Investing ain’t always smooth, and in 2022 it’s so far felt like going six rounds of Squid Game. Last week Netflix (NFLX) joined the game after surprising investors with news of falling subscriber numbers. The Netflix share price sure got given the red light, plummeting 35% in one day. 🚦 Watching investments drop is a horrible feeling. But it helps to remember even the best investors sometimes get it wrong.

After publicly declaring his own monster shareholding in Netflix this January, famed hedge fund manager Bill Ackman took an equally monstrous US$430 million loss, dumping shares just 3 months after buying them. But that’s relative peanuts to the man once called Baby Buffett. Ackman once lost almost 10x that – around US$4 billion – on an investment in Valeant Pharmaceuticals (now known as Bausch Health Companies (BHC)) over a two year period. Talk about a tough pill to swallow. 💊 

When it comes to losing bucket loads of bills though, it’s another ‘Bill’ that really takes the biscuit. Last year private investor Bill Hwang reportedly lost US$20 billion in two days when his investment fund Archegos Capital Management blew up in what Bloomberg has called ‘one of the most spectacular failures in modern financial history’.

But there’s one fail that just might beat ‘em all. Back in 1976, alongside Steve Jobs and Steve Wozniak, Ronald Wayne was the third (and most easily forgotten) founder of Apple (AAPL). 🍏 Wayne designed the first Apple Logo, but less than two weeks after starting the company he sold his entire 10% share of Apple for just US$800. Apple has had their fair share of ups and downs since then, but 10% of Apple today is worth a whopping US$270 billion. 😲 Yep, even the biggest and brightest make mistakes.