Heat 2 teaspoons of olive oil in a small skillet over medium-high heat.
Season both sides of the tomato slice with sea salt, freshly cracked pepper, and a pinch of crushed red pepper flakes, if desired. Add the thick tomato slice to the small skillet and cook for 2 minutes per side.
While the tomato is cooking, combine 1 ½ inches of water and 1 teaspoon of white vinegar in a wide medium-sized saucepan and bring to a simmer.
Break 1 egg into a small bowl. Once the water is at a simmer, stir the water with the bottom of your slotted spoon clockwise to make a swirling motion in the water.
Quickly and carefully slide the egg into the water. Cover and turn the stove off. Poach until whites are firm and yolks are still runny, 3 minutes and 45 seconds. Remove the egg using a slotted spoon and drain a bit over the pan.
Remove the tomato from the skillet and place it on a plate. Spoon a dollop of pesto on top followed by the poached egg. Season with sea salt and freshly cracked pepper, to taste. Serve immediately. Enjoy!