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Everyone makes mistakes, but what does one do when those mistakes cost you hundreds of thousands of dollars? What do you do if it costs millions? Mistakes are one thing, but throwing away millions to buy failing tech companies or buying entire towns (yes, like in Schitt’s Creek) nearly ruined some of the world’s biggest stars.


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Some were conned by fraudulent financial planners, like the infamous Bernie Madoff, while others just overestimated their influence on the market (see the section on Planet Hollywood). Many stars have made terrible investments, some have bounced back while others were far less lucky.

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9/9 Justin Timberlake Bought MySpace

MySpace was well on its way toward obscurity by 2011. This was not enough to deter the former N*Sync star from purchasing the drowning website. Myspace’s creator, the notorious Tom, originally sold the site for $508 million to Rupert Murdoch’s company Newscorp in 2005. Timberlake and the company Specific Media got it for just $35 million. Such a low price tag for what used to be a site with hundreds of millions of users should have been a huge red flag, Justin. Myspace is still around by the way, but now it only focuses on music streaming.

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8/9 Ashton Kutcher And Diddy’s Video Chat App

The star of That 70’s Show has begun to make quite a name for himself as a tech investor and financier. He invested in companies like Uber early on and it has paid off, but not all of his ventures have worked out. Along with the musician Diddy, Kutcher invested over $1 million into Tinychat, a video chat and streaming platform similar to Chatroulette or Snapchat. Unfortunately, because those sites already exist, along with several others like Skype or Zoom, there was little demand for their product.

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7/9 Kanye’s (Allegedly) Buying Parler

Kanye West, who now just identifies as Ye, has been melting down before the public’s eyes. For over a year the world watched him stalk his ex Kim Kardashian and harass her boyfriends, and in late 2022 Ye suffered his worst fall from grace yet when he made a constant series of antisemitic comments which ultimately cost him his contracts with Adidas and caused a massive decline in his net worth.

Now, with conservative pundit and alleged grifter Candace Owen’s in his ear, Ye doubled down on his new right-wing slant by announcing he will buy Parler. Owen’s husband is the CEO of Parler, a far-right alternative to Twitter and Facebook that has been failing ever since it launched. The site is notoriously glitchy and critics have pointed out that while it advocates for “totally uncensored free speech” users who have been critical of Donald Trump and the right wing have been banned. There is still time for Ye to get out of the deal.

6/9 Jay-Z And The Tidal Fiasco

Tidal was meant to be a “luxury music streaming service,” whatever that means. Tidal originally was a medium that would stream higher-quality sound and was going to be the only online home for some of the world’s biggest musicians. Madonna, Daft Punk, and of course Beyoncé were all initially part of the venture and were a part of Tidal’s launch. The problem was, no one cared enough or even really noticed the difference in sound quality between Tidal and other music streaming apps. Jay-Z would eventually sell Tidal to Square, the company owned by Jack Dorsey, the former owner of Twitter.

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Related: This Is Why Tidal Completely Flopped As A Streaming Platform

5/9 Guess Who Invested With Bernie Madoff

In 2008, just as the economy crashed and the recession began, many Wall Street crooks were outed for being the frauds they are. Among them was Bernie Madoff, who ran the largest Ponzi scheme in American history. When the scam all came crashing down, thousands of people lost everything, and some of them were huge stars. Among the people who have lost money thanks to Bernie Madoff are Kevin Bacon, Kyra Sedgwick, Steven Spielberg, Zsa Zsa Gabor, and Kim Basinger to name just a few. While Speilburg was able to recover (he is now a billionaire) stars like Bacon and Sedgwick have had a much harder time recovering their losses.

4/9 Kim Basinger’s Schitt’s Creek Moment

Basinger did not just lose money to Madoff. The star was forced to declare bankruptcy in 1993 for a variety of reasons, most of which were poor investments. One of Basinger’s most outrageous investments was the time she purchased an entire town in Georgia for $20 million in 1989. The plan was to build movie studios and tourist attractions but it eventually all collapsed. She resold the town for a measly $1 million.

3/9 What Ever Happened To Planet Hollywood

Ever wonder why you don’t see Planet Hollywood restaurants anymore? Well, a few still exist but the time when they decorated almost every major American city is long gone. While the idea of eating at a place owned by Arnold Schwarzenegger, Demi Moore, Bruce Willis, and other stars while surrounded by real props from their movies might sound like an appealing business plan, the public eventually grew weary of the schtick. Also, following the economic crash of 2008, many did not have the kind of disposable income that eating at places like Planet Hollywood needed.

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2/9 Donald Trump’s List Of Failed Ventures

Politics aside, Donald Trump is not the great businessman he sells himself as. There are many more failed ventures with the Trump brand on them than there are success stories. Trump Vodka, Trump Steaks, Trump Airlines, Trump Mortgage, and Trump Water are just some of the many failed businesses of the disgraced former president.

Related: Before Becoming President, Donald Trump’s Biggest Enemy Was Kristen Stewart

1/9 Elon Musk Spent $44 Billion For An App He Uses For Free

Elon Musk bought Twitter for $44 billion, and almost immediately upon taking it over the app lost over 1 million users. Musk bought the company promising it would be a beacon of unhindered free speech and that he would revitalize the tech to purge the site of trolls and bugs. So why did millions quit the app? Well, within hours of Musk’s takeover the use of racial slurs skyrocketed by 500%, and he launched an idiotic “pay for your verified checkmark” plan that allowed anyone to become verified (causing a slow retraction of his “no content mediation” policies) and within days more than half of Twitter’s employees quit. Many now believe the collapse of Twitter is imminent.

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