Tony Stubblebine: CEO of Medium Discusses Writing Authentically, Thinking Beyond the Content Treadmill, and Crafting a Lasting Author Brand

In today’s ever-evolving literary landscape, writers often wonder where on the internet they should be spending their time. Where can they share their ideas, build their writer’s platform, and find the audiences that will follow their careers and buy their books? 

How about Medium.com? 

Tony Stubblebine, who stepped into the role of CEO of Medium in 2022, has been working hard to ensure that this writing platform allows writers to create content that is worth paying for.

We spoke over Zoom about his writing life since taking on this new position, how to think beyond the content treadmill, and how to write with authenticity and consistency to connect with readers. 

Kailey Brennan DelloRusso: I’d love to hear about your journey as a writer. When did writing become an interest or focus for you? 

Tony Stubblebine: I just sent a thank-you note to my humanities professor because it dawned on me that she’s the one who got me into writing. The note started, “Dear Professor Cummins, thank you for being such a difficult person to write for.” I knew that would resonate with her because she really was the person who opened my eyes to what it takes to be a good writer.

You know, everyone writes—we write emails, thank-you notes, to-do lists—but writing for an audience requires an extra level of effort. She was the first person to help me see that, and it was important for someone to do that for me. I originally went to college to be a computer science major, fully intending to become a programmer. 

I knew I wanted to work in tech. I knew I wanted to work for startups. There’s a version of my life, in a parallel universe, where all I ever learned was how to be a programmer, and that’s all my life ever was. But by having writing as part of my skill set, it opened up so many other opportunities. I feel like I’ve gone as far as you can in that direction, where now I’m running a writing company.

Honestly, none of that would have happened without a professor who saw her job as more than just teaching the subject.

KBD: I love that. I had a similar experience with a professor who totally helped me, too. I love hearing those stories, and like you said, who knows what would have happened if you hadn’t met that person?

TS: I think my life would’ve been much more boring, which is what I told her in my thank-you note. So, that’s where it all started for me.

KBD: With your busy schedule as CEO, how do you find time to write? And is there a specific routine or process that you follow?

TS: I saw this with my predecessor, who’s also a fantastic writer. But when he was in the CEO seat, you almost didn’t see any of his writing publicly. What I realized is that all of his writing was internal. A CEO ends up writing things like strategy memos, and those memos need to be convincing and evocative. So, ironically, my best writing now is a business memo, which feels a bit sad to me because, before I became CEO of Medium, I was a prolific writer on the platform. I think I was doing a daily newsletter, and at one point, I did it for 280 straight days.

That level of consistency as a writer is what I miss now, given my other responsibilities. My writing process has stayed the same, though—I’m not great at forcing myself to write, but I’m good at working from inspiration. I usually have a lot of drafts going at once. There’s an inspiration to start a draft, and then a separate inspiration to finish it. So, what I’m always looking for is either the idea that sparks a new draft or the realization that I’m ready to finish one I’ve already started.

KBD: So you are a believer of the “shitty first draft?” 

TS: (Laughs) A hundred percent.

KBD: That's so important. I think a lot of people, especially when they’re new to writing, don’t realize how much of the process is drafting. It’s so much of that. 

TS: You know what scared me? When you meet really successful writers and realize how many drafts they go through. I saw Atul Gawande, the author of The Checklist Manifesto—which is a pretty popular business book—give a talk. That book actually came from a New Yorker article, and he said the editor at The New Yorker made him do 26 different revisions. Wow. I was like, “Who has time for that?”

I usually plan for three drafts. Sometimes even the first version involves multiple drafts just to work out what’s in your head. I follow what might be Neil Strauss’s advice: “you write the first draft for yourself, the second for your fans, and the third for your haters.”

I think that’s a great way to approach it. First, you get the idea out of your head—it’s hard to do that while thinking about an audience. But once you’ve worked it out for yourself, it’s still not complete. The second draft is about asking, “Is this clear? Will my core audience understand it?” That’s where you fill in the gaps that you skipped over when writing just for yourself.

The third draft is where the phrase “write for your haters” comes in. There’s always a group of people who might misunderstand what you’re saying. So my final draft is about making it as clear as possible to reduce the chances of being misunderstood. For the time that I have available, I can do three drafts, but never 26. 

KBD: As someone who has built a career around habit formation, do you apply any of these principles to your own writing practice or when you were writing these consistent newsletters all the time? 

TS: The newsletter was a really good learning curve for me. The first 50 were just straight off the top of my head—I had things I’d been dying to say and could just pump them out. But after that, I had to start manufacturing content, which is the word I use. I think that's kind of the difference between an amateur writer and a professional writer: can you write on command?

As time went on, the systems became more important. I needed to have more ideas, more ways to generate ideas, and more note-taking. There had to be multiple things in the works at all times. But I also found that it got easier because I had more to reference.

You write to get an idea out, and often there’s a follow-up. That’s something I tell other writers, and something I’ve practiced myself: try to write in a way where you can get paid twice for your writing. I mean that metaphorically, since I’ve done a lot of business and coaching writing. It’s one thing to write and have people read it, but through writing, I also developed a deeper understanding or mastery that I could use again.

This creates a flywheel effect—I’m out there practicing what I’ve written about, learning something new in the process, which then gives me more to write about. That’s what really helped me: writing was always paired with something else that naturally generated more things to write about.

KBD: Yeah, I think that’s really helpful now because, you know, so much of our audience and so many authors I interview are published, but now, you really have to have a newsletter and a social media presence. You have to balance your literary work with generating ideas on how to talk about your work in ways that grab attention. 

TS: Yeah. But there’s a difference between the type of writing I was doing and literary writing. Even literary writing involves a lot of research, right? So, what drives that research for you?

There has to be some kind of impulse behind it.

KBD: Exactly. And later, when you're promoting your book, you have to pitch essays that incorporate research or expand on elements of your book in ways that connect with wider audiences to generate interest. So many people now have newsletters just to share who they are. I hear questions about this all the time—how to build an author brand.

TS: That’s the thing—so much of it is about having systems for generating ideas because the pressure is on to constantly create. You really need a system for idea generation. I’ve gone through phases where I cared more about my personal brand or my company’s brand than at other times. Recently, we’ve been in a period where we’ve focused on getting our name back out there, so I’ve been more active on one platform.

Now, because of that, my brain always has this background process running, thinking, “How could I spin that into a short post?”

KBD: You’ve talked about the importance of creating content that provides real value to readers. With so much content everywhere, how do you think writers can better connect with their audiences on a platform like Medium?

TS: Well, Medium especially went all in on quality and authenticity. I think it’s a mixed bag. On the one hand, the downside is that people have built a lot of muscle for quantity—they tend to think that way. Then they come to Medium and get frustrated when just pumping out a new post every day doesn’t do anything for them. But the pro is that the content treadmill is awful, and it’s unfortunate that it worked better for a period of time.

People did high-volume content because it worked, but I think that drew them away from why they wanted to be creators in the first place—to write deep, authentic pieces about something that really meant something to them.

It’s not any easier to write that way, to write authentically. It didn’t get easier. But to me, the good news is that the distraction of being on a content treadmill is starting to go away. It’s impossible to keep up—it’s too competitive, especially with AI-driven tools. It’s a race to the bottom. The wins have gotten smaller while the competition has gotten greater.

So yeah, I do think the future is all about writing in a way that creates a really powerful, authentic connection with readers. You have to find ways to be authentic everywhere, and that’s harder—maybe sometimes not possible for everyone. But the good news is that it’s way more fulfilling. It’s a better way to live.

KBD: Yeah, I totally agree. I’m also interested in Medium’s subscription model. For writers and artists, asking for money for their work has always been daunting or uncomfortable, especially when, as we were saying, there’s so much content, and a lot of it is free. With Medium’s subscription model, the focus is on content that’s worth paying for. Do you have any advice for writers who want to meet that challenge?

TS: I think the first thing to remember is to think of Medium as a wide open first step. There are communities here, readers here, and a profit share where people do make money on Medium. So, there’s no reason not to be here—it just might not be the entire picture for someone aiming to be a professional writer. But it’s a great opening step because you get feedback, some amount of money, and you still own everything you write.

That’s what I tell people who want to be professional writers: think bigger. Don’t view platforms like Medium or others as just an ATM to get all the money you need. Think of it as part of a bigger strategy that ladders up to something larger. The people who do best financially on Medium are usually working on something that will end up being a book, a personal brand, or something more.

It’s worth noting, though it’s not necessarily literary, that the people who make the most money on Medium are often consultants. They use Medium to build an online portfolio and attract new clients. We might pay them $500, but their clients are paying tens of thousands of dollars.

It’s always valuable to start on Medium—to get distribution and feedback early on. You can post anything here, and you won’t really know what’s going to succeed until you come and try.

KBD: I meant to ask this earlier when we were talking about your own writing: writer’s block—some people believe it exists, some don’t. Creative burnout, though, I think that’s real (laughs). How do you deal with challenges like that, especially in your role of leading a major platform like Medium?

TS: There are two quotes I keep in mind. One, I know who said it, and the other I don’t exactly remember. The first is from Cory Doctorow, the sci-fi writer and also a writing instructor for a long time. I once heard him say, “If surgeons can’t get surgeon’s block, why can writers get writer’s block?” Sometimes you just have to perform.

Then, I was close for a while with some people in The Moth storytelling circuit, and there was a saying that came from that: “Everyone has one story to tell. If you can tell two stories, you’re a storyteller.” That’s not literal, but it’s the same idea—that a professional can write on command. They have tools to manufacture writing, which is the word I’ve used a few times now. And, yes, it’s way better to write when you’re inspired—that’s the best of it. But it doesn’t happen every day. So sometimes, you just have to dig in and produce something, even at your worst.

For me, unfortunately, that often means writing a letter to my board or something like that. But those deadlines don’t move. They need an update, and I have to give them the best available one.

KBD: I think that’s good advice. Everything you write, you just have to push through and get it done. A lot of times, if you can look beyond it as just work, you might surprise yourself and realize, “Oh, I guess I had more to say than I thought.” It turns out you don’t have writer’s block, or you’re not as burnt out as you thought. And that’s always a good day.

TS: Right. 

KBD: Do you have any book recommendations or anything you’ve enjoyed reading this summer that you’d like to share with us?

The Anarchy William Dalrymple, a history of the British East India Company.

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Tony Stubblebine is the CEO of Medium. Previously, he was the owner of some of Medium’s largest publications, including Better Humans, and is the co-founder and former CEO of Coach.me. He lives in New York.