Leib and his wife Isabelle invited Dalio to their Park Avenue apartment for family dinners and holiday gatherings.

Commodity futures had low borrowing requirements at the time, and Dalio knew he could profit more handsomely than with simple stocks.

[20] In 1974, he became a futures trader and broker at Shearson Hayden Stone, a securities firm[16] run by Sandy Weill, who later became famous for building up Citigroup.

At the firm, Dalio's job was to advise cattle ranchers, grain producers, and other farmers on how to hedge risks, primarily with futures.

[21] Dalio was fired from Shearson Hayden Stone after punching his boss in the face while drunk at a New Year's Eve party in 1974.

[22] Bridgewater started out as a wealth advisory firm, which it served numerous corporate clients, mostly retained from Dalio's job at Shearson Hayden Stone.

The company began publishing a paid subscription research report, Daily Observations, in which it analyzed global market trends.

"[7] In 1991, he launched Bridgewater's flagship strategy, "Pure Alpha", a reference to the Greek letter that, in Wall Street terminology, represents the surcharge a money manager can earn above a particular market benchmark, such as the NASDAQ.

[26] By 2005, Dalio was managing money for extremely large entities, including the $196 billion California Public Employees' Retirement System (CalPERS), the $27 billion Pennsylvania State Employees' Retirement System (Penn SERS or SERS), Melbourne-based National Australia Bank Ltd. and the pension fund of Hartford, Connecticut-based United Technologies Corp.[25] In 2007, Bridgewater predicted the 2007–2008 financial crisis,[11] and in 2008, Dalio published "How the Economic Machine Works: A Template for Understanding What is Happening Now", an essay assessing the potential of various economies by various criteria.

"[29] Researchers at the firm examined the public records of most of the world's largest financial entities and discovered that estimated future liabilities related to bad debts totalled $839 billion.

When Dalio met with U.S. Treasury Department staff and other White House economic advisors in December, these findings were disclosed but were largely ignored.

[30] In 2008, a disastrous year for many of Bridgewater's rivals, the firm's flagship Pure Alpha fund rose in value by 9.5% after accounting for fees.

In 2009, when economic growth was higher than expected and the Dow Jones Industrial Average increased by 19%, the company's Pure Alpha fund reportedly earned just 2% to 4%.

[32][33] By that same year, Dalio was managing money for the SERS, Kodak, General Motors and the Government Investment Corporation of Singapore.

A stake in Bridgewater Associates Intermediate Holdings, LP was purchased by the Teacher Retirement System of Texas (TRS) for $250 million in February 2012.

[36][37] Dalio has controlled Bridgewater Associates alongside co-chief investment officers Bob Prince and Greg Jensen since its inception.

[41] In reference to the personality that led him to investment success, Dalio has said that he considers himself a "hyperrealist", and that he is motivated to understand the mechanisms that dictate how the world actually functions, without adding in abstract value judgments.

[26] According to Dalio, Bridgewater Associates is a "global macro firm",[42] investing around economic trends, such as changes in exchange rates, inflation, and G.D.P.

Dalio implements this strategy by using leverage to evenly distribute exposure across various asset classes while maintaining the best risk target level.

[53] In November 2019, he posted a blog entry stating that excess capital, unfunded social liabilities, and government deficits had created a recipe for disaster in what he called a "paradigm shift".

[56] Dalio said that the odds of a low-wage earner moving to a higher level of wealth were decreasing over time and that this demonstrated Americans' lower economic and social mobility.

[55] In October 2020, Dalio cautioned people to not be blind to China's rise,[57] arguing that it had continued to emerge as a global superpower.

He claimed that China had succeeded in "exceptional ways", including high economic performance in spite of the COVID-19 pandemic, some of the lowest COVID-19 case rates, and being the center of half of all listed initial public offerings globally.

[58][59] Dalio asserted that when he visited China in 1984, high-ranking officials would marvel at basic technology such as calculators, calling them "miracle devices".

[58] He discussed the growing population of well-educated citizens, as well as China's continued growth in the absorption and processing of data, which many headlines have called "the new oil".

While stressing that things could always go wrong, Dalio stated that he believed China's path of economic reform would continue, bringing it unabated prosperity.

[68] Dalio has suffered from Barrett's esophagus, a form of gastroesophageal reflux disease (GERD), a pre-malignant condition that if not treated properly can lead to cancer.

[69] In 2014 he reportedly earned $1.1 billion, including a share of his firm's management and performance fees, cash compensation and stock and option awards.

[70] In 2015, Forbes estimated his net worth at $15.4 billion, making him the second-wealthiest hedge fund manager after George Soros.

[75] In January 2022, Bloomberg News reported Dalio's net worth as $15.7 billion, making him the world's 123rd-richest person according to their rankings.