Never though of running cable on outside of house, how do you then enter the cable into the house?

Yeah, that's the part you'd have to examine your house to find a way in. For me, I did it right next to where my cable service line and my AC coolant lines come into my basement, so I knew it was a good path, and also wouldn't look out of place. It comes into my basement just above my foundation, but below the floor of the 1st floor. Through what they call the rim joists. Like what you see in this image where the plumbing goes through the wall. So you might want to look for any utilities you have coming into the house near your foundation... cable, phone line, etc (avoid power lines of course though).

If you have siding, you could use clips like these so that you don't have to screw into the house to contain the cables. Of course, some here would say that will leave your cable vulnerable to being cut, so you may want to put it inside conduit. I don't do that though, because any place my cable is run is also in view of a camera. So it would at least alert me before the cable is cut.

Also, livingwaterRed has a good recommendation. Hiring someone to do it may not be a bad idea, they're experts at that sort of thing and would probably be able to run it through your insulated walls, or at least find a way to hide it better than you can as an amateur. I've read the typical rate is about $150 per drop... so that might be worth it to have it done right. I had some electrical work done at my house recently and they had to fish some of the wiring down insulated exterior walls, something I never would have attempted, but it was a piece of cake for them.