Dan's saying that the political machine is so rigged that it's very difficult for a third party to succeed. He gets right down into the gory details of the electoral system, it's eye opening.
You probably caught him at a bad time. He's also argued that third parties are the only way forward in America (which I think is not true). At this point, his Common Sense podcast is somewhat repetitive of his previous stuff, but he's trying to say new things each time, which is tough.
His Hardcore History stuff, on the other hand, is mind-blowingly awesome!!! And not repetitive.
In what way is it not? I'm a firm believer that the two-party system sucks and we need electoral reform to make third parties viable, and every time I vote I wish it were already so... but there's no escaping the reality that the system, as it is built today, makes third-party votes as useful as drawing a spaceship on your ballot.
Because the nature of the system makes it unstable with more than two viable parties. It is possible for a third party to attain a critical mass and become viable, but it would displace one of the current major parties and we'd be back to a two-party system.