The NYC singer/songwriter found himself playing a tiny North Carolina coffeeshop in front of a bored waitress, a couple of college students sitting on a couch trying to read, and a guy typing away on his laptop. While other performers might have bolted for the door and the nearest bottle of Jack Daniels, Goldstein decided to play to the audience that was there.

He put the guitar aside, turned to the laptop guy, and earnestly tried to talk him into logging onto teddygoldstein.com to order his self-titled CD and see if it would be delivered by the end of the show. Laptop Guy, clearly startled, wasn’t going for it, but Goldstein did get a laugh from the waitress and the students on the couch.

Over the next several weeks, in front of much more attentive audiences, Goldstein mined laughs from that story, enhancing his growing reputation as a dark-humor storyteller who rolls with the punches as well as he delivers them in his songwriting. Playing to the audience he’s given, no matter what kind of audience it is, is just one of Goldstein’s promotional rules not always remembered by more seasoned artists. Now with two studio albums available at his web site and a live one being mixed for a summer release, Goldstein is once again focusing on his more creative efforts at self-promotion afforded by the sometimes biting, sometimes sad, often defensively funny aspects of his songwriting.

Take a track like "Off Road Automobile," which compares the dating scene to cars. A self-professed car freak, Goldstein saw a promotional opportunity in one of his favorite NPR talk radio shows, Car Talk.

"I was listening to the show a lot," he remembers, "and I noticed that before and after commercials, they were playing songs that mentioned cars. So I just decided to send ‘Off Road Automobile.’ All of a sudden, people started calling me, saying, ‘I’m hearing you on Car Talk!’ It was great, but I never did get to hear them play that one on the air."

Nevertheless encouraged, Goldstein sent the program’s producers another car-themed track, "The Love Lot," and almost wound up totaling his own car when he heard them play it. "I was on the road," he says, "and I was listening to the show and heard the song, but I was going out of range and losing the signal! I was literally driving in reverse along the shoulder of the highway, trying to get the signal back, and I heard them play the chorus."

Goldstein also finds promotional opportunities in the funny stories he tells during his shows. He uses the laughs to get his foot in the door of unconventional gigs like the Funny Songwriters Festival in Massachusetts last March. While he enjoys such opportunities, he’s quick to say that he doesn’t try to write novelty songs or go for the joke.

"The thing about the humor is that I never really try to write a funny song. But generally, if I’m being completely honest in the moment of songwriting, it tends to go toward some kind of humor. Any good comedy is based more in tragedy. If I write something that makes people laugh, I want to write something next that punches them in the stomach. And them once they’re down, I want to find another lyric that’s going to bring them back up. I try to make it like a roller coaster. The song ‘Widow’ off my second CD is a good example. It’s a serious song about the heaviness of marriage, but it’s sort of a joke, saying that the thought of marriage scares me so much, I’d rather wait until I’m dead. So instead of proposing, I’m asking her to be my widow."

Such unusual songs get Goldstein noticed on the more commonly traveled avenues of promotion. Through a publishing deal with a New York company, several of his songs were used in an independent film called Three’s a Crowd. But Goldstein quickly learned it also never hurts to go after the guilty pleasure. He got a big kick out of the emails he received after his tongue-in-cheek "Lucky in Love" was recently featured in the NBC reality show Meet My Folks.

"People were saying stuff like ‘I just happened to be flipping channels, and I heard your song!’" Goldstein laughs. "Nobody will admit to watching that show! But I got tons of responses from people who heard it, and they couldn’t have all caught it by accident! What I find really funny is that in real life, the couple that got together on that show will probably last about as long as the song itself."

As Goldstein prepares to release his live CD, he feels that he’ll be offering the best promotional tool of all: the full experience of his live show captured on CD. The promotional proof is in the resulting sales. Goldstein finds that after he plays a town, he sees an increase in website CD sales from that particular place.

"My fans aren’t real impulse buyers," he says with a shrug. "My show seems to stay with them, and they order CDs later because of it. At the end of the day, this is about a full show. I know from watching artists that I’m inspired by that at the end of the evening, when you go home, what you remember most are the stories they told between the songs. You might remember a song here and there. And I don’t mind that, I really don’t. We indie artists may not be playing stadiums, but we still try to give a good show and have a good time."

And that can sell a CD faster than any talk radio or reality show.