O'Shaughnessy started his career at Lario Oil & Gas, a family-controlled oil and gas company based in Wichita, Kansas. Lario is involved in oil and gas exploration and drilling operations in the Permian Basin in West Texas, the Bakken oil patch of North Dakota, and parts of Kansas, Oklahoma and Ohio. After O'Shaughnessy turned day-to-day operations over to his sons in the 1980s, he formed a series of investment groups to develop projecs around the world, including Russia and Latin America. He is the Chairman of Frontier Wealth, an energy investment group and Chairman of Horizon Oilfield Services.
Gerald and his wife Priscilla contributed at least $202,000 to federal candidates and PACs in the 2012 election cycle, including $100,000 to the Romney Victory Fund. The couple and their sons -- Tim and Michael (the CEO of Lario) -- have all attended at least one of the Koch brothers' secret strategy retreats.