What’s Inside
How writing still cuts through in the AI era
Why storytelling isn’t just about reach
What the CEO of Medium had to say about voice and transformation
I’ve been writing online in some form or another since the 1990s.
Back then, we saved our files on floppy disks. And writing online felt experimental, a private electronic journal before blogs were a thing and long before anyone called themselves a “creator.”
At the time, I was a reporter covering venture capital, startups and other business stories. When I wrote for myself, I didn’t call it storytelling. I just thought one day I’d publish something outside of my day job.
I wanted to be a writer. And I wanted the freedom to write in a voice that better reflected who I was. My early writing was closer to personal journaling, as I was trying out ideas, seeing what stuck.
Long story short, I never got published in The New Yorker. But I kept writing.
Then came social media, and everyone got a phone. We started telling stories in tweets, photos and videos. Medium emerged in the mid-2010s as a space for longform thinking.
Eventually, like everything else online, it got noisier, too.
But recently, I had the opportunity to interview Tony Stubblebine, the CEO of Medium, for my podcast. I wasn’t looking to talk scale or Growth strategy. I wanted to talk about writing.
What it means to write today, why it matters if we write, and whether it still cuts through the noise.
I also wanted to know whether a writing platform in the AI era could still elevate people who have real ideas and without turning them into content machines.
Tony’s Clarity on those topics surprised me. In our short podcast interview, he sounded grounded in the belief that writing matters. Not because it drives traffic. But because it helps people think.
And honestly, it doesn’t matter if it’s Medium or Substack. The platform isn’t the point. The writing is.
“A blog post is the smallest amount of work that also has meaningful impact,” he said to me. “A tweet doesn’t change lives the way a 1,500-word essay can.”
What Tony said about storytelling stuck with me. Not just because I continue to write, or coach others on how to tell stories, but because I’m also navigating a world where writing often feels flattened.
It’s been chunked into summaries. Optimized for keywords. And then dressed up with em dashes, bullet points and emojis to feed the GEO.
Tony and I talked about AI, naturally. These days, every conversation about content eventually leads there. I asked Tony whether AI was changing how people read. He didn’t hesitate.
CliffNotes didn’t kill books, he said. Summaries have a use case, but they don’t take you on a journey.
“The [AI-generated] summary doesn’t transform you.”
Transform is an overused word in tech, but I kept coming back to it when I thought about my podcast with Tony. Because he’s right! Good writing transforms the reader. And Tony isn’t trying to build a platform that replaces that. He’s trying to preserve it.
A few days after our episode dropped, Tony published his own post on Medium. His lengthy Medium story, called Fell in a hole, got out, offers an honest look at Medium’s investment history, the leadership handoff to Tony and the site’s financial comeback that no one is really talking about.
His Medium piece fills in the backstory. It’s not the kind of corporate recap you’d expect from a CEO of a tech company. It’s raw and unvarnished, more like a founder’s private notebook than a corporate update.
I didn’t ask Tony much about the turnaround directly. But I realize now that it was hanging in the air over everything we talked about:
— How platforms shape the behavior of the people who use them.
— How easy it is to veer off course.
— And how much harder it is to build a place where regular people, and not just full-time creators, can share something meaningful.
There’s a line he dropped midway through our podcast that I keep thinking about, even weeks later:
“Everything you write has two topics, what you’re writing about, and who you are while writing it.”
It’s easy to forget those words in the content Economy as everyone’s chasing reach.
But what makes something memorable isn’t polish.
It’s honesty.
It’s voice.
It’s someone saying something real.
That’s what I hoped to surface in our conversation.
And it’s what I tried to hold onto as I wrote this post.
So go ahead. Write something of your own. Even if your audience is small. Even if you’re out of practice.
And it doesn’t matter whether you write on Medium, Substack or a Google Doc. The point is: writing still matters. It helps us think.
The internet still welcomes people who have something to say.
To hear the full conversation when I interviewed Tony Stubblebine, CEO of Medium, the podcast episode is on The Venture Variety Show YouTube channel. Let us know what you think.
