Not sure what a CS degree is supposed to help with if this guy wants to pursue the "scrappy SV tech startup" world.

He shouldn't be wasting time learning from professors who have never done anything real and have lived in an academic insulated bubble for decades.

Instead he should be building and shipping product after product until something sticks. And spending just as much time on marketing as development, and putting a lot of time and energy into hiring out and training a team to scale up to the next stage.