#16. Edward Lampert

Master of Contrarian Investing

Edward Lampert

Edward Lampert is one of the most successful investors in the world, known for his unconventional approach to investing and his ability to identify undervalued companies.

Lampert is the founder and CEO of ESL Investments, a hedge fund that manages over $4 billion in assets. He has made a fortune by investing in troubled companies and turning them around, and his strategies have made him a legend in the world of finance.

In this article, we will explore Lampert’s investment philosophy, the strategies he uses to identify winning stocks, and some of his most famous deals. We will also delve into some little-known trivia about Lampert, providing a comprehensive look at one of the most influential investors of our time.


Lampert’s Investment Philosophy

Lampert’s investment philosophy is based on contrarianism, the idea that the best investment opportunities lie in companies that are currently unpopular or undervalued. Lampert believes that most investors are too focused on short-term gains and fail to see the long-term potential of companies that are currently facing challenges.

In a 2016 interview, Lampert said, “I think it’s important to be contrarian because the market is often wrong. Markets are driven by emotions, and emotions can be very powerful things. So, when everyone is panicking and selling, that can be a great opportunity to buy.”

Lampert is also a big believer in value investing, the idea of buying stocks that are undervalued based on their intrinsic worth. He looks for companies that have strong fundamentals, including solid earnings, low debt, and a competitive advantage in their industry. Lampert is known for his meticulous research and due diligence, often spending months or even years studying a company before investing in it.


Lampert’s Strategies for Success

Lampert’s success is due in part to his ability to identify undervalued companies and turn them around. He is known for taking large positions in companies that are facing significant challenges, such as bankruptcy or declining sales, and then using his expertise to help them recover.



One of Lampert’s most famous deals was his investment in Sears Holdings, a struggling retailer he took a stake in back in 2004. Lampert saw value in the company’s real estate holdings, which included some of the most valuable retail properties in the country. He also believed that the company had a strong brand and a loyal customer base that could be leveraged to turn things around.

Lampert took an active role in managing Sears, serving as CEO from 2013 to 2018. He implemented a number of initiatives aimed at cutting costs, improving efficiency, and increasing revenue. However, despite his efforts, the company continued to struggle, and in 2018, Sears filed for bankruptcy.

While Lampert’s investment in Sears ultimately did not pan out, he has had many other successful deals over the years. He has made significant investments in companies such as AutoZone, Gap, and AutoNation, all of which have delivered strong returns for his investors.


Lampert’s Famous Quotes

Lampert is known for his insightful quotes about investing and business, many of which reflect his contrarian philosophy. Here are a few of his most famous quotes:

“Opportunities are often disguised as problems.”

“I’m not afraid of making mistakes, and I’m not afraid of failing. If you’re not making mistakes and you’re not failing, you’re not trying hard enough.”

“Contrarianism is not a guarantee of success, but it is a way of thinking that can be very helpful in identifying opportunities.”


Little-Known Trivia About Lampert

Despite his success, Lampert is a somewhat enigmatic figure, and there are many little-known facts about his life and career.

For example, Lampert is an avid chess player and has been since childhood. He has even competed in professional chess tournaments and is known to use chess strategy in his investing approach. Lampert is also a philanthropist and has donated millions of dollars to various causes, including education and healthcare.

Another interesting fact about Lampert is that he is a major art collector. He has a vast collection of artwork, including pieces by famous artists such as Picasso and Warhol. Lampert is known to be highly knowledgeable about art and has even given talks on the subject.



Edward Lampert is a highly successful investor whose contrarian approach to investing has made him a legend in the world of finance. He has made a fortune by investing in undervalued companies and turning them around, and his meticulous research and due diligence have been key to his success. While Lampert has had some notable failures, his many successes speak to his abilities as an investor.

Lampert’s famous quotes about investing and business reflect his contrarian philosophy and his little-known trivia highlights his diverse interests and philanthropic activities. For investors looking to learn from Lampert’s success, his investment philosophy and strategies offer valuable insights into the world of contrarian investing.

Patrick Woodcraft - Wholesale Investment Specialist Profile

About the Author: Patrick Woodcraft

As a wholesale investment specialist, I help Certified Financial Planners and Qualified Financial Advisors with the information and education they need about investment funds that are poised to perform best for their clients through the volatile economic seasons ahead. Book a free 15 minute discovery call with me to see what value I can bring to your business and establish if we’re a good fit to work together.



Talk soon,

Thanks for reaching out. I’m looking forward to connecting with you to understand your needs and discover how I can serve you best. 


*Patrick Woodcraft does not provide financial advice or investment advice. Nothing on this website may be construed as financial advice or investment advice. Past investment performance is no guarantee of future results. 


© Patrick Woodcraft 2023