Iasson Tsakonas graduated from Cornell University, Statler School of Hotel Administration, in 1994 and worked as an analyst for Prudential Securities in New York until 1996, when he moved to Baku, Azerbaijan.

In Baku, he started his own business in finance and property development, remaining active until 2006. In 1999 he also entered the start-up technology sector both as a project manager and an investor.

In 2002, he established OLIAROS Properties, introducing a novel approach to property development in Greece with his first project, award winning AntiparosDesignProperties on the island of Antiparos, Cyclades.

To date OLIAROS has developed 45 properties in 1.000.000m2 of land, setting an example of development ethos and methodology: high-standard contemporary architecture, low density, within the natural context and the community.

In 2013, with the launch of Beach House Antiparos, a high quality no frills, boutique beach hotel and restaurant, OLIAROS inaugurateda new development model for the Greek tourism industry.  This innovative model enables OLIAROS to develop, sell, manage and rent villas, all serviced by its own Beach House, which also acts as a meeting point and recreation hub on the island.

In 2007 OLIAROS launched KM (Kerameikos Metaxourgeio) Properties, an urban regeneration project in the Athens city center that included development of 42 buildings, in 36.000m2. In collaboration with 20 architecture practices, OLIAROS put together a holistic approach to turn the area into an innovation district, seeking to address a new urban reality and instill a present-day identity into Athens. The project was stalled for a number of years but is now being considered as a unique opportunity to develop a city Center Airbnb type Hospitality development.