Aleksander Chan is bootstrapping the media revolution
8 min read

Aleksander Chan is bootstrapping the media revolution

The former Splinter editor-in-chief talks Discourse Blog, an experimental project built on Substack and inspired by the spirit of Gawker.
Aleksander Chan is bootstrapping the media revolution

A song to read by: “Gente Aberta” by Erasmo Carlos

What I’m reading: “Team of Rivals,” by Doris Kearns Goodwin

Now readers, as you are well aware I hardly like to mention myself in this newsletter. In fact, if I could, I would have constructed these emails to be sent anonymously, that’s how badly I wish this newsletter never had to involve me. The day that artificial intelligence gets sentient enough to passably mimic my writing, I’m out of here. Lil Miquela will be penning all missives henceforth.

But, until we reach that point, you are stuck with me as your humble Virgil and traveling companion as we swamp through the infernal darkness that is the modern media industry.

So, given that we are stuck in this sojourn together, I feel that I should reveal that I am graduating from grad school this morning. In fact, as you are reading this very sentence, I will likely be sitting at the computer in my bedroom, wearing full cap and gown, sipping coffee and watching a pre-recorded commencement speech. What a time to be alive!

However I should say that a large part of the reason I came to graduate school, where I’ve studied media innovation and entrepreneurship in journalism, was so I could learn about the most innovative media companies and practices in the business. And, as fate would have it, I got to interview one of the people behind one of those businesses for this week’s Vibe Check: Aleksander Chan.

First and foremost, Aleksander is a San Antonian. Being from the Countdown City myself, I would feel remiss if I failed to note that.

More importantly, he is also part of the team of writers and editors behind Discourse Blog, an exciting new media site being constructed using Substack. That Aleksander and his team are doing the bold thing of launching a media startup in 2020 is laudable enough, but on top of that they’re doing it in an intriguing new way.

It might not sound mind-blowing, but launching a startup media company on the back of a startup newsletter company is certainly something to note. Indeed, besides their team, only one group of writers has done this successfully before, and I don’t like them very much, so it hardly counts.

The site’s writing, in classic ex-Gawker fashion, is sharp, smart, opinionated and funny, and it should be reason enough for them to succeed. That’s not really how things work anymore, unfortunately, but it still counts for something. (This is a good time, by the way, if you’re interested, for you to read the tragic story of the life and death of Gawker.)

So we’ll see! Discourse Blog is a promising new venture, staffed by smart people who have a higher-than-average shot of succeeding, animated by a spirit of irreverent genius almost a decade in the making. If they don’t make it, who should?

The interview

Who: Aleksander Chan, co-founder of Discourse Blog


Discourse Blog Twitter:

To catch everyone up quickly, you were formerly the editor-in-chief of Splinter, a Gawker offshoot covering politics. G/O Media sunset Splinter in October, and since then you’ve been working with former colleagues on Discourse Blog, a kind of hybrid Substack publication. Is that all correct?


So how was Discourse Blog born?

It kind of grew out of this unrelenting anxiety that me and the rest of the former Splinter staff were feeling, seeing so much happening in the news. Around the time the Democratic Primary was heating up, we were texting each other every day about what was happening and talking about how we would cover it.

Then in March, we were just shooting the shit again, talking about stuff in the news, and we started thinking, “What if what if we just put this up somewhere? Like, who cares? We'll do it for us.” Then we started getting really great feedback, with people saying, “Wow, we're so glad you're doing this. We've missed you guys.”

So that went on for a month or so, and slowly my editor brain began reactivating out of cold storage. I thought, “Okay, I'm seeing something here. Something's coming into focus.”

We had all worked together before, so that really cut the learning curve down; everyone kind of just fell into the roles that they’d had before.

What would you say Discourse Blog is trying to do? What are you covering and how are you covering it?

I think Discourse Blog is very similar in spirit to what Splinter tried to do: We're covering capital “P” politics, lowercase “p” politics and quote unquote “politics.” I think publications should be the purest expression of their writers’ beliefs, so yes, it’s about politics, but it’s also about what we're interested in. It’s politics, but it's also about the way we live now.

So much of the beauty of the project is that we’re not owned by anyone. We're not being told how to do anything. We decide every day what we want it to be.

It seems like, in many ways, rather than offering a highly defined product, you’re hoping to capitalize on the following Splinter and Gawker created. Would you agree?

We're definitely marketing ourselves, at least at the beginning, as “Brought to you by the former staff of Splinter.” It’s the easiest way to give new readers a sense of what we are.

We’re deciding every day what it's going to be, and I think we won't know what it’ll look like a year from now. It could be totally different, but I think that's part of what inspires and attracts us to this specific format.

We're publishing once or twice a day, at most, and only five days a week. We only write about the things we are really passionate about, as opposed to the stuff that you would have to do to feed the machine.

Publishers all have to contend with the demands of scale in their own way, and we’ve definitely been in places where we were publishing 30 - 40 posts a day. Now we don’t have to do that anymore.

The challenge and the opportunity there is that we’ve had to de-program ourselves. We have to recalibrate and pave new cognitive pathways for ourselves. Instead of thinking, “We have to get eight things up this hour,” we’re learning how to back away from that mentality to make something smaller but better.

Do you have an intended readership? Who is it, in your head, that will read Discourse Blog?

First, anyone interested in the greater Gizmodo Media Group universe. More specifically, we want to write about people experiencing politics at the frontlines. It’s asking questions like, “What’s happening with the pandemic? What's happening with these uprisings across the country? What’s happening in the newsrooms covering these stories?” These are the people who are on the frontlines of politics, not the people glad-handing on MSNBC.

We also believe that if you're upfront about what you believe, whether that's political, ideological or whatever, that that engenders more trust with your readers than pretending that you have no thoughts or ideas about what’s happening in the world.

That sort of mission is realizable in a way with Substack that hasn’t really existed before, right? Your only stakeholders are your readers, and that upends traditional business models and even content strategies, in both good ways and bad.

It's such a different way of engaging with your audience, compared to what any of us are used to or have seen before. The people who choose to read you have very deliberately chosen to be there. They’re reading it because they want to read it. We see this reflected in the emails that we get, in the comments on the website and in tweets, in the language people use when they share our articles. It’s all very supportive.

We’re also learning about our audience every day. We posted yesterday asking, “Hey, we're launching a paid program soon. What do you guys like? What do you dislike? What do you want from us?”

It’s exciting to build a community of people who want to be here and are interested in learning more and reading more and have ideas for how we can grow. It's just such a stark contrast to a general commentary, where you blast posts into the universe and some people really hate you and some people really love you.

You’re touching on one of the primary disadvantages of Substack: Its lack of analytics tools. You can see basic metrics, like views and subscribers, but beyond that you’re pretty blind. In some ways that contributes to the sense of editorial freedom that Discourse Blog is championing, but it also presents a lot of challenges.

It's definitely hard to get a sense of where you stand in terms of your audience. I didn't realize that we were taking that for granted so much, having the visibility and access that working at a big publisher can give you.

We were used to knowing where readers came from, how long they were there, how long they stayed, where else they clicked. I do miss having some of the information, because I know it's helpful for making long-term strategies.

And it's frustrating in some situations, like if we get a huge rush of subscribers. Where did they come from? Who tweeted that led to these sign-ups?

I've spoken with some of the people from Substack a few times, and they know that some users would love a more robust analytics dashboard. But I know that requires a certain level of engineering investment, so we’re coming to terms with the fact that we’re not going to know how people got to us or how long they read us for the foreseeable future.

Another disadvantage of newsletters is that it’s hard for new readers to find you. Newsletters are very siloed. There is no serendipitous discovery; you never “stumble upon” a newsletter, which can handicap growth. Is that something your team is concerned about?

Not really, but I mean we’re still in the early stages of this project; we’re still trying to figure out what kind of potential this whole thing has.

I think the second one person pays us any money to do this, it becomes successful to me.

The second anyone says, “I will give you money to do this,” that's wild. I've never worked with paid products before.

We intentionally wanted this to be small and thoughtful and just us. We want to be the internet version of the sustainable mom-and-pop shop, owned by a family, not so much something that we hope to grow big enough to be acquired by Home Depot or something.

You are planning to launch a paywall product in July. What’s the plan for that?

Price-point-wise, it's going to be comparable to what most other paid Substacks charge, maybe even a little less. In terms of what goes behind the paywall, it’ll be the more deeply reported stuff, the features, the in-depth journalism. Just anything that takes more time to produce, essentially.

And that’s honestly where a lot of user feedback will come into play. What are people willing to pay for? We’ll just ask them.

Is the dream to be able to do this full-time?

God, wouldn't that be incredible? I think our expectations are a lot more modest, frankly, at this point. Right now, if Discourse Blog helped everyone get a few hundred bucks a month to put toward rent, that's our near-term goal.

Substack is still kind of the Wild West, but a few publications operating on the platform have turned into full-time operations, so it’s not a completely unreasonable prospect.

Exactly. In practice, it is actually possible to make this a full time job. We’re not going to get ahead of ourselves, but that would be great.