I like "How to Make it" and think the writing is good and the acting is good. Yes, it could be better, but the first season (watching it On Demand) has kept me coming back. Bryan Greenburg, Victor Rasuk, and Lake Bell put in fine performances and I can see this as a real story line in New York. There is plenty of realism in the writing and acting.
It is not fair to compare this to Entourage, and I think those comparisons are partly why the show only lasted 2 seasons. People who were drawn to the show by this comparison and expectations of what the show would be like were disappointed. Entourage brought flashy people, a fantasy life in Hollywood, and lots of naked women, bare-chested fit men, and sex. It was a fantasy world with a few hints of reality.
"How to Make it ..." was more about reality and with no nudity and sex. So right there the majority of the Entourage audience started tuning out once they realized they weren't going to see Lake Bell, Florence Faivre, or anyone else naked. As superficial as it sounds, there are a number of people that watch the HBO shows because there is nudity. Without that, it's "just another show". They picked it up a bit in season 2 with a few nude shots - and the famous Lake Bell scene in Episode 3 that won her a Mr Skin award - to try to boost viewers. But by then it was too late, they lost a lot of the HBO viewers and ratings were down 25% in season 2.
So I think "How to Make it" didn't quite fit the bill of a paid cable channel show. If it were on a network, it might have fared better because the expectations of the audience would have been different - not lower (or higher) just different.
There are some ways where it did compare to Entourage, but that doesn't mean it was good. It was the typical up/down story line - things are going great, then disaster strikes. They work their way through it, things look good again, then something else goes terribly wrong. Then the first season ends on a high note to get you hooked for season 2 - where things go wrong again soon. That was the type of story line throughout Entourage which started turning people off after a few seasons - but the promise of hot naked women kept them coming back. As I stated above, without that lure, this type of story line got old fast and viewership dropped.
You can create drama in other ways then this constant up and down in every single episode (look at Boardwalk empire, Sopranos, Breaking Bad, etc.) but it seams that is the only way this production team knows how to operate.
So in the end, I liked the show and think Lake Bell is a beautiful and talented actress. I watched both seasons and would like to have seen more of it, but I think it just didn't have enough to keep a pay channel audience watching.