It is more to do with scale than the actual figures. In using sums like "million dollar", "10 million dollar" and then terms like "home run", "swing" etc. you're actually trying to define different scales of startup ideas that don't have a better terminology - but probably should.
There is a completely different risk profile in small businesses, then paid apps, then freemium products, then ad supported products. They are distinct, we just don't have a good way of communicating the differences.
One school of startup advice advises against raising money while another says to raise as much as you can. Rather than being in conflict, it is clear that they don't actually contradict each other but rather apply in different situations.
The don't-raise-money school that DHH et al preach is suitable for paid products and services, while an ad supported idea like a search engine or social network, or an idea with heavy R&D requirement requires that money is raised.
One million / 10 million / home run is a very imperfect way of classifying this distinction. The differences are all in the cashflow model - atm we refer to a flat cashflow model, a linearly increasing cashflow model, an exponentially increasing cashflow model and cashflow models that go negative for 2-3 years and then go either linear or exponential all as 'startups'.
