What I’ve learned working on editorial projects

What do I know about all this?!

Over the last decade, I’ve worked on a lot of editorial projects that have the goal of entertaining and enriching the smart, ambitious, thoughtful people that hang out on the internet. By editorial, I mean longform content that is tied to an idea (as opposed to a product).

Those projects include: standing up Stripe Press, supporting the launch and distribution of Increment magazine, playing editor for Stripe’s blog, launching Stripe Atlas Guides, researching and writing for The Kool-Aid Factory, publishing my weekly newsletter, Founder Fodder, conceiving of and launching two new publications you’ll see in your feeds very soon, and co-conspiring with many who are looking for guidance on their editorial strategy.

I have also written for First Round Review, Every.co, Are.na, and ghost-written blog posts and landing pages for tech companies you’re very likely familiar with (and hopefully love as much as I do). In a past life, I wrote two novels (both were published by Harper Collins, one was recently optioned for a limited television series) and told stories for The Moth (once in front of a live audience at San Francisco’s historic Castro Theater).

Doing this work has also led me to become a great appreciator and student of the great work others are doing in the space. And with that, here’s what I know and think you might be interested in knowing, too.

What does an editorial project entail?

All editorial projects, regardless of their scale or scope, engage in the following activities.

• Editorial/Production: deciding what to cover, who covers it, getting the ideas to their full expression, and getting the material into its final format
• Marketing/Distribution: getting the ideas out in front of those who will love it
• Operations: keeping the whole operation on the rails

Each activity comes with its own considerations, questions and quirks and requires its own set of skills and resources. I’ll share more about how I think about all that, and some examples of what I think Great looks like in the sections below.

More on editorial/production

• Your raison d’etre: So many people come to me saying they want to have an editorial strategy (“it’ll be great for brand or lead-generation!”, they say). Starting with wanting a pat on the back or leads isn’t enough. A great editorial strategy starts with having something you’re dying to say and then building a strategy around that. (It also helps to consider who you want to attract by way of consumers). Most importantly, an editorial strategy is distinct from a product marketing strategy and should be treated as such–different goals, resourcing approaches, talent, etc.
  • Like, Introducing Increment, Why Stripe Press exists (scroll to the bottom of the page)
• Idea/Topic Space: What is on-the-table for you to cover and what isn’t?
  • For Stripe Press, every book had to fall under one of three broad topic areas (Technology, Economics, or Society) and fit into one of two topic types (Turpentine–tactics for practitioners, or Big Ideas–inspiring stories or concepts that shape the way we think about things). If it didn’t fit, we wouldn’t publish.
• Format: What is the right format for your ideas/your audience? Blog? Newsletter? Video? Podcast? Landing page? Tik Tok? Long? Short? This will drive your editorial strategy (and production calendar/budget) in a major way. Team’s typically under-invest in this at the outset.
  • More in its own section below because there are so many cool options available!
• Look and feel: How do you want it to feel for your consumer?
  • Print magazines I find beautiful include: Kernal, Are.na Annual, and Logic Magazine
• Quality: The name of the game in editorial is quality. It beats quantity any day. (The metric I think about here is will my audience want to read every single thing I put in front of them?) And, there’s no shortcut to a great editorial (well, maybe there will be once GPT-3 goes into GA).
  • companies with editorial programs I’m consistently impressed by include Browser Company, Stripe (Stripe Press, Increment, blog), Are.na, and read.cv
• Your author(s): What voices will tell these stories? Author <> content fit matters more than you think. Great writing has a perspective, a personality, penance, a particular way to express a thing. In the world of editorial, getting the content right is almost the same as getting the authors right.
  • One cool thing about Stripe’s blog is that posts are always written by the people closest to the work, not some marketer. It was both a privilege and a form of recognition to be published on the blog.
• Style guide: How will you keep the voice and tone “on brand” and consistent?
  • Check out Aesop’s Style Guides here.
• Editors: There are two kinds of editors: concept editors and line editors. The skills required to do each are totally distinct. The role of a concept editor is to bring ideas to their full expression. Even if you don’t have a single or an officially-appointed editor, great feedback is a requirement for great writing. There’s such a thing as a good match here–the perfect editor for one person may be the wrong editor for another. The role of the line editor is to ensure there are no distracting errors–grammar, spelling, typos, etc. Doing a great job should be author and subject-matter agnostic. Editing always takes longer than you think. If it doesn’t you’re probably doing something wrong.
  • This requires cultivating a network of talented and available folks! (If you want to throw your name in the hat for mine, please DM me @zebriez on Twitter!)
• Fact-checking: You don’t want to inject falsehoods into the idea space, especially when your brand is on the line.
  • Here’s Evan Osnos on being fact-checked by the New Yorker (a publication known for their meticulous fact checking)
• Paying fairly: There are a lot of people involved in producing great writing. Decide what paying fairly means for you and then do it. Consistently. Also, don’t not do this. It’ll make you a jerk and you don’t want to be a jerk.

Formats to explore (with examples)

• Curation
  • Roundups like The Brower or 80,000 hours job board
  • Scrapbook (as collection of ideas) like Good Sign Off’s, Why Are We So Wimpy, or My Favorite Things At The Moment
•  Prose
  • Collection of longform (basically, a magazine) like Kernal or Increment or Works In Progress
  • One-off longform (basically, a blog post) like Stratechery or Bits About Money or Farnam Street. Some of my favorite riffs on this format include:
    • Research digests from Matt Clancy’s
    • “Letters from the Lab” from Andy Matuschak’s
    • “Comment letters” from Carbon Plan’s
    • Waxings like Marginalian (fka Brainpickings)
    • Interviews with the greats like Will Larson’s Staff Eng or Polina Marinova’s The Profile
  • Collective longform like Every bundles
  • Shortishform like Marginal Revolution or One Helpful Idea (from Spencer Greenberg, gotta sign up for the email)
  • Advice Column like Tech Support or Dear Sugar
  • White papers or peer-reviewed academic papers
  • Zines like Wizard Zines
  • Workbooks like The Artist’s Way (we also often see these in tandem with other works like Tim Urban’s Picking A Career)
• Video
  • Longform like Masterclass or Great Art Explained or Gourmet Makes or Restore Machines
  • Talk Series like City Arts and Lectures
  • Shortform (like TikToks that I shamefully don’t have any recommendations on)
• Audio
  • Interview like Ezra Klein Show or Conversations with Tyler or Tools & Craft
  • Well-Researched Deep-Dive like Acquired or Huberman Lab or Song Exploder
  • Listener Questions like A Way with Words or Car Talk
  • Roundtable like The Rewatchables
  • Debate like Both Sides of the Story
  • Voice memos
  • Quick updates like The Daily
  • Storytelling like Invisibilia or Beneath the Surface

 

More on marketing/distribution

I would say this is chronically under-invested in. People spend so, so much time getting the material created and then forget to promote it! Nothing beats word of mouth. Good things do spread. The marketing/distribution work is about getting it in front of the people that are likely to help you do that.

It’s also very, very noisy out there. How are you going to cut across?

• Promotion strategy: just having one, tbh.
  • What I’ve seen work: Direct outreach to family and friends, Twitter, Authors on podcasts, Reaching out to potential champions, Traditional media, outlets with very wide distribution (caveat: they’re hard/expensive to get slots in), Newsletter with targeted distribution, LinkedIn, Targeted Watering Holes, (sometimes) Amazon/LinkedIn ads, Talks to captive audiences (conferences, companies) (caveat: if there’s travel involved this could be very time-intensive for not as much upside), Hosting discussions around the materials (over meals, Zooms), Hacker News!
  • What I haven’t seen work (though would love to be convinced otherwise): Scaled giveaways of physical artifacts, “Blurbs” from people that won’t actually promote it,  Re-formatting (ie-doing a video trailer for a book), Reddit
• A way to stay in touch with consumers: Collect information that will help you reach them again. If they liked what you did once, chances are they might like you again.
  • Lenny Rachitsky built a Slack Community around his newsletter (currently sitting at almost 10k members).
• Launch checklist: Defining (and evolving) a set of activities you reliably do at launch will help you stay disciplined about doing the marketing/distribution work.
• Defining Target outcomes: If your editorial project is successful, what would happen? Often, these will be longer-term, harder-to-measure, outcomes. But, it’s still worth articulating what those are. And, making those things as observable as possible.
  • Some good examples I saw in my work for various book projects: My book appears on a course syllabus at $university, Invited to speak at x conference, I’m invited to do a lecture at a university, The New York Times reviews the book, I’m asked to do an op-ed on a related topic for a national newspaper, I’m asked by Netflix to do a series on the themes of the book, My book appears on Obama, Bill Gates, Reese Witherspoon, or Oprah’s reading list
    
• Drumbeats: Particularly if you’re producing evergreen material, you can re-circulate it. Keep things in circulation.
• Co-creation as a promotion strategy: Those who participate in the creation of the content will be more likely to promote it later. This includes everyone from the authors to the editors to anyone contributing to the look and feel.
• Geographies: Things are global by default when they’re published on the internet. If you’re dealing with a physical artifact, there’s a lot more work to do.
• Big Swings: It’s probably worth doing these every now and then. But, over-investing in them can get exhausting for everyone involved.

 

More on operations

• Editorial calendar: what gets published, when? What else needs to get done to launch, and by when?
• Budget: How much are you spending on this project? How are the funds best allocated?
• Charging to consume: will you ask people to pay? how much?
  • Derek Sivers has a cool model for charging for his books, more on that here.
• Tracking (and communicating) outcomes: Is it working? How do you know? How is it all communicated to stakeholders?
  • When I ran Stripe’s blog/Atlas Guides I would always, always tell authors about their readership numbers and authors always said it was the first time they got those. That shocked me. Now that I write a lot for other publications, I know that’s true 🙂
• Systems and tools: What do you need?