In a large bowl, combine the olive oil, granulated cane sugar, brown sugar, and eggs. Beat for 1-2 minutes, until frothy and doubled in volume.
Add the pumpkin puree, sourdough discard, yogurt, buttermilk, and vanilla extract. Mix until smooth.
Add the cinnamon, pumpkin pie spice, baking soda, and salt. Mix until smooth.
Add the flour and chocolate chips. Mix just until combined.
Transfer the batter to the prepared loaf pan, then add the streusel topping.
Bake for 60-65 minutes, until a toothpick inserted in the center comes out clean.
Let cool for at least 15 minutes in the loaf pan before transferring to a wire rack to cool completely. If desired, drizzle on the icing glaze after transferred to the wire rack. Enjoy!