Medium CEO Tony Stubblebine: The Future of Digital Content

Hi Grace. Thank you for having me here.

Use Varavine by the way. Okay.

Yes. Love that. I love a supportive gang.

I'm an engineer. I've written significant code — not this year, but let's say in 2022, I actually wrote a fair amount of code that year. I'm a computer science major and I got my start as an engineer right after the first bubble burst, so my career kind of starts in 2000 and onward.

I was thinking about Odeo because it's so related to Medium. Odeo was this really hot podcasting startup in 2005 that was founded by Evan Williams, who at the time was famous for being the founder of Blogger, but then he went on to find Twitter and now Medium, and he's my boss as chairman of the board. So that through line goes for a really long time. Odeo is what Twitter spun out of. I was the head of engineering there and helped launch that first version and helped do the spinout. That was the first big thing I ever saw. Even now, you know, we're seemingly 20 years past that moment, and there's a documentary on CNN. People can't stop talking about Twitter.

There's so many lessons from that time. One of them is that you have to be really careful about the hype cycle. Sometimes the hype cycle's too early, sometimes it's too late. Podcasting obviously now is a big deal — it was not a big deal in 2005. You basically had two podcasts that mattered. One was a former MTV VJ, the Podfather, Adam — I'm blanking on his last name — and the other was two venture capitalists recording podcasts while driving in their car down 280. One was very polished and one was like, oh, the value of having direct access to experts. I always gravitate towards that even though the audio quality of that was terrible. One of the top things I'm always looking for is: is this a real hype wave or not? Because I got so burned by being part of podcasting in 2005 when it was too small to matter, but the press thought they were too late to cover blogging so they reacted by being too early to cover podcasting. Honestly, we should have waited another 10 years. It took us a little while to realize, so we should do something different, and that's where Twitter spun out of.

I was the boss of all the engineers, and one of the engineers — the one that had the idea for Twitter — is Jack Dorsey. I was his boss. I did his one-on-one meetings. I gave him a $6,000 raise. That's what we were doing back then. I got to track his career, and I was like — he did such a good job of turning himself into a visionary. I always think about him, his management style. There's this story about him running Square — he takes the whole team out on a field trip to go look at the Golden Gate Bridge and goes, 'See, this Golden Gate Bridge is both beautiful and functional. That's what we're doing for finance.' That's the vision. That's the motivation. That's capturing that story. I don't do any of that. I'm like a terrible visionary. I'm terrible at painting that picture or inspiration. My career is such the career of an operator where I've been in the weeds of so many things.

When I left Odeo, I ended up starting a company that I bootstrapped. To me, that's the missing virtue of so many entrepreneurs — you're starting companies without knowing how a company operates. I had a five-year period where I took something from scratch to profitability. I had to make payroll, do the bookkeeping, the legal, the design, the marketing, the sales. Did I do any of those things well? No. It was not a good company. But because I had to figure it all out, I never — when I later had more money to spend, when I had investors, or even now at Medium — there's never a time where I'm confused about how all of the pieces fit together. My first time as CEO, I had to run the whole thing. When you give a founder $10 million, there's a whole part of what business is that they don't have to deal with. That's probably the most specific thing about who I am. I'm an engineer who's now been in the weeds of a lot of different parts of how a company works. That's how I lead even at Medium.

Wait, did you just say I mentored Jack Dorsey? I would never claim that. I had one-on-one meetings with him as a boss. I was a 27-year-old first-time manager. I mean, I think we mentored each other, I guess. It was a mess. I might be his last boss, actually.

Jim did a better job because Jack was willing to keep working for other people. After me, he's just refused to have another boss. The experience was so toxic for him, I think, that he just had to be independent.

There's a company I worked for and that I met my partner Sarah at — my significant other — O'Reilly, which did a really good job of organizing people. That was their business for a long time: to be in the center of tech. They're a tech publisher and a conference organizer. Maybe they're not as culturally relevant as they were when we worked there, but basically they were a major connector for all of tech. As a result, Sarah and I both have had very good networks and overlapping networks. The two of us had very similar careers. At home, I say my first personal advisor is my partner. I don't necessarily recommend this — this is just how we did it. We're not super publicly visible about how we help each other, but I can name several people at Medium that are quietly referrals from Sarah. She sometimes will say, why don't I get a referral bonus for this? I don't know. So she's number one, and the O'Reilly network is number two. We just always had a lot of friends — work friends that we kept in touch with and can call on for favors.

I'm very lucky to say Evan Williams is in my personal advisors. I worked for him at Odeo. He was on the board of my last company. Now, you know, CEOs have bosses — he's my boss. So I work with him again. That's now almost 20 years of on-and-off work relationship. We know each other pretty well, trust each other. Not just trust — when you know someone well, you trust that you understand how they will react. You see each other well.

It's funny how often I end up relying on other people for help. I would say probably the most valuable thing beyond that that ever happened to me is I got invited to an every-two-month CEO group. I want to talk about it because it's a format that anyone could recreate. One person organized it, and his job was to bring people that he trusted because there needed to be good trust within the group. This is a very small-scale version of YPO or something — there's like 15 of us, eight of us would show up. The format was just go around the room and say, 'What's your biggest problem?' And then the rest of the room would comment on it. We would get to see the patterns of our peers and for the most part feel less bad about ourselves, because this is just a job where you're always sucking. It's nice to see that that's how normal that is. Then it's nice to get so many different viewpoints. What became funny about that group is that 80% of the time the biggest problem was a business problem. But then 20% would be like personal — hey, I'm ready to propose to my girlfriend. That would come up twice a year. That says how much trust was in the room.

The organizer did. That was one of his superpowers. But also, I think it gave him power. It was elevating for him — 'Hey, I run a CEO group. Do you want to come?' is a nice gift to be able to give someone. That's probably played out in his career for a long time. This is a relationship business. Maybe it's not that obvious in your early 20s and you don't have to be perfect at it, but a lot of opportunities come from who you know, because so much of the information you need to know is not public. So much of working together is about trust, and you want to work with people you trust. He did all that work and I was really lucky to be part of it. Now a lot of my real deep friendships actually come from them.

That group was all pretty much struggling seed-stage companies. A common question would be, if I could just raise $50,000, I could make it. It was so on the margin. Then if someone was doing too well, we basically kicked them out. It was too uncomfortable. Like, 'Oh, I just raised a big series C and I'm taking money off the table.' Well, you got to get out of here. None of us are there. We don't want to hear how good your life is. So it was all kind of traditional startups at a similar stage.

If I could find other CEOs — maybe that are listening right now — that are running companies in the sort of $40 to $100 million a year range. Medium is a $50 million a year business with 75 people. Hey, I'm looking for the same thing. It can be done over Zoom. It was better in person, but it could be done over Zoom and it's just super valuable.

Coding.

The word I keep saying all the time actually is alignment, and I feel like sad saying it. It seems so corporate, but it's just an unbelievable amount of work to get everyone going in the same direction. One of the things that makes it a lot of work is a lot of times I don't know what direction we're going in, and I can't get there without help. So it ends up being more fun than it sounds to me. It sounds so corporate, but it's pretty collaborative — what are we really trying to do here? How are we trying to sequence it? We have this aspiration to be great at whatever, but we're terrible at it today. So we can't go from zero to 100. What is the first step? If I were faster at it, we would be doing better. I think of that as kind of the limiter. We did well — I think we'll talk about it — executed a pretty amazing turnaround that is rarely done. But I'll never not wonder if I could have done it six months faster, you know? That just eats away at me. So that's my answer.

We did the turnaround. The thing that made it hard, and the thing that people told me would be hard, is they said there's a lot of people that can lead cost cutting and there's a lot of people that can lead growth. It's very hard to do both at once. And it is, because cost cutting is demoralizing and it's paralyzing. People wonder, can I not do this because there's no budget for it? And it's like, you're saying we're cutting costs, but you're also at the same time saying spend money to make money. That part ended up being the challenge. I think that's the thing that's rarely done, and that's the thing I think the team is really proud to have accomplished — that we were also able to innovate. We changed the whole nature of Medium. Medium when I took over had been really swarmed by content mills, clickbait, low-quality content that were off-mission for us. So we had to change how we did recommendations and curation. All of that is kind of new and original to Medium to get where we wanted to go. But then we also had to take the cost way down, and then we also had to figure out where growth can come from. That took three years.