What The F*ck is Tony Stubblebine Thinking?

6 lessons from my interview with Medium’s new CEO

Do you ever ask yourself what the heck is Medium’s new CEO, Tony Stubblebine thinking?

Other bloggers do. It’s all I ever read on Twitter (the place for nuanced dialogue and cordial conversation).

I’ve seen everything from “Medium is changing” to “how I know Medium’s broken” and a whole lot of speculation in between.

To get to the bottom of it all, I decided to sit down with Tony and ask about his plans for Medium. Here’s what he had to say (and what I learned):

1. The Creator Economy is Dying

Endless content is dead, at least on Medium.

According to Tony, in the past many Medium creators would find a popular story online, a good angle, and rehash it for their own benefit.

“I’m not getting value here,” said Tony. “I’m getting tricked into reading these articles — they got a great title, maybe an interesting intro but by the time I get to the bottom they didn’t deliver.”

The algorithm was rewarding stories for clicks rather than for quality. Dead and buried as far as he’s concerned

Tony says he was lucky to inherit a subscription model from the past CEO, Ev Williams. Going forward, he’ll be happy if the platform can deliver a single life-changing article once a week or once a month.

2. Medium Authors Fear the Word “Expert”

According to Tony, nothing has been more contentious with Medium authors than the word “expert.”

Listening to past interviews with him, it’s the first question that comes up — followed by “why are my earnings down?” I second that. Please send me a $20,000 check for our interview, Tony.

But in all seriousness, Tony’s standards for what gets monetarily rewarded are higher than ever before.

“There are very few things that I feel shouldn’t have been written, but there’s a lot of things I feel like shouldn’t have been promoted.”

Don’t fret if you’re not Ryan Holiday or as eloquent as Jessica Wildfire. Tony says “expert” could also mean a massive amount of research into a topic or life experience you can share.

So don’t be afraid to try something new because you never know how it could pay off.

3. Medium’s Payment System Isn’t Your Only Reward

Medium didn’t always pay. That meant the genius of “How I made X amount of dollars in one second” were still incubating like a turd cupcake.

Even now that writers shamelessly showcase gaudy grotesque paychecks — such as myself — Tony says that the best writer’s work pays off for them in multiple ways.

“We talked to this one business consultant on Medium and asked: ‘how much does it matter that we pay you?’ He just laughed at us.”

Tony explained that the writer was netting a $500,000 contract from his Medium work once a year.

(I wonder if it’s Tim Denning? Tim, you lavish bastard, can you confirm?)

I can attest to this. I got a 9–5 job from my Medium articles. They also fired me because of my Medium articles, but that’s a different story.

The upshot is don’t think of Medium as just a payment platform; use it to create other opportunities for yourself.

4. The Best Writing on Medium is Better Than the New York Times

Tony says journalists are researchers, not experts.

By definition, a journalist working for the New York Times doesn’t know what they’re talking about.

I disagree with Tony here.

Sometimes an expert is too close to the story, lacking the means to tell the story properly. Kurt Cobain wouldn’t have been a blogger or journalist. Most athletes, chefs, businessmen, celebrities, and entertainment personalities don’t blog. Moreover, it’s also why we don’t expect experts to always know how to articulate what they do.

It’s why journalists are more craftsmen than artists.

And it’s why, as my journalism mentor taught me, getting the details right is paramount.

That’s not to say Tony is wrong — I’m just biased.

5. Tony’s Thoughts on AI

“AI is hard to spot from an algorithmic perspective; it’s starting to swamp SEO results already. You need someone to look at a piece and say this is new, this is fresh.” — Tony Stubblebine

Curation is the biggest change that Tony wants to emphasize for Medium.

In the past curation was formatted toward formatting and readability. Now with AI, the curation team is looking for trends in expertise, style or an author’s voice.

The recommendation algorithm also received a substantial change to ignore overgeneralized content. Tony believes human curation is still the best way to discern which content should be rewarded.

6. Productivity and Mindfulness

My greatest takeaway from the Tony Stubblebine interview was the first question: “Is Spotify mindless listening and vinyl better, and how does that affect mindfulness?”

Tony is a productivity coach who founded Better Humans.

He argued that listening to vinyl is a mindful activity. You must actively select the vinyl, find it in a store, and focus on the artwork.

We got into a discussion about how many mindless activities we do:

• Watch TV while we eat
• Half-listen to Spotify playlists littered with junk songs
• Checking emails and text messages while we’re in a meeting

He argued that if we can be more intentional and mindful about the things that slip into our lives, then it will make us better people.

A Final Thought

Tony says all journalists always get some details wrong.

I’m sure I did.

So listen to our entire conversation below and let me know your thoughts.

I’m sure Tony would love to hear from you!

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