What was the riskiest investment you made that paid off?


riskiest investments

The following guest post is courtesy of Adinah Brown, content manager at Leverate.

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Recently, there was an interesting article about several of the early employees at Google. Obviously we all know the story of Google from its humble beginnings as a research project at Stanford, to its current iteration as one of the most important tech companies in the world. Two stories in particular stand out, employee number 20, Marissa Mayer, and employee number 56 Charlie Ayers.

Charlie was a successful chef who got his start preparing meals backstage at music festivals. This exposed him to musicians who fell in love with his cuisine and asked him to be their exclusive chef. Charlie toured with several groups as their chef and was well on the way to financial success when a pair of 26-year-olds asked him to be a corporate chef for their new startup, with a funny name of “Google”. Against the recommendations of family and friends, he decided to take the job.

Marissa Mayer is probably well known enough not to need an introduction. In 1999, after graduating from Stanford, she received 14 job offers. Famous for her attention to detail, she analysed that Google has a 2% chance of succeeding, which was enough for her.

Charlie Ayers received 40,000 Google shares. When Google went public, his shares were worth $3.4 million.

Marissa Mayer was listed at number 6 on Fortune’s ’40 under 40’ list. Her net worth has been estimated as between $430 million and $540 million.

These are two prominent examples of financial moves that were incredibly risky at the time, but still showed a lot of amazing foresight or luck.

We asked a few of our friends about their riskiest investment that paid off.

Trevor Resnick, 29, Marketing analyst.

My riskiest investment that paid off was in Bitcoin, in 2011 it was selling at 43 cents. I don’t even know why I invested in Bitcoin, but I didn’t have a lot of money and was into penny stocks and the like. I think I held it for about 6 months and sold at $22.59 in June that year. I timed the market almost perfectly and sold pretty much at a peak. I thought I was so clever, that I reinvested that money into some other penny stocks that I found. They crashed and I lost all that money. When I next checked Bitcoin a year later, it was hovering at about 5 or 6 dollars, so I still felt pretty good about my trade. A year and a half later it was threatening the $1000 mark. Since then, I wince every time I think about what could have happened if I simply left my money in Bitcoin.  

Carl Masons, 66, Creative Design Executive

I am a pretty conservative person and I’ve always been a buy and hold type of guy, with mostly bonds and term deposits. In the early eighties I was introduced to a friend of my uncle’s called Charlie who was in investing. It turned out that he and his friend had this textile company that they were turning into an investment company. We talked about his business and he really left an impression on me, so I decided to buy a few shares. I didn’t have much money to invest in those days, and those shares were expensive. I actually had to take out a loan to buy just two class A shares for $260. After a few months it went up a bit and seemed to be doing well, but I started thinking about the cost of the loan and got worried about the risk, so I sold one of the shares. The profit covered most of the loan, and I did what I do with all my other shares, I hold. I still have that one share, and it’s worth $250,000. The company is Berkshire Hathaway. At the time, in my mind, it was a big risk, but today it seems like it wasn’t such a big risk, considering the reward. I often regret selling the other share and not buying more in the intermediate years. I guess in hindsight that was the biggest risk.

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What was the riskiest investment you made that paid off?

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