Archaeological excavations and field surveys carried out since 2001 at Olba have led to significant results for both the region and the city itself. As a result of the excavations, hundreds of coins have been discovered and detailed studies of the earliest of these have begun. Of these finds, the most prominent are the silver obol and the Macedonian coins found in 2010. The coins that have been dated to the second half of 4th century B.C. shed light on the early history of the Olba acropolis. These are interpreted bearing in mind the developments in political history and the location of the Olba acropolis. Undoubtedly, one needs much more evidence to explain the earliest stages of the history of settlement in Olba and to reach definitive conclusions. However, the coins that this article introduces; which date to the 4th century B.C. - and are the earliest coin finds of Olba - are significant not only for the city but also for the region as they are the earliest finds to be recovered so far in the region as well and hence the author's belief that they should be introduced to the scientific community, especially the experts studying the region. In order to evaluate these coin finds that offer information about the early history of Olba, one first has to consider the geography, the topography of the region and, the structure of the terrain. In this context, one should first state the fact that the Olba acropolis, a high land settlement located in the Eastern Rough Cilicia region, is above 1040 meters above the sea level. The hill upon which the acropolis is located is approximately 50 meters above the plain. This elevated position appears as a natural fortress and also provides natural protection with its rough structure. Specifically, the bedrock that is located near the peak of the acropolis surrounds the acropolis like a wall. Some parts of the acropolis are steep, making it near impossible to climb to the top of the acropolis. On the other hand, the Olba acropolis is notable for its strategic location. The acropolis is situated in a commanding position relative to the surrounding valley and the hinterland as well as the roads that connect the Olba region to the coastal areas via alternative routes. Nearly all of the roads that lead to the interior of the Olba region from the coastal area are connected to Diocaesarea via Olba. It is possible to reach the Olba acropolis through two different routes, one from Kesliturkmenli and the other from the Seytanderesi Valley. The Seytanderesi Valley connects Olba, Korykos, and Elaiussa Sebaste to one another, while the Kesliturkmenli road, via intermediate routes, connects Olba to Narlikuyu, Korasion and, Seleucia ad Calycadnum. These connections show that the Olba region is naturally connected to the coastal settlements that have ports. As the direct route from the coastal region to Diocaesarea is rough and steep, the routes that lead via Olba to Diocaesarea, the capital as well as an important spiritual and administrative center of the region, must have been frequently used. The Kesliturkmenli-Olba-Diocaesarea route also connects the Olba region to the Anatolian interior via Claudiapolis-Laranda-Ikonion. This indicates the strategic importance of the location of the Olba acropolis. Based on a coin that belongs to the Mazaeus period, and on the Macedonian coins found at Olba, one can propose that the strategically important location of the Olba acropolis has been recognized in the third quarter of 4th century B.C. by the Persians and in the last quarter of 4th century B.C.