Bill Grundfest, co-founder of the Comedy Cellar, the New York comedy club that served as a launchpad for some of the world’s most famous comedians (including Jon Stewart, Bill Maher, and Ray Romano), joins Stew Fortier to discuss why leaning into what makes you unique wins in the long term.

1. The first question you need to answer is, “Who’s my audience and what do they care about?”.‍

Learning who your audience is and what they care about is the first step to finding success as any artist who hopes to make money off their work. A standup comic and writer, Bill Grundfest has seen this play out again and again, whether in terms of his work or others’.

“Ask yourself, ‘Who’s my audience and what matters to [them]?’... When you're in a commercial art, that is a really important piece of the puzzle. If you're in a fine art, create what you want. Sculpt, paint, express yourself with no parameters or restrictions, do what you want. If it sells, if it doesn't, you don't care. You're an artist. But when you're writing for money, it is a commercial art.

And the first thing that you need to do is ask yourself, ‘Who's the audience?’ That doesn't mean that you pander. It doesn't mean you go, ‘Oh, who's my audience? I'm going to do whatever I think they want.’”

2. Write about the things that resonate with you deeply. Anything less won’t get much of a reaction.

Knowing your individual worth and what you bring to the table (or page, or stage, or screen) is just as important as knowing who you’re communicating with. In the Venn diagram of you, your audience, and where you’re similar, the overlapping area of shared passions is the sweet spot that will propel your work to the next level.

“Just write something that makes people feel. And the only way to do that is if you feel it. You've got to feel it a thousand times more than the reader is going to end up feeling it. The reader will feel a thousandth of the passion that you bring to it. So if you don't bring it, if it's not something that you genuinely care about, then it's going to turn into what most things turn into, which is a big pile of nothing, a big pile of ‘who cares?’

And in terms of the ‘signature move,’ it is so important… What you need is a clear point of view that makes you different from all the other people…”

3. Be different.‍

Being different is almost as important as being good.

“It's almost more important these days to be different than to be good. And it's almost like being good is on you. If you can sleep better at night knowing that you have honed your craft to the best level that you can, great. But we all have seen comics that are successful that stink. We've all read nonfiction and fiction pieces that are very popular: they sell a lot of books or they get a lot of clicks, or whatever the metric is, and they stink. But they're different.”

4. Writing great stories is not complicated.‍

Hollywood is filled with screenwriting teachers with grand theories about how to write great stories. The problem? None of them have actually sold a script. Writing great stories is actually quite simple.

“‘Story’ is just another word for ‘conflict.’ Who wants what and what stops them from getting it. If you can describe your story in that one sentence, ‘Who wants what and what stops them from getting it,’ and if you pick your ‘who’ properly so that your hero is somebody that we care about — not somebody that we are told by the author we should care about or somebody that we need explained to us why we care about them…

They're actively trying really hard to get something, and they'd rather die than not have it… We feel why they want it, and we hope they get it. And they reach the obstacle that thwarts them, that causes them to escalate…

Don’t even think about the theme of what you're writing until you've written at least the first draft. If you've written something that's interesting, I promise you, it has a theme...this isn't about getting an A in a class. This is about selling. This is about selling something.”

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5. Rejection happens.‍

Not everyone is going to like your work. There’s nothing you can do about that except continue to have faith in your material and move on. If you’re able to please everyone, that’s when you should worry that something is wrong.

“You’ll get a lot of rejection letters as a writer. Don't necessarily take those to heart. That just means that person was not right for you. [It] doesn't mean there's something wrong with you. You got to ask a lot of people to dance before somebody says, ‘Okay.’”

6. Don’t let anyone replace you.‍

Be good, yes, but be so different that they can’t ignore or replace you. Bill Maher had to learn that the hard way when he got replaced on one of his early shows. As Bill Grundfest told Jon Stewart in his early days, “You are not the vehicle for your material. Your material is a vehicle for you.”

“The reason they replaced [Bill Maher] with David Brenner is because they could. [Maher was] doing something that a lot of guys can do. When you pick ‘your signature move,’ when you pick a ‘what is that thing that makes me,’ then you'll be able to create a niche that nobody can compete with.

And will you be successful in that niche? I don't know, maybe, but I know that you'll have zero competition because nobody else can do what you're doing... Being different is the most important thing. Be good, too, but be different.”

7. At the end of the day, to get paid, you gotta solve somebody’s problem.

Capitalizing on your niche is almost like creating a sales funnel: let people know you exist, engage with them, and have them coming back for more. You may be an artist, but when you’re trying to make both art and money, you’re also a businessperson. And no, that doesn’t necessarily have to be a bad thing.

“Nowadays, you need to be entrepreneurial. And I know that rubs creative people the wrong way a lot of times, but it is as creative an endeavor as the actual creating. You're still engineering ideas. You're still working in the design of just end up pressing different buttons on your keyboard.”