[6][7] De Oliveira has a background in maritime transport;[7][8] he has since been the owner of Dili's two casinos, and has made investments in other industries, including aquaculture and agriculture.

[6] The airline's first income-earning activity, under a memorandum of understanding with the government made in January 2018, was to acquire and make available to the Timor-Leste Defence Force (F-FDTL) a Cessna 172P aircraft, together with pilots to fly it.

[11] Later that year, Aero Dili was the first airline in Timor-Leste to be granted an air operator's certificate (AOC) to conduct civil domestic services.

[10] On 11 August 2022, the airline carried out a successful experimental international technical landing, using its Cessna 207 aircraft, at El Tari Airport in Kupang, Indonesia.

The first two negotiations had not been able to go ahead, because the prospective lessors had been concerned about the weaknesses of East Timor's aviation system and its legislative framework.