One cool thing about this is what it does to the marginal cost of travelling. Assuming the place he would travel to has rooms for about the same as what he's paying in SF, the marginal housing cost of traveling becomes 0, which would make it a lot more financially feasible to travel frequently, especially to places nearby enough that travel costs are low.

Now, he's a startup founder and probably doesn't have a whole lot of time to do so, but if someone with a less demanding life did it, they could travel a lot.