[6] His father, Antonios Markos Kounalakis,[7] was an underground guerrilla fighter against the Nazis on the island of Crete during World War II; he fought with Constantine Mitsotakis, who later became Prime Minister of Greece.

Antonios and Vasiliki arrived in the United States as beneficiaries of the displaced persons refugee program and sponsored by the World Council of Churches.

[8][9][10][11] Kounalakis received a public education in the San Francisco Bay Area and earned his bachelor's degree in political science at the University of California, Berkeley in 1978.

[12] In 1988-1989, Kounalakis was a Robert Bosch Foundation fellow in Europe, attending the Bundesakademie für öffentliche Verwaltung in Bonn, Germany in 1988 and the École Nationale d'Administration in Paris, France in 1989.

He served as vice chairman of the board of advisors at the Southeast Europe Project at the Woodrow Wilson International Center for Scholars and was a trustee of the World Affairs Council of Northern California.

[25][26] In 1995, Kounalakis became the executive producer for Visible Interactive, a start-up technology company that used Newton handheld devices for immersive interpretive experiences in venues like the Smithsonian Institution museums.

"[30] His many columns identified Putin’s ambitions and warned that the Russian president’s unchallenged killings at home[31] as well as extraterritorial aggression and murders would increase in frequency and scale.

[32] In 2018, Kounalakis asserted that Putin used Russia’s oil and gas as a strategic weapon against the West and that “instead of punishing bad behavior, however, the world has both financially rewarded Putin and shown him new incentives to continue his aggression — both at home and in Ukraine.”[33] Ukraine’s vulnerability to Russian aggression was called out in his multiple columns identifying Kyiv’s deterrence weakness as well as threats to global nuclear disarmament He argued that “the U.S., NATO and others must do what it takes to prove a nation like Ukraine can remain sovereign even though it gave up weapons of mass destruction.

[35] In 2017, Kounalakis identified early that fentanyl was a cheap and lethal street drug and cutting agent emanating from China, strategically targeting vulnerable American citizens.

Russia Today (RT), China Global Television Network (CGTN), and Xinhua were organizations he suggested be registered under the U.S. Foreign Agents Registration Act (FARA).