-minute reunion special to WarnerMedia, and executives, seeking ways to promote that HBO Max was the exclusive streaming home of all six seasons of the 1990s sitcom, immediately bit."

That reunion special for The Fresh Prince of Bel-Air became an opportunity for Will to address his 27-year-long feud with Janet Hubert, the show's original Aunt Viv. The only thing missing was Jada's red table! And when the reunion show dropped, The Fresh Prince of Bel-Air released a merch store to capture the timely interest in the show.

To further capitalize on the hit show's popularity, Peacock ordered two seasons of 'Bel Air,' a new dramatized version of the sitcom which came from a 2019 fan fiction short film. Fresh Prince is the Westbrook Media machine running on all cylinders.

This is today's entertainment model. This is why Spotify and Chernin Entertainment announced a multi-year first-look partnership. Chernin's film and TV production company now has access to Spotify's podcasts. It can bring the best ones to life on the big screen. This is also why Drake drops smaller EPs and singles before he releases his albums. The most successful tracks influence the album's sound and are more likely to make the final cut. In both cases, iP is the farm system for IP.

Build the audience, then sell the products

Social media has revived their entertainment careers, but it also upped their investment game. In 2018, Will Smith launched Dreamers VC, a Los Angeles-based venture capital firm.

Here's Vik Sasi, a partner at Dreamers VC, in an interview with Entrepreneur's Handbook:

"We’re living in this peak of influencer marketing right now. In an environment where something like 30 to 40 percent of venture dollars trickles down into Google and Facebook just given how much paid media these startups are spending on. So when you bring along an influencer, especially someone of Will’s caliber, you can bring the marginal cost of acquiring a customer to $0 if they do an Instagram post, mention you on their YouTube, etc.”

Every company wants to lower its customer acquisition cost—whether it's a film studio, an email newsletter, or a venture-backed startup. This is why audience-first products have become popular. It's a relevant strategy for both an A-list Hollywood actor's production company, a superstar rapper, a company like Trapital, and everything in between.

Here's a visual of how it works for Westbrook:

In March 2021, Will told The Hollywood Reporter, "We have seen this company in our minds for decades — the artistic quality, the synergy of our team, the service and healing aspects of our content and the revolutionary approach across the board."

They built the company they wish had existed.

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If the 2001 version of Will and Jada Pinkett Smith met the 2021 version of Will and Jada, they would be shocked. "Y'all just put your business out there?" "Why do you keep saying 'content'?" "Do you live on that phone?"

But they would also be impressed. Like the characters they play in movies, Will and Jada overcame obstacles and found a way to stay on top.

Their transformation is remarkable. But before long, they'll have to go back to that drawing board. The landscape keeps changing, now more than ever.
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