I'm here today with Tony Stubblebine, and I've been really looking forward to this episode because he's previously the founder of Lift Worldwide, which was, as I understand it, the first habit tracking app on the iPhone as well as the first habit coaching company with Coach.me. And after that he took over as CEO of Medium.com from Ev Williams. So he's had a really interesting journey, and I'm really looking forward to digging into this together. Thanks so much for joining me on the podcast, Tony.
Yeah, I'm happy to be here, Will. It's cool that you wanted to talk.
Well, let's start with — we could start in a lot of places, and so I was kind of struggling with where we should begin. But why don't we start with the company you co-founded, Lift Worldwide. How did that come about?
But I feel like I have to start 10 years earlier, really.
Well, you know what? Let's start 10 years earlier if you want to. You start where you want to. We'll end up with Lift Worldwide though. I think one of the things I like to expose for people is that there's two ways to become the CEO. One is to be a prodigy, and I have no advice on how to do that.
The other is to pay your dues.
And I'm on a pay-your-dues trajectory. So I would say one of the key moments that led to starting Lift was — maybe six years earlier I had been the head of engineering for a small podcasting startup called Odeo, and it was started by this guy Ev Williams, whose name is going to come up because he's the founder of Blogger, founder of Twitter, and the founder of Medium, the company I run now. But at this moment in time I had been his head of engineering, and pretty quickly we realized that we were building the wrong thing. It's sort of like at first they thought the problem was they weren't shipping enough software — they weren't shipping fast enough. So I solved that problem for them, and then they realized no matter how much they shipped it was never going to work. And so they started looking for a pivot, and the pivot famously that came out of Odeo is something we've all heard the name Twitter. Like we built the first version of Twitter in that company — this 12-person company — and you know, grew it to let's say 150 users. It was just this prototype of a small group of people that really liked each other. We saw some promise in it, and it got spun out at that point.
But I thought I was there to be the head of engineering, and so when we spun it out, I was like — we're spinning out a product with 150 users and one of the engineers is leading it. You don't need a head of engineering. So I left. I left on good terms obviously because I stayed in touch with those people for a long time. And when they left Twitter, when they were done with it, they wanted to build new products, and I just happened to be ready to start a new company for myself at that moment. And I came to them — I hope we get to be business nerds — because there was this moment in time in startup land where it's just like you could have an idea and say, 'What if this worked?' and you didn't have to have any more justification than that. And so I came to them, I said, 'What if we could build a positive reinforcement layer for behavior change — essentially a psychologically savvy habit tracker?' And they're like, 'Wow, if that worked, that would change everyone's lives.' In hindsight, I would not start a company without a really clear view of distribution and business model. I think that kind of throw-it-at-the-wall-and-see-what-happens approach is kind of nuts, actually. But it was an incredibly fun journey. We did basically pioneer this genre of software. There's probably a hundred variants of habit trackers now. We made the most noise and set most of the patterns that people use.
Yeah. So did I hear you correctly though to say that you started by kind of throwing stuff against the wall, seeing if something stuck, but you don't like that approach anymore?
No. Terrible. Because what happens is you get into this — you spend all of this time on the product thinking. I think all of us are just obsessed with a better mousetrap. But if you don't know the business model and you don't know the distribution, you don't know the parameters that you have to design the product for. You just end up building a product that works but could never grow and could never make money, and that just feels like a mistake. And I always tell other entrepreneurs when they ask me for advice, especially about behavior change and habit tracking apps — whatever product idea you have is going to work. It will change people's lives. So I don't even want to talk to you about that. I want to talk to you about how you're going to grow it, because if you don't build that into the design of your company, it's all just a waste of time. It's not that we didn't build nothing. I mean we did eventually build a business. We did eventually get to profitability, but it was a small profitable business. And it was interesting enough for me that I ran it for a pretty long time. But oh — the connection I sort of missed — the connection to Ev Williams is like he funded it, he was on the board, he co-designed the first version with me.
And so at around the time that I was ready to leave it, he was ready to leave Medium. And I had just out of friendship basically always been really active on Medium, had been an adviser, and later had done kind of a business partnership with them and knew and loved the platform. I might even be underselling it. So Medium — our goal is just to be a place where people can write and publish and make it simple. Get rid of all the complexities. You shouldn't have to download software, you shouldn't have to install anything, you shouldn't have to build an audience first. Just write, and Medium will take care of helping you reach and build an audience just on the strength of your writing. So I had been part of that, and I loved it. And I had kind of backed into being a business partner with them and then turned into by far the most successful person on the platform — not just as an individual but as a publisher. Something like 2% of Medium traffic was going through things that I owned.
And the whole time, because I'm friends with Ev, I'm not just succeeding, but I'm like Babe Ruth-ing it. He's like, 'I think it should work this way.' I say, 'Ev, you're wrong. It should work this way and I'm going to prove it to you.' Just like point at the fence and then hit a home run. And I'm not — I wouldn't describe myself as particularly smart or talented. I just happen to be very good and interested in this one thing. I followed Ev Williams a lot early in my career, you know, when I was just starting out. I don't remember exactly where he was and what stage, but it was late enough that he was able to describe how he spent six years, I think it was at Blogger, kind of learning this first-person writing system. And then he spent years thinking about it for Twitter. And I remember that was really eye-opening to me to just think about, wow, this is not somebody flying by the seat of his pants when it comes to designing this. He's thinking about the same thing for years at a time. And it really kind of showed me what you needed to do if you're thinking about this kind of product development.
Right. I mean that goes back to kind of my suspicion around throwing things against the wall, and I think you're exactly right. Ev is a huge luminary in online publishing. I mean he helped make blogging a thing at all, and then he helped invent the category of short-form blogging — micro-blogging — which is Twitter. And even though Twitter has gone through its own chaos, it's like now we have three Twitters — Threads and BlueSky are on the same trajectory. And basically no one has thought longer or harder or deeper about these subjects.
And there's value to that. I mean absolutely we see the value. It was weird to take over this company from such a luminary. I had some track record that I knew what I was doing, but it's this incredible career blessing that I got attached to him early in my career and got to learn from him for almost 20 years now.
So there are a lot of different directions I want to go, but since we started talking about Medium a little bit, can you just help me understand — when did Medium come out? Like it came out of Twitter, I assume. I guess he left Twitter, he started Medium. Medium obviously is longer form, but what was his motivation to go from Twitter to a company like Medium? You know, because obviously there were other blogging platforms at the time. Can you just talk a little bit more about kind of the origin of Medium?
You know, the name almost says it — they were obsessed with the length. It's one of the things you learn in social media platforms is that the format defines what type of content you see. So if you put a character limit, you get Twitter-like content. And so they were interested in what does medium-length content look like. That literally came up in a discussion. He wrote 'Medium' on the board and they said, 'Whatever we do next, that's the name of the company.' And I think in a lot of ways it's a reaction to Twitter because Twitter can be so emotional and so reactive, and sometimes really toxic. I've heard it described as the PvP area — the player versus player area — where it's just okay to really yell at other people and be mean to each other. Maybe some people occasionally want that experience, but most of us do not. We want a place for thoughtful and informed writing. And so they realized you need multiple paragraphs to really get in depth. You don't need a book, but even just a singular idea takes a while to express. So it's between a tweet and a book.
That's interesting. I like that. And what I loved about that team — I mean to me, I learned something about innovation. Like you always think, all right, if I start a new company, the logic is I have to build something better than they've ever seen. And then my kind of programmer brain, because I was a programmer originally, I always jump to a new feature that no one's ever seen.
Medium had no new features. What it had was this incredible level of design. And so they innovated not by inventing a new feature. They innovated by taking all of the features you expected and finding the essence of them from a design standpoint. I was like, oh, that opened my eyes to this whole new world of how you could innovate on something.
That's really interesting. So to talk a little bit more about just kind of the details of Medium. So it's obviously a writing platform. What about other types of media? Is there a role for video, pictures?
Nothing. We describe ourselves as a reading and writing company. And I guess I'll get on my soapbox to get this message out into the world. I think it's okay to be counternarrative. It's actually — and so I'll describe why it feels counternarrative to us. It seems scary, but your job as an entrepreneur is to innovate. And there's a business strategy writer on Medium, Roger Martin, who has this phrase, 'where to play.' And one of his observations is that competitively, from a business strategy perspective, a lot of times the best place to play is where no one else is playing. Like yes, it's possible to compete, but competing is a lot of work. You'd rather go somewhere where no one's really paying a lot of attention. And so I would say the current narratives right now are 'pivot to video' again — you know, all the media had a moment where that was a catchphrase, and it's just come up again with TikTok for all forms of user-generated content — and then the other is AI. And so we looked at all these trends and we're like, wow, people really think we're headed in the wrong direction. What do we think? And what we came to is essentially there's just two human needs that we think we serve. One is a desire to think, and the other is a desire to connect. And so like with AI and thinking — you can't have a robot think for you any more than you could have a robot lift weights for you. Writing is exercise for your mind and writing is inherently healthy as a way to organize your thoughts. Sometimes it motivates you to do a little episode research, but really just to think even if you never were to publish it. If you care about being smarter, you will be drawn to writing. It is the best format for that. And I think way more convenient than video. It's hard to edit video, it's hard to edit audio — or you probably like when you edit audio, you might be using a tool like Descript that converts it to text and you edit the text and the audio gets edited for you, right? Text is a great format for that. And then the other is that we just all have a need to connect with each other. And there's something that writing online has exposed, which is that it validates that each of our lives are really valuable. If you have this impulse to document your life and share it, you immediately begin to realize that there's other people like you that want to learn from you. And there's just nothing more validating than teaching someone else. And what I think is surprising to people who write online is there is no limit to what you can teach. You don't have to be a teacher. You don't have to be an expert. You don't have to be a master of anything other than just to share your personal experience a lot of times. So those two things are not made better with video, not possible by outsourcing to an AI — I can't connect with you by sending my robot avatar to this podcast. I have to be here with you. So we just got really clear on our own first principles and are completely comfortable being a reading and writing company regardless of whether it's part of a popular trend or not.
Is it a big use case for people to write and not publish on Medium?
More and more. Just speaking for myself, I have like 800 published stories, which is a lot more than most people, but I also have like 800 drafts.
That's interesting. Yeah, that's interesting. I did the same thing when I first started. I used Posterous a lot. I actually went through a lot of different platforms, and frankly now I'm kind of thinking through like where do I want to be, where do I want to write. But I remember I went through Posterous, I really liked that. It kind of had a built-in audience to an extent. But I remember one thing that was nice about it was you could email — it was one of the first I think that you could email your notes into and it would either publish it or not publish it. And I remember it helped me refine certain thoughts to whether or not I chose to publish it at some point. And I published a lot, but I also didn't — I probably had a 2-to-1 ratio maybe of unpublished to published.
Our ideal writer is not needing to write every day. I think there's something kind of inauthentic about having to manufacture content. It goes against this idea that everyone has a life experience worth sharing. Our ideal writer is out living, and then when they do something interesting they come and share it. But if you are someone that kind of has this impulse to be a regular writer, you get into this need to — I call it being able to manufacture it. Even some days you have your inspiration, but on a day that you don't, what do you do? And the thing that worked for me is I just have so many drafts. If I feel like writing just because I enjoy the act of it but I don't have a lot of time, I go to my drafts folder, I go to my emails, I go to long Slack messages, I go to answers from Quora back in the day, comments I've left other places, and be like, 'Oh, I wonder if I can expand that.' I think that is a productivity hack of a lot of people. I'll give you actually a Malcolm Gladwell example. I thought his MasterClass missed an opportunity to explain what really makes him successful. He gave a lot of tactics in his MasterClass lesson about the structure of his writing, but then just casually he was telling a story about a book that had come out of — one day he was digging through his file cabinet and found five pages of notes that he'd forgotten about from a day that he'd spent interviewing people in some town in Pennsylvania. And he was like — and then he went on to the writing process. But my head was like, tell me more about this filing cabinet. You spent a day of work and did nothing with it for five years. That just tells me that there's this incredible amount of unpublished volume before any of it gets published. I thought — everything I know from my prior life in habit coaching and coaching in general is that that productivity system was driving a ton of his success as a writer, and that's probably generalizable to even those of us that don't aspire to be a New York Times bestseller.
Yeah, I bet you're right. That's an interesting insight. So I want to turn back for a minute. Let's go back to habit — or to Coach.me for a second. So I've found that one of the most difficult things in business is changing people's behavior, changing their habits. And I'm talking about team members primarily, but I would imagine it would apply to anybody. It's tough to do, right? It's not an easy thing to change somebody's behavior. So what can you tell us about that?
Yeah, I totally agree. And you could think of this as a manager, but I'll start with it as a behavior change specialist. Here's a product that will change your behavior. We came from a world of habit research — we had been connected to BJ Fogg at Stanford, who wrote the book Tiny Habits and is one of the biggest proponents of this, and biggest researchers too. But he came at it from this very narrow lens of, okay, we define the habit — you know, there's like a cue or a prompt or a trigger, all the same word — there's a behavior, and then there's a reward. And this is like Pavlovian. If you can design your life this way, then you will rewire your brain. And then the slightly more advanced way is if you want to get rid of a habit — find the cue and get rid of that. Or if you can't do that, then you try to build replacement habits. That's essentially the box that habit design was living in at the time. So we came to think it was failing so much because it was actually so much bigger than that. You don't need habit design, you need a therapist. We were just so often running into this. The example I give usually is this guy that we were working with, and we had a real Tiny Habits mindset. He wanted to give up sweets. So he was like, 'Okay, my goal is no sweets at all any day. I want to have a streak.' Of course he failed right away — too big of a goal. So we make it tinier. 'How about no sweets before noon?' Okay, failed right away. 'How about just no particular kind of sweet?' And he said, 'Yeah, okay, all right, I can have sweets but no ice cream.' That's what he told us. The very next day he goes, 'Coach, you're not going to believe what happened. My family is vacationing in Vermont and they wanted to go to the Ben & Jerry's factory.' So no amount of making this goal tinier had any impact on him to the point that he couldn't even go a day without ice cream. And he didn't just fail a little bit — he went to an ice cream factory tour. Right. And so it took me a while to kind of wrap my head around a theory of this. And then eventually I ran into a coaching framework — Dilts' Logical Levels, I think is what it's called. And it talked about the levels that you can reach someone at. And the baseline that we had been focused on was behavioral, but above that is belief and identity. And so imagine you're a dad in a family unit and you have a service mentality — my job is to make sure the family is happy. And imagine that that is at war with 'I told my coach I'm not going to have ice cream today.' Actually, the thing that was getting in the way was an identity system.
I love this. This is great.
So that's why it's so freaking complicated. And it's actually — something trivial like a habit sometimes is better addressed with a therapist.
Yeah, that's interesting. So, and I don't mean to interrupt, but I've done some habit modifications. I've gone from a bad diet to a great diet, from not working out to working out, and I've maintained a lot of these good habits for me. And I wonder if I've done some of this unintentionally. I think I did do some identity modification a little bit. I thought of myself as somebody who's strong and so I want to lift weights and be strong. I started jiu-jitsu and I want to be somebody that can move well. And so therefore these habits — I've not changed any behavior for the sake of the behavior. It's for the pursuit of some, I guess, identity.
Yeah, I think that's a huge part of what's probably happening psychologically for you. And so the problem is that habit design is very concrete and easy to reason about. Identity design — this is tricky. And I don't know — the only thing I've really had any success with with people is not to change their identity, but to help them accept an identity. A lot of times you know who you are, but you don't like it for some reason because you don't think society values it. I totally relate to that. So we actually said this already about types of entrepreneurs — you can either be a prodigy or you can pay your dues. Right. And I think that we mythologize prodigies. And so it's hard to accept, 'Oh, I'm not a prodigy. I am a person that's going to pay my dues.' But if you could accept it, suddenly everything in your life gets way easier.
Oh my god, I've got to tell you this. So have you ever used the StrengthsFinder program?
I know of it. I haven't done it myself.
Yeah, it's a great — for anybody listening here, it's a good personality assessment. We will often give it to new employees, and the idea is that you want to discover your strengths so that you can grow your strengths and not worry so much about all the things that might be weaknesses. And so it kind of flips a lot of these types of assessments on their head. In any case, I remember the first time I took it, I was early 20s and I hated the results. I wanted to be like the classic CEO. And so I just remember there were a couple years, maybe more than a couple, where I kind of fought with my identity, and those were not super happy years. I was really in denial about what my strengths were. I wanted them to be some arbitrary strengths that I heard were really impressive or whatever. And then I don't remember exactly what changed, but I remember I did change that mindset. I took the assessment again and I just kind of embraced what these strengths were. I found that they actually made a lot of sense. They did feel very accurate to me, and just like you said, things got a lot easier after that.
Right. It's a work-with-your-assets strategy. Like why design a business strategy for assets you don't have. And I think one thing that's — as I've talked to other people who've gone through that process — is a lot of times there's a starting belief or fear or anxiety that more self-acceptance will make you less successful. It's like maybe your self-criticism is the motivator for action, right? And so you're like afraid to give that up. 'If I'm kind to myself, then I'll turn myself into a failure.' And in practice it's not true. I saw — maybe one of my happiest moments listening to a podcast — I saw Tim Ferriss and Brené Brown talking to each other. And I think Tim Ferriss is famously very tactical, very find-a-hack, very — I loved his 4-Hour Workweek, all of his books. He was an investor actually in my last company so I've co-written things with him. I really like him. Somehow he has family near me in the Hudson Valley and I ran into him at a country gas station the other day. I just really have a lot of fondness for him, but I also don't think of him as heart-forward. Whereas Brené Brown would be. But they had this exact conversation — that they had this fear that if they had too much self-acceptance they would stop being successful at anything. And that they were both having the same kind of realization in their own lives that the more they could accept themselves, the more they were able to accomplish. And that's — StrengthsFinder is exactly that. Because it's not just 'find your strengths' — it's 'bet on them' afterwards.
Right. Correct. Yeah. Correct. It's really kind of the — I think Warren Buffett and his partner Charlie Munger would talk about this periodically. They would talk about it as staying within your zone of competence. Charlie Munger would say something like, 'There's no level low enough to describe how bad I'd be if I had to make my living playing the French horn,' so he doesn't do that. And so we do have these examples. Literally, at one point the richest man in the world is very comfortable with what he's good at and what he's bad at. Warren Buffett — that's a huge part of his life story and the way he tells his own story is: I found this thing that's valuable and I only do it. I've heard that other things are valuable, but I don't know how to do them, so I don't do them.
