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Hannah Cole

Hannah Cole

Musical artist

Sep 8, 2026

27:54
What would you say to that person who's like, "It's just easier for me not to even think about having to pay d- pay quarterly taxes, then I don't even have to give away that, you know, 34% of my income"? Um, at what point do you think that person should get serious about kinda being more on the up and up?
28:13
Sure.
28:14
Well, I think it helps to know what the law says.
28:16
Um, the law says you have to report that income.
28:20
So do you wanna be a felon? [chuckles] Um, I think there's a lot of...
28:26
I think one of the biggest misconceptions about how, you know, side hustle works or just starting out is that you have control over when you start reporting.
28:39
But actually, the law is crystal clear that you start reporting when you get a dollar in the door.
33:34
And I'm curious, what have you noticed that are some of the most, like, recurring calls for support that you get when you're live with people?
22:23
... w- uh, typically what works best? What's the best arrangement for filing taxes? Is it joint? Is it filing, uh, married but, you know, separately? What have you seen work best for couples, where one is an entrepreneur and one is not?
22:40
Yeah.
22:41
So the tax code was written in theory to benefit married couples who file jointly.
22:48
Like, I'm gonna say, I'm gonna put a big asterisk on that as I say it, but it, in theory it benefits a joint filing.
22:56
You get the most access to tax credits.
22:58
Sometimes those can be cut off if you file married, filing separate.
23:02
Um, but I will say that the tax code was also written by, you know, white landed gentry, mostly men.

7 MINS LATER

30:06
Okay
3:02
Tell me how, how you've pulled this off and kind of how you got to where you are today.
3:07
It's been a journey.
3:09
I started out as a professional artist.
3:11
I'm still a professional artist, but really, that's just a small business.
3:14
Like, artists are just self-employed, so it's not actually...
3:18
It feels weird, but it's actually not very different from just a side hustler or a freelancer.
3:24
But I felt really frustrated at the kinds of approaches that I got from, like, money and financial people.

5 MINS LATER

8:37
Mm-hmm.
10:45
And people were probably like, what can we kind of run through like 10 99 from a gallery schedule C, like maybe just a couple of basic terms and like how we should think about them.
10:56
Oh, I love this.
10:57
Let's do that.
10:58
So a Schedule C, let's do that one right up front.
11:01
Pretty much everyone listening to this podcast, if you are running an art business, you most likely have a Schedule C.
11:08
Schedule C is the default place on your tax return where you put your income from your creative practice, your art business.
11:17
And it's also where you put your business deductions.

12 MINS LATER

23:02
What is your expertise on LLCs versus sole proprietorship? Do you want to dive into that? I'm happy to.

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