1. Social Silo-busters: Couple the evils of the garden walled social network approach with posts on how hard is it to make friends later in life, add a pinch of all that useless time spent in the car commuting (scraping the bottom of Spotify or Audible) and you arrive at: ad hoc voice-based social networks based on proximity, e.g. through limited range (100m) FM transmitters (one cheap way would be to use a rPi: https://www.raspberrypi.org/magpi/raspberry-pi-fm-transmitte...)
2. "Why can’t I manage waste pickup from an app? What might a re-invented garbage truck look like?" These are spot on! You see news of these everyday but they are very slow to appear. Make a DARPA like challenge to sort waste.
3. Sleeper Markets. Again, he's right in that there are vast markets relatively untouched by technology. Examples: The buzzer for restaurants, why can't it have a screen to display menu, or let your preorder? At a restaurant, why can't I see the most ordered 5 items and have to go through pages of menu? Similar idea for supermarkets: why not have a giant screen at the entrance showing most bought products, interesting product pairings and other data that may be useful?