Earlier today, we had the opportunity to speak with Ev Williams, a co-founder of both Twitter and Medium, and James Joaquin, an operator who now focuses on investment and oversees the daily operations of Obvious Ventures, the mission-driven venture firm they both established six years ago.

Our discussion covered a wide range of venture capital topics, some of which will be published next week, so please check back for updates. For the time being, we focused our conversation with Williams on both Twitter and Medium, as well as some of the most prominent news stories of the moment. The following are excerpts from that conversation, edited slightly for conciseness and clarity.

TC: Many tech industry leaders relocated from San Francisco in 2020. Do you believe this trend has received an appropriate level of attention, or do you think it deserves more or less focus?

EW: My family and I moved to New York City from the Bay Area just over a year ago. I had resided in San Francisco for two decades and had never experienced living in New York, so I thought, ‘Why not give it a try? Now seems like a suitable time.’ It turned out to be a miscalculation. [Laughs.] It was a particularly unfavorable time to relocate to New York. I spent six months there before returning to California, which is an ideal location when you aren’t frequently visiting bars, restaurants, and socializing with others.

TC: Did your move coincide with the onset of the COVID-19 pandemic?

EW: Yes, it did. In March, Manhattan suddenly appeared to be an undesirable location. I am now located on the peninsula.

I am originally from San Francisco. For me, it was simply a desire for a change of scenery. However, a contributing factor that may be common in similar situations is the fact that I was no longer required to be physically present in a San Francisco office every day. For the majority of the preceding 20 years, my professional life revolved around working in an office in San Francisco, typically for a company I had founded, and I considered it essential to be there.

This situation predated COVID-19 and the widespread adoption of remote work. However, remote work was becoming increasingly prevalent. Around 2018, I observed that the competition for talent among the numerous companies in San Francisco—both startups and established public and pre-IPO companies—had reached an unprecedented level. This prompted me, along with many other founders and CEOs, to consider whether the perceived advantage of hiring locally and having all employees in the same office was beginning to be outweighed by the drawbacks. Furthermore, the tools and technologies that facilitate remote work were continually improving.

TC: Considering your role as a co-founder of Twitter, I must inquire about the ongoing presidential transition, which may be nearing completion. In January, Donald Trump will no longer enjoy the privileges associated with the presidency. Given the consistent publication of misinformation by him, do you believe Twitter should have taken action against him sooner? How would you assess its handling of a president who consistently challenged its boundaries?

EW: I believe Twitter’s recent actions represent a fairly effective solution. I do not necessarily agree with the idea that he should have been removed from the platform altogether much earlier. The ability to directly observe the president’s thoughts in real-time, however unconventional, is valuable.

It is uncertain what he would have done without Twitter, but he would undoubtedly have found another means of disseminating his message. The company’s recent implementation of warnings on his tweets or outright blocking them is a positive step. It provides additional context and serves as a form of ‘buyer beware’ regarding the information presented. This is a more assertive approach than any platform had previously taken, and it strikes a balance between simply removing individuals and upholding freedom of speech.

TC: Having launched Blogger, Twitter, and Medium, and with a career largely centered on content and its dissemination, do you have any further insights into what Twitter or other platforms could do to address disinformation? Because there will inevitably be others who exhibit similar autocratic tendencies.

EW: I believe that society as a whole is becoming more discerning when it comes to information—that is one long-term hope. It wasn’t long ago that anything appearing in “the media” was accepted as fact. Now, I think most people are skeptical. We’ve learned that this isn’t always the case, especially online.

Unfortunately, we are now at a point where many individuals have lost trust in everything published or shared anywhere. However, I believe this is a step in the evolution of becoming more media-literate and recognizing the importance of sources. As we develop better tools, things will improve.

TC: Turning to content platforms, Medium charges $50 annually for users to access an unlimited number of articles from individual writers and poets. Have you disclosed the platform’s current subscriber count?

EW: We haven’t released a specific number, but I can share that it is in the high hundreds of thousands. It has been a couple of years since we implemented this model, and I strongly believe in its viability—not only that people will pay for high-quality information, but that it is a much healthier model for publishers, whether they are individuals or companies, because it creates a positive feedback loop where quality is rewarded.

If people do not find value, they cancel their subscriptions, which is not the case with an advertising model. If people click on ads, you continue to generate revenue, and you can potentially mislead or appeal to base instincts. There were a couple of decades where the prevailing belief was that ‘no one will pay for content on the internet,’ which now seems demonstrably false. But that was the accepted wisdom for a long time.

TC: Do you ever contemplate whether you should have implemented a paid model from the beginning? I sometimes wonder if it’s more challenging to introduce it later on.

EW: Yes and no. When we initially adopted this model in 2017, we introduced a subscription option, but the vast majority of content—and still is—remains accessible without a subscription. Our model differs from most because we are a platform, and we do not own the content. We have an agreement with our creators that they can publish content behind the paywall if they choose, and we will compensate them accordingly. However, they can also publish content outside the paywall if they are not interested in earning revenue and prioritize maximum reach. These models are actually complementary because the platform’s scale attracts a large audience, which then funnels into the subscription offering.

Scale is crucial for most businesses, but it is particularly important for a paywall because people need to visit the platform frequently enough to encounter the paywall and be motivated to subscribe.

TC: Out of curiosity, what are your thoughts on Substack, a startup that encourages writers to create their own newsletters using a subscription model and then takes a percentage of their revenue in exchange for providing various back-end services?

EW: There is a resurgence of creators happening right now, which is part of a larger trend of people being willing to pay for quality information and independent writers and thinkers establishing themselves and building brands and followings. I believe we will see more of this.

TC: Medium has secured $132 million in funding over the years. Do you anticipate raising additional capital? What are your goals for the platform over the next 12 to 24 months?

EW: We are not yet profitable, so I expect that we will raise more money.

There is a substantial business opportunity here. While an increasing number of people are willing to pay for content, I don’t believe that means they will subscribe to dozens of sources, whether they are websites with paywalls or newsletters. If you examine how most media categories have evolved, many have transitioned from free to paid, at least at the higher end of the market. This includes music, television, and even games. And at the high end, there tend to be dominant players who control a significant portion of the market, which comes down to offering the best consumer value proposition—one that provides people with a wide range of options, personalization, and value for a single price.

I believe the same will occur in this space, and the subscription service that achieves critical mass has the potential to become a multi-billion-dollar business. That is our objective.