Playing It Safe is the Riskiest Move You'll Ever Make

You should bet big - even if you probably end up failing

Jeff Bezos, the founder of Amazon, is widely known as one of the most successful entrepreneurs of our era. He built a revolutionary platform that reshaped global commerce and undeniably impacted our daily lives.

Because of this, it’s easy to assume Jeff Bezos is a genius whose every idea turns into gold. The first assumption is correct, but the second one is profoundly wrong.

Just take a look at the spectacular and expensive failures Amazon has had over the years: The Fire Phone, the short-lived Amazon Wallet, Amazon Local Register, Crucible, Amazon Destinations, Auctions, Spark, TestDrive, zShops, WebPay, or Unbox are all clear examples.

While these setbacks may seem like obvious mistakes, they actually reveal a powerful lesson articulated by Bezos himself: to achieve massive wins, you must be bold and willing to make unconventional bets, even if it means a higher likelihood of failure in the short term.

The relationship between failure and innovation

As Bezos explained in his 2015 letter to Amazon shareholders, experimentation and failure are the engines of innovation and success.

Failure and invention are inseparable twins. To invent you have to experiment, and if you know in advance that it's going to work, it's not an experiment. […] Outsized returns often come from betting against conventional wisdom, and conventional wisdom is usually right.

He goes on to say that even with a low chance of success, the potential payoff can make the risk worth it.

Given a ten percent chance of a 100 times payoff, you should take that bet every time. But you're still going to be wrong nine times out of ten.

We all know that if you swing for the fences, you're going to strike out a lot, but you're also going to hit some home runs. The difference between baseball and business, however, is that baseball has a truncated outcome distribution. When you swing, no matter how well you connect with the ball, the most runs you can get is four.

In business, every once in a while, when you step up to the plate, you can score 1,000 runs. This long-tailed distribution of returns is why it's important to be bold.

Big winners pay for so many experiments.

Big winners pay for so many experiments. The vast majority of events are insignificant, but a tiny number of events are extraordinarily impactful.

Many outcomes in life are driven by these tail-end events. For example, consider the world of Venture Capital (VCs). A VC firm might invest in dozens of startups, fully expecting the vast majority to fail or break even. They aren't trying to be right 100% of the time. They are searching for the one investment that returns 100x or 1,000x its value. That single, massive success pays for all the other experiments and generates the fund's entire profit.

Bezos’s philosophy is identical. The Fire Phone, Amazon Wallet, and Crucible were all costly experiments. But one of his bets wasn't just a home run—it was the 1,000-run hit he described.

The 1,000-Run Home Run

Back in the early 2000s, Amazon’s website kept crashing during busy shopping seasons. To fix this, they built an incredibly robust internal infrastructure—servers, databases, and systems that could handle massive traffic spikes.

Then Bezos had a seemingly crazy idea: "What if other companies could use our infrastructure too?"

Most people thought it was nuts. Amazon sold books online. Why would they pivot to become a technology company? And who would trust putting their most sensitive business data on Amazon's computers?

But Bezos saw something others missed. He watched startups struggle to afford expensive servers and saw large companies waste money on computing power they only used occasionally. He decided to let businesses rent computing power like they rent office space.

Amazon Web Services (AWS) quietly launched in 2006. At first, mostly startups used it. Then bigger companies started experimenting. Today, when you stream Netflix, listen to Spotify, or browse millions of websites, you're using AWS without even knowing it.

That one "bet" now generates over $100 billion in annual revenue, leads the AI revolution, and has a valuation that completely eclipses the financial losses of every failed Amazon project combined.

Take asymmetric bets

This lesson is powerful because it applies far beyond businesses. We are often taught to avoid failure and seek steady, predictable paths, a mindset that minimizes the risk of loss but also the chance for spectacular success, but the principle of asymmetric bets encourages us to think differently.

You can build nine failed projects, but the tenth might change your career.

You can endure nine failed relationships, but the tenth might be the love of your life.

You can invest in nine average companies, but the tenth could be a multi-bagger that secures your future.

You can be wrong over and over, but if your one success is big enough, it will redefine you. So play big. Don’t settle for incremental gains when a life-changing opportunity is on the table.

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