How Gilmore Girls Do Money: Grant the Troubadour

Gilmore Girls

When he had the idea, all those years ago, it was brilliant.

“You can’t be a panhandler if you don’t ask for money,” he told the woman he was dating at the time.

“So you’re going to quit your job?” she asked. “To not panhandle?”

“Nobody’s paying for music right now,” he said. “They’re getting the music for free, and then they’re paying later, because they like you.”

“I still think Napster is stealing,” the soon-to-be-ex-girlfriend said.

“No,” Grant told her. “It’s a cultural revolution.”

Grant already had plenty of people in Stars Hollow who liked him. It was the perfect town for a slightly nerdy retail associate, where he could hold court both in Taylor’s book club—most recent selection: Tracy Chevalier’s Girl With a Pearl Earring—and Kirk’s bi-weekly D&D game. (“Fortnightly,” Kirk always said. “Bi-weekly is too confusing.”) Grant played a bard named Lord Pegason, and he built the character out of the parts of his life he dreamed of making true.

So, with his status in the town already established, all he needed to do was provide the free music and then collect the money.

The next day Grant took his guitar and he stood by the gazebo and he began to play. This in itself wasn’t particularly unusual; he had often spent summer afternoons jamming, either by himself or with a few friends, in the park. But it was fall now, the type of fall that seemed to linger forever, and Grant had a plan.

He slowly began moving away from the gazebo: first a few steps, then a few feet, then to the edge of the sidewalk. That was when people started asking what he was doing.

“Haven’t you heard?” Grant said. “I’m the Stars Hollow troubadour.”

He had thought very hard about his sales pitch, and it worked. “Oh, I guess I have heard you out here recently,” they always said. Grant smiled and kept playing.

“Am I supposed to give you money?” Kirk asked, later that afternoon.

“No,” Grant said, singing the word to match his fingerpicking. “I’m the Stars Hollow troubadour. I’m giving the town the gift of music—for free!”

“Yeah, nobody pays me for half the stuff I do either,” Kirk said. “Well, have fun.”

Grant continued to play, and began leveling up exactly as he had hoped. First, there was a town meeting where Taylor acknowledged that he did, in fact, appear to be the Stars Hollow troubadour. “If nobody else minds it, I don’t.” Then, after a mild winter had turned into the kind of spring that still looked and felt like fall, after the entire town had seen their official troubadour stand outside in his fingerless gloves and his signature brown jacket for almost six months, Grant submitted an application for an arts grant, titled “Grant Grant a Grant” and then quickly retitled “Stars Hollow Arts Association Grant Proposal.”

He got it. After all, he had been providing a necessary service to the entire town for free, and artists deserved funding. Plus, the grant applications were pretty thin that year.

The grant money, if managed carefully, would cover his living expenses for four months. Grant began to make notes of all the other ways he could earn money:

Make an album

Monthly concerts, charge admission


Get businesses to pay me to sing about them (selling out though?)

Residency program, “host the Town Troubadour for a month!”

Tour other towns

Sell T-shirts and other merch (didn’t work for Kirk)

“Make an album” seemed like the most profitable enterprise, so Grant put a sign next to his guitar case that read “Ask me about my upcoming album!” and bought a microphone.

The resultant album, titled “Grant the Troubadour a Moment of Your Time” and then quickly retitled “Stars Hollow Songs,” was not great. Grant had recorded and mixed the entire thing on Audacity, because he couldn’t afford to pay anyone else to do it, and plus he was in the middle of a cultural revolution which was literally handing him the online tools to create his own destiny.

But it didn’t have to be great. They weren’t going to buy the album because it was great, after all. They were going to buy it because they liked him.

Grant put copies of his album, burned on his home computer, in front of his guitar case. He printed out a sign that read “also available on CD Baby!” but removed the sign after the first day because he thought it might be driving away sales. He added the album to his email signature. He wrote about it on his blog, and guest posted “how to make an album with just $100” on other musicians’ blogs. (His blog commenters were the people who got him to stop saying “cultural revolution.”)

He sold 473 copies, all in all, which wasn’t bad. It grossed him $4,730 before taxes and business expenses, and the business expenses turned into tax deductions. That kept him going for another three or four months, which gave him time to make the second album and figure out how to grow his market.

Grant decided that the more people he could get to like him, the better chance he had of becoming successful, so he began booking bus tickets to local folk, filk, and geek conventions. He paid for merch tables, setting up his two albums next to a guy who resold ancient paperbacks and a woman who designed corsets. He took out his guitar and started playing, and people came to his table and bought the albums—which still weren’t any good, there was all this background hiss that Grant couldn’t erase, but they’d find that out later.

Make “best of” album

Become official convention troubadour for mid-Atlantic?

Teach continuing education class on following dreams

Apply for more grants

Sell T-shirts with my lyrics on them

Get on Stars Hollow radio

Make friends with famous musicians who can help me

Grant spent every night coming up with more ideas to make money. It was the most exciting time in his life, sitting in his tiny apartment with the mold on the wall and the mattress on the floor. He was part of the new artistic revolution. He had become the person he always wanted to be. All he had to do was stay a few months ahead of the money, and he could be this person forever.

Previously on How Gilmore Girls Do Money: Luke Danes

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