Boardroom sat down with ItsTheReal to discuss the commercial parallels between their period piece podcast and hip-hop’s Web 2.0 pioneers.
In 2008, the economy was down but the Wi-Fi was on.
Convergence culture was at an all-time high online with rising rappers flooding the internet with unpaid freestyles over high-budget hits. All the while, the Western wealth gap was approaching Great Depression levels.
As America faced a recession, premium programming reflected the dire times. Especially on satirical sitcoms like Entourage.
In Season 5 of the HBO series, agent Ari Gold street-races his new Ferraris while actor Vinny Chase attempts to avoid bankruptcy. Courting a completely different financial future, the Queens creative has a moral dilemma: file for Chapter 11 and trust his taste or sell out for another Aquaman?
“Vince needs a studio movie,” Ari screams from his C-suite office. “Not an indie.”
As the tension between Hollywood hotshot and soon-to-be starving artist mounts, the scene breaks with the sounds of Charles Hamilton: an off-kilter MC straddling similar stakes.
In 2008, the Harlemite had become famous seemingly overnight, flooding the pages of NahRight with free mixtapes and genius-level freestyles.
Having inked a $1 million deal with Interscope, he was living the American dream amid a financial crisis. However, his dream became a nightmare, as his deal left him handcuffed creatively.
Unlike Chase, Hamilton’s story was not scripted for premium television. It was very real, and one shared by bloggers, artists, and managers stuck in the middle of changing times. Today, these times are known as The Blog Era.
Telling the tale of the “Brooklyn Girls” rapper, Upper West Side brothers Eric and Jeff Rosenthal — better known as ItsTheReal — dove into the explosion of collaboration, creativity, and commerce that the internet and industry seemingly forgot.
A time that evolved tastemaking, but has yet to capture a spot on Wikipedia. A period that produced Platinum artists off the backs of bloggers. An era when independent creators truly took the steering wheel from industry execs.
“A lot of people who are running pop culture today started in this time,” Eric Rosenthal told Boardroom. “But there’s no proof of this time.”
Sitting down with ItsTheReal, Boardroom breaks down the business behind the acclaimed Blog Era podcast and how the story of the series parallels that of the era itself.
The Roc & A Hard Place
Historically speaking, The Blog Era period peaked from 2006 to 2012, give or take a year.
For fans of hip-hop, the precursor to the season was the rise of Roc-a-Fella Records.
Operating as an independent before striking a distribution deal with Def Jam, the Roc epitomized building a brand that was as artistically sound as it was commercially viable.
“Jay-Z, Biggs [Burke], Damon Dash, all came into it wanting to remain independent,” Rosenthal said. “They worked out their own deal to be a true 50/50 partnership with Def Jam. But when you get to ’06? They are the standard.”
The Rosenthals were at the crossroads of this systematic shift. In 2005, Eric was freelancing for Roc-a-Fella in a sense, serving as the videographer for Roc signee Kanye West. Around the same time, Jeff was doing digital work for the likes of AOL and HBO.
Just as the two brothers were trying to find their footing, the entertainment industry itself was seeing the rug pulled out. CD sales were down due to online piracy as the internet democratized how an artist got hot — and rich.
“We were both too young to recognize the bigger picture, but it was exciting on both sides,” Eric said. “I went to the Grammys with Kanye and all of a sudden I’m at parties with Magic Johnson and Ludacris.”
Proximity to power was at their fingertips, yet gates remained high. Eric and Jeff were hustling to get their own ideas out in the transitioning content space, but couldn’t connect their forward-thinking visions to suits stuck on old models.
“At that time, Jeff and I were pitching a TV show,” Eric recalled. “All of the major companies appreciated the idea but didn’t see how it could make money. So it was like, ‘forget all these people, let’s find our own lane.'”
For the Rosenthals, that lane was the internet and their people was the NahRight community.
NahRight, a prominent hip-hop blog from Ahsmi “Eskay” Rawlins, was an online mecca for hip-hop heads.
Much like Roc-a-Fella at its height, NahRight was able to bridge bullies, backpackers, and bottle poppers in ensemble and audience due to revered taste. It was disseminating freestyles at the speed of dial-up, also offering a platform for one of hip-hop’s most storied forms of comic relief in skits.
Carving their own lane, the Rosenthals rebranded as ItsTheReal. The two acted as a sketch comedy collective quickly co-signed by Eskay as opposed to networks. Viral videos could connect Jeff and Eric immediately to their audience without the context of a corporate middleman.
“The internet was attractive to us because there was speed and you could get to somebody directly,” Eric said. “We couldn’t sell a 30-minute show with three different components but we could put out one of those components for free out of pocket on a regular basis.”
Backed by blogs and powered by platforms like YouTube and Vimeo, ItsTheReal ascended in a lane all its own.
“We’d put these videos out,” Jeff said. “And 30,000 people would tune in on the first day.”
Like their peers in the emerging space, dollars dangled as popularity soared.
In the early advent of The Blog Era, artists, domain managers, and sketch comics alike benefitted from the flattening of the world and democratization of content.
They also walked the tightrope between taking corporate cash and outright owning their own art.
Charles Hamilton hit a $1 million deal with Interscope and had his single featured on Entourage. Rising rappers like Drake were signing contracts with Cash Money and Universal while Roc-a-Fella alum Kanye West was building his own boutique label, G.O.O.D. Music, by going after blog-backed talents like Kid Cudi and Big Sean.
Artists were feeding off the buzz that blogs built off free mixtapes and homemade music videos. For their reach, the blogs were getting broken off, too.
Much like how Roc-a-Fella partnered with Def Jam, NahRight aligned with the Complex Media Network to earn ad revenue. With a 50/50 revenue split, Eskay soon cashed Complex checks derived by big spends from legacy brand sponsors that included Sprite and McDonald’s.
At its peak, NahRight could collect $90,000 a month in ad revenue.
Meanwhile, Jeff and Eric navigated the same space of making content and making a living. On YouTube, ItsTheReal was doing numbers thanks to spoof videos inspired by Jay Electronica’s major label decision and collaborative content with Bun B.
By the early 2010s, ItsTheReal was already eying what was next, pivoting to podcasting and performing parody rap at Bonaroo.
While major networks may not have seen the vision for hip-hop comedy in a 30-minute format in 2006, MTV was knocking down their door a decade later. The appeal built by blogs signaled dollar signs, but also the beginning of the end.
“We never wanted to be the last guys standing at the party,” Eric said. “Anything over the course of our career, we didn’t do it for a longer period of time than needed to be.”
The same passion that birthed The Blog Era burnt out many who built it.
By the end of the 2010s, the boom of The Blog Era had gone bust due to Web 2.0’s evolution of taste-making and the rapid rise of streaming services. The same labels and agencies that relied on the blogs — and gave financial structure to some — crushed those platforms by way of legal brass or outright ownership.
Heading into the next decade, NahRight joined many others as it was revered in memory but reduced to digital dust. Then in 2020, a chain of unforeseen events changed everything.
By the spring of 2020, the world as we knew it had stopped.
Prior to the pandemic, Jeff and Eric remained moving in the ever-changing landscape of content creation. From forming movie review podcasts with The LOX to doing a live Roc-a-Fella reunion at Highline Ballroom, the Rosenthal brothers continued to carve new lanes and feed core audiences on platforms such as Spotify and Patreon.
When COVID-19 put a pause on live shows and hit hard in their home of New York, an existing idea of what was next finally had the runway to become a reality.
“Jeff was interested in doing a narrative podcast,” Eric said. “I said, ‘It’s only going to be done if it’s something we truly care about.’ And it was this time.”
Reaching out to connections from the course of their careers, Eric and Jeff began dialing all the major artists, execs, comment section stalwarts, and domain managers that defined rap’s online rise. To tell the story correctly, they needed the man behind NahRight on board.
“Eskay was that guy,” Jeff said. “It couldn’t have worked without him, he’s the sun to this universe.”
From there, the stars began to align as remote interviews took place from NahRight regulars like Joe Budden to trailblazers of the times such as Mickey Factz. Managers, media executives, and tastemakers talked to the brothers while the world stood still. In that time, they compiled 150 interviews and endless hours of audio.
To clear their heads and let the narratives arise, Jeff and Eric embarked on an 18-day road trip to travel safely and test the material.
“We would listen to the audio on the trip,” Eric said. “It was getting a grasp of the storylines and the bigger picture.”
The prize for the long drives was an IRL filter of what listeners would experience when tuning into their first long-form feature podcast.
Jeff and Eric had a hit on their hands no different than the artists who proliferated the pages of NahRight at the height of its popularity.
Soon they found themselves facing a familiar creative conundrum: sign with a major or remain independent?
In 2006, the suits at TV networks couldn’t understand the vision for ItsTheReal videos that NahRight patrons quickly grasped.
In 2023, they found the same struggle.
“It was sort of a throwback to that time in terms of selling an idea nobody really understood,” Jeff said. “We were taking meetings with labels and meetings with streaming companies. All of them sort of undervalued how important it was on a cultural level. What they saw was we’d spoken to too many people and they didn’t have ownership of it. It was a lot of very old thinking.”
It was an old friend who saw exactly what Jeff and Eric imagined.
“When we sat down with Scott Vener everything locked in place,” Jeff said.
Vener, the partner to Pharrell Williams in OTHERtone Media, is as nuanced in navigating corporate constructs and true taste as anyone in entertainment.
In 2008, Vener was the music supervisor on Entourage, handpicking Hamilton’s “Brooklyn Girls” as the song to score the scene where Vinny Chase debates his own artistic integrity before appearing at a 16th birthday party.
Now operating in a space where he hosts conversations with Quincy Jones and soundtracks Tiffany ads, Vener proved the perfect partner to take The Blog Era to a mass-market audience without selling out on its story.
“As long as we’ve known Scott, he’s always been the same person,” Eric said. “He was a fan of us at the very beginning of our careers, but we never had a chance to work with him. We brought him a fully fleshed-out story and I think he found it immediately compelling.”
The Blog Era finally arrived on streaming services in April 2023 after a panel preview at South by Southwest. By aligning with OTHERtone, Jeff and Eric were able to tell the story of major label motives and the fight for creative independence.
“If we took a deal with anybody else? The chances are that they would’ve put their hands in,” Eric said.
“There would’ve been much more of an agenda on the corporate side of things,” Jeff added. “With OTHERtone there was never any of that.”
Since commencing in June, The Blog Era Podcast has received near-perfect reviews with write-ups and praise from The New York Times to HOT 97. The passion project about the time that time forgot has reached listeners around the world while providing closure for the artists who were a part of it.
It’s a tribute to the same see-saw that countless creatives sit on today and a fight for artistic integrity that defies eras.
“It’s a music story, it’s a technology story, but it’s a cultural thing,” Eric said. “Capitalism, race, and the American Dream both realized and snatched away.”
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