The Top 11 Investing Legends

The Top 11 Investing Legends

Everyone is naturally interested in finding the investment fund or strategy that consistently produces the best annual returns. But while the performance of funds tends to ebb and flow, often with changes in the direction of the financial markets, there’s a small elite of individuals who have enjoyed almost phenomenal investment success. Below is my list of the highest 11 investors of all time. Many are names you almost certainly already know. But others may surprise you. I haven’t attempted to rank these investors but instead to supply a list of individuals who have found exceptional investment success through a wide variety of investment philosophies and strategies. As a private investor, it'll be worth following and studying several of these people. The maximum amount as anything, their success seems to be due to a commitment to their investment convictions. Which will be what the rest of us need to focus on. (Unless otherwise noted, all Total Net Worth figures are from Forbes - World's Billionaires List for 2021.)

1. Benjamin Graham

Benjamin Graham is considered the “father of value investing.” a minimum until the past decade or so… Value investing has been considered the foremost successful investment strategy over the long term. It’s the method of buying shares in companies that are fundamentally strong with promising prospects but overlooked by investors. It presents a real opportunity to find top-performing companies ahead of the crowd. Value investing may be a strategy employed by several of the other investors on this list. Though it's primarily fallen into disfavor in the past decade or so, value investing proved highly successful for Graham. His investment company posted annualized returns of about 20% between 1936 and 1956, which is well above returns within the general market. Graham was the author of two of the foremost popular books in investment history, Security Analysis, and the Intelligent Investor.
  • First Investment: Probably Northern Pipeline Co.
  • Best Investment: No information available
  • Total Net Worth: N/A – died in 1976 at the age of 82

2. Jack Bogle

Jack Bogle is the personification of the term “investment legend.” He was the founding father of The Vanguard Group. This $7.1 trillion investment company is the world’s largest provider of mutual funds and, therefore, the second largest provider of exchange-traded funds. But how Vanguard came to be may be Bogle’s most significant contribution to the investing world. While an undergraduate at Princeton University, Bogle conducted a study during which he determined most mutual funds didn’t earn any more money than popular stock market indexes. He found that the fees related to those mutual funds often caused them to underperform market indexes. Many years later, Bogle would launch the primary index fund, which was tied to the performance of the S&P 500. That was back in 1976, and therefore the fund is now called the Vanguard 500 Index Fund (VFIAX). And with nearly $740 billion in assets under management, it’s the most critical S&P 500 index fund in the industry. Bogle literally revolutionized the investment universe with the event of index funds. Because of their low cost and passive nature, they're now common in the portfolios of individual investors worldwide and, therefore, the mainstay of Robo-advisor portfolios.
  • First Investment: No information available
  • Best Investment: Launching index funds at Vanguard
  • Total Net Worth: $111 million at the time of his death in 2019 at the age of 89
“Time is your friend; impulse is your enemy.” -Jack Bogle

3. John Templeton

John Templeton may not be a household name among investors, but he’s another of the true legends of the industry. he's the founder of the Templeton Growth Fund, where he pioneered global investment diversification. (The fund is now a part of the $1.4 trillion Franklin Templeton firm.) Born in 1912, he began building his fortune during the good Depression of the 1930s. At a time when stock prices were crashing, Templeton saw it as a chance. When war II began in 1939, he borrowed money and purchased 100 shares of each company listed on the New York Stock Exchange that sold for less than $1 per share. He purchased shares in 104 companies altogether, including 34 that were in bankruptcy. As war II brought an end to the depression and super-low stock prices, Templeton’s wealth multiplied. Only four of the businesses Templeton invested in became worthless. Templeton was a relentless value investor and an enormous fan of another investing legend, Benjamin Graham. Templeton preferred fundamental analysis and even rejected technical analysis for stock valuation as a worthy investment.
  • First Investment: No information available
  • Best Investment: Bought 100 shares of every of 104 companies listed on the NYSE that sold for less than $1 in 1939
  • At the time of his death in 2008 at the age of 95, he had a net worth of $1.7 million, although he was known for donating the majority of his fortune to charity.

4. Peter Lynch

If this were the 1980s, Peter Lynch would probably win the title of the highest investor of all time. That’s when he was at the highest of his game as the manager of the Fidelity Investments’ Magellan Fund and the most well-liked mutual fund at the time. And it’s no surprise. During his 13 years managing Magellan, Lynch turned in a mean annual return of 29%, nearly doubling the return of the S&P 500. The fund outperformed 99.5% of competing funds in the last five years running it. When Lynch took over the fund, it had a mere $18 million in assets under management. But by the time he left in 1990, the fund had grown to $14 billion. Lynch was a champion of beneficial investing, the favored investment strategy founded by Benjamin Graham. But while Graham may have introduced the concept, Lynch played it bent perfection. Lynch was also a best-selling author with his 1989 book, One abreast of Wall Street, and originated the terms invest in what you recognize and ten-bagger (a stock that produces a return of 10-to-1 or more fabulous). Like a number of the other investment geniuses on this list, Peter Lynch came from humble beginnings. His father died when he was 10, forcing his mother to figure to support the family. Lynch himself worked as a golf caddy to assist and support his family. It had been the money earned from that job that enabled him to buy his first stock while he was in college. And yes, it clothed to be a ten-bagger. Lynch was on his way.
  • First Investment: Bought his first stock in college (Perhaps Flying Tigers) that provided a 10X return
  • Best Investment: No information available
  • Total Net Worth: $450 million

5. Warren Buffett

Warren Buffett may easily be the foremost popular choice as the top investor of all time on many people’s lists. After all, it’s hard to argue with a person who went from humble beginnings to a net worth of well over $100 billion. He’s currently one of the wealthiest individuals in the world, and sometimes he has been the wealthiest. He is so popular on Wall Street and in the financial media that he has been dubbed the “Oracle of Omaha.” Born in Omaha, Nebraska, and still living within the same home he purchased in 1957, Buffett may be a follower of Benjamin Graham’s value investing strategy. And within the style of John Templeton, Buffett lives a surprisingly frugal lifestyle, given his immense wealth. Buffett is the chairman and largest shareholder of Berkshire Hathaway, the $873 billion national conglomerate company headquartered in Omaha. Unlike traditional investment, Berkshire Hathaway takes significant equity positions in large companies, together with direct management of operations. Buffett features a 16.45% interest in Berkshire Hathaway. Buffett started as an investment salesman but quickly began multiple business partnerships. He eventually began performing at Benjamin Graham’s partnership; on the other hand, he started his own—Buffett Partnership, LTD—after Graham retired and closed his firm. Buffett met Charlie Munger (see below) in 1959, and by 1965, he began purchasing shares in Berkshire Hathaway, eventually taking control of the corporate. Berkshire Hathaway was originally a textile company, but Buffett moved into insurance, including Geico’s insurance giant. Though Buffett’s annual returns are falling in recent years, there’s no arguing with the long-term diary. Consistent with MarketWatch, Buffett’s Berkshire Hathaway stock has returned a mean of 18.3% per year—compared to 10.2% for the S&P 500—going all the way back to 1965.
  • First Investment: Purchased three shares of Cities Services Preferred at $38, later selling them at $40
  • Best Investment: Berkshire Hathaway within the early 1960s, taking control of it in 1965 and then converting it from a textile company to an investment company
  • Total Net Worth: $96 billion
“Rule No. 1: Never lose money. Rule No. 2: always remember rule No. 1.” -Warren Buffett

6. Charlie Munger

Charlie Munger is Warren Buffett’s partner in crime in Berkshire Hathaway. At the tender age of 97, he remains president of the company and is taken into account to be Buffett’s closest partner. He also is the director of Costco and chairman of the Daily Journal Corporation. Like Buffett, Charlie Munger may be a proud product of the state of Nebraska. Born and raised in Omaha, Munger indirectly came to Berkshire Hathaway. He served as chairman of Westco Financial Corporation, which eventually became a Berkshire Hathaway subsidiary. Apart from Berkshire Hathaway, Munger is an investment legend in his title. During the amount from 1962 to 1975, when the typical annual return on the Dow Jones industrial average was 5%, Monger’s own investment partnership had compound average annual returns of 19.8%. Munger’s name is hardly mentioned aside from Buffett’s. But had he continued his investment partnership as an independent entity until today, and he would likely be considered a standalone investment genius of the preliminary order. Despite his affiliation with the more popular Warren Buffett and his stunning investment success over the years, Charlie Munger’s estimated net worth is nonetheless estimated at but $2 billion, which will owe in part to the fact that Monger is a big giver to various charities and, by his own admission, has already transferred to a significant amount of wealth to his children.
  • First investment: Purchasing an investment property with the help of a lawyer, which yielded a 4X return on his investment.
  • Best Investment: I purchased Berkshire Hathaway shares for $16 per share and watched it increase to $300,000 per share.
  • Total Net Worth: $2 billion
  1. Nassim Taleb
Nassim Taleb is some things of an unusual candidate for this list like this because, in addition to being one of the most unconventional investors in history, he’s also a statistician and essayist. But on the investment side, one of his most significant contributions is his advocacy of what’s known as the “barbell investment strategy.” The barbell strategy is the opposite of the typical balanced portfolio. Rather than maintaining 100% exposure to medium risk/reward investments like stocks and bonds, the strategy promotes holding 90% of your portfolio in super-safe investments like cash and short-term U.S. Treasury securities and, therefore, the remaining 10% in high-risk/reward assets. You would keep most of your portfolio safe while committing only a sliver to the type of investments that seem unlikely to pay off but can pay off big if and when they do. The strategy isn’t universally accepted, but there's plenty of evidence of its success. A former hedge fund manager and derivatives trader, Taleb started his risk management firm, Universa Investments, in December 2007 and returned a fantastic 115% by late 2008—which was one of the very worst years in stock market history since World War II. That return was possible because the portfolio was designed on the bet that the stock exchange would take a significant plunge. (Taleb is the scientific advisor to the fund, which Mark Spitznagel manages). Taleb’s book, The Cygnus atratus, focuses on the acute impact of rare and unpredictable events and taking advantage of these events to produce big investment profits. The book has been described as the most influential investment book in modern history. Still another of his famous books is Antifragile: Things That Gain from Disorder, which emphasizes the necessity to prepare a portfolio for the very disasters the investment community prefers to ignore.
  • First Investment: No information available
  • Best Investment: Crisis-proof investments made beforehand of the 1987 stock market crash
  • Total Net Worth: $80 million

8. Ray Dalio

I’m mixing up this lineup by adding a pair of contrarian investors. Ray Dalio is best known for being the co-chief investment officer of Bridgewater Associates. That’s notable because Bridgewater Associates is the third-most prominent hedge fund globally, with quite $154 billion in assets under management. At various times, it's been ranked as the biggest hedge fund globally. A hedge fund may be a type of alternative investment employing various strategies to minimize losses during market downturns. Techniques employed include short-selling, leveraged derivatives, and options. Dalio founded Bridgewater Associates back in 1975, and he’s now considered one of the most significant financial innovators of our time. Therefore, he and, therefore, the company gained fame by turning a profit during the 1987 stock market crash and later by turning a 9.5% profit during the disastrous fiscal year of 2008. the corporate provides services to pension funds, foreign governments, central banks, university endowments, charitable foundations, and other large organizations. Dalio’s personal wealth is listed at $20.3 billion, making him the 88th richest person globally, consistent with Forbes. What makes that wealth level astounding is that Dalio is listed as “self-made,” meaning he built a fortune performing from the bottom up. He started investing at age 12, getting investment tips from golfers at a club where he caddied. He’s rumored to possess started Bridgewater Associates from his two-bedroom New York apartment.
  • First Investment: Bought 60 shares of Northeast Airlines at $5 at the age of 12 and tripled his investment
  • Best Investment: Launching Bridgewater Associates at age 26
  • Total Net Worth: $20.3 billion

9. Peter Thiel

This is another top investor you’ve probably never heard of, but his story may be a compelling one. A Stanford school of law graduate, he started off working in the legal field for several years. Born in Germany in 1967, his family moved to South Africa for a time, then to the U.S. in 1977. Thiel himself emigrated to New Zealand in 2011. That’s not precisely the kind of background you’d expect for a future superstar investor. a piece of writing in Propublica, describing Thiel as “The Lord of the Roths,” reports intimately how he turned a $2,000 investment during a Roth account in 1999 into $5 billion. As an enormous fan and promoter of Roth IRAs, this story guarantees Thiel a cherished spot on my list of the highest 11 investors of all time. Talk about tax shelters! Thiel is 53 years old, suggesting he’ll have access to entirely tax-free withdrawals from his $5 billion Roth IRA in only about six years. Of course, not everyone can do what Peter Thiel accomplished with a Roth IRA or the other investment account. As a co-founder of PayPal, he was ready to purchase shares in the company before it went public, including some through his Roth IRA. That wasn’t Thiel’s only accomplishment. He was also the founding father of Clarium Capital, Palantir Technologies, and Founders Fund. As a minimum of some of the most successful investors, Thiel may be a combination of investor and entrepreneur.
  • First Investment: No information available
  • Best Investment: Co-founder of PayPal, purchased shares before it went public, fetching him $55 million
  • Total Net Worth: $4.9 billion

10. Carl Icahn

Carl Icahn may be a bit of a controversial figure. He’s the founder and principal shareholder of Icahn Enterprises, which purchases companies in distress and turns them around for big profits. Part investor, part corporate raider, it’s his skills within the latter that have enabled his success in the former. He functions similarly to Warren Buffett in this regard. He not only invests in businesses, but also manages them. Icahn began his career as a stockbroker in 1961 and purchased a seat on the New York Stock Exchange in 1968. it had been then that he formed his own company, a brokerage engaged in risk arbitrage and options trading. But it wasn’t until 1978 that he began buying interest in companies. Perhaps his most famous acquisition was the troubled airline, TWA. He purchased the corporate in 1985 and began selling off its assets to repay the money borrowed to buy the company. Afterward, he took the corporate private, which netted him nearly a half-billion dollars. He has had—significant investments in several large companies, including PayPal, Yahoo, Lyft, Xerox, Clorox, Netflix, and Hertz. Other acquisitions included US Steel, King Pharmaceuticals, Motorola, and lots of others. His personal net worth is estimated at $16.7 billion.
  • First Investment: No information available
  • Best Investment: TWA netted him $500 million
  • Total Net Worth: $15.8 billion
“You learn during this business: If you want a friend, get a dog.” -Carl Icahn

11. George Soros

George Soros’s personal net worth is estimated to be $8.6 billion. But that’s after making a donation of over $32 billion to the society Foundations. If Carl Icahn is a component investor, part corporate raider, Soros is a component investor, part philanthropist. On a more practical level, he’s a hedge fund manager and began a Quantum Fund fund. It had $12 million in assets under management when it was created in 1969. By 2011, it had risen to $25 billion, eclipsing Soros' total fortune. But what Soros could also be is the world’s greatest speculator. He’s perhaps best referred to as “The man who broke the Bank of England.” That stems from his 1992 short-selling of $10 billion worth of British pounds, creating a currency crisis for the united kingdom that netted Soros a $1 billion profit. Soros’s immediate success as an investor has come from the Quantum Fund. Since 1973, the fund has produced net gains of $43.9 billion. In 2018, the fund was ranked the second highest-earning hedge fund of all time, behind Ray Dalio’s Bridgewater Associates.
  • First Investment: No information available
  • Best Investment: Shorting British Pound for a $1 billion profit
  • Total Net Worth: $8.6 billion

Final Thoughts

How great wouldn't it be if you could invest equal allocations in 11 funds run by each of these investors? Unfortunately, they don’t usually offer funds to the general public, concentrating instead on institutions and enormous investors. That’s largely because the sort of investing they do also involves high risk. If you’re like most investors, high risk is some things you want to avoid. But maybe—just maybe—you want to think about investing a small slice of your portfolio the way some of these investment geniuses have. Are you up to it?

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