[6] In 1995, Dokolo returned to Zaire to join the large family business of his father – in total 17 companies (banking, breeding, fishing, coffee exportation, real estate, consumer goods distributor, merchandise conveyance, printing, insurance, mining, and the selling of automobiles).

[12] Dokolo had invested in various sectors, including diamonds, oil, real estate, and telecommunications, in Angola, Portugal, Switzerland, the United Kingdom and Mozambique.

In an interview with Jeune Afrique, he stated that his aim was not "to build a large integrated group", but rather to have the opportunity to see "Angola and the Democratic Republic of Congo as a complementary complement" – "a Luanda–Kinshasa axis that could create a counterweight to South African supremacy".

[13] In January 2020, leaked documents indicated that Dokolo had made millions from a suspiciously one-sided partnership with the Angolan state diamond company, SODIAM, to buy a stake in Swiss luxury jeweller De Grisogono.

When the German collector Hans Bogatzke died, the curator Fernando Alvim suggested to Sindika Dokolo that he buy the 500 piece collection.

The collection was secured for a low price because Hans Bogatzke's widow, despite loving her husband, didn't want the responsibility and was pleased knowing it would be shown in Africa.

A number of artists and celebrities, such as the model Alek Wek or singer Keziah Jones, publicly expressed their support and appreciation for his work, and the role of Sindika Dokolo Foundation in the development of contemporary African art.

[35] Located on Casa Manoel de Oliveira building, the new headquarters were to become a place to "promote artistic thinking networks and strengthen ties between Portugal and Angola, as well as Europe and Africa, celebrating art as an unifying element for people and nations," said Dokolo.

[36][37] On 10 August 2017 Dokolo founded the movement Les Congolais Debout, which opposed DRC President Joseph Kabila's continued stay in power beyond the two terms set down in the 2006 constitution.