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Revue Creator Highlight: Meet Kevin Roose

Anna from Revue
Anna from Revue
Hello all,
Great to have you here. You’ve made an excellent decision in opening the newsletter today, because you’ve landed on our second ever Revue Creator Highlight. This is a new series where we’ll hear from brilliant authors on Revue — and talk to them about their experience of newsletter creation.
Today we’ll hear from Kevin Roose, creator of the truly excellent Futureproof newsletter. You may also know him as a technology writer, author and renowned columnist at The New York Times. Find him online:
You can also meet Kevin in person by tapping in to our Twitter Space. We’ll make sure to talk about the relationship between newsletters and traditional media, and you’ll be able to ask your follow-up questions. Follow me @aemelliott, my colleague @derjarjour, or our official handle @revue to join the Space. We’ll go live on Friday May 7th at noon ET, 6pm CET. See you there!
This interview is full of fascinating insights on the trends we’re seeing in the newsletter realm today. Let’s jump in.
First things first: how did you start writing your newsletter?
I released a book in March, and as part of my shameless self-promotional blitz, I decided I needed a newsletter. I had an old Mailchimp list I used to use to make announcements about new projects and major stories, but a lot of the addresses were stale and I basically never used it.
Revue sounded like a good way to get back into the newsletter game, and the team was very friendly and offered to help me get set up. I started writing a few days later.
What was the hardest thing about getting started, and how did you overcome it?
I’m used to writing for a newspaper, where everything is edited and re-edited and meticulously combed over — and at first, the lack of supervision was both freeing and a little terrifying. (You mean I just… hit send, and it… goes out?)
But I’m a former quick-turn blogger, so I got over that pretty quickly. I write my newsletter on the weekend, and when I sit down to do it, I imagine I’m writing an email to a smart friend. (Sometimes I even put “Dear [friend’s name]” in the header, just as a tool to get my thoughts going.)
You’re super savvy connecting with your audiences on all sorts of platforms, but working in newsletters is relatively new to you. What do you see as the main opportunities of this space?
It’s exciting to me for a few reasons. As a book writer, it’s exciting to be able to turn a one-time transactional event (“I spent three years writing this, please buy it!”) into a more casual, ongoing conversation with an audience.
And as a newspaper writer who is used to tailoring my ideas to a mass, mainstream audience, it’s been fun to use the newsletter as a space to get a little more niche, to go a little wonkier on something like robotic process automation, or add some context and depth to stories I’ve written.
Plus, in a much more pragmatic sense, it’s a great way to find and keep in touch with sources.
How do you see the role of newsletters in the changing relationship between traditional media organizations and their talent?
Are you trying to get me fired? Look, it’s no secret that legacy media organizations (including mine) are worried about the rise of subscription newsletters. I understand that concern — talented, big-name writers really are leaving prestigious publications to start their own independent media companies with email newsletters as their centerpieces — but I worry that the people who run big media companies (except my bosses, who are perfect) are conflating two separate things.
There’s the actual medium of the email newsletter, which has been around for decades and is frankly pretty boring and non-threatening. News organizations already encourage their writers to promote themselves and their work on platforms like Twitter and Facebook, so I’m not sure what a reasonable managerial objection to email newsletters would be, other than that writing on yet another platform might cut into productive work time. 
The actual thing news organizations are defensively reacting to, I think, is the economic model underpinning the newsletters — and the possibility that the big-name writers who work for them will soon discover that they could be making 2 or 3 times their salary if they left their jobs and went solo.
That kind of thing is already happening, and it’s a very real challenge to the business model of a lot of legacy media organizations, which depend on a kind of cross-subsidy flowing from the stuff that is popular and cheap to produce to the hard, expensive news-gathering that doesn’t pay for itself in ads and subscriptions. (There used to be a saying at the NYT that “the crossword puzzle pays for the Baghdad bureau.” I’m not sure what the modern version of that is, but it probably involves Spelling Bee.)
That model still works for now, but it gets harder if a lot of the people doing the cross-subsidizing leave to start paid newsletters. There are still plenty of good reasons to work at a large media organization — especially for writers who like collaborative work, who need editors and lawyers behind them, and who want access to a big, mainstream audience — but there are also reasons to want to go independent, especially when there’s already an ecosystem of independent writers proving that it’s possible to make a living doing this.
Someone on Twitter compared Revue, Substack, etc. to a price discovery mechanism for writers, and I think there’s something to that. Before a few years ago, most big-name media personalities didn’t really have a way to quantify the value they created for their employers. Now they do, and it turns out that a lot of them have been substantially underpaid.
That’s a fascinating development I’m sure we’ll all be agonizing over for years.
We’ll try not to get you fired! How do you think about your newsletter in the context of the work you do at The New York Times?
Right now, it’s more closely related to my book work than my newspaper work. But in the future, I’d like to use it as a kind of proving ground, sort of like how famous comedians test their material in small, intimate venues before doing it in front of 20,000 people at Madison Square Garden.
I can see using the newsletter as a way to test new ideas with a smaller audience before putting them in the paper, or to put stuff that might be too esoteric or weird to survive an editor’s pen, or even just to send out feelers for a bigger story I’m working on. 
What is your process for building a newsletter issue?
I set a recurring calendar reminder every Saturday called “write newsletter.” When that goes off, I start writing. Typically, I’ll have thought about a topic during the week and started jotting some thoughts, so the weekend process is mostly assembly. When it’s in a good place, I usually put it down for the day, and come back to it on Sunday with fresh eyes, and to add the image and section headers and stuff. I don’t A/B test subject lines or anything fancy, and I barely look at my analytics, so it’s all feel. I should probably look at that stuff more, come to think of it.
Newsletter audiences look very different from social media followings. How are you experiencing that disparity while growing your newsletter?
Honestly, I dig the disparity! I’d obviously love for my newsletter to blow up and be read by millions of people, but right now, it’s pretty great to have a smaller space for public writing that has an explicit opt-in requirement.
It means I’m writing exclusively for people who have chosen to keep up with my work in the last 3-4 months, whereas with Twitter, I’m writing for those people plus all of my social and professional acquaintances, plus the people who heard me on a podcast or liked some dumb joke I made in 2014.
It feels a little like starting over at a new school — I can be goth if I want to, mom!
Love that. Thank you, Kevin, for sharing your thoughts with us!
I’d love feedback from all of you on what you thought of this Creator Highlight. Did we ask the right questions? Did you learn what you wanted to learn? How was the length? Let me know by replying to this email.
Looking for even more inspiration? I got you.
Newsletter inspiration
I loved how clear Emily Drewry’s value proposition is to the readers of her new newsletter, Little Tweaks. Every week, she offers actionable tips and advice on how to smooth over small life annoyances and holdups.
That’s a great way to get subscribers excited about opening the next issue. Find out more and sign up here:
Little Tweaks
The week in newsletters
More news from the newsletter space this week:
Twitter acquired Scroll, “a better way to publish and read on Twitter”
Flipboard shifts from programmatic display ads to selling newsletter sponsorships
Email marketers are leaning in to diverse representation
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Have a great week,
Anna
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Anna from Revue
Anna from Revue @revue

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