[6][7] Dame Gruev was born in 1871 in the village of Smilevo, Monastir vilayet, Ottoman Empire (present-day North Macedonia).

[9] Following yet another revolt, Gruev and his associates were excluded from the Great School and emigrated en bloc to Bulgaria.

In 1891, Gruev was expelled from the university as he was suspected in the assassination of the Minister Hristo Belchev, but subsequently, this allegation turned out to be groundless.

In order to carry out his plans more successfully, and possibly to avert the suspicion of the Turkish authorities, he decided to become a Bulgarian school teacher.

The first two years after his return to Macedonia region he spent teaching, first in his native village of Smilevo, and later in the town of Prilep.

Gruev visited the cities of Resen, Ohrid, and Struga as well, and found the local population to be accepting his organization's revolutionary ideas very well.

In the fall of 1895, Gotse Delchev arrived in Štip with the idea of laying the foundations of a revolutionary movement seeking autonomy for Macedonia and Adrianople Thrace.

The expansion of the IMRO at the time was phenomenal, particularly after Gruev settled in Thessaloniki during the years 1895–1898, in the quality of a Bulgarian school inspector.

Gruev's tirelessly travelled throughout Macedonia and the Vilayet of Adrianople and systematically established and organized committees in villages and cities.

At Stoilov's insistence that the forced collection of money from the population be stopped, Gruev requested that the Bulgarian government allocate additional funds for weapons, but it was refused.

[17] At Gruev's insistence, the forcible collection of money from the population in Bulgaria continued, and the firm position that the Bulgarian government against these actions led to serious disagreements.

He organized a system in which money was collected from Sunday schools through a special "revolutionary tax", and a quantity of war materials was purchased.

Gruev hastened to Thessaloniki and there he found that the Central Committee, which was in charge of the IMARO, had already resolved to declare a general insurrection which was to take place during 1903.

Gruev, Boris Sarafov, and Anastas Lozanchev were elected by the Congress as the three members of the General Staff and empowered to direct the insurrectionary forces in the Bitola region.

Gruev put himself on the task of touring various revolutionary districts, disarming the insurgents, and storing up the war materials for future use.

In the autumn of that year, Dame was captured by the Serb's leader Micko Krstić, but was set free, with the assistance of Gligor Sokolović, after his negotiations with Pere Toshev.

On 23 December 1906, Dame Gruev and his detachment were discovered by the Turkish authorities near the village of Rusinovo (Maleševo district).