How AI Is Changing Writing — With Tony Stubblebine

31:21Not all of it, but some of it behind the subscription. And that's how we've made a business. And so that's what you're saying is our partner program. So for them, we were just like taking a stand and saying like the thing that we want to pay for to make sure it exists on the internet is your real life lessons. And this idea of paying you to spend 15 seconds generating a ChatGPT transcript just doesn't even make sense to us as a worthy thing to pay for. But that's different than saying whether or not it's valuable. It's like we're saying we're paying to make something exist on the internet that otherwise wouldn't exist.

32:07I see. So what does the web look like if we're going to have a lot of writing that's generated by AI, like thinking about your event calendar sitting alongside and probably outnumbering human content, human generated content? Yeah. Yeah. If it doesn't already, probably does already. but the quality question it will keep getting better though it could um do we are we going to my head originally went straight to relationships right are we going to get tired of having relationships with each other are we going to prefer an ai for a relationship too and of course that's like the weird edge of ai right now too um you have an ai girlfriend ai boyfriend and Because it's like the degree to which that shifts, that's one of the other reasons that people write and share online is because we're trying to create connections with each other.

33:05I mean, I don't think that will ever disappear. I hope it never disappears. I still like connecting with people. So I think that'll continue to drive a lot of activity. But the question I've been posing to friends and advisors is if Google Gemini reduces search traffic enough that there isn't an incentive to post in public, will people retreat in private? And the example I usually give, because we already see this happening, which is we think Twitter, there was a Twitter exodus and it went to, like most people think, the Twitter exodus went to Blue Sky and to Threads and originally a little bit to Mastodon.

33:52I would make the case that a lot of it went to Discord. and that's an example of the public internet retreating into private spaces where it's safer to be yourself and to be weird and to be um uh um yeah it's also less noisy well i've never seen a discord that didn't make my head explode but you should i mean you should join we have one for big technology subscribers i think it's excellent i mean seriously like But I was going to say that I've seen exactly the same thing that you've seen. I could go weeks now without tweeting or a week, let me be realistic. But I'm in the Discord all the time.

34:32And it is less noisy. It's friendlier. Not all of them are. But it is friendlier than Twitter, which it's easy to be friendlier than Twitter. And it's more information-dense and less madness-inducing because you don't have that home tab driving you nuts. Right. All right. You've convinced me. smart people join the big technology discord. You heard it here first. Yeah, I think I'm not worried about like the end of civilization or something. I just think the internet is shifting a lot right now. Right. And that's probably one of the shifts that will happen is if you don't, if the incentives for public discussion disappear, or you're going to see people shift into different ways to get kind of the same thing that they have been getting.

35:22Yeah. On the AI relationship thing, it's interesting. And I'm curious about the way that you put it because it's not necessarily a preference that people prefer AI girlfriends over human girlfriends and boyfriends. It's more just like it's a substitute when those relationships are not there. Sure, right, right. I wonder if something can be said for content as well. Yeah, it could be a yes and, right? Yeah, I think there's a lot of placeholder content. Fill your time.

35:58But it's not the pinnacle of a deep, substantial experience. I think that's true in human relationships, and it's, I think, true in certain writing. Yeah, well, for now. Let's see how things change. Okay, I do want to talk a little bit about the approach that you're taking at Medium to sort of, we've had Matthew Prince on in the same chair talking about how Cloudflare is trying to force AI companies to pay if they want to crawl publisher content. You recently started a similar program along with a number of others. So talk a little bit about your way to protect the content from human content creators.

36:38Matthew is like my hero. I really, I see it very similarly to how he sees it. And so I think to go back to this, like we're in antisocial relationships between with the AI companies right now, right? Like it's not, it didn't start collaborative, it started antagonistic, right? So what I read in his announcement with Cloudflare, which was that we need to make it easy at Cloudflare for a lot of our customers to block all the AI crawlers. And if we do that for enough content sites, then they're going to have to negotiate. And it really sounded like what he was saying was leverage first. Like everything else can be figured out later, but first you need enough leverage to bring them to the table.

37:24So that makes perfect sense to me. What is not ideal to me is that doing that would rely on a single service provider. that we could only bring them to the table if we're Cloudflare customers. Now, Medium is a Cloudflare customer and a happy one. And we do use Cloudflare to block basically any crawler that isn't crawling in a way that drives traffic back to us. We're blocking right now. And it's because the Cloudflare tools are so good. But I always would have preferred an open license. And so there is one that just launched, a real simple licensing standard, RSL.

38:14And what it's getting is a coalition of platforms and media properties. Quora and Reddit are part of it. Yahoo is part of it. To say, here's an internet standard that we're going to put out that lays out how we want AI companies to use or not use our content. and of course the default thing we're going to say is no, we don't want you to do anything until you talk to us but at least now we can say that in an official way and for people that are not, for AI companies that are not respecting it, then we use tools like Cloudflare to block it. Then there's this other reason why Cloudflare doesn't work for us, the initiative that they put out because they have this one where they'll negotiate the payment for you.

39:10It's that Medium, and I think we're the only platform that wants to do this, is we want, if we get any money out of these AI companies, we want to give all of it back to the creators. Like so far, every other platform has been doing side deals and then just pocketing the money. and like I don't know that doesn't make sense to me medium's never been in the sell your data business anyways and it's not our like we don't own this content I don't know even know how we could sell it but you know people are are other companies have tried to do it that way and so we're which others like reddit I think so yeah that's what it that's what the press releases made it seem like.

39:53And so I think not only, I don't know why I'm so combative. It's like, not only are we trying to shame the AI companies, we're trying to shame the other like social media platforms that like, it's like, we're all in a position to negotiate on behalf of our content creators. Like I'm in the business of negotiating for our writers to get some compensation out of these AI companies. And if we can do that, the intention is just to pass it directly back to them. My CFO is like, just shake me every time she hears me say this. She's like, well, shouldn't we? Take that money. Not just that, but it's like, okay, look, if we have significant legal fees, yes.

40:38We'll cover costs, fine, fine. But yeah, I think it's just really important that we get back to those incentives for all creators, not just writers. Otherwise, they're going to disappear. The thing that we love, this internet, it will disappear if you take all the incentives away.

41:01I actually don't understand why the AI companies aren't more worried. I think they're building something on a very shaky foundation because these new rag-based searches where they're doing all this research for you like the the information they're pulling in it is literally going to stop showing up on the internet and it's like chat tpt will give you good advice for 2025 and earlier but nothing beyond that i don't think they care because they could just hire people to write directly for them that's what they're already doing that basically through third parties like with scale so it doesn't seem like they're too worried they never present as worried about anything other than i guess when you're you're happy to raise$40 billion a year and then lose$100 billion in a five-year period.

41:47I wouldn't. You chill. That style of business is beyond me. Not your thing. Yeah. All right. I want to take a quick break and then talk to you a little bit about why I, as an independent publisher, am happy to play ball with AI companies and want my stuff to appear even without compensation in places like ChatGPT. And then, of course, I want to talk to you a little bit about what Medium is and how it's different from Substack, which is something that I'm sure some of our listeners have questions about. So let's do that right after this. Capital One's tech team isn't just talking about multi-agentic AI.

42:23They already deployed one. It's called Chat Concierge, and it's simplifying car shopping. Using self-reflection and layered reasoning with live API checks, it doesn't just help buyers find a car they love. It helps schedule a test drive, get pre-approved for financing, and estimate trade in value. Advanced, intuitive, and deployed. That's how they stack. That's technology at Capital One. Did you know your credit card points and miles can lose value to inflation? Credit card companies often reduce the redemption value of your points and miles. Now, imagine a credit card with rewards that can grow in value.

43:02With the Gemini credit card, you can earn Bitcoin or one of over 50 other cryptos instantly with no annual fee. Every swipe at the store or gas pump earns you instant rewards deposited straight to your account. Plus, sign up now for a$200 Bitcoin bonus to kickstart your rewards. Visit Gemini.com slash card today. Check out the link in the description for more information on rates. Again, if you're looking to invest in Bitcoin but don't know where to start, the Gemini credit card makes it easy. The Gemini credit card is issued by WebBank. In order to qualify for the$200 crypto intro bonus, you must spend$3 ,000 in your first 90 days.

43:42Some exclusions apply to instant rewards in which rewards are deposited when the transaction posts. This content is not investment advice and trading crypto involves risk. The Gemini credit card cannot be used to make gambling-related purchases. And we're back here on Big Technology Podcast with Medium CEO Tony Stubblebine. Tony, before the break, I talked a little bit about how I am an independent publisher. I'm on Medium. I'm on Substack. And I kind of want these AI bots to crawl. I think I'll have an advantage if the AI bots crawl my content. And that is because it seems to me more and more that the way that people are getting information is through these AI chatbots.

44:22It's not a majority of search by any means. It's not anywhere close. But Chattapiti does have 700 million monthly users or weekly users. And Gemini has lots of users. Meta's tool is starting to increase in usage. If people are talking to these bots more and more about things that I cover, I want my work to be a source there. A, because it is already starting to drive some referral traffic. I'm seeing ChatGPT as a source for paid subscribers for big technology. But also, if you think about, again, this reason of why people who write and create content do what they do is they want to have it reach other humans.

45:02And now a good channel is through these bots. So here's the I've data. I'm happy to share it. So ChatGPT is about 1 % of what we see from Google right now. So not nothing. but the thing that's really important to us is that it converts into paid subscribers four times higher than Google traffic so I think it may be more accurate to say for what you know from a business standpoint and like what you're saying too about having paid subscribers is that chat GPT is like four percent as big as Google right now already I don't I'm we're a little bit confused by the growth curve because it was on a tremendous growth curve from the fall of last year to the spring of this year and then leveled out.

45:50And a bunch of people said, oh, it's all college students and it'll pick back up when school starts again. We haven't seen that. So ChatGPT jumped so fast and then it's just flat since. Google is almost the opposite. And I'm hopeful and I think they're making noises that they don't want to destroy the internet and they're going to find some way to be a better partner to the world. But right now, I would estimate that we lose about 100 clicks from traditional Google search for every one click we get back from a Gemini summary. And that's huge. And what is less good than ChatGPT is that there's no difference in conversion rate.

46:44These aren't like somehow higher intent visitors. It's just suddenly a lot less traffic. And I would say my worry is even if they paid, I think a lot of the writing that I'm most interested in reading wouldn't care. It wouldn't be enough because most of the writers on the internet are not even doing it for money. They're doing it for validation. And if they don't get readers, sort of the point of it goes away for them. But this is what I'm saying, that they will get maybe even more readers by having their work summarized into an AI answer. Well, sure. Why should they not want that? Well, this is what I'm getting at with that data is that ChatGPT maybe feels additive.

47:31It's like, oh, here's another way that another traffic channel. But if you look at it just through the lens of Google, it's diminishing, right? That overall Google traffic to most sites has dropped quite a bit. And like the way that Medium sees it actually is that our SEO optimizations, which you were noting earlier, have been effective enough to grow Google traffic. but that the click-through rate when Gemini launched dropped nearly in half. And so I think that that trade-off is not a good trade-off. It's 100 to 1 against us. Let me run this by you. If most people, like you say, are writing for validation or connection, does it matter that people are going to their actual website or reading their thoughts and experiences at all?

48:21Because if it's really connection and validation, and I'm just like throwing this out there because it's worth talking through. It's subtle. We have to tease it all out for sure. Then they're getting that. Their arguments are just being distributed instead of their website through ChatGPT where people are still reading that. Do you think you'll change how you write to focus less on depth and more on like kind of a memeable idea that can travel through the AI summaries? So I would say no. To me, actually the best performing story and it's not always like this, but the best performing story that I wrote this year has been this story, this profile that I wrote on the Dario piece.

49:01Dario Amelde, the Anthropics CEO. And that went through all channels. So through Substack, through Medium, thank you. You guys highlighted it on Medium. And the SEO is better on Medium, you're saying. Yeah, great SEO on Medium. Obviously, we put it on YouTube. We put it on the podcast. You don't always get that return on a story that you work a couple of months for, and that's really frustrating. But when it works, it's really great. So that to me was indicative of maybe that's the direction and this idea of writing this memeable content that gets produced, that gets put forward in AI engines is less exciting to me, I guess.

49:37Well, I got my start in media, essentially working for this tech publisher, O 'Reilly, back before Stack Overflow existed. Like the internet was built by people that had O 'Reilly books on their shelf, right? And I was there in that era. And what I liked about the founder, Tim O 'Reilly, is like, you know, essentially the business was selling the most in-depth information possible. like the best books with the best authors and the best tech reviewers, like really good, high-quality stuff. But he was also in the business of trying to name things because he thought, I think, if he could name it, he could then build a business underneath it.

50:17So O 'Reilly coined the phrase Web 2.0 and then had a conference business behind it. And so it is the modern internet kind of works both ways sometimes and maybe sometimes people specialize. But it is true that both ways can be powerful ways to kind of get that validation of you changed people's minds. Yeah, I went and visited Tim in his Oakland home a couple of years ago. Let's see, 2022. So three years ago already. And the story I wrote, and I wrote it for Medium, was Tim O 'Reilly, CoinWeb 2.0. He thinks Web3 hype is naive. I think he was right. He said, if the bubble pops, are we going to find value in those bored apes?

51:01I don't think we did. So, okay. Tim has been right about things for a while. Yeah, for a long time. But, you know, it's interesting. I'm looking at this story, and it's on Medium. And it was part of, like, this program that Medium was running to get, I guess, journalists and folks of that nature to write exclusively for Medium. And that has since gone away. Yeah. And so obviously, you know, I'd say looking from the outside, it seems like Substack has, you know, has emerged and picked up a lot of that energy. And it leaves me wondering where, what Medium is for and who Medium wants to serve. And now that I'm sitting across from the CEO of Medium, I thought this would be a good opportunity to ask.

51:43I think Medium is a place for real people to write. And I think that there is a space on the Internet for professional writers. And it's kind of amazing how that class of writers is growing right now. But those people should be using specialized tools. And I think Substack is one of them. Patreon, Kit, Gumroad, right? Like these are all paths to professionalize your life. But your average person, most people, the majority of people, are not trying to quit their day job to be content creators. And what it looked like to us is that the internet had really shifted to serve content mills, content creators, independent media people, which you would qualify for.

52:35Yeah, I'm definitely in that category. You've gone into it. Not content mill, but independent creator. You qualify as indie, to be clear. Right. And like and you must like feel like so much opportunity that you don't have to be, you know, like doing your profession in this like big corporate ecosystem that maybe is like stifling and also not always stable. Right. That's a good read. And but that's not the majority of the Internet. And that's not the part of the internet that I fell in love with. What I fell in love with was the idea that every single person is learning something just through the act of their life that's worth sharing and that other people would get value from.

53:16We threw the word validation around a couple times. That's really validating just about the act of living. And sometimes the lessons are quite trivial. But this is the thing I learned from Tim O 'Reilly is you don't get a journalist to write a book about programming. You get a programmer to write a book about programming. That's not that idea of I could learn how to do my job because someone else who's better at my job just happens to be writing about it on the internet. That's the most commercially viable content on the internet. Like, I hate to break it to you, to anyone that's like trying to like make a go of it.

53:56Dude, like people with killer jobs sharing how to do it. Like everyone makes money on that because it's like the readers want to pay for it. The people publishing it, they get paid in the secondary. Like they get paid on reputation. They get paid. A lot of times they're just a lot of great writers are doing it to try to get people to come work for them. So they're advertising like, hey, I'm a good person to work for. Or they go independent and they're working as like business consultants or whatnot. So like that group is not trying to be on the content treadmill. Because by definition, their value comes from not being on the content treadmill.

54:41It comes from being like living somewhere, right? And I'd always rather hear from someone that's so busy living that they don't have time to learn all these internet games. And so the number one thing I did at Medium, which was all based on lessons that I'd learned by being a partner to Medium before I was the CEO, is just to switch us and be clear. we're not uh um we're focused on real people and regular people which does not mean average i mean a lot of them are spectacularly informed but if we can serve them and be the best place for them to write then we're golden and so then all of this like the professional class you're you're um a small but welcome part of our community but not the core of it yeah no it's not news to me that those the programmers are the best folks to write about programming because i mean the proof is if you look at the substack leaderboard actually like they're two of the top three um are gergay orsos and alex you who both write about gergay writes about engineering alex writes about systems so what you're saying is instead of having the people who've left like those programming jobs and want to do that professionally you would rather have like one programmer who like is doing this full time look at medium as a place to write about something that they know expertly but without the interest of being a professional content creator so they wouldn't want to start a sub stack there's um this there's a skill in being an everyday writer so you have to manufacture some something to write about and i i like hearing from people that didn't have to like manufacture anything it's just like when you have something to say say it and if it's a while till you have something to say again that's fine too that's healthy yeah i mean that was my original use case for medium i've been writing on medium so it's 2025 yeah i think since 2010 11 and it was these i was i was not a professional writer i was marketing and sales and just like doing these one-offs like um you know things that i observed that i thought might be interesting i was using a lot of different platforms medium and tumblr and stuff but i was like putting some good stuff i think some of my best stuff on medium because i knew that there was a chance that that algorithm would show it to more people it worked well with twitter and yeah and i think it's actually what got me like um yeah when i got hired at buzzfeed to be a reporter in san francisco i was a reporter at age at the time but i'm pretty sure it was the stuff i was writing on medium that caught the attention of the editors there and got me that full-time job writing is like the universal portfolio.

57:26And that is also one of the innovations of tech is that people started moving from resumes to portfolios. GitHub is a portfolio for engineers. Dribbble is a portfolio for designers. But if those don't work for you, just write about your job and that can be a portfolio for you. And I love to hire people who I can read how they think and how they approach a problem before like that's way more informative than where they had worked right and what bullet points they put on their resume um yeah but but what my counterpoint would be that you need news on on any news on the platform like yours well i think so actually let's talk this through because to me like one of the biggest moments of medium history i'm curious what you think about this was like when uh was it jay carney at amazon and oh obama or no he was working for obama jay carney was doing this back and forth let me make sure i have this right not now i see i'm really showing because i can't remember exactly what happened i feel like i feel like i might fall down on some key part of medium history here okay okay so oh all right here it was the new york Times wrote a story about how people at Amazon were crying at their desks.

58:47And the entire battle back and forth actually happened on Medium, where Jay Carney, the person running public affairs at Amazon, wrote this post, what the New York Times didn't tell you. Then Dean McKay, the editor at the time, wrote a response to that. And then there's Jay Carney. He wrote a comment based off of what Dean McKay wrote. All this happened on Medium. And the interesting thing to me is that there was the urgency there because the news was taking place on it. And that when you saw people like Jay Carney and Dean McKay going back and forth, it made you want to write stuff on Medium because you knew it had that ability to blow up.

59:27But maybe I'm just looking at that from a journalist perspective and I'm not seeing the big picture. Well, this is the sort of the op-ed of the internet sort of vibe that Medium sometimes has. where, you know, Jay Carney is not building an audience. He's not hustling to be an everyday content creator. That's actually, this is one of the use cases. For Medium, it's just not the daily use case, right? Like how many people per month on Medium are fighting some, you know, public dust up? You know, very few. Like I don't even think, this doesn't even cross my radar like once a month but now that you like bring it up as a pattern yeah i mean look jeff uh jeff bezos had an affair that he posted about on medium right and uh because it was about to leak through the national inquirer i've seen tony robbins defend him was it an affair or was it the the maybe photos or something i'm sorry jeff bezos it was really it was actually quite a good yeah bezos speaking of good writing i mean bezos is a great writer exactly that was very well written I think it was, anyway, I won't say the title.

1:00:37I think it was someone else reading. I've seen the CEO of Carta use Medium that way. It happens, and I think what's nice is to go to a platform that's going to elevate a story based on the merit of that story rather than how much audience you've already built. So it is actually a good place to just land if you have just one major thing to write. And I was thinking, for us, what we would say the most newsworthy stuff stuff was the start of COVID because there was a lot of really big COVID information that was coming from people, thankfully, who weren't in the audience building game, but were doing pretty deep research and analysis and posting it on Medium.

1:01:20Yeah, I remember reading those posts. It was fascinating. Well, look, as a happy Medium user, publisher, and reader, I want to say thank you for your time. And I think you're profitable and it's not going anywhere. It's better than that. I think it's like we had a rough stretch. We got out of it. We were profitable. And then this like we're trying to say like we're not competing with the creator economy. And for a while, one of the things that people don't see is how many people are writing on Medium. It had been flat during our struggles. And it's like our writer numbers are 50 % higher than they were on January 1st.

1:02:00And that's because we got out of like kind of being in this weird competition that we didn't want to be in and now we're back to being just being like like a place to just go and start writing not having to worry about all that other stuff yeah it's interesting because uh for me so medium after starting big technology medium was my first contract yeah first so that was signing a contract with medium was like the first moment where i was like maybe this will work yeah that was in 2020 then you came in and canceled it and I said, you know what? I'm not the one who canceled it, but I agree with the cancellation.

1:02:32No, no. It wasn't right for us. Once you came in, the program that I was in went away. And you know what I said? Really? I said, it's fine though, because it's one of those things where I was like, I obviously would love to have kept, and I'm still publishing on Medium, just not as much. I would have loved to have kept going. But now, you know, seeing the direction you've gone here and you talk through, because we've spoken a couple of times now, both on mic and not, it makes a lot of sense that you're taking it this direction as opposed to what could have been and also ran Crater Economy Company that's just running after the sub-stacks.

1:03:10And who wants to do that? So anyway, yeah. I wish, I think because we had hired so many journalists and then let them go. There's this like lingering bad blood, which you're not presenting. I do not, I seriously don't, I respect the direction that you guys went. I have no bad blood and I think both of our businesses are okay. Yeah, I want to always try to have some yes and. It's like, yes, I want professional media to exist and thrive. And Medium has a different business. We're not the ones that are going to make that happen. Well, it's good to see everything going as planned. And good luck on your continuing fight against AI sloth.

1:03:46I appreciate it. Great discussion. Thank you for having me. All right, everybody. The website's medium.com. Go check it out. All right. Thank you all for listening. We'll see you next time on Big Technology Podcast.

1:04:24With a Gemini credit card, you can earn Bitcoin or one of over 50 other cryptos instantly with no annual fee. Every swipe at the store or gas pump earns you instant rewards deposited straight to your account. Plus, sign up now for a$200 Bitcoin bonus to kickstart your rewards. Visit Gemini.com slash card today. Check out the link in the description for more information on rates. Again, if you're looking to invest in Bitcoin but don't know where to start, the Gemini credit card makes it easy. The Gemini credit card is issued by WebBank. In order to qualify for the$200 crypto intro bonus, you must spend$3 ,000 in your first 90 days.

1:05:03Some exclusions apply to instant rewards in which rewards are deposited when the transaction posts. This content is not investment advice and trading crypto involves risk. The Gemini credit card cannot be used to make gambling-related purchases.