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Steve Anderson – Make Successful Failures Like Amazon and Protect the Downside
26th October 2020 • My Worst Investment Ever Podcast • Andrew Stotz
00:00:00 00:33:07

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Steve Anderson is an expert in strategic risk and business growth. Drawing on decades of experience in the insurance industry, he wrote The Bezos Letters: 14 Principles to Grow Your Business Like Amazon, a Wall Street Journal, USA Today, and international bestseller. With hundreds of thousands of followers, Steve has been handpicked by LinkedIn as one of the world’s most influential thought leaders.


“Measure what matters, question what was measured, and trust your gut.”

Steve Anderson


Worst investment ever

In 2007, Steve inherited a pretty good amount of money from his sister, who died from breast cancer. He wanted to invest this money in the smartest way possible. So he went to an investment advisor who advised him to invest in REITs and Class A office buildings, which he did.

Here comes the recession

A year later, the recession hit the US real estate market, and Steve lost his entire investment. He knew that he should have pulled out his investment as soon as things started to take a turn, but he opted to hold on for a year hoping for the best. Unfortunately, this turned out to be his worst investment decision ever.

His one mistake

While he had the right intentions and was even smartly investing his inheritance, Steve made the one mistake not to put measures in place to protect the downside.

Lessons learned

Think more about downside protection

Something will always happen that is outside your control. So think about what you’re going to do in case of uncertainties.

Protect your assets

Concentrate more on protecting your assets than growing them.

Andrew’s takeaways

Focus on the long term

A lot of times, we get caught up in the short term. Instead, focus on the things that will make money over a long period, such as stocks and bonds.

Shortfall risk is a huge risk

Very few people ever think about shortfall risk. Most people take comfort in putting all their money in the bank, thinking that it’s low risk. No, that’s high risk because your money will never grow.

Actionable advice

Do a better job than I did to protect the downside.

No. 1 goal for the next 12 months

For the next 12 months, Steve’s goal is to keep the book alive and keep the buzz going. Hopefully, this will lead to live in-person events.

Parting words


“Obsess over your customers. Think about that more because you’re probably not.”

Steve Anderson




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