Eight legendary investments that paid off big-time

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Unbelievable investments that actually paid off

Investing isn’t a risk-free way to make millions (or even billions). But for these people, a savvy gamble paid off big time.

From a shoe brand on the verge of collapse to a bookshop in a garage, read on to discover the incredible investment opportunities that made these people rich.

All dollar amounts in US dollars

Google’s 53rd employee and resident chef

In 1999 Charlie Ayers Jr was employed as a personal chef for a family in California’s Silicon Valley when he decided to apply for the role of executive chef at Google, despite not knowing what a search engine was. When Ayers didn’t receive a response to his job application, he started sending regular deliveries of his homemade bakes.

This tactic worked, and he was eventually given the job of cooking for the first 50 Google employees, who had only recently moved out of Google’s original converted garage office to the new Mountain View, California HQ.

Google’s 53rd employee and resident chef

After a couple of years catering for the growing company, one of Google’s financial analysts told Ayers that the business was about to go big, and that he should get stock options before it went public. To invest in Google, Ayers borrowed $14,000, the equivalent of around $25,000 (£19k) 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 (pictured) left Google in 2006, his 700,000 shares were worth around $40 million, the equivalent of $62 million (£47m) in today’s money. This allowed him to open his own restaurant and pay back his dad – and then some.

George Soros’ bet against the Bank of England

Hungarian-born George Soros survived the Nazi occupation of his home country and moved to the UK in 1947, where he was awarded a degree from the London School of Economics. After setting up several successful funds, Soros quickly became a millionaire.

But his investing success became legendary when he decided to bet $10 billion ($22bn/£17bn today) of his fund’s money against the British pound in 1992…

George Soros’ bet against the Bank of England

The pound was on the brink of collapse at the time, which Soros viewed as an investment opportunity. The investor 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 he could buy it back a lot cheaper. Soros is said to have pocketed $1 billion – $2.2 billion (£1.7bn) in today’s money – from the move and was hailed as the man who broke the Bank of England on what’s since been called “Black Wednesday”.

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His decision is said to have cost the country £3.4 billion (£7.3bn/$9.6bn today) and prompted the UK to pull out of the European Exchange Rate Mechanism.

Netflix and invest with Carl Icahn

Originally a service that posted DVDs to customers, Netflix decided to focus solely on streaming video 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.

In 2012, Icahn invested $321 million in the platform, giving him a 10% stake in the company. His investment would be worth around $440 million (£334m) in 2024 money.

Netflix and invest with Carl Icahn

Fast-forward 12 years, and Netflix has almost 270 million subscribers worldwide and it’s safe to say that the streaming service has definitely overtaken the now-old-fashioned notion of sending DVDs through the post.

According to Business Insider, the investment earned Icahn a tidy $1.9 billion (£1.5bn), but he didn’t cash in as much as he could have. The billionaire closed all of his Netflix holdings in 2015, but the company has continued to grow. It’s been suggested Icahn may have missed out on an incredible $6.4 billion (£4.9bn) by pulling out before the service really peaked.

Buffett’s billion-dollar sweets

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, which recently became the first non-tech company in the US to reach a market valuation of $3 trillion (£2.3tn), bought the confectionery shop back in 1972 for $25 million – the equivalent of $188 million (£143m) today – just after the brand’s founder Laurence See passed away, and the business was only just about managing to stay afloat.

The year Buffett invested in the company, it generated a $4.2 million profit.

Buffett’s billion-dollar sweets

Half a century later, the returns are beyond impressive. In 2019 Buffett told the San Francisco Business Times that his candy company has made well over $2 billion (£1.5bn) of pre-tax income, making his return figure a staggering 8,000% on the original investment.

And it’s not just the finances that Buffett is a fan of – See’s Candies sweets have become a staple at his Berkshire Hathaway gatherings, with the holding company buying a staggering 6,000 kilos of products in 2013 alone.

The Thai jet lag cure that went global

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 the drink’s inventor, Chaleo Yoovidhya, he invested $1 million, the equivalent of $3 million (£2.3m) in today’s money, into helping this magical liquid go global. And so Red Bull was born.

The Thai jet lag cure that went global

Red Bull has dominated the energy drinks market for years and sold more than 12 billion cans last year alone.

With an estimated brand value of around $17 billion (£13bn), it’s clear Mateschitz’s initial investment has more than paid off.

Nike saves Converse after bankruptcy

Footwear giant Converse filed for bankruptcy in 2001. Two years later, rival brand Nike bought the company for $305 million – the equivalent of $542 million (£412m) in today’s money.

Already well-loved for its Chuck Taylor and Jack Purcell tennis shoes, Converse’s annual sales soon began to grow under Nike’s control.

Nike saves Converse after bankruptcy

In 2023 alone, Converse sales hit $2.4 billion (£1.8bn), more than six times the amount 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 $16 billion (£12bn).

The family money risked on Amazon

With an eye-watering fortune of $197 billion (£150bn), it’s unsurprising that the world’s second-richest man, Jeff Bezos, gets a mention in our list of incredible investors. Bezos poured a lot of his own time and money into what initially started as an online bookstore based in his garage and grew into global e-commerce platform Amazon.

However, Amazon wouldn’t be what it is today without investments from his family members…

The family money risked on Amazon

Bezos convinced his parents, Jackie and Mike Bezos, to invest $245,573 in his fledgling business in 1995 – the equivalent of almost $507,000 (£386k) in today’s money. He warned them that it was a “big gamble”, and highly likely to fail. But Bezos needn’t have worried; Amazon became the second American business to achieve a market cap of $1 trillion (£760bn) in 2018 and is still worth over $1 trillion today.

If his parents had kept hold of their shares, their stake would have been worth around $30.7 billion (£24bn) by 2020, according to Bloomberg. Not bad for an investment in your son’s garage-based business.

Apple’s 3rd employee Mike Markkula

Mike Markkula (pictured) 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 $1.3 million (£990k) in today’s money – for a 30% stake in the company and became the finance guy behind Apple.

Apple’s 3rd employee Mike Markkula

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 (£760bn), and today it’s worth almost $3.4 trillion (£2.6tn).

Markkula retired from Apple in 1996, and it’s unknown what percentage of company shares he still owns (if any). Today, he’s estimated to have a fortune in the region of $1.2 billion (£913m) – not bad for someone who had to be tempted out of retirement!

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