On Selling Book #1 And Dreaming Rothschild Dreams

For today’s chat, Billfold pal Jason Diamond is here to talk with us about books, money, dreams, and one very particular pair of shoes.

Ester: Hello Jason!

Jason: Hi Ester! I’ve spent too much on lattes today. I’m feeling a little bit bad after hearing that one reader the other night.

Ester: Helaine Olen? But her argument was that no one goes broke getting lattes or gets rich giving them up!

Jason: I liked her argument, but I was thinking, “What if she’s wrong and I’m going broke drinking these things?” I’m really paranoid.

Ester: We all get paranoid that we’re DOING IT WRONG, I think, especially when it comes to money. But you’re celebrating this week, right? The day after you performed at Billfold Live, you announced some exciting news?

Jason: I found out on my way to Housing Works that I sold my first book. It was crazy to find that out and then get in front of so many people!

Ester: We should all have such problems! That’s amazing, though, congratulations. 🙂 How long did the process take? Were you trying to sell the book, or a book, for a while?

Jason: Thanks. Well, the thing is, the book idea evolved from failing to write a John Hughes biography, something I tried to work on for several years until a bunch of crazy stuff happened. So you take those five years and add about six months of my agent and I working on the proposal, and I guess you get a long time. In terms of trying to sell it, that didn’t take as long as I thought. The proposal went out and we heard a few rejections, then a few editors reached out. All told, I’d say that took two weeks. Two very long weeks.

Ester: Two very long weeks, plus five and a half years. And now you never have to worry about money again! That seems like a good bargain. JK, I know advances are awful these days. A tipster sent me an interesting, very candid blog entry on the subject by a Hugo-winning novelist called Why I’m Not Quitting My Day Job:

This is the first year that book advances, royalties, and my day job salary will all combine to bring me up over the $100,000 a year mark (likely $105,000 or so, depending on outstanding items). I was pretty much destitute in 2007 — laid off, sleeping in a friend’s spare bedroom, living completely on credit cards — so 7 years from penniless to $100k is a big milestone for me, and I intend to celebrate it by paying off a student loan.

The goal is to be debt-free (aside from the mortgage) in two years.
I also worked relentlessly to get here, and I’m aware it could all blow up tomorrow.
About 75% of that money I’ll make this year, still, comes from my day job.

Without getting into the kind of details that might make you uncomfortable, are you okay talking at all about the advance side of things?

Jason: Yeah, totally. Although I have to say that even if I made a ton of money from my advance, I’d probably still keep my day job as well. I need to always be doing something, and I pretty much spend my entire day writing about food, so it gives me a chance to escape a little from the book.

Ester: That makes sense. Especially these days, it seems a bit crazy to walk away from a day job you like, even if you come into money, and there are all sorts of studies about how people derive identity and comfort from having a job. Do you have a sort of secret fantasy about what would you change if you get really rich? Probably not from writing books about John Hughes — though he is an icon — but from winning the lottery, say, or getting an inheritance from a great-uncle you never knew? Would you stay in Brooklyn or would you do something vastly different?

Jason: I’m sure you know the song “If I Were a Rich Man.”

Ester: Are you kidding? I was Tzeitel in our middle school production of Fiddler.

Jason: I was Lazar Wolf! Anyway, Sholem Aleichem originally wrote it as “If I were a Rothschild,” and sometimes I have these weird daydreams where I find out I’m a Rothschild and I’m from the poorer part of the family with all the eccentrics, but I’m still worth something like a hundred million or something. Sort of like a Jewish King Ralph.

Ester: Ha! Yes, sure. So, what do you differently?

Jason: I think then I’d probably quit my day job. I’d also probably give a lot of money away, because I don’t think anybody needs that much money, and nobody likes a miser. If I see The Toast is doing a fundraiser, I’d be like, BOOM! Here’s fifty grand. Some non-profit that gives books to prisoners? BOOM! You get a bunch of money. An indie bookstore I like needs an investor? BOOM!

Besides that, I’d also probably buy a place in New York and a place outside of it.

Ester: Ah, philanthropy. I spent a couple of years writing grants for a non-profit and I thought frequently how much fun it would be to be on the other side, reading and evaluating grants, trying to make sure money reached the right people. I’m sure it would also be stressful and bureaucratic and annoying, too, but it would be so satisfying to be able to give things away, especially to good causes. And such an interesting challenge, to try to maximize investments and sort through applicants and figure out where I might be able to make a difference, vs where I wouldn’t be able to, no matter how hard I tried. Like that Menstrual Man in India — did you ever read about him? Think how gratifying it would feel to help fund that kind of innovation.

Jason: I did!

If I remember correctly, we both come from the Jewish non-profit world. I was the editor at a Jewish pop culture site for a few years towards the end of Jewish philanthropists being like, “Maybe art is the way to get young Jews to care,” before a lot of it became more about Israel and marriage and whatnot. It really bummed me out when I started to see that happen because that’s what I’ve always loved about being Jewish almost more than anything, the culture. I feel like if I had a lot of money, I’d try to right that wrong if I could. Then I’d be like a Rothschild!

Ester: Well, that’s just silly. The only thing to do is spend your money trying to make sure every young Jew in America 1) visits Israel; 2) has a part in a production of Fiddler on the Roof; and 3) hooks up with lots of other young American Jews or Israelis. In fact what you and I should do with our imaginary money is make Tinder for Jews. Jinder.

Jason: Why are we not talking about this brilliant idea on email? We could be rich?

I had to listen to a lot of ideas people had to get Jewish money. I might be ruining a potential piece by talking about this, but my favorite was this guy was trying to get ten grand so he could start some program that I swear was called “Challah Back” or something terrible like that. The idea was this: You get a room, an open bar for an hour, and a bunch of single Jews. They talk, and regardless of what happens at the end of the night, everybody goes home with a challah.

Ester: CHALLAH BACK. I love that idea so much I want to make out with it on a bus in the Negev. I want to have its children and make sure all of those children have Bar Mitzvahs, unlike that brat Ali on Transparent.

Jason: I just remember thinking, “It would be so awesome to be sad because you got rejected by a bunch of girls names Rachel or a bunch of dudes named Jared, but at least you get to walk home eating a challah.” But yeah, Jews and money, always a great topic!

Ester: I am indefatigable on the subject. 🙂 But I love books just as much. Is there an author-who-makes-money type of person whose career serves as a goal you’ve been working towards? When I was younger and people asked what I wanted to be when I grew up I said “Margaret Atwood,” because she got to write poetry and prose for a living and be taken seriously. Even now, I don’t think I have a better answer. Of course, Atwood doesn’t blog; but maybe she would have, when she was 30-ish, if it had been an option.

Jason: I think the one writer who always comes to mind is Nora Ephron. She could write great and funny essays, but she could also create the template for romantic comedies. I think Mindy Kaling is amazing because she’s really following in Ephron’s footsteps while also sort of deconstructing the Ephron formula. And she’s also a good writer.

Rosie Schaap is another one. She’s one of my favorites. I love how she can write about booze and make it personal. Drinking With Men is one of my favorite memoirs/personal essay collections.

Ester: These are such great role models. My only worry — which is true for Atwood too — is the “Oh God, am I reaching too high and setting myself up to feel like a failure” thing. Like, maybe I should have a more accessible goal. Myla Goldberg has a pretty good life, it seems: she teaches creative writing in MFA programs, even though I don’t think she has an MFA herself; she gets to keep writing books and appearing at literary festivals. And live in Brooklyn with her family.

Jason: I have a lot of respect for her. I think a lot of my favorite writers do that. Alexander Chee teaches and works on his writing. Roxane Gay teaches and writes. Porochista Khakpour, Justin Taylor, etc. I think that’s a really smart way for a writer to balance things if they can pull it off. Lord knows I can’t.

Ester: Totally. But I wonder if nowadays that’s as much of a pipe dream of dreaming that you’re a long-lost Rockefeller. Ah well. Either way, you’ve sold a book! That’s step one! What are you going to spend your advance on? Boring things like food and rent, or do you have grander plans? (DISNEY WORLD!!)

Jason: I’m going to buy my wife something nice. Besides that, I might buy a new pair of Air Jordans. Maybe I’ll get a pair of the 6s? He won his first title wearing those.

Ester: Excellent choice, sir! Enjoy.

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