In the bowl of a stand mixer, whisk together the warm milk, dry active yeast, and sugar. Set aside for 5 minutes to activate.
Add in the eggs and whisk for 2-3 minutes until creamy.
Add in the flour and sea salt. Using the hook attachment, knead the dough for 2 minutes.
Add in the extra virgin olive oil and knead for another 5 minutes. The dough should have completely absorbed the extra virgin olive oil. If not, knead for an additional 2 minutes.
On a clean surface (without flour), knead the chocolate chips into the dough by hand. This helps distribute them more equally.
Form the dough into a tight, round ball. Place the dough into an oiled bowl, cover with plastic wrap, and set aside in a warm place for 2 hours.
On a clean surface, separate the dough into three equal parts. Roll out each part in a log-like shape that is about one foot long. Braid the three parts together.
Line a loaf/bread pan with parchment paper. Place the braided dough into the pan. Lightly cover with a tea towel or plastic wrap. Set aside in a warm place for 3 hours.
Preheat oven to 350F.
Brush an egg wash (whisk one egg until one constant color) over the brioche loaf. Bake for 30-35 minutes, or until golden brown.
Allow it to cool for 3-4 minutes.