Mallory Ortberg: Yeah, I started it right around when I finished the book, and found myself at slightly loose ends, and I was sort of trying to figure out “where do I want to put all the weird jokes and thoughts and ruminations?” And I no longer had a website to force everyone to read them on. I had a couple friends who had started newsletters, and it seemed like a lot of fun especially because it’s opt-in. Not that The Toast was like forcing people to click on it, but I just kind of like the idea of, if you think you’re on board with this kind of thing, you can follow along, and if you’re not, you won’t. And it is a lot of fun.

I really just enjoy doing something that had sort of no editorial oversight and was just really whimsical. But we pretty quickly ran into the subscriber limit, which was a shame. I felt bad saying, “sorry, we’ve run out of people who can look at it. Now you have to stop.”

Ortberg: 7,500 people. We actually filled the first limit, which is 5,000, and TinyLetter was super nice and added another 2,500 people to the list. Again we filled that up pretty quickly. If you want bigger than that, you have to go to MailChimp (which charges the sender money for larger newsletters). And the idea of paying someone else money to do something that I used to do for money felt like, “OK, even I know that’s not how it should work. I’m not the most sound businessman alive but I’m pretty sure that’s bad business on my part.” I was still considering it, and then I stopped and I thought I am not like taking care of my own professional future. So for a little while, I thought, it will just have to be capped and that will be that and there will only ever be seventy five hundred members of the elect.

And then a while back. Hamish McKenzie from Substack got in touch with me and was like hey we’re we’re launching this thing where people can write a tinyletter. I mean, a newsletter. (I’m doing that Kleenex thing where I’m using the brand name to refer to the object itself.) And people can subscribe to it. And that sounded awesome, because that would like solve my problem of being able to make it available more widely. And also I could make some money doing it, because it’s my words and ideas and thoughts, and I was like, “that sounds great.” At a certain point, when you write for a living, there’s only so much time you can dedicate to do something for free before you’re like, “I should not only do that.”

It’s 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.

Ortberg: 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 the 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 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.