Internet marketing

It wasn’t just and eToys — 20 years ago, a slew of hip-hop and ‘urban’ sites became early casualties of the first dot-com bubble

At the very end, Adam Kidron needed a multimillion-dollar loan just to pay severance to the people he was laying off. Some of his employees at Urban Box Office, the company he had co-founded, had to be taught how to apply for unemployment. They were kids, really; many had never had a real job. “I was a twentysomething high school graduate from the Bronx,” says Steven Samuel. “UBO paid me six figures. It was about our worth, not our formal education.” Kidron even made sure all the content creators retained the rights to anything they did at UBO. But riddled with tech issues and mismanagement, UBO couldn’t realize its egalitarian dream.

It wasn’t alone. Between 1999 and 2001, with the greater dot-com era just beginning to spiral, hip-hop and “urban” websites and startups proliferated, flush with investment cash. Hip-hop impresario Russell Simmons, riding high in his Phat Farm/Baby Phat fashion heyday, staked his digital claim with media company RS1, later named 360HipHop. (“The site will utilize a multi-media approach to deliver content, providing the user with the latest in hip-hop trends and information, as well as connect users, and hip-hop celebrities/personalities, in a virtual hip-hop nation,” wrote one breathless article in 2000. “Especially interesting will be interactive sites devoted to ‘Puffy’s Gun Collection’ and ‘Snoop Dogg’s Greatest Spliffs.’”) Sony Music Entertainment and Universal Music Group both invested.

The finance world even got in on the founding. Investment banker Charles “Chas” Walker and his business partner Peter Griffith launched “netcaster” Hookt, later partnering with Sean “Puffy” Combs in hopes of leveraging the Bad Boy/Sean John impresario’s supernova profile. HBO launched Volume, a site that leaned heavily into video content and that many expected to spin into an MTV competitor.

And one by one, they all unceremoniously shuttered.

Just as with the larger dot-com bubble, the causes of death were many. Gross mismanagement. Bloated salaries. Unchecked spending. Buggy site design that ignored the fact that most users were accessing the internet by dial-up modem.

By now, the boom and bust is 20 years in the rearview. Media has had multiple other reckonings since then, from the recession that killed dozens of magazines in 2008 and 2009 to the recent closures and layoffs happening across digital journalism. And most of the major players involved in those early years have recovered and moved on to high-profile media careers. But the lessons, the facepalms, and the “WTF?!” moments remain fresh. When something sounds too good to be true? It probably is.

Starting in the mid-90s, a bull market turned into a frenzy of opportunity: Any idea with a dot-com suffix attached could get millions in a single round of funding, and then more rounds when that was spent — even when you had nothing to show for it. Sites and startups flocking to the still-young internet attracted trillions of dollars in investments. And hip-hop wanted in.

Adam Kidron (co-founder, Urban Box Office): I was supposed to have dinner with Clarence Avant one night — who was a legend, of course — but when I showed up to the penthouse, there was only one person there. He said, “it’s just me and you. I’m George Jackson.” I knew he had done Krush Groove and New Jack City. We ended up taking a walk, and we realized we had so many similar interests and outlook on life. From the outside, we couldn’t look any more different. But inside, we were the same. From that first day, we were inseparable.

Ntianu Eastmond (executive producer, UBO): There was a crew of us, Black women, who had all gone to The New School; one by one, many of us ended up interning at VIBE. Some of us moved out of journalism, but some stayed. One writer, Charlotte Smith, ended up at UBO and told me about it.

Adam Kidron: George and I did a few projects together. But then he got the job at Motown. (Jackson was appointed president and CEO of Motown Records in 1998) I said to him, “George, I’m sick of working for other people. Let’s go do something for ourselves.” George said, “Well how are we supposed to do that?” I said, “we’re going to have to raise some money.” We went out, raised a bit of money, and got an office inside of a garage at Chelsea Piers. I sit down on the first day and notice a sticker on the wall. It said, “If you can read this sticker, it means you’re going to get lead poisoning.”

“The way UBO was hiring people was like building a boat as people get on.”

Ntianu Eastmond: I interviewed with both George and Adam, which was so weird. They were actual grown-ups. I have never, before or since, walked into an environment where you interview with an actual grown-up.

Steven Samuel (co-founder, SOHH): The way UBO was hiring people was like building a boat as people get on.

Karu F. Daniels (entertainment news producer, Volume): I’m in my early twenties. I’ve already written for The Source and VIBE and other places. I got a signing bonus, doubled my salary, and had my own office. It was very cute. We had to work, of course. But yeah, it was nice.

Chuck Creekmur (news assistant, Volume): I had just recently launched AllHipHop and we were still grinding, going to everything. I was at a press day for Queen Latifah and I met this guy Karu Daniels. A few weeks after the event, he told me he was starting at this new place called Volume. It was backed by HBO. There wasn’t a lot of money but there was a space for me if I was interested.

Serena Kim (associate editor, 360HipHop): I was working at Notorious, which was Puffy’s magazine, and interviewing to be an associate editor at The Source. I go on a million interviews over there, and then [editor-in-chief] Selwyn leaves.

Selwyn Seyfu Hinds (editor-in-chief, 360HipHop): Leaving The Source [after months of tension with Source owner Dave Mays and his friend Ray “Benzino” Scott] was like a breakup. You pack your stuff over time. Wait for the right moment. So, there was an argument one day. I may or may not have thrown a chair at a wall. And at that point, I knew I was going to have to go. But I wasn’t going to just walk out and leave my staff. So for the next few months, I took meetings and thought about my next step.

Chuck Creekmur: Earlier in AllHipHop’s history, there was some talk of Russell Simmons and Lyor Cohen and Kevin Liles wanting to acquire a substantial piece of the site. It was a deal we quickly turned down. They didn’t respect us enough, compared to these other sites that were being funded. I just don’t think we were the cool kids like some of these sites with bigger names. But we had hit a sweet spot from a revenue and staffing point of view. So we held on.

Larry Hester, aka The Blackspot (editor-in-chief, Hookt): I was at XXL when the investors started coming around, talking about creating sites, about people retiring at 23, and having all these stock options. So yeah, we all wanted to get in on that. Investors were just throwing money around.

Selwyn Seyfu Hinds: Pretty much all the sites had come to me to talk about running their editorial teams. That’s not boastful. It’s just where I was in my career, running The Source, and the relationships I had. It makes sense.

Datwon Thomas (executive editor, Hookt): XXL was a dream job. I was so happy to be there. I was a kid who dropped out of college, got an internship at VIBE, and got hired at XXL — but XXL wasn’t paying anything. My name was starting to ring bells, but that wasn’t going to get me out of my grandmother’s apartment in Brooklyn.

Blackspot: I’ve always had a love for the digital space, going back to Vibe Online in the mid-90s. That was my specialty. But I wasn’t savvy enough on the back end to start my own thing. It was also expensive to start these things up. There was no WordPress — this is straight-up HTML, and you have to design everything from scratch.

“Like, sometimes I would look up from my desk and around the space and just think, I can’t believe this. This is the team I work for? This is the ’27 Yankees!”

Selwyn Seyfu Hinds: I’m close to deciding to go with Russell’s site. He has an event at his apartment for Hillary Clinton. All the bigwigs are there. At the end of the event, I’m about to leave, and I see Puff of all people. He says, “I’ll drive you home, I need to talk to you.” So we hop in the — I think it was a Navigator — and he pitches me on not going to 360HipHop. He wants me to run a site he’d just invested in called I turned him down nicely. But now I’m realizing how competitive this space is going to be. Puff is trying to poach me away from Russell — in Russell’s house? I didn’t even start yet! [Laughs]

Datwon Thomas: Reggie from Iced Media told us that these guys running a new hip-hop website were looking to staff up. It was [Hookt co-founders] Peter Griffith and Chas Walker. I’d worked with Black twice already, so the idea of working with him again was appealing.

Jon Caramanica (assistant editor, 360HipHop): I was literally working with all my journalism heroes. I’m now working with Selwyn Seyfu Hinds, who ran The Source. I’m working with Sheena Lester, who ran XXL. There’s kris ex, Serena Kim, Jazzbo, Jeff Chang. Like, sometimes I would look up from my desk and around the space and just think, I can’t believe this. This is the team I work for? This is the ’27 Yankees!

Paul Estevez (Marketing Director, UBO): I had started out at [clothing brand] Willie Esco. But I had a falling out with one of the backers over a handshake deal. I’m thinking on my next move, and my best friend Tony Martinez and his business partner are starting up It sounds interesting. But I’m like, where’s the funding? They say, “it’s under UBO.” This is 1999.

Adam Kidron: We wanted to build a platform that was really diverse and really multiracial and multicultural and we wanted to do it by respecting the creators. And we wanted to find a way of making it financially viable because we didn’t want to be vulnerable to the ever-changing mood of venture capitalists.

Omar Wasow (co-founder, Black Planet): When we were building Black Planet, we pitched some of these same investors as these sites and the answer was no. I’ll admit, it was hard to see places like UBO get this money when we were already growing and we thought we had this proven technology. But they had more sizzle.

Blackspot: I had a meeting with Peter and Chas. They told me I could hire a staff and it was on.

Datwon Thomas: I wasn’t sure if I was leaving XXL. Elliott Wilson was on his way to be the editor-in-chief. And I knew he was about to kill it. He was already known to be a powerhouse. I could do some ill stuff on that team. He told me I should stay. But Hookt was going to triple my salary. That was that.

Splashy launch parties and unlimited budgets fed into a growing legend around the upstart startups. Their young employees rubbed shoulders with the culture’s elite — and had blank checks to create whatever they wanted to.

Jon Caramanica: We went to Russell’s house for some 360HipHop party. It was the first time I ever saw a Basquiat in person, you know? I’m surrounded by priceless art and a team of people I respect the most in my field. You’re young and you’re just thinking. This is it. This is what I imagined. It was the first time I felt like I made it.

Ntianu Eastmond: I had already worked at one Black-owned startup with all Black investors and it went under really quickly and really badly. But when I walked into UBO, it felt like it was different. There was so much creative energy and positivity.

Paul Estevez: I had never seen anything like it before. All of these creatives packed into a warehouse with desks. It looked like there was barely enough space for all of us.

Adam Kidron: We literally didn’t have enough chairs. We had folks working on morning and evening shifts just so they could have a place to sit.

Steven Samuel: Either you came in mad early or in the middle of the day. I opted for the middle of the day. You could still go hours waiting for someone to leave so you could get their chair.

Ntianu Eastmond: The idea was that there were going to be all these different groups of people creating content in their own unique silos. Some were starting from scratch. I was a part of what would be known as Style Cartel, a fashion site with e-commerce.

Blackspot: We had [future XXL and VIBE editor-in-chief] Datwon Thomas, [future VIBE and LEVEL editor-in-chief] Jermaine Hall, [future MTV News hip-hop editor] Shaheem Reid, Mark Allwood, Mahogany Brown, Keith Murphy, Detox… Just an amazing team. I was proud we were about to do some crazy content. But honestly? I was even more proud that I was about to give these writers a decent fucking salary. We were gonna do what we loved and actually be able to live. People were able to move out of their parents’ cribs. People who already had spots were able to upgrade. So many of us, especially the women, were struggling to make a few bucks to do the thing we loved. I just wanted my people to have a better standard of living. So it was a dream come true.

Chuck Creekmur: The staff at Volume was incredible. I didn’t even realize it truly until much later. But you’ve got Karu, [Source editor and future Atlantic Records VP] Riggs Morales, [Source editor] Smokey D. Fontaine, [legendary stylist] June Ambrose. It was just this incredible amount of talent. I was still writing for hip-hop magazines that were barely paying. I was just happy to be there.

Serena Kim: I’m hearing I might be able to go to Selwyn’s next place, 360HipHop, and be an associate editor there. I start there — the same day as Jon Caramanica. I knew his work, so I was excited to be working on a team.

Adam Kidron: I believe you should respect people for their talents, not their education. George and I wanted to get rid of the elitist ideas of who can create and who cannot. You need to respect a 17-year-old who is sitting there making video games as much as someone who studied at Harvard. This was the root of everything for us at UBO. It was utopian and egalitarian.

Ntianu Eastmond: From day one, if you raised your hand and said you wanted to write something, make something, produce something, shoot something — the answer was yes, go for it. There were very few limitations to our creativity. I mean, part of it was because there was no infrastructure in place to actually make any limitations. But there was this underlying idea that UBO was about artistic freedom first. That was so exciting. I don’t think they ever denied any budgetary request that I ever made. Even the outrageous ones.

Esteves: We all got laptops. And I remember in the beginning, UBO was in the same building as Research In Motion, which was developing Blackberry. So we all got Blackberries when they were first released.

Adam Kidron: We started to look into having A-list celebrities involved with UBO. George and I went to Palm Beach to see about signing the Williams sisters to some kind of content deal. The father, Richard, opens the door. I’m like, “we’re here from UBO to meet with Venus and Serena.” He says, “Venus and Serena? They’re dead. Didn’t you hear the news?” And he slams the door. We’re like, stunned. We ended up talking to him and we did have the meeting and we did sign them. And after that, we’re able to sign a lot of celebrities to work with us. A lot. We spent the money we needed to spend to do it.

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Datwon Thomas: 360HipHop had these ads all around New York City: “I Am Not Hip-Hop.” And they had these huge photos of people like Rudy Giuliani in them. We were like, damn, they got all the money. Since Puffy’s fashion line, Sean John, had just dropped, it made sense to partner with him. But then, there was the shootout [at Club New York]. He just wasn’t the same after that. He still worked with us. But he wasn’t as focused. It was our chance to have a big name connected to us, like Russell and 360HipHop, but it didn’t really work out.

Blackspot: There were so many sites doing similar things, we had to bring in celebs and give them these deals to work with us. I wasn’t crazy about the Puffy deal. Hookt also did a deal with Eminem, and that was even worse. We weren’t even allowed to say his name in conjunction with the site. We were just getting an animated video from “The Real Slim Shady” that we could post. It was ridiculous.

Ntianu Eastmond: At one point, I told them I needed to buy a dozen Prada bags to sell on the site and the answer was, “sure.” Then, and this was my first business trip ever, I went to the Magic [fashion trade] convention. We were looking for apparel companies to partner with and perhaps sell on the site. They sent a stretch limo to pick me up. I stayed in a suite at the Bellagio. It was all just outrageous.

“Any idea you could think of, you could do it. My department was responsible for pulling off the launch party. We’re like, ‘What about renting Ellis Island?’ And it’s approved.”

Blackspot: We realized we needed cameras to make some content. We’re literally walking around trying to borrow a camcorder from someone. The professional standard at the time was a Canon XL-1. I’m like, can we get one of those? And the answer is, “you might as well get two.”

Paul Estevez: Any idea you could think of, you could do it. My department was responsible for pulling off the launch party. We’re like, “What about renting Ellis Island?” And it’s approved.

Adam Kidron: I never understood why people thought we spent a million dollars on that party. We did not. Not even half a million. It was $350,000. And even that was insane to me. I had not planned to spend that much. We got a sponsor, they pulled out at the last minute, I was left holding the baby. We probably got a little carried away. But a million dollars? Rubbish.

For all the editorial enthusiasm, experts were few and far between. Many of the sites had the same kind of wide-eyed optimism approach to technology that they had for the content side. So they built Flash-heavy sites with bells and whistles—only to realize that not only did it take too much time to upload their content, but most of their audience didn’t have fast enough connections to see it anyway.

Siddiq Bello (digital consultant): So you have people like Chas and Peter at Hookt; these are really savvy, smart, well-experienced cats. But they didn’t start from a base in technology. They started from a base in a revenue model that they attempted to layer on top of technology.

Omar Wasow: Folks like UBO came from the media world, they had a really good story and they understood the urban consumer. They had great marketing materials and they had sizzle with their pitch books and concepts. If you were a media investor, it made a lot of sense. If you were a tech investor… it looked a little thin.

Adam Kidron: It was kind of ludicrous. You have the three of us — me, George, and [co-founder] Frank Cooper — and there’s no technologist between the three of us. I’ve had projects that didn’t work for tons of reasons. But I’ve never had a project where I just had no idea how to execute an important part of it.

Steven Samuel: Yes, there were issues. But our lead tech guy, Tyrone Thomas, was actually way ahead of his time. This guy was talking about XML structures in 1999 when that wouldn’t really be fully utilized until 2002 or so.

Jon Caramanica: We had kris ex interview Nelly—a video interview. We had built a custom video player on the site. And we’re like, wait, our video player can’t support the length of this video. There was no out-of-the-box [online publishing system] in 2000, so they were all custom. There were four slots for video clips. But it was still heavy to download. This is early internet. Even if we solved one problem, we immediately had another one.

Paul Estevez: The vision was brilliant. We were doing comedy, animation, cultural work, fashion, and culinary. Everything. But the tech just wasn’t there.

“You could make beats on Hookt. Like, what Genius is doing now? We were doing that in 2000. I don’t know why we did this, but we had a page where you could do graffiti. It even made the sound of spray cans.”

Omar Wasow: The money was sloshing around. But at some level you have to figure out, is this an information technology or a social technology. It’s not to say you can’t have a successful tech company built around content. But If you’re UBO competing against a magazine like The Source, what was making your site essential and distinctive? And if you have it, can you execute it?

Karu F. Daniels: The launch date just kept being pushed and pushed and pushed. I think some of the powers that be were waiting to see what others are doing.

Ntianu Eastmond: For UBO’s Style Cartel project, we had tons of content. But we never had a URL or a site.

Datwon Thomas: You could make beats on Hookt. Like, what Genius is doing now? We were doing that in 2000. I don’t know why we did this, but we had a page where you could do graffiti. It even made the sound of spray cans. [Sighs]

Steven Samuel: I made a bet with Kidron that if he couldn’t import SOHH into UBO, he would cancel the Ellis Island party. I worked with tech for months to make that happen. It didn’t happen. But that party still happened. So, I didn’t go. I stayed in the office and upgraded my computer.

Karu F. Daniels: Listen, Smokey [Fontaine] was a fucking visionary. The things we were doing at Volume were so ahead of its time. We literally had June Ambrose working in the office. Volume was sending her to the Caribbean for photo shoots. We had behind-the-scenes videos of Jay-Z’s music videos and Puff’s videos. That is the kind of content we had. We were the site with gravitas.

Blackspot: Our entire site was built with Flash. So to put up one story was just such a strain on resources and our services. We could have a month’s worth of content, but it would take forever. And then, if people actually started coming to Hookt, it would start acting wonky and have design issues. It was the technology that we really underestimated.

Datwon Thomas: We decided to make music videos for songs we thought should have been singles. The first one was “Chickenheads” by Lil Cease. We shot it all through Brooklyn. It was amazing. It was this song no one was supposed to know because it didn’t get the push from the label. But everyone on the street is coming up to Cease and singing along. The video was amazing. It’s gone now. No one has it.

Karu F. Daniels: We never got out of beta.

Adam Kidron: UBO had a very optimistic idea of what you could and could not do at that time. Did we hire the right tech people? No. Did we know how to hire the right tech people? No. We looked at people’s potential. So we had kids running the infrastructure.

While these high-profile sites are burning through cash with little output, a mysterious website appears to chronicling the confusion — and it’s naming names.

Adam Kidron: We were making progress but there’s also tension. There was this website crucifying us daily, especially me. It was called Urban Exposé.

Blackspot: I had no idea who was behind that site. No one did. But whoever it was had all the gossip about every site. The bosses were pissed because they were being talked about on the site. But I thought it was genius. They called me into the office one day and told me to grill everybody on staff and see who was feeding them information. I’m like whatever. I paid that no mind. But we all checked it religiously.

John Lee (aka Crispus Attucks, founder of Urban Exposé): I have a strong tech background. I was on the cover of Wired as a teenager. Like, I’m ready for this. I hear about these sites and I can’t wait to get on at one of them. And every place — UBO, Hookt, Volume, 360 — every single one of those sites were like, would you get out of here? I guess I just didn’t look the part. I’m showing them how I could do content and tech. And these people are staring at me like, why is he in my office? I was like, okay. I’ll do my own thing.

Datwon Thomas: Someone mentioned it in a meeting. Have y’all seen this shit? They weren’t talking about Hookt at first. They were talking about the other bigger sites. But eventually, they started talking about us too.

Omar Wasow: I had some thoughts. But we really didn’t know. But after it became more and more popular I started digging around.

Datwon Thomas: People thought it was Blackspot. But I was with him every day so I knew it wasn’t him. But the person had this slick, funny way of covering our world. It was insane. There would be stories about investors and what sites weren’t doing well. It reminded me of The Rap Bandit at The Source: This anonymous person who knows everything. And whoever it was, he was pissed and coming for all of us.

John Lee: 360HipHop was a beautiful site. But they were dogged with a lot of technical stuff. I’m not going to shit on anyone over there because everyone is doing well today. But I do remember they had specific tech issues. Around that same time, Russell Simmons did an interview with Forbes. And he said Urban Exposé was his favorite site.

Serena Kim: It was the first time that hip-hop journalism actually was the story instead of reporting the story. Honestly, people were both scared and flattered. The junior staffers were kinda excited to get name-checked. You made it if they were talking shit about you on Urban Exposé.

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Some of the headshots that appeared on Urban Exposé. L-R, from top: Russell Simmons; the ventriloquist dummy Lester; Source owner Dave Mays; UBO co-founder Adam Kidron; Magic Johnson; 360HipHop editor-in-chief Selwyn Seyfu Hinds; Darien Dash, whose company, DME, was the first Black-owned internet company to be traded on Wall Street; Hookt president Brett Wright; Black Planet founder Omar Wasow. Photos courtesy of John Lee

Adam Kidron: In a society where people with privilege have exploited others, things like that site will happen. It didn’t bother me. But I just thought I was taking a lot of punches for other people.

Datwon Thomas: They’re talking about hirings. Firings. Investment deals. Partnerships. And then in the comments, people are talking about everything. We just knew this person was brilliant — and fast.

“I just remember thinking, well shit, if we had this Urban Exposé guy here, maybe we could get something done.”

John Lee: I decided to name myself Crispus Attucks. Like, these motherfuckers hate me and this site but they don’t see that I’m giving them the keys to the kingdom. These sites are blowing through millions and couldn’t do the tech side properly. I put urbanexposé up in an hour and had more traffic.

Serena Kim: I just remember thinking, well shit, if we had this Urban Exposé guy here, maybe we could get something done. [Laughs]

John Lee: I’m into Black rebellion. It’s in my DNA. So Urban Exposé was my chance to show my full rebellious side.

Omar Wasow: I started asking some questions. A media reporter and I started trying to figure out who it was.

Serena Kim: I refreshed the site literally every 20 minutes. No lie.

John Lee: Urban Exposé was very simple, and it’s what these sites should have been doing. These sites were supposed to be an easy interface for writers to put their content up: Just press a button and manage it. That way, a writer could do their fucking thing and not worry about contacting the webmaster and technical leads to get the story up. There’s enough blocks to writing. You don’t need to go through 3,000 poindexters before you can put your article up. That’s the antithesis of content creation.

Datwon Thomas: We just didn’t know how this person was getting this information. That was the crazy part.

John Lee: I dressed up as a janitor and snuck into some offices and listened for info. And I dated someone at one of the sites so I could ask her about her day and get some information. Just a couple of dinner dates. I really did like her, though.

Omar Wasow: So, the media reporter I knew came to me with this random SMS grid. He had messaged with Crispus Attucks. I looked up the numbers in my phone — it was John. It matched an old burner number I had for him years ago.

John Lee: Omar Wasow and Harry Allen were the only two people who figured out it was me. And neither of them said a thing. I always appreciated that.

Omar Wasow: I was doing tech reporting for NBC. I convinced them to let me break the news of John Lee being Crispus Attucks. It was this super-insider Black media story. But I persuaded them that it was breaking news.

John Lee: It was legendary. But it’s difficult to stay in business. A site like Urban Exposé gets a lot of clicks, it’s kind of like Spy magazine, which I loved back in the day: You can go hard on people, but eventually you start running out of friends. And that’s exactly what happened.

UBO, the site with the biggest dreams, declared Chapter 11 bankruptcy and folded in December of 2000, months after George Jackson’s death hobbled the site’s morale. Hookt never recovered from its tech issues or its ill-timed partnership with Sean “Puffy” Combs; after nine months and a series of layoffs, the site shuttered in May of 2001. In October of that same year, after stories predicting Volume’s demise, HBO announced that it was shutting down the site — which had never actually launched.

But the shortest tenure belonged to Russell Simmons’ 360HipHop: Just three months after launching the site, Simmons sold the site to BET.

Ntianu Eastmond: I have this image in my mind of Adam telling us that George has passed away, and just breaking down crying. I knew it was pretty much over at that point. I didn’t get the sense that Adam wanted to run it without George. Well, that, and the fact that they were burning through money very very quickly.

Steven Samuel: I remember coming off the elevator and I saw wall to wall niggas crying. And none of us recovered from George’s death. Depending on who you were, he was either like a dad or a big brother. We had one verbal issue and he corrected me with respect.

Adam Kidron: I knew we weren’t going to make it after this investor pulled out of a deal that was already set and binding. He reneged on the binding term sheet. And that was $20 million. Gone.

Paul Estevez: Did we need to have a launch party on Ellis Island? No. But hindsight is 2020. It was a different time and a different culture.

Adam Kidron: I went to Chase and got $2.5 million just to pay [severance for the layoffs]. And there wasn’t a single penny left. We were just conjuring from a stone at that point. There was a lot of anguish and anger.

“I just looked around one day at all the empty desks and thought, ‘Oh my god. There’s no one here. Now what?’”

Serena Kim: So we go from 75 employees, and everything is popping — then we start having round after round of layoffs. Everyone is terrified of getting laid off. We’re like, did she just walk into HR? What about him? Eventually, all those people became two people: Me and Jon Caramanica. I figured they kept me because they were barely paying me anything. Then, BET bought the intellectual property and I had to go to D.C. every week and upload old shows from BET to 360HipHop.

Blackspot: The bosses at Hookt wanted me to start firing people, and I couldn’t do it. I would push back. “So-and-so has to go.” And I would say, “Nah, he just got a new apartment.” But then it was making me look bad to my bosses. I wasn’t experienced enough to handle that. That was a weakness on my part.

Serena Kim: I started working 12 hours a day. And I remember there was this window near my desk that didn’t close. It was wide open. So I started wearing my huge winter coat to work and leaving it on all day.

Datwon Thomas: There was this slippery slope of talent leaving. We had real bonafide stars in their youth. Jermaine Hall went to The Source. Blackspot left. Shaheem Reid left for MTV. I just looked around one day at all the empty desks and thought, Oh my god. There’s no one here. Now what?

For the most part, the survivors of the urban dot-com boom and bust have done well for themselves. Most remain in media in some form, from major newspapers and journalism outlets to tech companies like Apple to film and television.

Ntianu Eastmond: I think UBO was destined to fail the way it did. Ultimately, it was branding over quality — and I don’t think that was unique to UBO. Or the era.

Chuck Creekmur: Volume taught me the value of having a network, the value of having friends in the industry. I went on to write for all the places those people went to and that was not possible beforehand.

Siddiq Bello: I say we didn’t fail enough and we didn’t fail fast enough. We keep forgetting that we learn the same lessons again and again. Those people weren’t the first to raise that kind of money. It’s happening right now, too.

Ntianu Eastmond: Adam and George really tried to not stand in the way of creativity. They tried to create an environment where people were empowered to do their best. But that put a lot of personality on the individual to actually do that when no one was over you. The resources were there. But there was just not a lot of instructure.

Chuck Creekmur: Volume expanded my horizon out of just writing about entertainment. They were trying to set a precedent for online journalism in hip-hop and beyond. They were taking a magazine approach to the internet.

Paul Estevez: The beauty of that kind of atmosphere was that it took me out of my comfort zone. When UBO moved to a new space, they separated us from our teams. All the marketing people sat with the marketing people from the other sites. I hated it. But it ended up being the best thing for my career. I met people I ended up doing business with for years. And I learned how to handle that kind of discomfort. It was a great lesson for me. I was so young.

Adam Kidron: When I think of UBO, I don’t think of it as lost potential or anything like that. All I can say is that some of the most exciting days of my life were there. It was priceless.

Datwon Thomas: Before I came to Hookt, I’d pitched a lifestyle magazine to Harris Publications, which owned XXL. I knew my audience, young Black men, wanted three things: women, cars, and clothes. Long-ass white tees, big rims, and a video chick. A magazine focused on that man never existed. But they turned it down. So it’s years later, I’m looking around Hookt after everyone has gone. I get a call from Don Morris, the editorial director at Harris — he says, “Why don’t you come back and do that magazine you pitched?” And that’s how KING was born. We mostly all drifted back to print. Took a lot of lessons with us.

Adam Kidron: My whole life, I’ve been trying to build a platform where creatives who contribute to the culture can get a fair shake and actually get paid. That’s still not the case: Spotify and YouTube are shitty platforms to get paid. To this day, I haven’t fulfilled the promise of what George wanted in UBO. I’m not regretful of anything we did. I just regret that it didn’t work out better. And I’m doing more to fulfill that promise as soon as I can.

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