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Tony Stubblebine moved Medium from losing $2.6 million monthly to achieving its first profitable month in August 2024, after 13 years of losses. The CEO, who previously founded habit-tracking company Coach.me and helped develop early Twitter, has refocused Medium on serving writers more interested in sharing their expertise than profiting from their words. For Stubblebine its about the expert economy, not just the creator economy. Known for viral productivity techniques like Interstitial Journaling and his 75-minute guide to iPhone optimization, Stubblebine has grown Medium to over one million paid subscribers while maintaining its ad-free, quality-focused approach. Now the company is launching a new app for notes and writing, called (fittingly enough) TK, in a bet that strong design will distinguish it in a crowded marketplace. Stubblebine spoke with Fast Company about why he still prefers paper notebooks for meetings, and how Medium differentiates itself from creator platforms like Substack. The conversation has been edited for length and clarity. Youre launching a new writing app. Why does the world need another writing tool? I had to make this case to get people inside the company excited. There are four things I want that I don’t see right now. First, the Medium design ethos matters to me. I want my words to look and feel beautiful. I was already drafting things in Medium’s editor that I never intended to publish just because I like the typography better. Second, this world of second brain apps exists, but the idea of a second brain is a mainstream concept without mainstream implementation because you have to do so much manual organization. Most people are not that organized. A messy system almost always beats a regimented system. This is a great use case for AIour view is it’s meant to elevate people, not replace them. AI can completely alleviate all the manual organization that would typically go into Roam or Obsidian. Third, theres a way to use AI as a writing assistantnot to write for you, but to do your bidding. A lot of what I publish needs citations. The other day I was writing about an old Medium program launched by founder Ev Williams. I highlighted the paragraph and said to the AI assistant: Ev wrote about this on the Medium blog in 2017. Find the link and add it. It figured out the core concept, found the link, and added it. Im easily distractedif I had to find that link myself, I would have been lost for an hour. Fourth, I’ve never seen any note-taking apps attached to a distribution network. My writing is very sensitive to the idea that you could share it and get validation and help someone else. Sometimes youre working on something and realize this could be helpful to other people. We’re excited to attach Medium’s massive network of readers to this genre of software. Youve taken a strong stance against AI training on creators work. Why? Were the only social media platform that if we can get money out of the AI companies, is planning to give 100% of it back to the creators themselves. We refused training deals with AI companies worth low single-digit millions because we heard from our writers that they felt it was unfair for companies to make money off training on the Medium network without giving anything in return. Theres still an ongoing negotiation across the industry about whether these companies will pay creators. We just supported an initiative called the Really Simple Licensing standard. We hope that gives consent and control back to the creators. How do you compete with Substack when writers can earn more there? The people who actually make the most money on writing are not charging for the writing itself. We sort of forgot in the rush to the creator economy how lucrative the expert economy is. Some of the best-paid writers on Medium are technical leaders who post twice a year, but those postings are their calling card when they go get jobs that sometimes pay upwards of a million dollars a year. The creator economy is kind of a content treadmill and doesnt always pay that well. Meanwhile, building yourself up as an expert authentically often opens up really interesting work opportunities. If you’re committed to the creator economy, you should follow a strategy of publish once, syndicate everywhere. Medium folds into that as a place to syndicate, to get additional traffic and subscribers back to your main mailing list. But if youre not in the creator economy, you’ll build an email following on Medium faster than anywhere else because you have a built-in network of people you don’t already reach. We’re much more built for that group, which is the majority of the internet. How did you engineer Medium’s turnaround? The key thing is, even if you turn around the business, you have to end up with a business that you’re proud to be running. A lot of the turnaround was in the product itself, making Medium a place where smart amateurs write regularly. Until that point, we’d either been a place where professional journalists were writing or where the new wave of content creators would write for small dollar amounts. We looked at that as paying to create more content mill stories that otherwise wouldn’t exist, and that felt bad to us. Beyond that, its run-of-the-mill business. Every dollar you spend is meant to bring back at least a dollar. If you dont have a theory on spending money, you shouldnt spend it. The startup industry was very lax about how it spent money for a while, and Medium was definitely in that boat. Just getting tighterpeople call it cost cutting, but I think of it as role clarity. Every person needed a role connected to how we work as a business. What advice do you have for technical founders transitioning to CEO? The bar for companies has gone up. It used to be build it and they will come, or you only had to be good at one or two things. Now people are so savvy about how to build a company that you really have to plot the whole business model through. Its not just can you build a better mousetrapcan you build a distribution channel? Can you build a business model where you can make money? The last company I started in 2011 was just like, I hope if I build something cool, people will use it. I came to regret that pretty quickly because I didn’t know how I was going to market it, let alone make revenue. When people come to me and say they built a better habit tracker, I tell them: I believe you, but how are you going to get people to use it? How are you going to make money? Why is this a business? If you don’t design that into the plan, good products just get abandoned because they don’t work as businesses. What does your current daily tool kit look like? I have a pretty simple work life. I’m mostly meeting with people, so I’m spending a lot of time either in Zoom or Google Meet. I typically have a paper notebook in front of me because my view on note taking during a meeting is that it’s a form of active listening. I have a strong opinion about the ideal paper notebook. We found notebooks that are landscape format, which means they’re wider rather than taller. The thing I lie about wider is that I caught myself thinking deeper about my own notes. It’s like taking the idea of writing in the margin and blowing that up. I end up with almost always three columns: raw notes as Im trying to follow along, a second column for things I need to come back to or how I want to participate in the meeting later, and this empty third column for total epiphanies. The way that form factor interacts with the way your brain works, I found fascinating. What’s your current relationship with your iPhone after writing that viral optimization guide? I still basically believe the premise of that postthat it takes 75 minutes to reconfigure your iPhone for productivity. The meta point was that these software tools are not preconfigured to make your life better. The worst offender is notifications, which should be called interruptions. If an app asked you, Is it okay for me to interrupt you mid-meeting? you’d think harder about whether thats okay. I keep basically all my notifications off unless its text messages from certain people or phone calls from my favorites, which is three people. I always try to keep in mind that the iPhone is meant to be a tool for me. My front screen is all Google utilitiesmaps, calendar. The action button is set to photos. Youve mentioned considering going even further offline. Whats your experience been with that? I did a four-month camper van trip around the U.S. and drove 9,000 miles. The thing that blows people’s minds is that I didnt listen to anything during the drive, unless I was tired. I tried to have quiet time for thinking and seeing where I was going. That was one of the happiest periods in my entire life because my brain was not buzzing all the time with brain candy that exists on your phone. If I wasnt working, I would probably opt to be nearly fully offline beyond extremely helpful things like Google Maps. Opting out seems like a good way to live for most people.
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In YouTubes early days, the odds seemed good that the platform would be destroyednot by a competitor, but by its own popularity. How could any young video startup ever cover the cost of streaming so much content across the internet? Or avoid the fate of Napster, another media-sharing startup of the era that was sued out of business for rampant copyright infringement? Even being acquired by Google in 2006 posed a risk: YouTube could have been mismanaged into irrelevance, as often happens after tech giants acquire shiny new toys. But over its first 20 years, YouTube didnt just surviveit revolutionized media, redefining what TV could be. By letting anyone upload video for free, it empowered a new generation of creators to cater to every imaginable audience and attract fan bases in the millions. It taught marketers to appreciate the value of reaching these viewers, and it used technology to give rights holders control over their content. The platform conquered PCs and then smartphones and was eventually available on nearly every new TV set. Today, with 2 billion logged-in users a month, YouTube is watched more than any traditional TV outlet. According to Nielsen, the company has grown its total viewers by nearly 50% since December 2023, bounding past Paramount, NBCUniversal, and Disney to take the top spot among media companies. Its now the U.S.s most-watched video provider, not just among streamers but cable and broadcast TV channels, too. Its 2024 ad revenue was $36.15 billion, a figure that doesnt include subscription revenue from its YouTube Premium and YouTube TV businesses. YouTubes story is still unfolding, and new twistssuch as the arrival of generative AIhave yet to play out. But to understand where business, tech, and culture are heading, there may be no smarter place to look than YouTubes past. We talked to dozens of employees, creators, and other eyewitnesses to tell the story of where YouTube has been, and where its going. (Their comments have been edited for length and clarity.) In this articlethe first chapter of an oral history Fast Company will be publishing in five partssome of those interview subjects recall key moments in YouTubes earliest days, from tiny startup to category-defining phenomenon. Its story, like so many others, began at PayPal. The payments startups early employees, whod be known as the PayPal mafia, began to infiltrate the tech industry and start new companies, particularly after PayPal went public in 2002 and was acquired by eBay soon after. Steve Chen, cofounderwith Chad Hurley and Jawed Karimof YouTube: The three of us and most of the early YouTube hires, that original core team, all came from PayPal. We had had at least three or four years of experience working together. Chad, I think, I met on the first day that I landed in Silicon Valley.Roelof Botha, former PayPal CFO and partner at Sequoia Capital, YouTubes first investor: PayPal was a bit of a cauldron of an experience. We had a very small team in the office, next to the Palo Alto dump. I remember being there on weekends and seeing Steve standing outside smoking, because he was still a smoker back then. I worked with Jawed on a project in 2000. While Chen, Hurley, and Karim hatched plans for a video-sharing startup in early 2005, an entire field of such services was sprouting up, including Google Video, Revver, Veoh, and Vimeo. All leveraged Macromedias Flash software, which shipped with most web browsers and had simplified the formerly gnarly process of streaming video over the internet. In Chen, Hurley, and Karims initial conception, their service would focus on letting people upload videos of themselves to find dates. Casey Neistat, filmmaker whose 2003 video iPods Dirty Secret had been a rare pre-YouTube viral phenomenon: When I first started making movies in the very early 2000s with my older brother, there was no appropriate venue for the kind of videos that we made. Felicia Day, actress, singer, writer, and YouTuber: Its so strange to think that people didnt watch videos online. I remember seeing the lightsaber kid, and thats pretty much it. Mike Downey, senior product manager, Flash: In the early days of Flash, the player was bundled with Netscape Navigator. Microsoft then knew they needed to bundle Flash with Internet Explorer. Because IE couldnt succeed if it didnt have everything Netscape had.John Harding, Google software engineer (2005-2007); YouTube engineering manager, director, VP (2007-present): Before [Flash], you needed either desktop software or complicated browser plug-ins, and it didnt work for half of the people half of the time. Downey: The alternative was RealPlayer or Windows Media Player, or a couple of others. You were taken out of the web and into the RealPlayer experience or the Windows Media Player experience, and it wasn’t a seamless thing.Billy Biggs, Google/YouTube software engineer (2006-present): Flash video is what made this all possible. Suddenly the internet had video as a thing. Harding: We did some pretty cool things with Google Video that we hadn’t seen other people do. Like, we let you jump all the way to the end or any point within a video, which was something that Flash didn’t actually support.Dmitry Shapiro, founder and CEO, Veoh: I started pitching Veoh to investors in mid-January of 2005. And the first person that I pitched [to] was a guy named Roelof Botha at Sequoia. Im not suggesting that Roelof took my idea and gave it to Chad and Steve. But the history shows that we were there at a similar time.Chen: We started development in February of 2005. Even during that phase, we were not sure whether Macromedia Flash would be sufficient.Botha: I was at a gathering of former PayPal people in San Francisco, and somebody mentioned, Hey, you should check out what Jawed and Chad and Steve are working on. And so I went home and typed in the URL and discovered YouTube. They were still in Chads garage in Menlo Park at the time, the three of them. I reached out, and we started to chat about the business.Chen: When we originally released it, we thought that it was going to be a dating site. After a week passed by and zero videos were uploaded, we thought, Okay, before we give up, why dont we just open it all up and let the users decide what they want to upload? It wasnt that we saw a spike in traffic right away, but we started seeing sprinkles of content come in. Me at the Zoo April 2005 In the first-ever YouTube video, the platforms cofounder Jawed Karim informs us that elephants have really, really, really long trunks, and thats cool. Its a start Shapiro: Veoh believed that it was going to be extraordinarily expensive to host and stream video from our servers, and therefore we needed to build a peer-to-peer network to dissipate the costs. Chad and Steve didn’t try to solve the problem. They got to market fast and became a hit. As the service gained traction with creators, there was more stuff to watch. As more people watched, there was more incentive for creators to post. This virtuous circle propelled growth. Chris Maxcy, YouTube VP of business development (2005-2013): When I started, my hypothesis was, this is a young company thats going to have to work with the AOLs of the world, the Yahoos of the world, because its going to be all about getting traffic. That premise quickly changed. Evolution of Dance April 2006 In under eight minutes, Judson Laipply prances his way through decades of American pop music, from Chubby Checker to Eminem. Winningly energetic and goofy, this was the most-watched YouTube video of all time as late as October 2009. Chen: We started seeing a spike in activity through the social networking sites out there. At the time, MySpace was the biggest one, and they allowed you to take that same embed code that you see on YouTube today and embed it into your MySpace updates. Overnight, that video could get hundreds of thousands of other people putting it into their own profiles and sharing it with their entire network. Rhett McLaughlin, cocreator and cohost (with Link Neal) of Good Mythical Morning: People started asking us, Why don’t you have a YouTube channel? And we said, We don’t have one because YouTube channels are for people who don’t have websites. We didn’t understand anything about what was about to unfold. Ian Hecox, cocreator (with his high school friend Anthony Padilla) of the comedy duo Smosh, which got its start lip-synching TV theme songs: We started making these videos out of sheer boredom. And then, when we found out about YouTube, one of our main drivers [to post videos there] was just free hosting. Because every time somebody watched a video through our website or on MySpace, we would have to pay for that bandwidth. Justine iJustine Ezarik, YouTuber, whose first YouTube video was test footage showing her microwaving and eating oatmeal: I was posting videos everywhereMySpace, Yahoo, Revver. There were just a bunch of places that were hosting videos. I started posting to YouTube mostly just to store the videos. Botha: Part of what YouTube did was they had the comment section. They were able to cultivate a community. Anthony Padilla, cofounder, Smosh: You could see the audience feedback immediately. You could refresh the page and see the views go up immediately. Seeing those numbers increase when we made something better helped us refine what we made so we could continue doing what we liked. Ezarik: I was like, Oh, this is so cool. Theres a whole community of people here. So I started posting for [the YouTube] audience, and then finding other people who were making videos. And thats where it got interesting. There werent many people doing it. Hecox: What initially attracted people to our content was the accessibility of it and the relatability of it. Any kid that ever had a camera could relate to what we were doing. They’re like, I also have access to a camera and I make silly skits with my friends. Mia Quagliarello, YouTube senior product marketing manager, content and community (2006-2011): Skateboarding dogs was the [term people used to] be derogatory about the kind of content that was there. There was a lot more content than skateboarding dogs. Lonelygirl15 June 2006 Bree, a 16-year-old who broadcasts from her bedroom, becomes YouTubes most popular creator. It turns out shes fictional, and her videos develop into a serialized science-fiction story. Chen: A video of [soccer star] Ronaldinho juggling a ball off a goalpost was one of the first videos in 2005 that really took off. Botha: We reached out to the person who uploaded it. It turned out to be one of the marketing people at Nike. Chad, Steve, and I flew up to Oregon to meet them. To me, it was a very interesting window into how brands would use this platform, and it wouldnt just be Americas Funniest Home Videos done on the internet. In August 2006, YouTube hit the Comscore Media Metrix top-50 ranking of the largest web properties. Still wincing from their encounters with Napster and other file-sharing services widely used for piracy, media companies eyed the new phenom warily, though some chose to engage with it. Unauthorized sharing of copyrighted content abounded. Jack Flanagan, EVP, Comscore (2002-2010): When those reports came out, people would jump into them immediately just to see how they ranked. The fact that it was the first time that YouTube broke into the top 50 was just huge accomplishment. Michael Fricklas, general counsel, Viacom (2000-2017): It had started to become pretty well known in the movie and television industry that there was this new pirate site. Maxcy: I remember talking with a very, very, very large studio down in L.A. This one particular individual said, We love YouTube. We think this is really going to help our business, particularly from a promotional standpoint. But when I leave this room, I’m going to have to say, loudly in the hall, that we’re going to reserve the right to sue you. Chen: Even Lady Gaga playing in the background is technically copyrighted content if its more than a few seconds. We were very aware of the Napster issues. Zahavah Levine, YouTube general counsel, chief counsel (2006-2011): Many users were uploading videos of themselves, either alone or with friends, singing songs or dancing to music playing in the background, or maybe of their kid dancing in their living room to music playing in their house. Hecox: One of our first videos, the Pokémon theme song music video, quickly became the most viewed video on YouTube. It stayed there for about a year and a half before it was removed for copyright infringement. That was a catalyst for us to push ourselves into original content that didn’t have copyrighted content, because we didn’t want to see our videos removed. Maxcy: Warner Music Group was our first label partner. That really helped us build credibility with some of the other larger labels. Levine: I still remember sending an email to our main contact at WMG proposing that instead of removing all the user-uploaded videos identified as containing WMG recordings, we instead monetize them with ads and share the money with WMG. To our great surprise and joy, Warner agreed. Lyor Cohen, Warner Music Group CEO of recorded music (2004-2012); YouTube and Google global head of music (2016-present): [WMG chairman and CEO Edgar Bronfman Jr.] had a lot to do with it. He was quite receptive to experimenting and pushing the boundaries. We saw an opportunity to push the accelerator rather than pump the brakes. Levine: Until that moment, music companies had always negotiated and approved the right to use a piece of music in a video on a song-by-song and a use-by-use basis. This was the first time ever that a music company granted blanket sync rights for an entire catalog of compositions to be used in unknown video content. A historic firstand a huge milestone. Additional reporting by María José Gutiérrez Chávez, Yasmin Gagne, and Steven Melendez
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E-Commerce
The entrepreneur Sara Mauskopf has a big voice on X but not in real life. Tens of thousands of people follow her account, where she goes by @sm. Outside social media, she is an introvert who prefers to stay in with her husband and three kids, only attending industry happy hours when she feels its critical for her business. Allow me to bust the myth, which I have heard repeated by peers and colleagues throughout my working life. The myth? To build a following as a storyteller, you have to be self-centered, self-promoting, or extroverted. In reality, its often the opposite. It might seem counterintuitive, but Mauskopf gravitates to social media because she doesnt crave the spotlight in her personal life. Self-effacing, witty introverts like Mauskopf are far more commonly found on the internet than you might think. In truth, you can be thoughtful and low-key yet still find success as a storyteller. Many of the people I interviewed who had the largest followings online were also the humblest. I sum up people like Mauskopf with the term quiet influencer. These are people who arent trying to draw attention to themselves but can find a following online because of their ability to listen and absorb information. When they do share, its to educate, inform, or entertain others, not to build up their egos. Often, they follow the golden ratio of social posts: the 9:1 rule. I came up with this formula early in my career, when I was starting out on social media. I havent changed it in over a decade, simply because it works, and I share it with companies I advise daily. So here goes: For every one braggy post related to an accomplishment, milestone, or achievement, share nine that are useful contributions. Think of the contributionsthings that are interesting, valuable, entertainingas earning the brags. Sometimes it is helpful to share something positive that happened on a personal or professional levelI totally understand that but this lets you do it without it coming off as self-absorbed or generic. Companies are guilty of this toohave you ever scrolled a CEOs LinkedIn profile and viewed nothing but updates about funding milestones, customer wins, and key hires? These are important to share every once in a while, for the purposes of company morale and external validation, but a big opportunity for contribution content has been missed. If theres anything to remember, its this: To be a successful storyteller, both online and offline, its important to think about what the audience wants and needs. Many of us, as we move through our lives, welcome helpful information that we wouldnt get elsewhereinformation that helps us do our jobs better, learn something new, or feel less alone with the challenges we face. If you can meet that need, youll be a much more engaging storyteller. Contributions in this vein might include: A hilarious personal anecdote that will make someone laugh when they need a little bit of levity in their day An insight about what is really going on in the news beyond the headlinessomething people in the industry would find helpful A piece of analysis that explains a complicated topic in an accessible way or provides a step-by-step for how to accomplish something that others find challenging If you are sharing something self-promotional, it can help to provide context around why the milestone means so much to you. One example: When the Joe Biden administration highlighted Kaitlin Christine, a CEO in my network, for her companys work in breast cancer detection, I helped her share the news with her community. She initially wrote that it was an important milestone, and she described how honored she was without going into much detail. Because I knew a little about her story, I prompted her to share a little bit about how she felt in the moment when the White House reached out and what it meant to her. Christines company, Gabbi, builds breast cancer risk detection software. She started it after losing her mother to the disease at a young age. After getting screened herself, Christine ended up getting a double mastectomy given her profile (genetics, family history, and so forth). So, to hear from the Biden administration felt like her lifes goals were being realized and her mother would have been truly proud. Once reframed to talk about how personal the experience was for her, her post hit a nerve with her following. The beauty of reframing content in this way is that even something promotional, like an important new milestone or new hire, can become a useful contribution and/or a moment to truly connect with an extended network. That turns the viewer from a passive liker into a true believer or ally. Likes become comments and reshares and, more importantly, offers of support. I genuinely appreciate when CEOs talk about not just the great things theyve accomplished in their roles and daily activities but how they got there. Some people refer to this trend as building in the open. Imagine a scenario where a CEO doesnt just post something bland on LinkedIn about the stellar new chief technology officer they just hired. How about sharing instead how they found this amazing candidate? What tools did they use? Did they retain a recruiterand if so, who? What kinds of interview questions did they produce to assess each candidates technical prowess? What geographies did they focus on? Perhaps this information could even be viewable to anyone via an open document like Google Docs or Notion. Likewise, rather than announcing a venture capital funding round, a leadership team could talk instead about how they were able to raise money in a difficult funding environment. Authenticity works because it shows vulnerability or provides others with a potential lesson they can use in their own professional pursuits. If you follow the 9:1 golden ratio, no one will begrudge you the odd self-promotional post that highlights your fantastic accomplishments. Those are important to share occasionally, because the industry may want to know what youre up to. The important thing is to use your voice to give back to your community most of the time. If you are a resource to others, they will follow you, and you will build influence. Excerpted from The Storytellers Advantage: How Powerful Narratives Make Businesses Thrive. Copyright 2025 by Christina Farr. Available from Basic Venture, an imprint of Hachette Book Group, Inc.
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