The Big Flop - Ozy Media: Fake It Till You Break It with Mara Wilson and Nish Kumar | 68

Episode Date: December 30, 2024

Carlos Watson built Ozy Media on a foundation of lies, fake views, and impersonated executives. From star-studded festivals that never happened to a $40 million con call, Carlos built a multi-million dollar media mirage. Ozy’s story proves that in the world of startups, sometimes the biggest disruptor is reality itself.Mara Wilson (Matilda, Where Am I Now?) and Nish Kumar (Pod Save the UK, Mash Report) join Misha to invest some of their time into this promising business... flop.Follow The Big Flop on the Wondery app or wherever you get your podcasts. You can listen to The Big Flop early and ad-free on Wondery+. Join Wondery+ in the Wondery app or on Apple Podcasts.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to The Big Flop on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/the-big-flop/ now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

You know what's even better than listening to the big flop? Listening to the big flop without any ads! With Wondery+, you can enjoy the floppiest of flops, completely uninterrupted. It's like having a front row seat to the world's biggest train wrecks. Join Wondery Plus in the Wondery app or in Apple Podcasts and upgrade your listening experience today. On Groundhog Day 2021, managers from Goldman Sachs, the very wealthy bank, sit down to a Zoom call. It's a typical reference meeting to see if a recommended company, Ozymedia, is a good investment.

If yes, they'll happily throw in $40 million to see if this news startup gives them that sweet ROI. But the meeting is delayed. Alex Piper, the Google executive who's supposed to talk up Aussie media, is missing. Alex seems to be running late and requests to shift from a live Zoom call to a simple phone conversation. Perfectly normal business stuff. Alex tells the Goldman Sachs crew that he loves Aussie media, like really loves them.

He stumbles a bit and weirdly refers to Aussie as us rather than them. That's fishy, but no deal breaker. Executives aren't always the most articulate. Little do the Goldman Sachs folks know that Alex isn't really Alex. He's a guy named Samir Rao, who's actually the number two at Ozzy Media, and he's speaking through a voice modification app. Sitting next to him is his partner, Carlos Watson, the face of Ozzy. LOL. This is technically a bank heist. On the phone, Alex's voice starts to sound kinda odd. Like it's changing in unnatural ways. Man, there are bad tech days and then there are bad tech days. At least that's what

the Goldman Sachs employees assume. They couldn't begin to imagine they're being conned or that Carlos is literally texting Samir every word he says. The call ends and some members of the team are impressed. 40 million is a drop in the bucket for Goldman Sachs. They just need to send a nice follow-up email and seal the deal. Except they send it to the assistant of the real Alex. Except they send it to the assistant of the real Alex. OZZY does serious journalism, serious storytelling. You raised almost a hundred million dollars and what do you have to show for it? Calling OZZY Media a dumpster fire is an insult to dumpsters and fire. We are on a sinking ship. From Wondery and at Will 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 who discovered TikTok. Don't look it up, just take my word for it. At Don't Cross a Gay Man. And today, we're taking a look at Aussie media. Now everyone, I'm so excited just like I am every episode because we have some fabulous guests. First, we have the author of Where Am I Now? and actor of some of your favorite films. It's Mara Wilson.

Welcome to the show. Thank you so much for having me. I love this show. Thank you so much for having me. I love this show. Thank you. Also not to be outdone, we have the host of Pod Save the UK and a comedian who's currently on his Nish Don't Kill My Vibe Tour. It's Nish Kumar. Welcome to the show. I'm thrilled to be here. Sometimes I get asked to do things. I think, I wonder why I was asked to do this. And then I remember that I made a show for Quibi. And so if you're talking about prominent failures, you've got

to get me on. If you make it a podcast about shipwrecks, get someone who was on board the Titanic. Come on. Yeah, we did Quibi at the very beginning of our series. I heard it. Bless you. It was hauntingly accurate. Yeah. Today, I mean, it does seem like all news media companies are struggling a little bit.

Serious outlets like the New York Times are offering silly games to desperately keep their audience while formerly successful video heavy disruptors like Buzzfeed and Vice are basically on life support at this point. But about a decade ago, one entrepreneur, Carlos Watson, thought he had the secret formula to beat them all and founded his own company, Ozymedia, to disrupt the disruptors if you will. He figured he could conquer all media, even live events. But very quickly, experts start doubting if Watson was anything but a con man, more so than all the other media moguls. I feel like there's such this like early Gen X,

late millennial fetishization of disruption. Yeah. And as somebody who often had a disruptive slash excessive talking on her report cards, disruption is not a good thing necessarily. Same. Like that can get you in some serious trouble with your parents. Disruptive children who spent like their entire childhoods being told off for being disruptive and have now spent their entire adult lives going, well, why are they allowed to disrupt everything?

Yeah, exactly. Well, before we learn about the company, let's learn a little bit about its CEO, Carlos Watson. Watson comes from a Jamaican-American family in Miami. And according to his bio, he grows up on food stamps, but is able to overcome his humble beginnings and gets a scholarship to Harvard. Okay. He's an overachiever. So of course he goes on to study law at Stanford where he is one of the editors of the law review, but not the editor. And this is a

important distinction because even though he's genuinely accomplished throughout his life, Watson tends to embellish a little bit. We'd never do that, would we? No, and you can hear about that in my book, The Man Who Never Lied. So, Watson graduates from Stanford in 1995 and moves to East Palo Alto, then known as the murder capital of America. Uh oh. There, he tries to do some good by starting a group called the Successful Young Black Men's Mentoring Program, rolls right off the tongue, offering kids advice on getting into and paying for college. So that's really great.

And this gives him the idea for his first for-profit company, Achieva, which later gets bought up by Kaplan, a test prep service, thereby wetting his appetite for entrepreneurship. It's actually through volunteering where he meets philanthropist Laureen Powell Jobs, wife of Steve Jobs. Now you might know Steve Jobs. He started this little company called Apple. They make something called computers. Of course I know Steve Jobs. He was friends with Seth Rogen. He was great friends with that guy who loves weed. Right. Right. But Laure Lauren Powell Jobs has a huge heart and she and Watson team up to co-found a nonprofit called College Track to help kids not just get into college, but also to finish it.

This is good stuff. Right. Yeah, that sounds like a good idea. Yeah. I've worked with a couple of youth development organizations and a lot of them do really great things, but sometimes there's some kind of eccentric people behind the scenes, you know, because you get a lot of like philanthropists who donate money and things like that. So you kind of end up sucking up to these people who, like, I remember being in ones like right after the, you know, 2008

financial collapse and having to like thank the volunteers and the people who donated money and knowing like, wow, you guys destroyed our country and really the world, but thanks for like giving kids scholarships. Yeah. Philanthropy is a weird world. Sure is. I'm very used to hosting charity events, but because I have no sort of administrative responsibility within the charities, I'm very capable to just go, give us your money, you rich turds. Yeah. I think maybe guilt and shame go a little bit further in the UK than they do here as well.

Yeah. I don't know if you know a huge amount about our country's history, Myra, but we are neither guilty nor embarrassed about any of it. That is very true. That is very true. Nothing ever happened in any of the Commonwealth countries ever. That was bad. Our museums are full of our own stuff. Well, in addition to his college prep projects, Watson does some consulting at companies like

Goldman Sachs and blue chip consulting firm McKinsey. And then he gets work as a political analyst for networks like Fox News, Court TV, CNBC, and CNN. I mean, he's hot stuff. Literally. People Magazine names him one of their hottest bachelors of 2004. And in 2009, that hotness lands Watson his dream job as an anchor for MSNBC. I think in the context of the news media, he's very good looking. Like, it's like when even people talk about attractive politicians, you're like, yeah, in context. Yeah. Like in the context of politicians, that's a good looking politician. Well, fortunately, he's good looking, but unfortunately, his show gets canceled.

Been there, brother. Been there. So right before he got hired and fired from MSNBC, Watson was inspired by the 2008 presidential election, yes we can, to start his own blog, The Stimulist, his first dip into media startup waters. Well, now that he's fun-employed, Watson thinks he can cause a stir by launching a media conglomerate that will shake the industry to its core. How? By catering to readers who are hungry for topics mainstream media simply ignore. Nobody's

ever done that before, except Vice, Buzzfeed, Gawker. Yeah, we had those things by then. Yeah. Sure did. It's sort of like in 2008 saying, I've come up for this amazing thing, right? It's a pod for your music. You just put all of your music in a little box so that you could listen to it. It's, it's, he's sort of arrived a bit late in the day to this, right? You're tapping on a theme that just goes right through this whole story.

But Watson, to his credit, says that he has a new angle to this. He thinks about how his grandmother, who was born in 1902 in Jackson, Mississippi, learned almost everything she knew about the world by reading Life magazine. His company will also broaden the horizons of curious young people in hard-to- reach areas and help them become well-rounded and savvy individuals. So he calls his venture Ozzy after Ozzy Mendeas, the sonnet from the poet Percy Shelley. Okay, just a second. Isn't Ozzy Mendeas, the whole point of that is that like there was this man who was famous and world renowned and now is nothing?

That's like the whole point of that poem. That nobody will remember you. You are absolutely right. Is it the last line, is it look upon my works you mighty despair? Like that's the phrase that people use from that poem to be like, I have really shat the bed here. Yeah. So for any of our listeners who haven't read The Watchman or watched Breaking Bad,

the poem tells the story of a pedestal next to the destroyed statue of King Ozymandias, where an inscription tells whoever reads it to gaze upon Ozy's grand empire and feel amazed and intimidated by all the great things he's made. Except, it's all destroyed by that point, so the inscription is a bit ironic and sad. Yeah. So, feels like a bad omen, no? Why would you do this? Why would you open a shipping company called Titanic Shipping? Like, it doesn't make any sense.

Yeah. Well, he explained that the poem inspired him to think big, which, gosh. And why not pick up on my new idea, Hindenburg Aviation? Well, for COO, Watson enlists his friend from Harvard and fellow Goldman Sachs alum, Samir Rao. And more importantly, he calls in a favor from his extremely wealthy acquaintance, Laurene Powell Jobs, to cede the company. So, by 2013, Watson receives $5 million from Powell Jobs and another $20 million the following year from a German media conglomerate. So Watson uses all that money to hire top tier journalists from places like the Wall

Street Journal and the Times of London. Now, to take back what MSNBC took away, Watson starts his own talk show, The Carlos Watson Show, on YouTube, featuring interviews with musicians like John Legend and politicians like Hillary Clinton and Joe Biden. The talk show has good numbers and Watson seems to have a knack for having his finger on the pulse of what's trending. So he and Ozzy's staff say they can predict who's going to make it big before anybody else. And to learn about Ozzy's talent for discovering new talent, let's play a game. Here are the rules. I'm going to describe some folks who Ozzy claims it discovered and you tell me their names.

who Ozzy claims it discovered and you tell me their names. This young, globe-trotting funny man could be the new Jon Stewart, according to an Ozzy headline from March 26th, 2015. Who is it? Trevor Noah? Ding, ding, ding! Yes, Ozzy Media claims to have found Trevor Noah. Here's the problem.

Here's the problem. This was published only four days before Noah was officially announced as the new host of The Daily Show. And he'd already been a correspondent. Yeah, we knew who he was. We knew who he was. Also, the name of the article was changed after the announcement. It used to be, What an African Finds Funny About America. Oh, okay.

Oh my god. Yeah, that's the first one. Next cue. This little-known comedian was super awkward when Ozzy ID'd her as the next big thing. And Ozzy was right, because she ended up starring in her own dramedy on HBO. Issa Rae? Ding, ding, ding! Oh my gosh, y'all are so good at this game. Yes, Issa Rae? Ding, ding, ding. Oh my gosh, y'all are so good at this game.

Yes, Issa Rae. Now Issa Rae's Aussie profile was posted in 2014, two years before Insecure premiered on HBO. But her YouTube show, Misadventures of Awkward Black Girl, was a huge deal by 2014. And she was listed in Forbes as one of their 30 under 30s. So I'm pretty sure that means she was already discovered. Yeah, they're pulling a British museum. He's discovering things that were already discovered. A part of me weirdly respects it. All right, one more.

She's just a bartender or is she going to take politics by storm? Who is this mystery woman on the go? AOC. Ding, ding, ding. When was that posted? Last month? Yeah. Yeah. Yeah. Ozzy profiled AOC a month before she won her congressional seat.

But months after Mother Jones and the Wall Street Journal already did the exact same thing. Yeah, this was like after we'd seen videos of her dancing. Like, there were like viral videos of her dancing when she was at Boston University, I think. Like, people were talking about her. Yeah. when she was at Boston University, I think. Like, people were talking about her. Yeah, Watson also takes credit for discovering the poet Amanda Gorman, pop star Dua Lipa,

baseball outfielder Aaron Judge, and bizarrely, Judge Brett Kavanaugh. Oh God. What? Why would you want to take credit for him? I don't know. Also, Dua Lipa's British. I don't want to play this card. But you can't claim you discovered Dua Lipa. What are you going to claim you discovered Oasis next?

Come on, America. So, anyone paying super close attention at this point catches some of these fibs and is already a bit skeptical of Ozzy, but nobody consequentially sounds the alarm. Like, not yet anyway. In public, Watson keeps chugging along, pretending to be an inventor that everybody loves and wants to work for. His main goal is to woo new investors and keep the old ones in line. And he can do that by capturing as much of an audience as possible so that the company can get acquired. So how about an in-person live event? Did someone say fire festival? I mean Ozzy Fest? Oh no. Because it's basically the same thing. It's 2016, Carlos Watson launches the first Ozzy Fest.

It takes place in a modestly sized venue called Rumsey Playfield in Central Park. The lineup includes comedian Phoebe Robinson, Broad City, Issa Rae, Corey Booker, and Karl Rove. What? Mm-hmm. Yeah, one of these things is not like the others. There are some musical performances, Y. Clefshon, Will.i.am, and others. And about 2,000 people show up.

Listen, if you're gonna lose a whole load of money, you gotta have a musical performance by Y. Clefshon. Yeah. Yeah. Yeah. Yeah. Yeah. Nothing soundtracks a debacle more than that man went on till November Live. But for his first live event, not bad, right? Decent lineup, okay attendance. However, problem, Ozzy and Sharon Osbourne promptly sue Ozzy Media for trademark infringement. Oh, of course.

Yeah, well, their Ozfest was founded in 1996. It's an annual heavy metal music tour. And the Osbournes feel the name Ozzyfest could confuse their audience. They even argue the logo is psychedelic, so fans of heavy metal might actually think they should go. Well, the parties eventually settle the trademark infringement case suit. Watson promises to make Ozzyfest as dissimilar as possible to Ozfest and even offers the Osbournes some stocks as a mea culpa.

Good Lord. Yeah. So in 2018, Watson tries OzzyFest again. This time, he leans on his famous friends and cuts some large checks to get bigger names for the event. Headliners include baseball stars Alex Rodriguez, Hillary Clinton, interviewed by Lauren Powell Jobs with performances by Common and Passion Pit. Why is Hillary Clinton at all of these events? Yeah, what year is this? 2018.

Okay, I think by 2018 we kind of had Hillary Clinton fatigue. Yes. We were like, you're not, you know, you couldn't do it. Why are you still everywhere? The country said no to those kitten heels, hon. Like, this Ozzy Fest also goes just okay, but Watson tells a more obvious lie than usual. In a press release, he claims Ozzy sold 20,000 tickets to the event, which was impossible because the venue only holds 5,000. And even then, former employees claim they practically

had to give the tickets away. The next year, in 2019, Watson announces that Ozzyfest is expanding. Oh my god. This time to Central Park's Great Lawn. What? He claims 100,000 people will be there. It'll be swarming with celebrities too, like Trevor Noah and Shark Tank's Barbara Corcoran and Mark Cuban.

What? What? This is the thing, like, is this supposed to be a concert? Is this supposed to be comedy? Is this supposed to be standup? Is this supposed to be like... And who is this for, really? I'll tell you who would have livened up Woodstock. Mark Cuban.

Exactly. Well, here, I hope I can clear up some of the confusion, because we do have a couple more guests where it might become more clear. Celebrated chef Marcus Samuelson will do a brunch event. And there's also going to be a, wait for it, petting zoo. There's lots of festivals that happen through the summer in the United Kingdom. There's all quite a big part of the comedian's calendar because there's always a comedy stage at all of these things. I've never heard a festival say,

you gotta check out our brunch. Not one time. While you're coming down from MDMA, why not have some poached eggs? So with an event that has 100,000 people coming, all of these events. So many people. From musical performances to panels to petting zoos

and don't forget the infamous brunch, how much time do you think Watson has to plan and put this festival on? I'm gonna say based on what we know about him, he announced this the week before. Yeah. Close. Yeah, it seems like that.

You would want to think like six months, but. Yeah. Right. At minimum. Yeah, at minimum. Two months. Oh, God. Two months. But even the Parks Department personnel are like WTF. Even Leslie Knope did not believe that it was possible to do this.

But they move forward with permit approvals due to pressure from above. So 500 ads are put out promoting the event, costing Aussie media probably like $2 million. And in true Aussie fashion, they mix some untruths into these ads. For example, one of the ads features a photo from a different, more popular gathering called the Global Citizen Festival. So here's the real Ozzyfest of 2018. Oh, okay. It's sort of, there's a sign with a... It looks like a sort of badly attended panel at a television festival.

And I speak directly from experience. Here's the picture Ozzy used in the promo materials. LAUGHS Yeah. It's just people stretching back as far as the eye can see. Phones out. Phones out. So in response to being called out for this, an Aussie spokesperson just says, one of our team members made a mistake and we apologize. This is great.

Which let's remember that because Aussie will use that excuse again, but we'll get to that in a few. So the festival. Fast approaching and more and more about it is clearly sketchy. A-Rod keeps pretending to be part of OzzyFest, but according to some close to him, he's reportedly paid to say that. Oh, my God. LAUGHS Ozzy organizers claim Trevor Noah is gonna do stand-up,

but he's actually just a panelist. The list of sponsors for the festival is strange as well. Besides names like JPMorgan Chase, there's Wellbeing Trust, a mental health nonprofit that denies being involved, and also listed is the European Wax Center. Will they be doing waxings there? Like by the petting zoo? Right by the petting zoo. Get a nice little landing strip right next to the donkeys. Pet something furry and then get rid of something furry.

There we go. Well, speaking of the money, the most worrying part is how expensive the festival is to produce. The two-day event is going to cost Ozzy at least $6 million. Oh my God. It sounds like the guests from previous years were more interesting. I would want to see Issa Rae and Phoebe Robinson and, you know, common like- Mark Cuban's probably listening to this like, Ouch, I was there. Sorry, Mark Cuban.

I spent all day nude in a petting zoo for nothing. So, that's probably the end of Ozzy, right? Not yet. Suddenly, it's the week of the scheduled festival, and NYC experiences a massive heatwave, and Mayor Bill de Blasio cancels all large outdoor events like the New York City Triathlon and, luckily for Watson, Ozzyfest. But since the cancellation was out of Ozzy's control, they get a huge insurance payout. Now that's something the subject of our Fire Fest episode Billy McFarland probably wished he had. Yeah. Right. So we of course know that in 2020, live events of all kinds are a no-go.

So Ozzy Fest doesn't have another go that year. Although Ozzy Media has raised $83 million in investments by this point, Laureen Powell Jobs and German publisher Axel Springer have now stepped down from the board or away from the company and have diminished their contributions. But Watson is still using their names to make Ozzy seem more important. The company is bleeding money on famous writers, celebrity appearances, and, as the world discovers a bit later, paid views. Paid views?

Yup. He's paying for fake YouTube views. Oh no. Yeah, he's one of those. Wait, you can do that? Hold on guys, I just gotta call my investments guy. To seem enticing to more investors and bigger buyers, Ozy has been inflating their numbers, basically all of them.

YouTube videos that have over a million views only have a few dozen comments. Red flag. They claim to have upwards of 50 million monthly unique users. Seems high. They tout 20 million newsletter subscribers, which is nearly 10 times the normal amount. They even valued themselves at $159 million. I'd literally never heard of them before. Exactly.

And I was like exactly their demographic, I think. I was, you know, I was a 20 something in this time. Like I was coming into my my 30s. Not only have I never heard of them, but I don't think anybody I know has heard of them the way that they'd heard of, you know, Buzzfeed or Vice or any of these actually big name outlets. Matthew Feeney couldn't agree with you more. That's all I've been thinking. Like I'm thinking, I am surely the exact target demo for this. Yeah. You know, also, I'm in comedy as well. And there clearly seems to be some, like, weird interest in comedy.

Obviously, my feelings are hurt. I haven't been booked for a single Aussie test. It's okay. You got the Quibi show. Yeah. Let's focus on the positives. You're just not as funny as Mark Cuban. What can you say? Not as funny as Mark Cuban, what can you say? Well sadly, despite being someone who positions himself as a practical progressive, Wasson

does turn out to be a bad boss. Like a cartoonishly bad boss. He misleads new hires about what their responsibilities will be, hiring college kids to do way too much work. He uses his fleet of underpaid grunts to churn out articles, videos, podcasts, and newsletters. Watson demands that people work 18-hour days, are available for meetings on Sundays, and that they answer their emails on holidays. He crams workers into a tiny open office in Silicon Valley where pretty well-respected journalists don't even have space to take private calls for their reporting. And the

budgets are miniscule. But these writers are supposed to be breaking stories that bigger news outlets with more staff and more money can't even think of. One Aussie employee even describes being pressured to take stock options over a raise. So unsurprisingly, the grind gets to people and Aussie has an extremely high turnover rate. In just two years, 42 out of 50 full-time employees either quit or are let go. One employee has to enter a six-week outpatient program after suffering a panic attack, which could have been avoided if she didn't have to work 18-hour days for two weeks straight

to make marketing assets for Watson's all-important YouTube show. Watson's COO, Samir Rao, then pretends to be the HR director and calls this employee's doctor's office to double check that she really needs the time off for her depression. Oh, God. Oh, my God. He did some character work. Oh, no. Yeah. It really is. I mean, this is like that time when bad bosses are being outed all over the place. And this is after, you know, Theranos where everybody's like, oh yeah, if something your

boss starts giving you stock options, that's a bad sign. Yeah. Yup. How did you think this would never get out is really the question. Girl, you tell me. But it does, unfortunately, get worse. Oh, no. So let's do a little scenario. Pretend you're completely unscrupulous. What sort of scheme would you come up with to fool a big investor into giving you a bunch of money?

I mean, do we have somebody like the HR person who can do some character work? I mean, do we have somebody like the HR person who can do some character work? Oh my gosh. Yeah, yeah, you do. Do we hire actors to be, you know, happy workers? I mean, clearly he knows some comedians. Or are you hiring like actors to make calls and be like, hello, this is, this is Barack Obama. This business is fantastic.

Yo, I think you all were born to be white collar criminals because that's kind of what he does. Really? Kind of pushing the button here. So on Groundhog Day of 2021, managers from Goldman Sachs join a Zoom meeting with Alex Piper, a Google content executive. Now this is just between Goldman Sachs and Google. It's a reference call to see if Aussie is a good place to invest in. So, Carlos Watson, he's not there. Unfortunately, Alex is running late and is having problems logging onto Zoom.

So he asks the Goldman Sachs folks to move to a conference call where Alex tells them how great Ozzy is, how much ad money Watson Show makes on YouTube, and how they plan to make more content with the company. I mean, it's definitely what an investor wants to hear. Well then, Alex's voice starts to sound funny. Some digital distortion creeping in. What, like auto-tune? Was it like T-Pain?

Or like the thing from Scream that the killer speaks into? Yeah. So after the meeting, a suspicious Goldman Sachs attendee does some Batman-level detective work and emails Alex's assistant to follow up about this call. The assistant gets Alex on the line and he reveals to Goldman Sachs that he was not at that meeting and someone must have been pretending to be him. Oh, so this is a real person they're pretending to be. This isn't just like, you know, what's a common name? Alex Piper. Yeah.

Hi, I'm Alex Piper. This is a real person. Real person. Yeah. The person pretending to be Alex Piper, that person, according to Google's investigation of the incident, turns out to be Samir Rao. No. Watson's number two, the COO of Ozzy.

Yeah. Oh, that's fantastic. That's at least twice that he's impersonated people to get something. So how do you think Watson covers for Rao's oopsie? He must have pulled the, I don't know who that is. Or, oh, they just made a mistake. Maybe he thought he was Alex Piper.

Ding, ding, ding. Mara, I'm telling you, you have a knack for this. This is scaring me. Remember the one of our team members made a mistake? Excuse. Well, Watson says Rao was having a mental health crisis and just decided to impersonate an executive. Rao, of course, needs to take a leave of absence to make this believable.

I mean, to get the help he needs. And because Watson is so charismatic, this somehow works with Goldman Sachs. That's not how mental health works. Yeah. He just had a crisis, believed he was Alex Piper, made a phone call. Yeah. Just hopped on a meeting.

But Goldman Sachs, they buy it. Not Google though. And they contact the FBI. Google the snitches, man. We know this. They're snitches. Google the snitches. Yeah.

Everyone, let's bring back Ask Jeeves. Yahoo would never. Jeeves has taken some of our darkest secrets to the grave. He sure did. So maybe Carlos Watson knows he's cooked or maybe he's oblivious. Either way, he acts as if the Google exec impersonation just didn't happen. In July of 2021, Watson announces a new Ozzy Fest, this time in Miami. Supposedly, they've partnered with TikTok and are sponsored by Chevrolet, YouTube, Clubhouse, Twitter, and others. But when Forbes reaches out to these companies for confirmation, They get no responses from half of them.

And YouTube and Clubhouse say, no, absolutely not. We are not involved with that festival. Well, yeah. I mean, I don't think that YouTube is still owned by Google, right? I think they've pissed off Google. They're not going to want to partner with them. Now, Ozzy does eventually postpone this festival due to the COVID Delta variant. Sure.

And it is never rescheduled. Imagine you're Watson here. Do you think you're in trouble? Or are you just like, I'm rich. I can do whatever I want. I mean, it's got to be a case of I'm rich. I can do what? Like, you would think at this point, self-awareness or shame

would have kicked in. Yeah, he seems like somebody who's just going to keep digging. Yeah. Well, regardless of what Watson is planning, journalists are already sniffing around Aussie media and nothing is passing the smell test. In September, a few weeks after AussieFest's latest cancellation, a bombshell profile of Aussie media is published by the New York Times. Oh no.

It's called Goldman Sachs, Aussie media and a $40 million conference call gone wrong. I mean, I do feel like this guy burned his bridges with a lot of journalists too. Yeah, absolutely. And that is specifically a dumb move because if you want to do some shady stuff, you don't want to be pissing off journalists left and right. Yeah. Yeah. If you keep saying stuff like we're way better than the New York Times, there's a chance the New York Times might have a little look and see what you're up to.

Yeah. Absolutely. And those people, besides breaking the news of the fake phone call, the author of that article, Ben Smith, puts into question all of Ozzie's tactics and potentially fake traffic stats. Even if other outlets had been thinking it, he is the first person to say it out loud. And the wheels come off the Ozzie bust almost immediately. Within days, sites like Axios are publishing articles like How Ozzie Fell. There is a dizzying amount of revelations. People learn that Ozzie's early backers have left the company. There are weird lies, like a claim made by Watson that Sharon Osborne became a friend and investor

after their Aussiefest trademark infringement lawsuit. I mean, even if the Osborne's had accepted free stocks during the settlement, which they say they haven't, they wouldn't technically have been investing anything into Aussie media. Listen, I've met all of my closest friends because they tried to sue me. How else do you people meet people now that Myspace is gone? Yeah. So Sharon, she calls Watson out, naming him

the biggest shyster I've ever met in my life. And Sharon Osborne said that. She's probably met a lot. She is a manager in the freaking music industry. Yeah. So anonymous sources start crawling out of the woodwork, saying more than 95% of the Carlos Watson Show's audience has been paid for through social media promotions that play automatically before the videos people actually want to see.

A writer and producer who were both hired to make a show for Ozzy say they were told it would air on A&E. They later learned Watson had no deal with A&E. So just like super weird lies. Now behind the scenes, Ozzy's board starts investigating. And by the end of the week, the board chair resigns and major donors jump ship. Big advertisers like Chevrolet, Walmart, Target, they all pull their ad buys. And by Friday, the entire Aussie staff, which was about 75 people, learns the company is shuddering via Zoom call. They get no severance and writers start hastily archiving their articles in the event the website goes offline.

Were they told about this by an actual person? Or was somebody fake on the Zoom call? Just AI Jesus. We've got to turn our cameras off, but we do have a treat for you. It's Christopher Walken. And Hillary Clinton. And Hillary Clinton. She's got to see it through. So in the middle of all this, Watson goes on NBC's Today and announces that the company's down, but not out. According to him, advertisers and fans of the company

reached out over the weekend and offered support. Is it another line? I don't know. Watson is also asked about the infamous phone call and here's what he says. Let's watch a clip. Did you know that your partner, the co-founder of this company, was going to impersonate a YouTube executive on a call. Yeah, no. And it's sad and it's difficult. It was wrong. Obviously, they figured it out very quickly. Why were you not on the call and how did you not have any knowledge of the call? Part of the fundraising process, you end up talking to a lot of people and I'm not on

every call. Almost that level of bullshit is actually something I admire. Because he is making total unblinking eye contact with a professional journalist and he is saying to him, I'm afraid I was taking a dump. Listen, I'm running a company. I can't be on every call like, are we going to get $40 million? I got things to do. Okay, I get the charming reputation now because yeah, it is very strange to see somebody like have very sincere eyes and, you know, and eye contact when they've just done something

this big and this stupid. In a different world, he would actually, I think, have been a very successful cult leader, who then ended up being the subject of one of these podcasts, just for a different reason. So I'm going to skip ahead past the couple of years where Watson keeps swindling people with weird PR tricks. Seriously, Google Carlos Watson Hugh Grant. I'll leave you to that. Ooh. So, in February of 2023, Watson, Samir Rao, and Aussie's former chief of staff, Susie Hahn, end up being charged by federal prosecutors with conspiracy to commit securities and wire

fraud. According to the indictment, Watson duped an investor into giving Ozzy $20 million by claiming that Google offered to buy Ozzy for $600 million. Wow. Watson's also charged with aggravated identity theft for that YouTube exec call. But wait, Watson said he wasn't on that call. According to Rao's testimony, the impersonation was all Watson's idea. He says Watson and Rao were in the same room

together on that call. He also says on the stand, he was trying to signal me at first, he was mouthing stuff to me that I wasn't understanding or receiving. And then after that, according to Rao, Watson started sending texts so he would know exactly what to say. Things like, I'm a big fan of Carlos, Samir, and the show. Oh my god. Yeah, I mean, they just needed to take one improv class. You know what I mean?

It's just, it's not that hard, guys. Well, I wish I could tell you that Watson and Samir tried to rip off a bank only once. But unfortunately, the 42-page federal indictment accuses Watson of forging a contract between Ozzy and the Oprah Winfrey Network for a supposed second season of a show. And then forcing his then

CFO to try to get a loan for Ozzy by showing this fake contract to a bank. Now to their credit, the CFO immediately quits and writes Watson and Rao an email where they say, this is fraud. And to be crystal clear, what you see as a measured risk, I see as a felony. The CFO was not implicated in wrongdoing or charged. Measured risk? Measured risk. That is incredible. We forged Oprah's signature and we consider that a measured risk.

Yeah. So, Watson, he's in big trouble, but he's a fighter. And during his trial, he gets a bright idea. So you remember Ben Smith, the guy who broke the YouTube Goldman Sachs story for the New York Times? Yeah. Yes. Well, Smith was at Buzzfeed when the company was looking at Ozzy for purchase.

And ever since the 2021 article went live, Watson has been claiming that Smith was out to get him. So as Watson trials heats up, he finds some emails where Smith is talking about Ozzy and uses these to sue Ben Smith along with Buzzfeed for a conflict of interest. I mean, brilliant idea, no? Jason Vale This is where I think I've lost my ability to be a white collar criminal because my instinct in that situation was he puts on a wig and a mustache and tries toly backfires on him. Watson is not supposed to

use anything from his criminal trial for any reason other than his trial. It's illegal. And it appears that yes, of course, those documents about Ben Smith were indeed from his criminal trial. So the U.S. attorney, Trying Watson, accuses Watson of trying to retaliate against witnesses. The prosecution even recommends Watson's bail be revoked since he can't be trusted to behave himself. Yikes. And unfortunately for him, a New York federal jury agrees. On July 16th of 2024, after an eight-week trial, Carlos Watson is convicted on all three counts and Aussie media, which Watson still owns, is

found guilty for conspiring to commit securities fraud and wire fraud. Watson faces a minimum of two years in prison and a maximum of 37 years. Wow. That's a big difference. But also this is America and America is known for, you know, kind of letting white collar criminals, you know, it remains to be seen how long he will actually serve. So let's do a little where are they now? Carlos Watson was just sentenced to almost 10 years in prison.

He maintains his innocence, of course, and argues that he didn't receive a fair trial and that he had been discriminated against. His prosecution and judge begged to differ. They said Watson violated a gag order by smearing his prosecution as a racist online, that he snuck phones into the courtroom, and that he illegally used discovery materials to retaliate against witnesses. And at his sentencing, his judge said, quote, the fact that we're here in this circumstance is tragic, but it's a tragedy of Mr. Watson's own making. Oh, and Lauren Powell Jobs, Alex Springer, and all of the other Aussie media investors weren't involved in any of these wrongdoings.

After his conviction, Watson also dropped his civil suit against Ben Smith and Buzzfeed. Ben Smith is still running his company, Simaphore, but he's currently being criticized for his downplaying of the Olivia Nuzzi, RFK Jr. sexting scandal. In defense of Nuzzi, who was critical of Biden while being friendly with RFK, Smith wrote, If you're not sleeping with someone in a position of power, how are you even a journalist? Oh my god. Wow.

I know. In response, NPR's David Falkenfleck said, that is pretty bananas. That's where everybody is. Good old NPR. That's such an NPR response. So here on The Big Flop, we try to be positive people and kind of end on a high. So are there any silver linings that you can think of that came about from Carlos Watson and Aussie media? I mean, here's what I will say.

There's the possibility of a silver lining. Because like, there's been a real vogue for like TV shows and movies about white collar criminals. I'm thinking of the Theranos one. I'm thinking of the WeWork one. What do those white collar criminals. I'm thinking of the Theranos one, I'm thinking of the WeWork one. What do those white collar criminals have in common? They don't just have white collars, they got white skin. This is an opportunity for us to make a show or a movie

that represents white collar criminals of color. The lack of diversity in white collar crime is stunning. We want to be represented in society as people of color. We can't be what we can't see. Hollywood, do your thing. They could call it the Wizard of Ozzy. The Wizard of Ozzy. The title's right here. It's right there. So now that you both know about Ozzy Media, would you consider this a baby flop, a big flop or a mega flop?

I'd say big flop. It's not mega flop because I feel like if it were mega flop, it would have disrupted our lives a lot more, I think. But it is a big flop in that like, these people are still very much screwed over and like these people are still, it doesn't seem like they've quite gotten away with it. And it does seem like a lot of lives were messed up in the process. So it is definitely, I would say, a big flop. Yeah. Big flop. No doubt this is a big flop. This is a big flop.

No doubt. This is a big flop. No doubt. Well thank you so much to our guests Mara Wilson and Nish Kumar for joining us here on The Big Flop. And of course, thanks to all of you for listening. If you're enjoying the show, please leave us a rating and review. We'll be back next week with another flop with an actor known for his stunts on and off the screen. it's Tom Cruise.

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