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Interview with Mallory Ortberg

posted by Tim Carmody   Dec 01, 2017

Hi everyone. Tim Carmody here. Jason and I are trying something new. I interviewed Mallory Ortberg, probably best known for the site she cofounded called The Toast, about her new subscriber-supported newsletter The Shatner Chatner. (It’s actually been in operation since March, but has a brand new home on the web.)

The full (well, fuller) interview is on my newsletter, which is called Backlight. Below, Kottke.org gets an exclusive, handcrafted, heavyweight gram vinyl excerpt, where Mallory describes what The Shatner Chatner is all about and its place in today’s simultaneously imploding and exploding media galaxy.

I hope you enjoy it, and if you do, check out my Tinyletter and keep coming back here to Kottke. It’s an experiment in collaboration we’re excited to try.

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Mallory Ortberg: I love the Shatner Chatner. It feels very important to me that this newsletter always be in some way connected to… not necessarily Bill Shatner the man, but William Shatner the persona. That’s always super important, for me to distinguish between the two. People keep trying to say, “did you hear that thing that William Shatner said on Twitter?” I’m like, “no, I never want to know about Shatner.”

Bill Shatner is just the flawed material manifestation of the spirit of Shatner.

It’s a fact. It’s a red herring you know. Let it be what it is. I am trying to commune on a different level with with the Shatner… I feel like I have a running list of male fictional characters that weirdly drive the engine of the Shatner Chatner where I’m constantly trying to figure out, “what is my relationship to you? Why are we kind of the same?” And Niles Crane is also one of those people. And I again don’t know why. That’s what I’m still trying to use Shatner Chatner to figure out.

So Shatner has emanations and penumbras not just on this planet, but fictional ones too, in other characters.

There’s like one body, with multiple incarnations.

[The new site] is a little more professional, but it’s not the same - it’s not like The Toast Part 2, where I have to also run a whole website. They run the website. I just get to make jokes. And it’s not to say that it is The Toast 2.0, content-wise either. It’s very much just like Mallory’s weird thoughts and feelings, for however many folks would be interested. It may be, you know, a smaller crew, but I also want to make sure that it’s like a reasonable amount of money and not something that like only really well-off people will be able to afford.

I mean, I can’t always necessarily convince an editor to publish, “Hey, I wrote a bunch of stuff about my weird inability to love Stephen Sondheim but I really want to, because it helps me understand my best friend Nicole.” That can be the hard pitch to make when outlets are cutting their editorial teams. Whereas I’m like, “ah, but I’m pretty sure at least 5000 people would actually be super into learning more.”

That makes sense, especially when you have a track record of being able to bring your audience with you; they’re interested in going wherever you’re going.

Sure. And if they don’t, you know, then I’ll get to do that too. whatever the experience is going to be, it feels just like cool to get to try something that’s not the same as either, “OK it’s going to be a full time job. I have to run this website, I have to do a lot of behind the scenes stuff as well as write a lot, and I also have to make sure that on a daily basis the site is close to profitable, or else we’re going to run into trouble.” And then at the other end something like a free newsletter is really really fun, and then after like six months, it’s like, “oh, but this is how I make my living. I should probably at least try to not write for free all the time.” Even though, again it’s my choice, it’s not like somebody was trying to get me to publish a newsletter and then not pay me. It’s just more of a sense of what’s the right balance here between getting paid for my time and work versus not overworking myself.

I was pretty jazzed about the possibility that I won’t have to like answer any more e-mails than I do already which is great. Very hard time doing that. But I will get to write some more.

Will the newsletter still be published weekly?

So my hope is, with some money coming in, I’ll be able to dedicate more time to it than just once a week. For me, as somebody who has kind of a high natural tendency toward output, I really like to write kind of a lot. You know I took some time off after The Toast to write a little less and rest, and it was great. But I love to write and I love to come up with a bunch of dumb ideas and make jokes.

And you know again I would make it really clear: It’s not The Toast, the Sequel, because you can’t like promise anybody else’s involvement. “Don’t worry, I’m reuniting the gang, I’m back on the road.” Can’t do it. I mean, if anyone listening were to say, “I have ten million dollars and I want to make you restart The Toast,” I’m sure I could talk Nicole into it in a couple of years. This isn’t that.

So it’s a solo project?

I think it’s going to stay mostly solo. It would be so fun to periodically have like Nicole and some of my pals stop by. But I think especially because I’m charging individually, I don’t want to ask anybody to be a regular recurring feature if they’re not also making money. So I think it is going to be solo in that regard.

I’m still going to be writing books, and it’s not affecting other projects that I’ve got going on. But it’s nice, especially as a freelancer, you know - I freelance for Slate, I freelance my books (that’s probably not like the way to look at it). I have a lot of independent projects. I don’t have like a day job where I get benefits and health insurance. So part of what feels exciting about this is at least the opportunity to try to have that home base.

As grateful as I am for all the opportunities I’ve gotten over the last couple of years, I’m also very aware that, like The Toast, which is something that I loved and did well, that could go away. Not necessarily in the next five minutes, but in the next six months or the next year and the next two years. And so I always want to have at least one or two things that I feel like “OK, if everything else fell apart tomorrow, would I be able to pay my bills next month?” “How am I doing my best to make sure that I am taking care of myself financially in a really hot and cold field?” I’m a freelance writer. That’s means sometimes things are really flush and sometimes are really not.

I know I hope it works out. If it doesn’t at least I give it a shot. Like, I’m always a little bit anxious to think ahead to what my next thing with my backup with my third fallback plan. All the way down to, you know, let’s assume the entire industry craters tomorrow. “Where could I try to go get a job that would give me dental insurance?”

It’s funny because, I don’t at all think “oh, the future best response to that is everybody go start a newsletter and become like a freelancer!” It’s part of what’s just like really painful is just a reality of: people get fired for trying to unionize; people get fired for reporting sexual harassment at work; companies are laying off a lot of people both in my industry and in other industries. Just systematically we’re removing workers’ protections and making sure that people who have to work to live don’t have to work. There are a lot of people who work 40, 50, 60 hours a week and who do not have health insurance or retirement plan or unemployment and don’t know how they’re going to pay for food this month.

I’m really grateful that that right now, I’m making decent money. But also, you know, starting a newsletter is not the answer to the fact that we live in a society where workers are just not taken care of, not prioritized, not given a fair exchange for their work. Which of course every conversation I feel like that everyone has about work right now comes back to “we need unions,” “we need workplace protection,” and all that.

So I don’t want to pretend like this is the correct response to the world we live in. It’s just the project I’m excited about. And I’m anxious, and I call my representative in Congress all the time but it feels weird and threatening.

At the same time, I have so many people I know, not really like personal friends but just people I love on line, who have newsletters, and I love it so much, and I wish there were more ways for people to charge like a small amount for it. Right? I have so many people that I would love to pay, like, a couple of bucks a month to read their thoughts about food or movies or feelings or you know all of the above and anything that makes that easier. I’m kind of jazzed to at least explore.

I know I was thinking, if I were giving advice to someone who was like, “I used to do this job for money and now I do it for free,” it would be, try to make some money doing it. Because you know can you can do it.