Connor O'Brien

In 2015 O'Brien and O'Leary formed O'Shares Investments, a firm offering investments to U.S. investors exclusively in ETFs.

In 2014, the Autorité des marchés financiers charged O'Leary Funds with failing to comply with various provisions under the Securities Act, namely, the restriction regarding securities concentration in a portfolio, the requirement to publish and file in a timely manner a press release informing the public about changes to a fund's fundamental investment objectives, the requirement to hold insurance coverage in accordance with regulations and the requirement to notify the AMF of any change to the information filed for registration purposes. With respect to the latter requirement, O'Leary Funds had failed to declare that it was the subject of a counterclaim for damages. O'Leary settled and agreed to pay penalties.

O'Brien teamed with Canadian businessman and reality-television personality Kevin O'Leary in 2010 to form O'Leary Funds. O'Leary Funds suffered losses in 2011, but initial reports of large losses and redemptions by investors were modified when analysts considered the way the funds were structured and the fact that the funds paid distributions, which increased value to investors. Both analysts and fund partners O'Leary and O'Brien acknowledged that the funds employed complicated strategies that made losses look larger initially than they were. The firm was eventually sold to Canoe Financial in 2016, when O'Leary Funds had about $750 million under management.

O'Leary Funds entered a legal dispute with Canadian energy company Boralex Inc. in 2010 over Boralex's proposed takeover of the Boralex Power Income Fund. Boralex owned 23 per cent of the trust, and O'Leary Funds held about 9.4 percent. O'Leary Funds contended that the proposed amendment to Boralex Power Income Fund's trust agreement was illegal, and petitioned the Montreal District Superior Court for the Province of Québec for a safeguard order (injunction), or ordonnance de sauvegarde, to prevent Boralex from proceeding with the sale. The petition was rejected, but the court ruled that O'Leary Funds had sufficient cause to seek damages in civil court. The case was still before the court as of February 2017.

O'Brien returned to Canada with his family in 2001 and dissolved Stanton Capital in the U.S. He founded Stanton Asset Management in Canada the next year, and in 2004 launched two funds of hedge funds, Stanton International Equity and the Stanton Diversified Strategies funds. After four years in which, according to O'Brien, fund investors saw accumulated returns of some 30% in addition to tax breaks, the funds suffered significant losses in late 2008. Some investors lost as much as 70% of their money, and O'Brien was forced to suspend redemptions.

O'Brien and Livanos also launched MaritimeDirect.com, an internet-based maritime information and e-commerce site, in 1999. MaritimeDirect weakened as a result of downturns in the dry-bulk shipping industry, overly optimistic projections, and the decline in tech-sector financing. Under pressure from creditors, it ceased operations in 2001.

Stanton followed the ESCO investment by teaming with shipping-industry executive Vassilios M. (Bill) Livanos in 1998 to form Millenium Seacarriers, Inc., a United States-based dry-bulk shipping company that eventually owned and operated a fleet of up to 22 bulk carriers. Millenium Seacarriers faced difficulties when market conditions and charter rates for the dry-bulk shipping sector deteriorated in the early 2000s. By 2001, bondholder Wayland Investment filed suit against Millenium Seacarriers and O'Brien claiming they "enriched themselves at the expense of the bondholders and other investors and creditors" by charging high management fees and executing a number of irregular sale-and-purchase transactions. Millenium settled the suit 2002 and gave up 17 ships, all but one of its remaining fleet. It eventually filed for restructuring in a bankruptcy proceeding.

Stanton ventured into shipping in 1997 when it assembled a team of investors to partner with the Norwegian shipping company Tschudi & Eitzen to acquire ESCO, an Estonian state-owned shipping company that was privatized through O'Brien's family links to Estonia. According to the business daily Aripaev, ESCO has in the last four years accumulated huge debt, and its main shareholders were suspected of siphoning capital out of the company. Stanton sold its interest to Tschudi & Eitzen in June 2001 in order to recoup some money after dismal showings in both MaritimeDirect and Millenium Seacarriers.

In 1995, he founded Stanton Capital Corporation, a private-equity investment firm. One of Stanton Capital's first ventures was in the privatization of the Peruvian state-owned steel company SiderPeru. Stanton acted as the financial partner of a team of private investors that included Acerco S.A., as industry partner, and Wiese Inversiones Financieras S.A., an affiliate of Banco Wiese, to acquire the Peruvian steel company SiderPeru. The consortium, named Sider Corp, acquired 96.46% of Siderperu in 1996. Siderperu's employees acquired the remaining 3.54% of Siderperu's share capital. Stanton sold its share to its consortium partners in January 2001.

O'Brien is a former alpine skier who represented the United Kingdom in the 1984 Winter Olympics in Sarajevo and Estonia in the 1994 Winter Olympics in Lillehammer.

O'Brien began skiing at an early age and has skied for four countries: Canada, the United States, the United Kingdom and Estonia. He was a member of the Middlebury College alpine ski team and skied for the United States while in college. Skiing under the British flag, he finished 33rd in the downhill at the Sarajevo Winter Olympic Games in 1984. Temporarily coming out of retirement and while working on Wall Street, he returned to the Olympic Games in 1994 to ski for his mother's native country, Estonia, which had recently gained independence from the Soviet Union.

Connor Olev Martin O'Brien (born 4 February 1961) is a Canadian investment-fund manager. He is president and chief executive officer of O'Shares Investments, a U.S.-based ETF adviser, as well as president, chief executive officer and chief investment officer of Stanton Asset Management, a Montreal-based investment-management company, which he founded in 2002. O'Brien had previously established a private-equity investment firm, Stanton Capital Corporation, in New York City. Before establishing his own businesses, he held positions at Merrill Lynch and Lehman Brothers.

O'Brien was born and raised in Montreal and holds British and Estonian citizenship, as well as Canadian. His father was born and raised in Belfast, Northern Ireland, and his mother immigrated to Canada from Estonia as a child in 1944. When Estonia gained its independence from the Soviet Union, O'Brien became an Estonian citizen by birthright.