Bring a small pot of water to a boil. Once boiling, add all of the tapioca pearls at once. Give them a stir to break up the clumps. Boil for 15 minutes.
Cover the pot, remove it from the heat, and let it sit for another 15 minutes.
Drain the water and transfer the pearls to a small bowl. Add brown sugar and stir to mix until the sugar dissolves into a syrup. Set aside.
In a serving glass, add the diced strawberries. Use a muddler, wooden spoon, or flat end of a rolling pin to muddle the strawberries until they become a rough puree.
Add the cooked tapioca pearls along with the brown sugar syrup to the glass.
Fill the glass halfway with ice and pour in milk until about ¾ full. Stir to mix it into strawberry milk and to loosen the pearls. You can keep the layers separate if you prefer.
In a chawan or small bowl, sift in matcha powder. Add hot water and use a bamboo whisk to whisk in an "M" motion for 15 seconds until frothy.
Pour the matcha on top of the strawberry milk layer. Serve layered but stir to mix before drinking!