The less expensive TV converter boxes (Homeworx, iview, Ematic, etc) don't have internet connectivity. They get their program information from the broadcast signal. A lot of broadcasters are kind of spotty on how much information they provide and how far ahead they show programming information. None of it goes past 24 hours that I have seen.
Is the Tivo capable of accessing this information included in the broadcast signal? If not, your brother should still be able to look up schedule information in TV Guide or sites like Titan.tv. He would then be able to program recordings by channel, time and date. That's how I do it with my cheap little Ematic converter box and it works just fine.