Behind Medium’s Growth: CEO Tony Stubblebine on Helping Writers Thrive

How can Medium’s unique platform help you reach new audiences and maximize your freelance potential?

In this episode we sit down with Tony Stubblebine, CEO of Medium, to explore how the platform is impacting the world of writing.

With over 1 million paid subscribers and recent profitability, Medium is becoming a powerful space where writers can thrive without the hustle and connect with new audiences.

Tune in to hear Tony’s take on how to maximize earnings through Medium’s partner program and the unique opportunities it presents to freelance writers.

In this episode, you’ll learn:

How Medium’s new focus on authenticity is helping writers stand out in a crowded digital market

• What profitability at Medium means for writers using the platform
• Key changes in Medium’s Partner Program and how they affect writer compensation
• Strategies for freelance writers to maximize their success and earnings on Medium
• Why community and connection with readers are more important than views or clicks
• How Medium’s distribution engine gives writers an edge 

ABOUT TONY STUBBLEBINE

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.

Read Tony’s writing.

ABOUT MEDIUM

Medium is an online publishing platform where writers from all backgrounds can share their stories, insights, and ideas with a global audience. Known for its clean design and user-friendly interface, Medium offers a space for thoughtful, high-quality writing on a wide range of topics. With a unique focus on authenticity, Medium connects readers to content that prioritizes depth and meaning over clickbait, while offering writers the opportunity to get paid for their work through its membership model.

Learn about Medium’s Partner Program.

Full show notes here.

Chapters

• 3:32 Medium’s milestones: 1 million paid subscribers and profitability

Transcript

Tony Stubblebine: 0:00

The only way you can stand out is by focusing on quality. And the thing that makes quality is authenticity the internet recently hasn't really been built for quality. It's been built for attention. So for two years now, we've been really just laser focused on building a platform that rewards the type of Writing that I think everyone wants to do anyways, and which readers are dying to read., and that's why Medium has been growing as a subscription business, we're standing out against what the rest of the internet is doing right now.

Ashley Cisneros Mejia: 0:39

Welcome to Talk Freelance To Me, the podcast for women freelance writers, 1099 independent contractors, and solopreneurs. I'm your host, Ashley Cisneros Mejia. For more than 20 years, I've worked as a journalist and freelance writer. Today, as a mom of three kids, I'm passionate about helping other women leverage the freedom that freelance offers. On Talk Freelance To Me, we're all about the business of freelancing. If you want to learn how to monetize your talents, make money on your own terms, and design a flexible work life that actually works for you. This show is for you before we get started. Don't forget to follow us on your favorite social media platforms, review us on Apple podcasts or wherever you listen. And don't forget to share this episode with a friend. Visit our website at talkfreelancetome. com for free resources. Join our email list to be the first to know about our latest offers. Today, I have an incredible opportunity to speak with Tony Stubblebine, CEO of Medium. com. If you're unfamiliar, Medium is a publishing platform that was established in 2011. Today, it has grown into a space that values high quality human writing over AI clickbait. Tony has been the CEO for about two years now. Under his leadership, Medium crossed 1 million paying subscribers, and the company is profitable for the first time. In our conversation, we chat about what makes Medium unique, how it compensates writers, and what freelance writers can gain from using the platform. What I found most interesting about Tony is his commitment to creating a healthier and more refreshing corner of the internet. Tony describes Medium as a place where writers can simply write and be heard, without the pressure of becoming what he calls internet hustlers, which I thought was a pretty funny way of putting it. In this interview, Tony will share the ways that the most successful medium writers use the platform and how Medium's built in distribution engine can help you share your writing with new audiences. Let's get into the episode. I am so excited to bring to you a special guest, someone that you may not have ever had, , an opportunity to hear from directly the CEO of medium. com. Tony Stubblebine. Tony, welcome to the show.

Tony Stubblebine: 3:06

Thank you, Ashley. Thank you for having me as a guest. I'm excited. Hopefully I can be helpful.

Ashley Cisneros Mejia: 3:10

Yes, I had the honor to experience Medium Day that you just had, and I got to hear your keynote address to everybody who was in attendance, and it was very cool. Under your leadership at the company, you've achieved some big milestones. I know in April, you crossed 1 million paid members. How would you define Medium's identity today?

Tony Stubblebine: 3:31

Yeah, that's a good place to start. So Medium is a blogging platform that rewards authentic writing. I'm going to get into what that means. This is like essentially the pivot that happened under my leadership, but it worked. And so you can count on us to stay in this direction. The benefit of focusing on authentic writing is it's this breath of fresh air for everyone, especially freelance writers. Because nobody likes this grind of finding new quote unquote content to manufacture every day, right? That's not an authentic way to write. Readers will click on it. Sometimes they'll go viral and they'll click on it, which works if you're running ads. But readers aren't impressed with it. And then now with AI, that sort of daily grind approach to content development, it's just not even defensible. Now anyone can do it. And it's impossible to stand out. The only way you can stand out is by focusing on quality. And the thing that makes quality is some authenticity about how you care about it or where it comes from your own life experience, right? It's like, the good news is we've all led interesting lives, and that can drive much better writing than the idea of just, oh, I need to manufacture an opinion today that will, you go viral. And like every writer that I've ever talked to that's on the content treadmill is dying to get off of it. It's just an exhausting, low reward place to live. But the internet recently hasn't really been built for quality. It's been built for attention. So for two years now, we've been really just laser focused on building a platform that rewards the type of Writing that I think everyone wants to do anyways, and which readers are dying to read. And yeah, like, that's been a stark contrast to the rest of the internet, and that's why Medium has been growing as a subscription business, is we're standing out against what the rest of the internet is doing right now.

Ashley Cisneros Mejia: 5:32

During your keynote, you also mentioned that for the first time since the company was founded, I think it was 2011, you're profitable. And that's been under the last two years that you've been CEO. Very cool. Congratulations. Thank you. What does this financial milestones, new stability mean for us as writers who are putting our thoughts, our authenticity, our stories and insights on the platform?

Tony Stubblebine: 5:55

Yeah, financial stability is stability for everyone. And that's why I said it. Absolutely. Inside the company, we're over the moon. It was this team that me and the team that I've worked with for the last few years, this was one of our major goals for just completely practical reasons. We want to do big things in order to do big things, we have to stay in business. And so it was a ton of work and we're all very happy, but like, why does that matter to everyone else? So the reason it matters is because you want to write with a company you can count on to be in business for a long time, not just be in business, but to be stable to work with, right? I think. Prior Medium had a little bit of history of pivots, but this is really the true for all startups. Before they have a business model that works, they're at risk for pulling the rug out from under you because they have to. You have, you either pivot or you go out of business. And so that's why you see so many startups change. their mode, but now mediums in a different category, we have a working business. And so all of our pressure is to keep doing what we're already doing, just do it better. And I think that makes us a much more stable partner for writers for one. And especially writing is so timeless. I think that You want to write something great and evergreen. And sometimes it can have a life on the internet that lasts for decades and you don't want to have to move it to the hot new thing every time platforms change. So yeah, I think it's a big deal for the whole community at Medium that we are now profitable because we're, as you say, it's easier to count on honest.

Ashley Cisneros Mejia: 7:30

To me, it's a very uplifting, refreshing message when you see AI and what I love AI, I use it for different things for this podcast production, for example, it streamlines things, but as a writer, it does feel a little disheartening when you're seeing even big legacy publications starting to use AI to create content, which is something that me and a lot of my listeners have done and what you've Created here what you're you and your team are working on and having all these members who are saying we are paying for good content for good storytelling for things that are going to make us feel something teach us something and you're showing that it still can be done that there's still a demand for that and. I think that's really cool. Cause that sends a message that there is still a demand for what we do. I think that's awesome.

Tony Stubblebine: 8:19

Absolutely. I think a lot of that message also really validates people that are hopeful that there's a better, there can be better places on the internet, that the internet can be better, that writing as we think of writing still has a future and a home. That's also one of the big messages here is hope that. Hey, it works. It doesn't all have to be as bad as it is in other corners of the internet.

Ashley Cisneros Mejia: 8:45

So you've done a lot of changes with your partner program and how you compensate writers work with your algorithm and also your internal team who looks at content and decides what to boost or what to not. Can you walk us through some of these big changes as it relates to writers looking to earn money on the platform?

Tony Stubblebine: 9:02

Yes, as you say, we do a profit share with our authors that's really focused on rewarding the very best stories. And that's been great for everyone who's trying to get off of the treadmill. You just flat out cannot earn a living on Medium if your strategy is to grind out a living with something new every day. It's like much more of a focus on find something that you can write about that's really meaningful and impactful. I think that has ended up guiding writers. in a different direction where they're thinking about what does their writing ladder up to. I think the most successful writers on Medium, if you're talking about financial success and I think also satisfaction, are writing often in a way that ladders up to either a book or to other employment. The people who make the most money are using writing to develop and show mastery of a topic. and then are getting paid even more for something related to that. So it's like they're a coach or they're a consultant. The people that are making the most money from Medium are all business consultants. And I think no one says that out loud. Instead, they're focused on, oh, how much does each piece get paid? It's like, no, we live in a world that will sometimes give huge rewards. to expertise. And how do you develop and show expertise? Writing. It's the best way to do that. Where that works with our community, with the readers, we're stewards of the money that our readers give us, is that's what they want to read. They want to hear from someone who knows what they're talking about. So we have redone all of our incentives, all of the way that our recommendation systems work. To get away from algorithmic attention seeking, algorithms are really good at spotting what you'll click on, but they're terrible at understanding whether you read something that was actually helpful to you. And that's where having topic experts. In our recommendation system, fundamentally, that's what made the current medium successful is now we're spotting and elevating a different type of writing and our readers love that. And I think more and more, so do our writers.

Ashley Cisneros Mejia: 11:21

Very cool. So what strategies would you recommend to writers who want to really maximize this engagement and earnings under the new model that you have for your partners?

Tony Stubblebine: 11:32

I'm always asking freelancers to think. Bigger, it's appealing to think that you can make a living just sharing whatever thoughts crossed your mind today, right? I think all of the freelancers that you work with find pretty quickly. That's a competitive. Flooded place to play, right? To succeed, you have to find a voice. Often you have to find a topic where you can be well known and, but then the good news is if you do that, you don't just succeed as a writer every day. It opens up the door for other things. Like example, sometimes I'll give is. Even if you're a successful writer like Stephen King, I'm pretty sure he makes more money on the movie rights than he does on the books. So it's like, even when you get to the peak, the, the extra is beyond the writing. There's a kind of a programmer term of people get lost in a local maxima and they miss the writing. The, there's something bigger next door. Like the idea is that you might get really excited for climbing a hill, but you don't realize that there's a mountain next door. And so we're just like constantly looking for ways to guide people away from the idea that being a creator is just write something new every day. No, there has to, you have to have some bigger vision for yourself or it doesn't like in our experience, watching writers on the platform, it just doesn't work out for you.

Ashley Cisneros Mejia: 13:00

So given the competition with other platforms, how does medium differentiate itself in terms of the business model and the value proposition to writers when there's lots of places that want us to write to get traffic or, yeah.

Tony Stubblebine: 13:14

I think there are basically three reasons that someone would pick medium as a tools, community, and distribution. And for the majority of people that makes medium a better choice than a standalone site, like WordPress or ghost or a newsletter tool, like convert kit or sub stack. And the way I would say it is. I can almost never think of a reason that someone that's using those tools wouldn't also use medium, but I can all, I it's often the case that you're on medium and it's not worth those other tools as well. And I think the main one is probably for a lot of people is just distribution. You're always hunting for distribution somewhere. We have a unique distribution system. Like we'll give you, we'll give different content distribution than like a Tik Tok would. Right. Then if you're killing it on TikTok, it might actually mean you won't do well on medium and that's fine, right? We're if, but if you're not doing well and you want to focus on quality and authenticity, then we're set up to reward that. At a minimum, our Google ranking is way higher than your Google ranking. This is just the benefit of being a platform. We get ranked so highly in Google. So if you're trying to set yourself up as an expert, or you're using your writing to build a portfolio because you want to do freelance writing somewhere else, and you want to be found, why build your own SEO credibility? Just use ours, right? A lot of people do that. And then if you want to find an audience, if you want to find a community, And especially if you don't already have one, Medium has a system of publications where you can just go and submit to a publication and get a built in audience that you wouldn't already have. And then on top of it, if you're trying to build an audience, an email list, Medium has that. Medium will collect email addresses for you. You can take those email addresses somewhere else. If you don't want to use our built in tool, a lot of people keep their newsletters somewhere else. I mean, there's a lot of tools now. It's not just Substack, it's Beehive, it's ConvertKit, it's MailChimp, and ButtonDown maybe. Tons of writers on Medium link out, like it's completely acceptable to put a call to action at the bottom of what you write so that you can send people to your course or your newsletter.

Ashley Cisneros Mejia: 15:31

That's the biggest thing that I'm seeing with a lot of the writers is when we do writing for clients to pay the bills to buy groceries and then coming up with the space, right? Like the intellectual space and to just to write something else for ourselves. You only have so much time, right? And brain power. And thinking if I have only this much left, should I write a book? Should I do a sub stack? Should it go on medium? Should I try to build my own empire and pay for it? And some people aren't techie. And so they're not going to know how to make their own WordPress website. And if you're just beginning. That's a long journey to rank in Google. And now I feel like Google is prioritizing Reddit and Quora. And so thinking, I guess it just depends on what your specific objectives are. I think for writers who don't want to learn, Maybe they just want to write for the sake of writing and maybe they're not wanting to create a funnel that goes to sell digital products. They just love the writing. I definitely see medium as a great way to jump in and to share your expertise. Right. Publish it and reach people quickly without worrying about all the other pieces. I

Tony Stubblebine: 16:49

agree. Uh, and we, the way we say it sometimes is you shouldn't have to learn how to be an internet hustler in order to have your writing successful. Red medium is a place that we just want you to be a writer. Just come be a writer and focus on that focus on living. So you have something to write about. And I think that the best voices are often people in that category. Like someone that has mastered SEO has mastered virality. That's all time. That is taken away from the writing itself. I don't think it's healthy for the writer. And I don't think it's healthy for the internet at large. Honestly,

Ashley Cisneros Mejia: 17:29

I agree with that. I hear that in some of the industry groups that I'm in of writers who are saying, Oh my God, don't give me another social media platform where I have to tap dance and learn how to be a whole. Video production person when that's not who I am. I just want to share my messaging without thinking about filters or what the trendy song. So it's all about reaching people. I definitely see this as if it's for the love of writing and you want to share a message and you're not trying to go viral. You're not trying to be an influencer. You may be not trying to get a brand sponsorships or whatever. And you want to have a message to share. I definitely see medium is a much easier, less painful way to connect with people. Thank you. Yeah. So as we look toward quarter four here, and we're getting into 2025, where's medium going next? You've hit this 1 million paid members milestone, the profitability piece, where are you going next?

Tony Stubblebine: 18:26

Our goal is to do what we're doing already, but do it better. And I think the thing that's probably hidden, and we even barely touched about it is the power of community on medium. It's one thing to get money. It's one thing to get, uh, views like, oh, here's 1700 views, right? But the thing that really drives writers the most is a connection with the reader. That's what we're writing for anyways, right? So Medium has, just as the basis of the community, this incredibly active publication ecosystem that people can submit to. And by submitting, you end up working with editors. I think on a given month, there's something like 9, 000 active editors working with authors to help those authors find an audience, sometimes help the authors give feedback to what they're writing, if that's what you're wanting. And then each of those publications has their own community where they're talking about what you wrote. And so I just think it's so powerful when I write. I think I judge the success of my writing so much more on the comments than I do on the number of pages, right? That's the most direct way you realize, did I write something powerful? And I think that's the secret sauce inside a medium. And it's just, it's a touch too hidden. And so I like a lot of our work coming forward is focused on making that. More visible. And I think that's something also writers crave is a human connection from their writing. So we're just trying to give more and more of that.

Ashley Cisneros Mejia: 19:58

I think that's exciting. I think a lot of people who are freelance, there's some folks who do something else for their nine to five and they love writing, writing as their passion. And so they have the space for it. Mentally, because it's not tied to living to explore more. And I think a lot of people who are freelance writers, I think they started where you're talking about writing something that's meaningful to them and seeing it resonate and experiencing that magic, that synergy with someone like, Oh, it hits someone. And if, and hearing that feedback and getting new ideas, that excitement, what gets us into this. And then there's other people who say, Oh, can you write for me? Can you do that for me? And so then unknowingly we become businesses, which is great. It can be great. But I think what I'm hearing too, as somebody that I write for companies, I write for people, two things is going on medium to, to observe what pieces are connecting, what it's studying that, what is it about what they wrote, how they presented it that elicited that engagement. Because that's what we're trying to replicate for our customers. And then the other piece is thinking of it as an invitation to be more playful again with our writing before it became so tied to, I have to work to pay for daycare. I have to write to pay for daycare. And that's the position that a lot of my listeners are sitting in because it is how we make our living. And we're not under, we're not working for a big media company where we have, some of us are. Freelancing on the side, but a lot of my audience, they're working writers. And so it's exciting to think about a place to return to what got us into this in the first place.

Tony Stubblebine: 21:48

The, the working, the craft authentic to be, to work the craft. I think there's a real hunger for that. I was a. Programmer originally, and then you end up being a corporate programmer. Wait a second. This was my hobby and then I became a writer, but yeah, that really resonates with me. The other thing you said too, it's, we're all trying to learn what better way to learn than immerse yourself in a community of writers. This is there's so many communities of writers here and around subtopics and genres and just to to learn and get inspiration from them has got to be incredibly powerful for people that are aspiring to be really successful freelance writers.

Ashley Cisneros Mejia: 22:30

Yeah, and the opportunity that you're creating on the internet to connect with people. And not a search engine, not an algorithm, because I think that was for many years and maybe we're coming out of it. Maybe I don't know, but it just felt initially it was you're connecting with the readers, the target audience, centering them, thinking about what's in it for them, what matters to them. And then it also became, wait a minute, we've got a rank. So here are these keywords, stick these in there, make sure you format your writing in this way, because we have to please Google too. And I think. That opportunity, that invitation to just connect with real human beings again, it's also pretty cool.

Tony Stubblebine: 23:12

Good. Yeah. It's like job satisfaction on top of it all. And we want writers to be more successful, but also happier while they do it.

Ashley Cisneros Mejia: 23:21

That's fantastic, Tony. I appreciate your time so much today. Thank you for sharing a little update on what's going on with medium and why writers like me, who are freelance writers should definitely consider writing on medium as well.

Tony Stubblebine: 23:36

Great. I appreciate the opportunity to talk to people and I learned a lot as well. So this was great. Just so much appreciation for you and what you do to educate freelancers.

Ashley Cisneros Mejia: 23:48

And with that, we've come to the end of another episode. Please make sure you hit subscribe and give me a 5 star review on Apple. Check out the show notes and grab my free Niches Get Riches freelance writing worksheet to brainstorm the best niches for your writing business. Until next time, this is Ashley Cisneros Mejia. Don't forget, we all get this Don't constrain yourself to a box that you were never meant to fit in. It is your right to profit from your own creative gifts. Our music was composed by Donna Raphael of World Instrumentals. Talk Freelance to Me is a product of Fenix Creative Studio.