Robert Friedland is a man addicted to risk and profit. His life has taken him from a first year classroom at Bowdoin, to a cell in federal prison, to a commune with Steve Jobs, to a gold mine in Guyana, to the Forbes list of billionaires. This career trajectory may be unorthodox, but his desire to accrue wealth is undeniable. In whatever endeavor he chooses, Friedland has repeatedly shown that he is not afraid to seize opportunity, no matter how hazardous.

Now the head of a mineral investment and development corporation called Ivanhoe Mines Ltd., Friedland, 61, has spent the past 25 years investing in mines in every corner of the world. His various international mining ventures have garnered significant rebuke from environmental and social groups, even as his companies' profits have soared.

His most famous and lucrative find came in northern Labrador's Voisey Bay in the mid-1990s, when he discovered what he called "the richest nickel, copper and cobalt deposit on the planet," according to an August 2006 article in the New Internationalist. The same article reported that in the span of two years, shares of Friedland's company vaulted from $4 to $167. Ivanhoe Mines did not respond to repeated requests to interview Friedland.

Voisey Bay was just one of a series of mining ventures Friedland has had his fingers in. Starting in the 1980s, Friedland invested in mines in the western United States, Burma, Angola, Sierra Leone, and Papua New Guinea. The New Internationalist reported that many of these countries had active mercenary groups and military regimes making mining a complex and dangerous affair. Friedland's subsequent partnership with some of these groups, such as the Burmese government, led to questioning of his personal and corporate ethics by political activists. Nonetheless, Friedland's companies have always sought out the riskiest ventures, the ones that other companies were not willing to pursue.

Risk-taking has long been Friedland's calling card. As a Bowdoin sophomore at the age of 19, Friedland found himself on the wrong side of the law. Along with two accomplices, he was caught on March 6, 1970 in the parking lot of a Portland, Maine motel with 24,000 tablets of LSD worth an estimated $100,000. In a New York Times article from March 6, 1970, the Justice Department reported it as the largest LSD bust "ever made in New England." A March 13, 1970 Orient article reported that Friedland was arrested along with Marc Heinlein, also of Bowdoin, and Kermit Sargeant of Berkeley, Calif. They were caught after Heinlein sold 8,000 tablets to an undercover federal narcotics agent in the culmination of a several-month long investigation.

The arrests sent shockwaves through a Bowdoin campus already embroiled with the anti-establishment fervor and experimentation of the 1970's anti-war protests. The same Orient article reported a general feeling of paranoia among students fearing that federal narcotics agents were seeking to limit their drug consumption, while Brunswick residents complained about the harmful effects of drug-loving students on their community.

While at Bowdoin, Friedland participated in an experimental arts community on the College's 80-acre Coleman Farm. The 1969 Bowdoin Bugle listed Friedland as a member of the 1968-1969 first year skiing squad and a cast member of the Masque and Gown show "Picnic on the Battlefield."

According to the Orient, Friedland resigned from Bowdoin "without comment." The LSD bust earned him, according to Walter Isaacson's 2011 biography of Steve Jobs, a two-year federal prison sentence.

Out on parole in 1972, Friedland entered Reed College in Portland, Ore, where he was eventually elected as student body president. There, Friedland set out on a new path. Isaacson writes that while Jobs, then a first year at Reed, was trying to sell his IBM typewriter, he walked in on Friedland and his girlfriend having sex. To Jobs' surprise, Friedland insisted that he stay in the apartment and wait until they were done. The two soon became friends, bonding over a mutual interest in Eastern spirituality, which Friedland had developed during a trip to India.

According to Isaacson, this bond prompted Jobs to join Friedland at a spiritual living experiment on a 220-acre apple orchard in Oregon that Friedland had become the steward of through a wealthy uncle. (It has been speculated in numerous media accounts that Jobs conceived the name of his company while working in the apple orchard). The communal lifestyle at the orchard apparently lost its appeal for Jobs when Friedland began focusing more on generating profit from apple products than on the anti-materialistic ideals of the commune.

Between the LSD and the apples, Friedland's focus on profit appeared paramount to all else. Many attribute Friedland's success to his uncanny ability to make deals and win over hesitant investors.

Friedland is well known for his aptitude at generating enthusiasm and financial backing for risky projects that are akin to multi-million dollar gambling bets. Isaacson writes that Friedland was "one of the few people in Jobs' life who were able to mesmerize him." It was Friedman's ability to manipulate people with a deep, silent stare that Jobs inherited and used to great effect. In Isaacson's book, Jobs is quoted as saying, "it was a strange thing to have one of the spiritual people in your young life turn out to be, symbolically and in reality, a gold miner."

While his departure from Bowdoin was ignominious, Friedland may have the last laugh. At an estimated $2.8 billion according to Forbes, his personal net worth is about three times the value of the College's endowment. As sometimes happens in the mining world, the line between riches and ruin can be thin. In 1993, Friedland ran afoul with the law again, this time with the potential for more serious consequences.

Friedland-owned Galactic Resources, a mining corporation, invested in a gold mine in Summitville, Colo., that spilled large quantities of cyanide into the tributaries of the Alamosa River. According to a December 24, 2000 New York Times article, the 1992 spill killed all flora and fauna in a 17-mile stretch of the river. The Crestone Eagle, a newspaper in Colorado, described it as the state's "worst environmental disaster." With the EPA on Friedland's doorstep, Isaacson mentions that Friedland tried to persuade Jobs to intervene on his behalf, but Jobs refused to do so and their relationship subsequently soured. It was this disaster that helped earn Friedland the nickname "Toxic Bob."

A June 12, 2001 article in the Seattle Post-Intelligencer stated that Galactic Resources agreed to contribute $27 million toward the cleanup, far short of the estimated $232 million the effort ultimately cost. Mines and Communities, a website dedicated to exposing the negative effects of mining, reported that "a timely resignation" by Friedland coupled with moving many of his assets outside of the country saved him from further personal liability. Although Friedland's maneuvering prevented the company from incurring the full cost of the cleanup, trouble continued two years later when Friedland again became embroiled in an environmental disaster, this time in Guyana.

According to the New Internationalist, one of Friedland's companies, South American Goldfields—along with the World Bank and the Guyana Government—was responsible for perhaps the worst cyanide spill ever when a mine leaked "3.2 billion litres of cyanide-laced tailings" into two Guyana rivers. He reportedly avoided financial ruin through another resignation. The nickname "Toxic Bob," however, took on a whole new meaning.

With this unsavory history behind him, Friedland is looking to roll the dice again, this time in rural Mongolia. In a country roughly the size of Alaska, he hopes to once again amass a fortune by building an operation in a country where even industry speculators are skeptical.

Friedland's complex financial puppeteering is well underway, and seems sure, as always, that the project has the potential to make a huge windfall. According to Mining Weekly, Friedland's Oyu Tolgoi Project is expected to account for 33 percent of Mongolia's GDP by 2020. In the wake of some local protests and after years of extensive geological investigation, Friedland has reportedly started a massive public relations campaign to improve his standing with the locals.

In a 2007 interview with Xecutivetv, Friedland highlighted the cultural and natural assets of the country: "We are in love with Mongolia as a country and we really love what we do," he said.

While the hospitals and schools he is building are surely helping win public opinion, he has by no means achieved wide popularity. Friedland's casual smirk, monotone voice, and icy stare give off the image of a James Bond villain more than of a benevolent capitalist.

Regardless, it seems that Friedland is once again poised on the brink of huge success. Whether the result is an environmental disaster, a billion dollar fortune, or both, Friedland is likely to get his way. As his high-stakes gambling continues, Friedland is securing his legacy as one of the greatest manipulators of money, minerals, and men.