The Big Flop - Myspace and its $580 Million Mistake with Erika Ishii and Brennan Lee Mulligan | 87

Episode Date: May 12, 2025

Before there was Facebook, there was MySpace – and Tom Anderson was everyone's first friend. With his iconic profile pic and revolutionary platform, Tom turned social media into a cultural phenomenon. But when corporate suits came calling with fat checks and even bigger expectations, Tom went from being everyone’s first friend to the internet’s first cautionary tale. Erika Ishii and Brennan Lee Mulligan (Dimension 20, Dropout.tv) join Misha to get the lowdown on how Tom from Myspace fell out of everyone’s top 8.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Before we dive into today's tale of catastrophe, I have to tell you about Wondery+. If you're someone who craves the juicy details behind the biggest flops, Wondery+, is exactly what you need. Add free episodes and early access to new stories that will take you even deeper into the world of business blunders. Trust me, it's a game changer. Join Wondery Plus in the Wondery app or in Apple Podcast. Can y'all remember who your first friend on MySpace was? For a second, I thought it was this frenemy I had when I was in middle school, but weirdly they might have just been on my top 8 choices. It was actually Tom, the creator of MySpace.

Still not ringing a bell? Well, my guest describes him as the default guy on the posters of your community college. Cute. In Tom's heyday, he truly could have had it all. Could have been a household name like Rupert Murdoch or Mark Zuckerberg, the execs who once vied for his attention. So what went wrong? Why is he only somewhat remembered as the guy who friended me on MySpace when I was 14? Let's get into it, besties. and

the long-term news That's what News Corp. to sell off the struggling site for 35 million dollars. Facebook had no chance to win. The only reason we won was because of the gross confidence of MySpace systematically over a period of many years. Did I just say that publicly? We are on a sinking ship where strategy meets top-tier gameplay. Drop in on the exciting Sugar Rush and Crazy Time slot games, or play the dazzling MGM Grand Emerald Nights, a slot experience that captures the magic of MGM.

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Get an instant price today at zenSurance.com. From Wondery and AtWill Media, this is The Big Flop, where we chronicle the greatest flubs, fails, and blunders of all time. I'm your host, Misha Brown, social media superstar and king of coding at your bestie Misha. And on our show today, I'm so excited because we have two amazing guests that you can catch on Dimension 20.

It's Erika Ishii and Brennan Lee Mulligan. Welcome to the show. Very glad to be here. Very excited to hear about Brennan's MySpace days. Okay, so before we jumped on, we were chatting and Brennan, you said that you were like a MySpace connoisseur. So what, can you describe what was your MySpace persona?

So my MySpace persona was really dedicated to the community I built at my summer camp. Yeah. So MySpace was a way to keep the candle lit. You know, it was a way to hold hands across vast physical distance in digital space and keep bits and inside jokes alive. My God, who would we have been but for Myspace?

It was revolutionary. It was. And Erica, do you have any memories of the site? Now, I'm no snitch, but I seem to remember that at its height, I might've been too young to actually create an account. I think you had at some point had to be 18 or older. Is that correct? Not back in my day.

The lawless land of MySpace. But today we are talking about the man who created MySpace and made it the biggest social media site on the planet before sending it spiraling into relevance. Now the man who starts MySpace is also the guy who becomes the literal face of the site and that's right everybody it is Tom from MySpace aka Tom Anderson. So as you may recall back in the day when you signed up for MySpace, Tom automatically became your very first friend. And that made Tom and his profile pic synonymous with the site. So let's take a look at that iconic picture of Tom. Brennan, can you describe

what we're looking at for the listeners only? Well before the advent of artificial intelligence, the internet rendered the most normal white man you have ever seen in your life. A brunette wearing a nondescript white t-shirt, turning to look over his shoulder as if to say, what am I writing on this whiteboard? Whatever it is will be the advent of a new information ecosystem and paradigm that will disrupt American democracy in less than two decades. And for that, we have to take our hats off to Tom Anderson.

Yeah, I think Tom actually went around friending everybody on Facebook as well, which is where my familiarity with Tom came from. But also, I thought he was another, I thought he was one of maybe two friends of mine. When you live in LA, you have a friend that looks like this, just sort of the default guy that's like on the posters for your community college. Sure.

I particularly really like the description in his profile. Just says, woo, with a little smiley face. That's genius. There's a degree of you're saying woo, but your emoticon has a closed mouth. So which is it, Tom? You know what I mean? Yeah. Woo!

It's not, it's not semi-colon D, like I have an open mouth, I'm saying woo. It's woo only behind the eyes, mouth shut. That's creepy. Or even XD, XD would have been the woo for me. XD. For the youths listening or watching this, XD was when you were like so excited that you're like,

ah, and then if you turn it sideways, if it comes an excited face. Before he becomes everyone's first MySpace friend, Tom is a 13-year-old hacker who is deep into web culture. And Tom even has his own hacker name. Now, if you've seen The Matrix, you might expect this hacker alias to be something badass, like Trinity, Neo, maybe even Morpheus.

But Tom goes by the name, wait for it, Lord Flathead. Yeah. Wow. Yeah, so cool. But at just 14 years old in 1985, so this is the 80s, Tom hacks into one of the computers at a Chase bank and winds up getting raided by the FBI. They do let him off the hook, but the feds do take away his computer. So I think for a young nerd that may be a fate worse than jail. Now you would think that this brush with the law would give Tom a sense of importance of being thoughtful and responsible about using the internet. But as we will see, that is not the case.

He's going to keep having that move fast and break things ethos that defines the early days of the internet and social media. So let's fast forward through the growing pains of his life to 2003. And Tom is in sunny Los Angeles working at an online marketing company called eUniverse, which sells a totally normal range of things from skin cream to printer ink to diet pills. Fun. Fun.

Fun. Tom is also involved in a whole bunch of other sus side hustles. He sells spy cameras, gets involved in spyware, and sells shady ebooks that cover subjects like how to hypnotize people and how to grow taller. Oh, anything that was like in the back of an old fashioned comic book. Yeah. He's such a strange character.

But Tom is eyeing an opportunity that's even bigger than sketchy ebooks, the brand new social media sphere. He and his friend, Krista Wolf, who also works at eUniverse, start thinking they should build their own social media site. So what do they do? Well, basically they make a new and improved version of a popular site that already exists. Friendster. Do you remember Friendster? Yes, yes, yes, yes. What, but Friendster, that's like a contemporary of live journal, right?

Because I remember Friendster didn't even register to me as like, MySpace was the first thing I remember growing up with that registered as social media. You are here to collect friends, manicure an online presence, and Friendster felt a lot more like, oh, this is like a Craigslisty vibe, right? Yes, okay.

Right. Yes. My journal was where you'd go to like, read your friends' blogs and short stories and things. I never really delved into Friendster at all. Me either, but from all we can gather and what we'll hear, it doesn't seem like we're missing out on much. So this is a moment where a Friendster competitor has a real chance to break through because Friendster is having some technical struggles with load times and errors when people send messages to each other. But more importantly, from Tom and Chris's point of view, Friendster is just too dang rigid about how it lets people use the site.

So let's take a look at a Friendster profile page. Oh, huh. Yeah, Eric, do you want to describe for the listeners what a Friendster page looks like? This is, well, it's the beta, I guess, and it looks very like an early GeoCities business' website where there's like a box with all of your data. It has, you know, some of your favorite things and interests and yeah, this is not conducive to interaction. I can't believe we're not seeing any ska under favorite music,

given where... Look at this guy and you tell me that he's not going, -"Pick it up, pick it up, pick it up." -"Pick it up, pick it up." Yeah, totally. I think what Erica's trying to get at is it's boring. It's very dull. Although, you know, I'm picking up every single profile that we've snapshot it in any social media site, whether it's MySpace or Friendster, they all love Weezer. So Weezer was like, really, really big at the time. So Tom and Chris, they

want their site to be a cooler, less buttoned up social media platform. And that's going to drive a lot of their approach, including one key difference between their site and Friendster. On Friendster, they do boring things like checking to make sure that users' profiles are accurate and getting rid of fake accounts. How boring. And on Tom's site, you're going to be allowed to create any kind of profile you want, even if it's fake.

Any of us who have large social media followings today, we are like, fuck you. So now, as they're building the site that will become MySpace, Tom and Chris make a huge mistake. They don't quit their day jobs. Instead, they launch MySpace as part of the company they work for. Keep that in mind for later. So, MySpace debuts in August of 2003. By the way, before they landed on MySpace, Tom and Chris considered two other names, comingle.com and yopeeps.com. And to think we could have had yopeeps.com. Why?

Why aren't we in that timeline? I mean, that domain probably already taken. I mean, I feel like that would have been snatched right up. For sure. And here's what the MySpace looks like when it launches. Man. That was your landing page. Oh, the landing page looks like when you go to an unowned domain. Yes.

Yes. Very GoDaddy. Yeah, 100%. Oh, wow. God, I forgot how this deep dive into the history of the internet, even a few short decades ago is like, so crazy. It all looked like this. Everything was like AOL dial up. It was just gray and corporate for no reason. Yeah. Yeah. It's got the little meatballs.

They got cute little smiley faces. So for the listeners only, it says there's three easy steps to MySpace. We're creating a profile, inviting your friends, and then meet your friends' friends. So, it's all about connection, everybody. So right now, MySpace might not seem much more exciting than Friendster based off that landing page, but that will change once people start making

MySpace accounts and building their profile pages. And as we already know, when you sign up for MySpace, you do get that one first friend for free on the house to start you off, Tom. And because everybody on the site will be seeing his profile, whether they want to or not, Tom also makes a decision to be less than honest when it comes to one aspect of his profile. What do you think he lies about? He lie?

Why would Tom lie to us? Why would, what? Well, if it's to mirror sites that come after this, I will say he lies about his height. He says he's six foot, but he's actually 5'11". Ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha Oh. Wow. Yeah, he claims he's five years younger than he really is. Younger? Yeah.

I was gonna say, how old is this, if he's hacking computers at a bank in the eighties, how old is this guy? Well, on his site, I remember from his profile picture, we looked at it, said he was 29, so he must've been 34. Wow, oh my God. Yeah. Oh my God.

Have you ever lied about your age? Yes, I did. You're like, I'm not proud of it. I'm not proud of it, but I have. I lied to say I was a year older so that I could go to overnight camp. When I was 11, I said I was 12 years old. Aw. Aw, that's cute.

A lie is a lie in the eyes of God, so don't aw. It's not cute, all right? I deceived, I bore false witness. Well, it wasn't church sleep overnight camp, okay? No, it was pagan overnight camp, it's true. Settle down. If it's a flat or a squeal, a wobble or peel, your dread's worn down or you need a new wheel.

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in modern criminal history was targeted premeditated and meant to sow terror. I'm Jesse Weber host of Luigi produced by law and crime and twist this is more than a true crime investigation we explore a uniquely American moment that could change the country forever. He's awoken the people to a true issue. I mean maybe this would be rich and powerful people to acknowledge the barbaric nature of our health care system. Listen to law and crimes Luigi exclusively on one degree plus

enjoying one degree plus the one degree at Spotify or Apple podcasts. Luigi exclusively on Wondery Plus. You can join Wondery Plus in the Wondery app, Spotify, or Apple podcasts. Well, light cat fishing aside, when the site launches, MySpace explodes. In addition to looking cooler than Friendster, it also just works better. MySpace page is loaded in just a second or two, where over on Friendster you'd sometimes have to wait 20 whole seconds for a web page to un-hurl. So, ugh, the early internet. Now, music is a major part of the success of the platform. The site allows fans and artists to share and download songs.

Up-and-coming acts like My Chemical Romance and Lily Allen used the site to boost their popularity and eventually established musicians like Depeche Mode, Weezer, Madonna and U2 all get on board as well. Now, as one person in the music industry at the time says, being on MySpace is a mandatory thing bands must do to get promoted. So this was like a really big like turning point in the music industry and advertising themselves on social media. I remember during Facebook taking off while I was in college

and it was a college only site that the reason MySpace stayed relevant even after it had started to crater was because of musicians. That like it was still a place where you're, I remember way after I had started to crater was because of musicians. That like, it was still a place where you were, I remember way after I had stopped using it, I would talk to friends that were musicians and they were like, go check out our MySpace page.

And that was the little tail that MySpace retained for relevancy for a few years after the writing was very much already on the wall. Absolutely, and not to get too far ahead or give any spoilers, but when we see what MySpace evolved into, I think that makes a lot of sense that bands and celebrities specifically kind of kept that going. But MySpace, it also let users pick a song

that automatically plays when someone visits their profile page. Okay. What track would you have automatically been playing on your page? I think I had this. I'm trying to remember what it was. I think it was either the house that Jack built

by Aretha Franklin, or it was, it might've been a battery by Aesop Rock, which is not the same as Aesop Rocky. Aesop Rock is a different other rapper. One of those two tracks was what greeted you when you came to my MySpace page. It might have been something from American Idiot or it might have been something from My Chemical Romance.

Actually, no, because I had a old Nokia phone and a custom cell phone ring of a Cowboy Bebop's tank. So it probably would have been tank. Those are fascinating because I feel like I was very much probably trying to mask my homosexuality and would have had something so stupid like Stacey's mom from Phelan's of Wayne playing.

Oh, that was such a banger. It's a great song. It's a great song. It's still on my workout playlist. Yeah. Well, another iconic feature of MySpace is, as Brennan alluded to, the top eight, which lets you feature eight of your friends on your page and also rank them, which is diabolical. As you can imagine, this leads to some major drama among MySpace users. Like, Lisa, I used to be your number one and your top eight and now I'm number seven.

How could you? I thought we were besties. But let's be real. If there's one thing that keeps people coming back to social media, it is drama. Brennan, did you have any top eight dramas that you remember? I feel like a lot of me and my friends who were fellow, young fellows, young adolescent men, the rate of change was glacial. Your top one was the same from the,

like top one, two, three, spoken for, these were the other boys that were like born in the same hospital ward as me. Like it's not changing anytime soon, but when a change did happen, it was profound. Making a very good new friend, having that friend be like, Hey, can I add you into my top eight? And the conversation would be like, I add you into my top eight? And the conversation would be like, I must never touch my top eight. Let me be clear. I no longer speak to six of the top eight.

They are gone from my life. But if I remove them, there will be phone calls, there will be drama. This is frozen in ice. We can't touch this anymore. That was my experience in the top eight, was basically you do it once, you are locked in, it reflects no part of your lived reality. So I went to a really small high school.

I graduated with 66 people. And I distinctly remember a couple who had been together for a while and the guy moved her from number one on his friends to move one of his like guy friends into the number one spot. They broke up. It was a huge thing.

Over that? Over that. Yeah, they never got back together in the rest of high school. They are married today. What? Yeah. Wow.

But like what is happening in your mind as you're designing that feature? How do you not understand? Wow. But like, what is happening in your mind as you're designing that feature? How do you not understand? I mean, was that the point? Was the point to create a functionality that would drive hatred and destroy marriages? Different time, different time.

So Tom and Chris, they also get celebs like Tila Tequila to join the site. Oh God. It's all these things where you see the seeds of fascism. Like being seated here in MySpace. It starts with midi files and it ends with storming the Capitol. Absolutely. Now, to be fair, she had like 40,000 friends on Friendster.

So it was like they were like, please come over. So another feature of MySpace that makes the site incredibly popular actually happens by mistake. MySpace runs on a super basic coding language. So Tom and Chris also build the site really quickly. They're trying to ramp up to compete with Friendster as fast as possible. And because of the slapdash way they put the site

together, Tom and Chris accidentally give users permission to code their own MySpace pages. This was the thing. This taught all of us how to be little coders and HTML and all the other things that I actually don't understand as an adult. Because people can completely customize their pages. And this winds up being something they love about MySpace. No more boring corporate pages. We can make this ours. So Tom and Chris are happy to let people have this control.

Remember, they are trying to set MySpace apart from Friendster. But let's not forget this is the early 2000s and this means that MySpace users are going to be making some extremely questionable design choices. Now these pages may make your eyes hurt but one thing that's not hurting is MySpace's growth. The site is exploding in popularity and that means some big opportunities are heading Tom's way. But as we'll see, those big opportunities also have some big risks. Now just six months after launching, MySpace is the most popular social network site, completely eclipsing Friendster. They're adding over 23,000 new members every single day. Now, as you can imagine, corporate America,

they start taking notice of the site. People with big money see big opportunity here and they start reaching out to try to buy MySpace. Tom and Chris get their first chance to sell MySpace when a rando company called MatchNet offers $40 million for the site. So if you're Tom, how tempted are you to take a $40 million payout? I would assume very tempted.

I would assume so as well. But Tom and Chris, they do pass on the deal, probably thinking that MySpace is hot enough that they can hold out for a better offer. And in 2004, they do get another offer. Friendster decides if you can't beat them, join them and they propose a merger that would evenly divide everything up 50-50. Now, if you're Tom, how do you feel about this deal? We already got Tila. It's over for you guys. Okay? It's over. We got Tila. That's such an insane, you know, I have this very successful thing and you don't and you want to merge it and then split like, what did Friendster bring to the table? Well, I can tell you, MySpace obviously has the upper hand.

By the end of 2004, MySpace is getting over 2 billion page views in just one month. And at the same time, Friendster gets just 150 million page views. That's about a tenth of the traffic. Wow. So you can say they do not take this deal. Also in 2004, another potential deal

presents itself when Chris takes a meeting with some guy named Mark Zuckerberg. Who? I don't know. Mark offers Chris the chance to buy his company, a little college site you probably never heard of called the Facebook.com. But Chris turns down the deal. This Zuckerberg guy is asking for way too much money. $75 million. Ridiculous. No, I'm just, uh, it's, you just see places where history could have gone differently and you go, no, do, do that.

Do something different, whatever, whatever you need to do. Okay. Oh boy. Like now, obviously looking back, how do you feel Tom and Chris feel about making the decision to pass on Facebook? Well, it's a wild thing because I'm trying to think what would have happened.

When was that offer made? Would they have kept it a separate thing that was like college oriented or would they have made different? separate thing that was like college oriented or would they have made different? Anyone who's embedding MIDI files on pages, maybe shouldn't be entrusted to shepherd the next, the next. I remember like opening pages and having like your laptop blast out in the student library because you're like, Oh God, that's right. Every time I go here, it's going to be system of a down. Like, it's like, oh no.

But yeah, I have no idea. That is 75 million for what is now Facebook is crazy. That is crazy. Oh my God. I mean, yeah, I don't know all the numbers or what the presentation looked like there, but I feel like asking for $75 million for Facebook what it was at the time is crazy.

It sounds crazy. But also, Tom was like a coder. He was a hacker. He wasn't necessarily a businessman. So I assume at this point he had business or financial advisors. But then again, you know, who knows? A lot of times tech guys don't feel like they need

assistance or input. Any amount of money to have avoided the timeline where Mark Zuckerberg goes on Joe Rogan and goes, we have an absence of masculinity in the modern corporate workplace. It would be worth any sum of money to not get in that timeline. Any sum of money.

Yeah, I mean, at the time, MySpace is top dog. So, you know, there was no way of knowing that Facebook would become what Facebook would become. It is obviously a huge mistake in hindsight, but he is feeling very good about keeping his focus on MySpace. By April of 2005, two years after its launch, MySpace is getting over 13 million people visiting the site each month. And this means the site is

becoming even more irresistible to buyers and it's starting to attract the attention of more mainstream companies. And soon enough, in summer of 2005, two major companies, News Corp, owned by Rupert Murdoch, and Viacom, start competing to buy MySpace. Remember, social media is brand new right now, and companies like News Corp and Viacom, which own more traditional legacy media brands, are terrified that they're going to miss the social media boat, and that boat in their eyes is going to sail them directly to Money Island. Now these stodgy old media companies are also desperate to get something else from MySpace, the cool factor.

It's 2005 baby and nothing is cooler than MySpace. So who wins this bidding war? News Corp winds up putting together the better offer after what is described as a marathon weekend deal. Like, sorry everybody, you'll be missing your summer cookouts with kids in Little League and games this weekend. We've got to buy that website that lets users make the ugliest profile pages on the planet. In the end, Rupert winds up buying MySpace for $580 million. winds up buying MySpace for $580 million. And to think you could have had 50% of Friendster's traffic.

Too big. Yeah. Man. Wow. If you are Tom, what are you doing with all of your millions? Getting a different shirt. Get a different shirt. Time to hang up the old white tee.

Let's get something with a collar on it. Let's go. I'm just going to follow Weezer around for years. I feel like if I had that much money, it would have gone directly back into combating Rupert Murdoch and whatever sinister plans he had on my social media platform. I would have put in the deal that now Rupert has to be the new Tom. So like you make a MySpace page

and it's just Rupert Murdoch staring at you. You like go on his page and it's him in a suit, but it's still, if you want to destroy my sweater. Oh, I guess Rupert loves Weezer, too. All right. In the early hours of December 4th, 2024, CEO Brian Thompson stepped out onto the streets of Midtown Manhattan. This assailant starts firing at him and the suspect suspect... He has been identified as Luigi Nicholas Mangione. ...became one of the most divisive figures

in modern criminal history. I was meant to sow terror. He's awoking the people to a true issue. Listen to Law and Crime's Luigi, exclusively on Wondery+. You can join Wondery+, in the Wondery app, Spotify, or Apple podcasts. In the early hours of December 4th 2024 CEO Brian Thompson

stepped out onto the streets of Midtown Manhattan. This assailant starts firing at him and the suspect he's been identified as Luigi Nicholas Mangione became one of the most divisive figures in modern criminal history was meant to sow terror is awoking the people to a true issue. Listen to law and crimes's Luigi exclusively on Wondery+. You can join Wondery+, the Wondery app, Spotify, or Apple podcasts. Well, turns out Tom should not start spending hundreds of millions of dollars just yet. Remember how he and Chris started MySpace

as a work project? Well, that means their old employer can claim a big piece of their new company. And that means they don't have as much control over the final terms of the deal to buy MySpace, and that winds up costing them big time. Chris and Tom wind up having to split just over $21 million between them. Wow, my God. Okay, hey, is $10.5 million a lot of money? Yes, but not compared to $580 million.

That's wild. Now, this also means that Tom and Chris have to answer to Rupert and News Corp. On the plus side, they also get salaries. They both get a two-year $30 million deal each, which certainly softens the blow. But by 2006, MySpace has become the United States' most popular website. Whoa. Like, it's even bigger than Google.com, the previous title holder. But under the new management of Rupert and News Corp, it's not going to be smooth sailing for much longer. So how do you think Tom likes being an employee

of Rupert and News Corp? I would say probably despises it. This is what do they call this in the Silicon Valley kind of lingo, it's like golden handcuffs, right? Yeah. You've gone from being a founder to now being kind of what, a mascot, right? You've sold your, yeah.

Oh, tough. Yeah. You sold, yeah. Yeah, you, you guessed it. Tom is not doing, not doing great under this new regime. He's used to doing things his own way and he's not happy about having to answer to Rupert and co. Now one major early conflict comes when Rupert and the News Corp team move

Myspace offices from cool Santa Monica to one of the offices of a News Corp subsidiary in much less hip Beverly Hills. As if Tom is horrified by the move and he goes all the way up the ladder to take his complaints directly to News Corp President Michael Churnin, which is maybe not an attitude that's going to make your new boss is happy to work with you, though it seems like that's the last thing that Tom cares about. So what do you think about that strategy, being the problem employee? You simply have to understand that the principled stand is to not sell. That's the principled stand. If you're making money and you're doing your own thing and you're free, that's the value. It's wild to sell. People have opined on this before that the term selling out has gone out of vogue or out of style. But that's what that

is. You went to Palpatine, you went to Rupert, you took the cash. You work in Beverly Hills now baby. That's what you wanted. That's what you wanted, big guy. That's what you wanted. And so that's my question is didn't like surely he would have anticipated this is how it would work out. I'm not the most financially savvy person, but also, like, I would simply not have done this. Or I would sell that and then, like, go immediately and make a better site because I have the actual coding ability

to do so, right? It's also wild just to be, like, in this situation where you're like, Beverly Hills! It's like, dude, some people get a promotion in Singapore. Like, you're talking about, this like a slightly different commute. So, yeah, Tom is not the most tactful person. And despite working at a social media company, he does not have the best social skills. When he doesn't want to deal with one of his coworkers, he just starts to ignore them, which fair. But just another thing that's going to cause friction with these higher-ups.

Tom also isn't shy about sharing the problems he has with News Corp, even with the press. He complains to one reporter that the new situation is a pain. Which babbling to the press about the company, you have to imagine, is a real no-no for any member of the News Corp family. So Rupert also reportedly gets a tip that Tom has been working on a secret side hustle. What do you think Tom's other gig is? Your space, the follow-up to my space. Well, it is reportedly a porn site.

Okay. Yeah, okay. Yeah. So you can imagine that News Corp is not happy. It's problematic enough for Tom to be having a side hustle at all. But if word got out about Tom's porn site, that is a major embarrassment for the very stodgy and stuffy Rupert Murdoch. Surprisingly, Rupert does not decide to fire Tom. Instead, he works to keep the whole thing under wraps. Maybe he went to visit the site

and he really enjoyed it secretly. Maybe he has a top eight there. Maybe he has a top eight or just a couple tops. One reason why... Girl. One reason why Rupert might be willing to look the other way, for the time being at least, is that he still thinks that MySpace has the potential to make him even richer. So much so that he makes an extremely bold prediction.

He says that in 2008, MySpace will generate $1 billion in ad revenue. So that means Rupert wants to see a return on his investment ASAP. And that means the pressure is on for Tom to make sure the site is making that money. As a result, in 2006, MySpace signs a three-year deal with Google worth $900 million. That sounds like a major victory for MySpace, but it does come with some strings attached.

Google gets to be the go-to search engine service on MySpace, but MySpace has to hit certain targets for site traffic every year. That's a big ask. In other words, Google is paying to get their search boxes on MySpace, but in exchange, MySpace has to promise that more and more people are going to be using those boxes on MySpace, but in exchange, MySpace has to promise that more and more people are going to be using those boxes every year. The pressure to make MySpace profitable also means added pressure on Tom. He needs to be like crushing it. And right now he is not. An example of Tom not delivering goods, what's one thing that Tom considers

to be an important part of his job? Secret porn site. Secret porn site. It's keeping up with the music industry and bands that are on MySpace. And that sounds really reasonable. After all, music is a huge part of the site. But what Tom is actually doing is just like staying up till 2.30 in the morning listening to music on MySpace. Tom is spending a ton of time trying to add some totally rando features. Tom wants MySpace to have instant messaging, which is a good thing, a classified section like Craigslist, and even a virtual karaoke machine, whatever

that is. Hmm. I don't hate any of these because these are all features that Facebook has that were very popular, you know, like the Facebook marketplace, DMs. And, you know, I mean, listen, I'd never say no to karaoke. Yeah, same.

Well, the thing that is a little bad about these new features is that they're being developed in-house by MySpace, which is hugely time consuming for the people who work there. Like by contrast, Facebook is doing all of these things at the same time, but they're letting developers from outside the company create these applications for the platform. Like Farmville, that was huge for Facebook and they were able to get it on the platform without making a bunch of their engineers spend all day designing pixelated chickens. Right, third party stuff. Third party stuff. Another big problem is also starting to rear its ugly head. Remember how when Tom and

Chris built the site they used that extremely basic coding language? Well, that choice is also starting to catch up with them. The site has gotten so big that code is no longer good enough for what they need it to be able to do. One person who works at MySpace says it took literally 10 to 15 times longer to build code on the MySpace system than it would on any other technical platform. Ironic twist, right? The thing that initially let them move so fast is now preventing Tom and MySpace from making big essential changes. In other words, the break things part of move fast and break things, it's catching up with them. These days, we'd say, you know, if you look around, then you find out.

Yes, yeah, and they're they're finding out. But if you can believe it, it's not just the rise of Facebook that sends MySpace to the grave. The end of MySpace is kicked off by an investigation. Dun, dun, dun. An investigation. Dun dun dun. Ooh. I know. So in 2006, the attorney general from Connecticut announces he is opening an investigation

into pornography on MySpace. Specifically, whether minors are seeing pornography on the site. One CBS News anchor says, quote, there are fears that this popular social networking website and others like it have become places where sexual predators easily prey on children. Another attorneys general around the country,

not wanting to miss out on the media frenzy, start their own investigations. It's just a windfall. And Tom's reaction to all of this, his take is that it's not MySpace's job to keep tabs on what kids are doing. That's a job for their parents.

Great. That's going to be awesome to say in court. Now these investigations definitely aren't helping the situation at the company. The MySpace team, which has already stretched thin by working on all of Tom's wacky features, now has to work on trust and safety and privacy features as well. And this also creates an opportunity for Facebook. Zuck and Co. capitalize on the chaos at MySpace and the media panic by presenting themselves as the safe alternative social media platform. Oh my god.

This all happened so fast. This is like we're talking about like three years. This is crazy. Yeah. This is in three years time. So in short, Myspace's reputation is starting to tank. And you know what else doesn't help the site's reputation? That Google ad deal we mentioned earlier.

According to Chris, this deal makes them have to double the number of ads on the site and a lot of these ads are really low rent. One is just a picture of gross looking teeth. Another incredibly scammy ad has the text, want a girlfriend? View hundreds of pics here. And as one analyst puts it, MySpace has become an eyesore. Yeah. Do you remember any of the like terrible ads back in the day? Yes, it was haunting.

And again, because people could customize their pages, you couldn't be sure what was an ad and what was like some bizarre decoration created by the person whose page you were on. So where's Tom as all of this is happening? Well, it seems like he's either unwilling or unable to find a way to turn things around. And as far as News Corp is concerned,

the problems with MySpace are Tom problems. One exec totally throws him under the bus saying, Tom was responsible for the product, but ended up being a complete bottleneck on getting things done. So, sorry Tom. He is now skating on thin ice, and that ice just keeps getting more cracks in it. So the site's sloppy coding.

Because of it, MySpace has a reputation for being notoriously buggy and has become an easy target for hackers, taking another major hit in 2007 when a bunch of musicians, including Alicia Keys, have their pages compromised. And when the hack happened, if you clicked on basically anything on the hacked pages, you'd get taken away to another page selling scammy software and filled with malware. Oh, God. Yeah. Myspace even got earlier threats from hackers about taking down the site so someone in charge like Tom absolutely should have seen this coming, but nobody, certainly not Tom, was

able to prevent this majorly embarrassing incident. If I clicked on the page of a beloved performer and was swept off to, you know, malware.blogspot.co.uk, I would never forgive them. And that, and ultimately if I was legal representative of some of these artists, I would be making that case in court. I would say, I would say people trust Alicia Keys with their sensitive financial information. And you allowing her page to become compromised. I keep on falling deeper down a hole of malware at this point, okay?

I wouldn't have it. I don't want it. Is this a, potentially, I mean, this is all very much in line with what I would do if I were a former hacker turned corporate sellout in golden handcuffs. I'd just keep working at that job and, you know, making these kinds of decisions. It feels like Tom's riding a $30 million wave to fuckster or whatever the secret porn site is. Yeah.

Yeah. But Tom, they keep him around, but only as a consultant. So now that might not sound like such a bad deal for Tom, but it seems like this is a way to fire him without actually officially firing him. So Tom is not feeling good about this new arrangement. Even if he's still technically a part of MySpace, Tom no longer has any real control over the company. And you have to imagine for a guy like Tom, this has got to be pretty frustrating. But Tom hangs in there for a bit, maybe trying out an early version of quiet quitting.

But a year later, he no longer has any role at MySpace. Do you think there's anything that he could have done to not be sidelined? Not sell your company. If you love something, you don't sell it. So Chris and Tom are now gone, but there's a ton of chaos and turnover in MySpace's management, and the site just continues its decline. In a truly ominous sign, in July, Facebook dethrones MySpace as the number one social media site. In a desperate effort to turn things around, the new MySpace team decides they need to revamp the site. And so in 2010, they debut a new and maybe improved MySpace. Here's what the new version of the site looks like.

Oh dear. Oh, it looks like Facebook. I see. They made a Facebook. It does look a lot like the OG Facebook. Yeah, it looks like the front page of a Huffington Post. It looks like those old digital news sources that's just three columns of posts

of people you don't, like current events people you don't follow. But yeah, heavily skewed towards music. Yes, it doesn't feel very like friends of my friends. It feels a lot more like, I don't know, TMZ. Yeah, a lot of TMZ. So yeah, people who are trying out the new version of the site, they are not impressed.

One tech journalist writes, it's a vaguely decipherable mess of pop culture, status updates, thumbnail photos and usage data. I'm terrified by the mere thought of hanging out there. Okay, drama queen. Yeah, I don't know if I would go so far as to say I'd be terrified, but I feel safe in my home looking at this page, but also it does not spark joy. I love a digital media critic being like, I can't stop screaming, even thinking about this website.

I'm shaking in my boots boots imagining this website. Wow. There is one more change they make to the site in 2010, and this has to upset Tom more than anything else. Brace yourself. Tom is no longer the first person you become friends with when you sign up for the site. Is there a replacement, Tom? Well, instead you automatically become friends with a profile page called Today On My Space. This page is referred to by its acronym, Tom,

which is so petty. Oh! Today On My Space, no. See, that is like the most classic corporate takeover redesign thing, where you take something that is asymmetrical and quirky and bizarre. I remember the fact that someone was like, oh, the first person you become friends with on MySpace is Tom who made MySpace.

And it's so bizarre, but you love it. I remember signing up when I was a teenager and being like, oh, some random guy who made the thing as your first friend, that's fun. And the fact that in their last bit, they're like, we will crush the original spark of joy associated with this website in a desperate attempt to reclaim relevancy.

God, terrible, terrible, terrible. So cosmetic changes, good or bad, after the MySpace debuts, the site loses almost a third of its users and the amount of ad dollars it's bringing in plummets going down 40%. They also lay off like a third of their workers in the US and two thirds of their overseas employees.

So what's Tom up to as MySpace is circling the drain? Not a whole lot. He's become a prolific social media user, posting about tech trends on social media. So from founder of head of a major company to Twitter reply guy, ouch. Meanwhile Rupert is looking to sell MySpace. His investment has not panned out the way he'd hoped. Far from making a billion dollars like he predicted, the site is losing tons of money for News Corp. I mean, it was embarrassing to still be on MySpace in 2010.

It's now more embarrassing to own it for Rupert, so he's looking to get rid of it. And in 2011, 600 more people lose their jobs at MySpace, and just a few months after that, Rupert finally finds someone to buy the company. Rupert sells MySpace for a pathetic $35 million. That's a huge loss. He's only getting back around 6% of the $580 million

he paid for the site only six years ago. Later, Rupert would call buying MySpace a huge mistake. So let's do a little, where are they now? MySpace bounced back and is now once again the most popular social media site in the world. We're all on MySpace, right? Oh my God. No, obviously not.

The site has only continued to decline. In 2019, everything uploaded to the site prior to 2016 was accidentally deleted. Oopsies. Awesome. But in some ways, that's the best thing MySpace has done in years. The site has basically completely shut down between 2022 and 2024, though apparently this year it's become active. Once again, here's what the homepage looks like in 2025. Whoa, it's just a news site.

It's a news site. It's a music news site. Wow. Yeah. Yeah. Celebrity gossip and news. That's what it is. Maybe in a few years, I'll eat my words and I will be asking you guys to friend me and follow me on the big flop on my MySpace page. I don't know. I mean, listen, I think, you know, everything old is new again.

History and fashion is cyclical and Neopets are back. So that's about the same. Maybe it's due for a comeback. You know what? If I had to predict what's going to happen with MySpace, here's what I'm saying. 35 million, it got bought for. We don't know who it got bought for. I think next year it gets bought 700 million by Friendster. Big comeback. Ooh, big comeback. As for Tom, he is apparently worth 60 million dollars,

which is not too shabby. He mostly stays out of the public eye and seems to spend a lot of time on landscape photography so that's him. He's very much known, remembered as a meme and a symbol of an earlier era of the internet but he will always be associated with MySpace and ultimately the site's failure. He is MySpace Tom after all. So here on the big flop we try very hard to be positive people and end on a high so are there any silver linings that you can think of that came about from Tom and MySpace? For the world or for Tom? Because he's worth 60 million dollars and he gets to live his landscape photography dreams. For the rest of us, I mean, we have my chemical romance

and a lot of musical acts that we would not have had without the popularity of MySpace. You know, I think for Tom, I would say each of us only gets to light our candle for but a brief window in the turning of ages. And for Tom, there was a shining moment where he was king of the hill and had more friends than any man before him. If we cannot raise a glass to that, then what can we raise a glass to? Cheers to that. For the world, huge net loss, social media, enormous mistake. So now that you both know about MySpace Tom, who built the most popular social media website

in the world, but let it become a completely irrelevant punchline, would you consider this a baby flop, a big flop, or a mega flop? This is a Skype level mega flop. You were way out in front, baby. You were way out in front, baby. You were way out in front.

How did this happen? You got overtaken. It's that don't, don't take your eyes off the ball. You got zucked, come on. I would say, like I'd say this was a big flop, a medium to big flop. Overall, like, there was no world in which he could have made all of the right business decisions and had all of the technology available to make it Facebook.

But I think, as Brennan said, the first guy over the top, and he, you know, came out wealthy and, you know, can be remembered as somebody who founded a social media platform that didn't directly become evil. Also, it's like the only person who really got hurt was Rupert Murdoch. He's the only one who really lost out. Which I think, okay, that's a super- And he's also doing fine.

He's also doing fine. Actually, Misha, great point. Can I retract my answer? Net positive. Net positive. You said can I retract? Can I retract? Net positive.

Yeah, wait, actually fuck that guy. Net positive. Well, thank you so much to our guests, Erika Ishii and Brennan Lee Mulligan for joining us here on The Big Flop. You two deaf would have made my top eight. Oh! And thanks to all of you for listening and watching. If you're enjoying the show, please leave us a rating and review or subscribe. We'll be back

next week with another flop. Watch out, this flop is a little… moist. Remember when we were all mailing a company our spit in a tube? Well, that company ran out of customers willing to give away their genetic information. It's the DNA testing company that launched everything from billboard hits to Barbie dolls. 23andMe. Bye! Goodbye! If you like the big flop, you can listen early and ad free on Wondery Plus. Join Wondery Plus in the Wondery app or on Apple podcasts. Prime members can listen ad free on Amazon Music. Before you go, tell us about yourself by filling out a short survey at

Wondery.com slash survey. The Big Flop is a production of Wondery and AtWill Media, hosted by Misha Brown, produced by Sequoia Thomas, Harry Huggins, and Tina Turner, written by Anna Rubinova and Luke Burns, engineered by Zach Rapone, with support from Andrew Holtzberger. The video podcast is edited by Olivia Vessel. Managing producer is Molly Getman. Executive producers are Kate Walsh and Will Molnati for At Will Media. Legal support by Carolyn Levin of Miller,

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