The most incredible investments of all time

Investing isn’t a risk-free way to make your millions – or even billions – but for these people it was a gamble that paid off. From a shoe brand on the verge of collapse to a bookshop in the garage, these weren’t all sure-fire places to put large amounts of money, but their backers had the last laugh with these incredible investments. Click or scroll through to discover the most incredible investments ever.

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In 1999 Charlie Ayers Jr was the personal chef to a Silicon Valley family when he decided to apply to work at Google, despite never having heard of it or even knowing what a search engine was, during the dotcom bubble. When Ayers didn’t receive a response to his job application he started to send regular deliveries of his homemade bakes. This tactic worked, and he was eventually given the job of cooking for the team of 50 Google employees who had only recently moved out of Google’s original converted garage office to the new Mountain View, California HQ.

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After a couple of years of catering for the growing company, one of Google’s financial analysts told Ayers that the company was about to go big, and that he should get options in the company before it went public. To invest in Google Ayers borrowed $14,000, the equivalent of $20,000 (£15k) in today’s money, from his father who warned him that if it was a scam he would have to pay every dollar back. When Ayers left Google in 2006, his 700,000 shares had soared in value to $40 million, the equivalent of $51.2 million (£39.4m) today, allowing him to open his own restaurant and pay his dad back, and then some.

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Hungarian-born George Soros survived the Nazi occupation of his home country and moved to the UK in 1947, where he started his business career after getting a degree from London School of Economics. After setting up several successful funds, Soros quickly became a millionaire. He really became a legend in the investment world, however, when he decided to bet $10 billion against the British pound in 1992.

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The pound was on the brink of collapse, which Soros saw as an investment opportunity – he bought and sold off as much of the currency as he could, knowing that it was about to suffer a huge depreciation in value and that he could buy it back a lot cheaper. Soros is said to have pocketed $1 billion – $1.5 billion (£1.2bn) in today’s money – from the move and was hailed as the man who broke the Bank of England. As a result, the UK pulled out of the European Exchange Rate Mechanism and it is rumored to have cost the country £3.4 billion ($4.4bn). An incredible investment for Soros, but a devastating one for the UK.

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Originally a service that posted DVDs to customers, Netflix decided to focus solely on online streaming in 2011. This came as a shock to many and 800,000 people hurried to cancel their subscriptions. Investor Carl Icahn wasn’t one of them however, and he decided to invest $321 million (£247m) into the platform in 2012, giving him a 10% share of the company.

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Eight years later and Netflix has over 167 million subscribers worldwide and it’s safe to say that the streaming service has definitely overtaken the now-old-fashioned notion of sending DVDs though the post. The investment earned him a tidy $1.9 billion (£1.47m) according to Business Insider. Icahn didn’t cash in as much as he could have done however – the billionaire closed all of his Netflix holdings in 2015, but the company has continued to grow. It’s been suggested that he may have missed out on around $6.4 billion (£4.9bn) by pulling out before the service really peaked. Read more: Netflix’s journey to global domination

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Warren Buffett is known to have secured hundreds of good investment deals over the years, but his purchase of See’s Candies was one of the sweetest. Buffett’s investment company Berkshire Hathaway bought the confectionery shop back in 1972 for $25 million – the equivalent of $152 million (£118m) today – just after the brand’s founder Laurence See had passed away, and the business was only just about managing to stay afloat. The year Buffett invested in the company it had generated a $4.2 million profit.

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Fast forward almost half a century and the returns are beyond impressive. In 2019 Buffett told San Francisco Business Times that his company has made well over $2 billion (£1.5bn) of pre-tax income, making his return figure a staggering 8000% on his original investment. And it’s not just the finances that Buffett is a fan of – See’s Candies sweets have been a staple at his Berkshire Hathaway gatherings and 6,000 kilos of products were bought by the company in 2013.

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The best ideas can come from the strangest places. In 1984, Austrian businessman Dietrich Mateschitz was in Thailand suffering from jet lag when he was offered a native sugary concoction, Krating Daeng, which seemed to give him the energy boost he needed to get over his flight. Partnering with local businessman Chaleo Yoovidhya, he invested $1 million, the equivalent of $2.5 million (£1.9m) in today’s money, into making this magical liquid into a global product. And so Red Bull was born. Read more about CEOs’ eureka moments

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Red Bull has dominated the energy drinks market for many years and as of 2019 the company had sold 75 billion cans across the globe, according to Forbes. With that level of success and a brand value of $9.9 billion (£7.7bn), the initial $1 million investment was certainly one that paid off.

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In 2001 footwear giant Converse filed for bankruptcy and two years later, Nike scooped up the company for $305 million, the equivalent of $438 million (£338m) in today’s money. Already well-loved for its Chuck Taylors and Jack Purcell tennis shoes, Converse’s annual sales soon began to grow under the control of the sportswear brand.

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In 2019 alone, Converse sales hit almost $2 billion (£1.5bn), which in itself is more than six times the amount that Nike spent on acquiring the company. Converse now makes up around 10% of Nike’s total revenue and based on Nike’s current market cap, that puts Converse’s worth at around $15.9 billion (£12.2bn).

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With an eye-watering fortune of $131.1 billion (£100.9bn), it’s unsurprising that the world’s richest man, Jeff Bezos, gets a mention in our list of incredible investors. He poured a lot of his own time and money into what initially started off as an online bookstore based in his garage until it grew into the global e-commerce platform Amazon. But Amazon wouldn’t have become what it is today however, had it not been for the investments of his family members.

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Bezos convinced his parents, Jackie and Mike Bezos, to invest $245,573 in his fledgling business in 1995 – the equivalent of $413,000 (£321k) in today’s money. However, he warned them that it was a a “big gamble”, and highly likely to fail. Bezos needn’t have worried, and Amazon went on to become the second American business to achieve a valuation of $1 trillion (£770bn) in 2018. If his parents still had hold of those shares, their stake could be worth around $30.7 billion (£23.8bn) according to Bloomberg. Not bad for a relatively small investment in your son’s garage-based business.

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Today Chinese company Tencent (TCEHY) is a big player in the tech investment sector with a current value of $505.8 billion (£389.5bn), but that wasn’t always the case. Back in 2001 South African media and tech investment firm Naspers paid $32 million – $46 million (£36m) in today’s money – for a large stake in the relatively small tech start-up, in what was seen as a “bet”.

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Since then Tencent has flourished, with over a billion people using its social media and payment platform WeChat. And Naspers bet certainly paid off: when it sold off part of its stake (reducing it from 33% to 31%) in 2018, its share was found to be valued at $175 billion (£135bn). That’s a huge increase on its intial investment of $32 million.

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In 1995, investment extraordinaire Warren Buffett put $290 million – $486 million (£376m) in today’s money – into struggling bank Wells Fargo. Since Buffett became involved with the bank, profits have soared and it now has a market cap of $198.7 billion (£153bn). It is one of the most profitable banks in America.

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Buffett is thought to have made billions out of the deal, so although he usually refrains from investing in banks, this one seems to have been a good decision. That said, the bank has run into trouble recently with lower income reported in 2019, and Buffett is fuelling the speculation as he has been selling off small portions of his shares piece by piece, making investors wonder if he knows something they don’t. Read more: Who earns the world’s biggest companies?

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Mike Markkula was lured out of early retirement by the first two Apple employees Steve Jobs and Steve Wozniak (also known as ‘the two Steves’), and was fundamental in the company’s beginnings. On joining the team in 1977, Markkula invested $250,000 – around $1 million (£773k) in today’s money – for a 30% stake the company, and became the finance man behind Apple.

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It goes without saying that the initial investment was a worthwhile move for Markkula: in 2018, Apple became the first company to achieve a valuation of $1 trillion (£770bn), and today it is worth $1.4 trillion (£1trn). Markkula retired from Apple in 1996, and it’s unknown whether he still owns any Apple shares. But if he did keep his 30% share he would have a cool $420 billion (£323.4bn) to his name, which really isn’t bad for somebody who was roped in after already retiring. Now discover From Apple to Walmart: how the world’s biggest companies looked 10 years ago

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