Not at all. Jobs is not implying that you should, like, jump from minimum wage job to minimum wage job until you find one you like. He is suggesting that if you put in effort, like learning deeply about something, that will close the gaps that are necessarily closed to find true love. Which is the same thing Cuban is saying.

Perhaps you can interpret Jobs' statement that way in a vacuum, but fortunately we don't need to evaluate what Jobs' said in a vacuum. He also said a lot of other things that allow us to build up context around his intent. He spoke a lot about how he found his love.