Talking tech’s exodus, Twitter’s labels, and Medium’s next moves with founder Ev Williams

Earlier today, we had the chance to talk with Twitter and Medium cofounder Ev Williams, along with operator-turned investor James Joaquin, who helps oversee the day-to-day of the mission-focused venture firm they separately cofounded six years ago, Obvious Ventures.

We collectively discussed lot of venture-y things, some of which we’ll publish next week, so stayed tuned. In the meantime, we spent some time talking specifically with Williams about both Twitter and Medium and some of the day’s biggest headlines. Following are some excerpts from that chat, lightly edited for length and clarity.

TC: A lot of tech CEOs have been saying goodbye to San Francisco in 2020. Do you think the trend is attracting too much attention or perhaps not enough?

EW: I moved away to New York from the Bay Area a little over a year ago with my family. I’d lived in San Francisco for 20 years, and I had never lived in New York and thought, ‘Why not go? Now seems like a good time.’ Turns out I was wrong. [Laughs.] It was a very bad time to move to New York. So I was there for for six months and quickly came back to California, which is a great place to be in a world where you’re not going into bars and restaurants and seeing people.

TC: You moved when COVID took hold?

EW: Yes. In March, Manhattan suddenly seemed not ideal. So now I’m on the peninsula.

I’m from San Francisco. It was really, for me, just honestly looking for a change. But an enabling factor that could be common in many of these cases is the fact that I no longer have to be in the office in San Francisco every day, [whereas] for most of 20 years [beforehand], all my work life was in an office in San Francisco, generally with a company I had started, so I thought it was important to be there.

This was pre COVID and remote work. But remote work was becoming more common. And I noticed in 2018 or so, with this massive number of companies that were in San Francisco —  startups and large public companies and pre IPO companies — that competition for talent had gotten more extreme than it had ever been. So it got me —  along with a lot of founders and CEOs — thinking about maybe the advantage of hiring locally and having everybody in the same office [was a pro] that was starting to get outweighed by the cons. . . And, of course, the tools and technology that make remote work possible were getting better all the time.

TC: Given that you cofounded Twitter, I have to ask about this presidential transition that is maybe, finally happening. In January, Donald Trump will lose the privileges he enjoyed as president. Given the amount of disinformation he has published routinely, do you think Twitter should have cracked down on him sooner? How would you rate its handling of a president who really tested its boundaries in every way?

EW: I think what Twitter has done especially recently is a pretty good solution. I mean, I don’t agree with the the notion that he should have been removed altogether a long time ago. Having the visibility, literally seeing, what what the President is thinking at any given moment, as ludicrous as it is, is helpful.

What he would be doing if he didn’t have Twitter is unclear, but he’d be doing something to get his message out there. And what the company has done most recently with the warnings on his tweets or blocking them is great. It’s providing more information. It’s kind of ‘buyer beware’ about this information. And it’s a bolder step than any platform had taken previously. It’s a good version of an in-between where previously [people would] talk about just kicking people off, [and] allowing freedom of speech.

TC: You started Blogger, then Twitter, then Medium. As someone who has spent much of your career  focused on content and distribution, do you have any other thoughts about what more Twitter or other platforms could be doing [to tackle disinformation]? Because there is going to be somebody who comes along again with the same autocratic tendencies.

EW: I think all of society gets more information savvy — that’s one hope over the long term. It wasn’t that long ago that if something was in “media,” it was accepted as true. And now I think everyone’s skeptical. We’ve learned that that’s not necessarily the case and certainly not online.

Unfortunately, we’re now at the point where a lot of people have lost faith in everything published or shared anywhere. But I think that’s a step along the evolution of just getting more media savvy and knowing that sources really matter, and as we build both better tools, things will get better.

TC: Speaking of content platforms, Medium charges $50 per year for users to access an unlimited amount of articles from individual writers and poets. Have you said how many subscribers the platform now has?

EW: We haven’t given a precise number, but I can tell you it’s in the high hundreds of thousands. It’s been a been a couple years now, and I’m a very firm believer in the model — not only that people will pay for quality information, but that it’s just a much healthier model for publishers, be they individuals or companies, because it creates that feedback loop of ‘quality gets rewarded.’

If people aren’t getting value, they unsubscribe, and that isn’t the case with an advertising model. If people click, you keep making money, and you can kind of keep tricking people or keep appealing to lowest-common-denominator impulses. There were a couple of decades where the mantra was ‘No one will pay for content on the internet,’ which obviously seems silly now. But that was that was the established belief for such a long time.

TC: Do you ever think you should have charged from the outset? I sometimes wonder if it’s harder to throw on the switch afterward.

EW: Yes, and no. When we first switched to this model in 2017, we created a subscription, but the vast majority of content was — and actually still is — outside of the paywall. And our model is different than most because it’s a platform, and we don’t own the content, and we have an agreement with our creators that they can publish behind the paywall if they want, and we will pay them if they do that. But they can also publish outside the paywall if they’re not interested in making money and want maximum reach. And those models are actually very complimentary because the scale of the platform brings a lot of people in through the top of the funnel.

Scale is really important for most businesses, but for a paywall, it’s especially important because people have to be visiting with enough frequency to actually hit the paywall and be motivated to pay.

TC: Out of curiosity, what do you make of Substack, a startup that invites writers to create their own newsletters using a subscription model and then takes a cut of their revenue in exchange for a host of back end services.

EW: There’s a bit of a creator renaissance going on right now that is part of a bigger wave of a people being willing to pay for quality information and independent writers and thinkers actually breaking out on their own and building brands and followings. And I think we’re going to see more of that.

TC: Medium has raised $132 million over the years. Will you raise more? Where do you want to take the platform in the next 12 to 24 months?

EW: We’re not yet profitable, so I anticipate that we will raise more money.

There’s a very big business to be built here. While more and more people are willing to pay for content, I don’t think that means that most people will subscribe to dozens of sources, whether they’re websites with paywalls or newsletters. If you look at how basically every media category has evolved, a lot of them have gone through this shift from free to paid, at least at the higher end of the market. That includes music, television, and even games. And at the high end, there tend to be players who own a large part of the market, and I think that comes down to offering the best consumer value proposition — one that gives people lots of optionality, lots of personalization, and lots of value for one price.

I think that the same thing is going to play out in this area, and for the subscription that’s able to reach critical mass, that’s a multi-billion dollar business. And that’s what we’re aiming to build.