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.
