Cleveland and San Jose are about 2,145 miles apart by road. Split the difference and you arrive near Denver, the city closest to the halfway point between them. That puts roughly 25 hr 40 min of driving on the Cleveland side and 19 hr 26 min on the San Jose side — the fairest single meeting point among the cities near the middle.
Over this distance most people will fly rather than drive the whole way. Denver still makes a fair, central place for Cleveland and San Jose to converge, splitting the travel instead of asking one side to cross the country.
If Denver doesn't have what you're after, Omaha and Oklahoma City are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Cleveland and San Jose.
City descriptions adapted from Wikipedia (CC BY-SA); photos via Wikimedia Commons, credited above.