Tony Stubblebine moved Medium from losing $2.6 million monthly to achieving its first profitable month in August 2024, after 13 years of losses. The CEO, who previously founded habit-tracking company Coach.me and helped develop early Twitter, has refocused Medium on serving writers more interested in sharing their expertise than profiting from their words. For Stubblebine it’s about the expert economy, not just the creator economy.
Known for viral productivity techniques like Interstitial Journaling and his 75-minute guide to iPhone optimization, Stubblebine has grown Medium to over one million paid subscribers while maintaining its ad-free, quality-focused approach.
Now the company is launching a new app for notes and writing, called (fittingly enough) TK, in a bet that strong design will distinguish it in a crowded marketplace.
Stubblebine spoke with Fast Company about why he still prefers paper notebooks for meetings, and how Medium differentiates itself from creator platforms like Substack. The conversation has been edited for length and clarity.
You’re launching a new writing app. Why does the world need another writing tool?
I had to make this case to get people inside the company excited. There are four things I want that I don’t see right now.
First, the Medium design ethos matters to me. I want my words to look and feel beautiful. I was already drafting things in Medium’s editor that I never intended to publish just because I like the typography better.
Second, this world of second brain apps exists, but the idea of a second brain is a mainstream concept without mainstream implementation because you have to do so much manual organization. Most people are not that organized. A messy system almost always beats a regimented system. This is a great use case for AI—our view is it’s meant to elevate people, not replace them. AI can completely alleviate all the manual organization that would typically go into Roam or Obsidian.
Third, there’s a way to use AI as a writing assistant—not to write for you, but to do your bidding. A lot of what I publish needs citations. The other day I was writing about an old Medium program launched by founder Ev Williams. I highlighted the paragraph and said to the AI assistant: “Ev wrote about this on the Medium blog in 2017. Find the link and add it.” It figured out the core concept, found the link, and added it. I’m easily distracted—if I had to find that link myself, I would have been lost for an hour.
Fourth, I’ve never seen any note-taking apps attached to a distribution network. My writing is very sensitive to the idea that you could share it and get validation and help someone else. Sometimes you’re working on something and realize this could be helpful to other people. We’re excited to attach Medium’s massive network of readers to this genre of software.
You’ve taken a strong stance against AI training on creators’ work. Why?
We’re the only social media platform that if we can get money out of the AI companies, is planning to give 100% of it back to the creators themselves. We refused training deals with AI companies worth low single-digit millions because we heard from our writers that they felt it was unfair for companies to make money off training on the Medium network without giving anything in return.
There’s still an ongoing negotiation across the industry about whether these companies will pay creators. We just supported an initiative called the Really Simple Licensing standard. We hope that gives consent and control back to the creators.
How do you compete with Substack when writers can earn more there?
The people who actually make the most money on writing are not charging for the writing itself. We sort of forgot in the rush to the creator economy how lucrative the expert economy is. Some of the best-paid writers on Medium are technical leaders who post twice a year, but those postings are their calling card when they go get jobs that sometimes pay upwards of a million dollars a year.
The creator economy is kind of a content treadmill and doesn’t always pay that well. Meanwhile, building yourself up as an expert authentically often opens up really interesting work opportunities. If you’re committed to the creator economy, you should follow a strategy of “publish once, syndicate everywhere.” Medium folds into that as a place to syndicate, to get additional traffic and subscribers back to your main mailing list.
But if you’re not in the creator economy, you’ll build an email following on Medium faster than anywhere else because you have a built-in network of people you don’t already reach. We’re much more built for that group, which is the majority of the internet.
How did you engineer Medium’s turnaround?
The key thing is, even if you turn around the business, you have to end up with a business that you’re proud to be running. A lot of the turnaround was in the product itself, making Medium a place where smart amateurs write regularly.
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Until that point, we’d either been a place where professional journalists were writing or where the new wave of content creators would write for small dollar amounts. We looked at that as paying to create more content mill stories that otherwise wouldn’t exist, and that felt bad to us.
Beyond that, it’s run-of-the-mill business. Every dollar you spend is meant to bring back at least a dollar. If you don’t have a theory on spending money, you shouldn’t spend it. The startup industry was very lax about how it spent money for a while, and Medium was definitely in that boat. Just getting tighter—people call it cost cutting, but I think of it as role clarity. Every person needed a role connected to how we work as a business.
What advice do you have for technical founders transitioning to CEO?
The bar for companies has gone up. It used to be “build it and they will come,” or you only had to be good at one or two things. Now people are so savvy about how to build a company that you really have to plot the whole business model through. It’s not just can you build a better mousetrap—can you build a distribution channel? Can you build a business model where you can make money?
The last company I started in 2011 was just like, “I hope if I build something cool, people will use it.” I came to regret that pretty quickly because I didn’t know how I was going to market it, let alone make revenue.
When people come to me and say they built a better habit tracker, I tell them: I believe you, but how are you going to get people to use it? How are you going to make money? Why is this a business? If you don’t design that into the plan, good products just get abandoned because they don’t work as businesses.
What does your current daily tool kit look like?
I have a pretty simple work life. I’m mostly meeting with people, so I’m spending a lot of time either in Zoom or Google Meet.
I typically have a paper notebook in front of me because my view on note taking during a meeting is that it’s a form of active listening. I have a strong opinion about the ideal paper notebook. We found notebooks that are landscape format, which means they’re wider rather than taller. The thing I like about wider is that I caught myself thinking deeper about my own notes. It’s like taking the idea of writing in the margin and blowing that up.
I end up with almost always three columns: raw notes as I’m trying to follow along, a second column for things I need to come back to or how I want to participate in the meeting later, and this empty third column for total epiphanies. The way that form factor interacts with the way your brain works, I found fascinating.
What’s your current relationship with your iPhone after writing that viral optimization guide?
I still basically believe the premise of that post—that it takes 75 minutes to reconfigure your iPhone for productivity. The meta point was that these software tools are not preconfigured to make your life better.
The worst offender is notifications, which should be called interruptions. If an app asked you, “Is it okay for me to interrupt you mid-meeting?” you’d think harder about whether that’s okay.
I keep basically all my notifications off unless it’s text messages from certain people or phone calls from my favorites, which is three people. I always try to keep in mind that the iPhone is meant to be a tool for me. My front screen is all Google utilities—maps, calendar. The action button is set to photos.
You’ve mentioned considering going even further offline. What’s your experience been with that?
I did a four-month camper van trip around the U.S. and drove 9,000 miles. The thing that blows people’s minds is that I didn’t listen to anything during the drive, unless I was tired. I tried to have quiet time for thinking and seeing where I was going. That was one of the happiest periods in my entire life because my brain was not buzzing all the time with brain candy that exists on your phone. If I wasn’t working, I would probably opt to be nearly fully offline beyond extremely helpful things like Google Maps. Opting out seems like a good way to live for most people.