Scaling the Paywall

The dilemma of information access in dark times

AI generated image

Yesterday, a post of mine on Substack’s Notes app regarding paywalled content sparked quite a bit of positive discussion. For subscribers who may have missed it, you can read the original post here. I’m sharing a few excerpts from it here, along with some additional commentary and links to other relevent essays. As usual, the comments open to all. Also, I’ve extended the 20% discount for paid subscriptions through the month of May. ~MSW

A few years before the housing crisis, I was hired by a Black-owned investment bank to build and manage an equity trading desk. The company was a startup and as it happened, their minority partner was Cantor Fitzgerald, which until recently was headed by Howard Ludnick, the current Commerce Secretary in the Trump administration.

I envisioned a bespoke trading desk that made use of the latest algorithmic tools. My plan was to develop a desk capable of handling the most complex quantitative transactions with minimal risk. If I could accomplish that, I knew our firm would be able to compete with just about any competitor.

From the start, I had two hurdles. What I had in mind was a very expensive proposition. The customized high-frequency trading system I needed cost $10,000 a month for each trader I planned to hire.

But there was another problem to deal with: at the time, no other minority-owned investment firms were trading at this level of complexity. So finding clients willing to trust my untested desk with their business was a tall order.

Aside from the fancy hardware, I knew that turning my vision into a viable business required an additional component—a champion. I had to find a client, not the kind who tossed the occasional trade, but a “true believer” willing to support the kind of trading desk I was attempting to build.

It took weeks of meetings with some of Wall Street’s biggest investors, but eventually I found what I was looking for: a global asset manager that bought into what I wanted to achieve.

Do You Come Here Often?

They agreed to commit hundreds of thousands of dollars in business to help me get my trading desk off the ground. Before long, others came. Huge quant desks and mutual funds gave my desk a shot at their most difficult trades.

All it took was a champion.

My counterparts on the right side of the political spectrum are well-funded by a right-wing political apparatus. Many have found a home on this platform. Substack has literally helped some of them build out their media teams. Meanwhile, I operate on a non-existent budget, literally banging out thousand-word essays on an old iPhone, juggling news subscriptions.

~An excerpt from my 4/24/25 Notes post

When I started this newsletter five years ago, I approached it in much the same way as building a trading desk. But instead of one huge champion, I’d need lots of individual believers who were willing to contribute financially to making my fledgling project sustainable.

So what’s the best way to accomplish it? That’s what I mused about in yesterday’s post on Notes (emphasis added):

[T]he reality is this: to produce a quality product, especially given the areas that I explore, The Journeyman needs more paid subscribers. So I have a decision to make. Do I take the approach that most publishers have and go back to paywalling everything?

I happen to believe honest and accurate information should be openly available for free as a counterweight to the daily stream of misinformation and conspiracy theories we encounter, especially from our government.

That’s why, a few years ago, I abandoned paywalls. I know not everyone can afford financial support, which is part of the reason I’ve taken this approach. But here’s the thing: this only works if enough people who can afford it are willing to lend their support to this project by becoming paid subscribers.

As of this writing, this newsletter is a few hundred away from 10,000 subscribers, with thousands more who follow on Substack’s app, but about 250–fewer than 3%—are paid subscribers.

Don’t get me wrong; I have immense gratitude for every person who has joined me on this journey. But here’s the thing: if only five 5% of the subscribers to this newsletter chipped in financially, I could afford subscriptions for research, and maybe even buy a refurbished laptop.

Lies, Damned Lies, and Misinformation

Each year, Harvard’s Nieman Journalism Lab selects a group of journalists to offer their predictions for the upcoming year. In her piece predicting the growing irrelevance of mainstream media, Alice Marwick, a researcher of far-right disinformation, points out the financial resource imbalance faced by those of us on the left. Compared to the flood of disinformation and outright lying on the right, voices like mine are at a distinct disadvantage:

[T]he right has capitalized on the decline of legacy media, expertly curating a profitable and thriving ecosystem of podcasters, influencers, alt-tech platforms like Rumble, and media companies like the Daily Wire propped up by conservative billionaires and funders. Young talent is found in spaces like TikTok, developed and incubated in spaces like PragerU, promoted by other influencers, and amplified by social media spaces that prioritize conservative content…their leftist equivalents are often stuck working on a shoestring. No matter how liberal they are, left-wing billionaires are unlikely to support creators who advocate for socialism or the abolition of wealth hoarding.

A Note to Free Subscribers: February 2025

In her prediction that free news “will be increasingly synonymous with AI slop and other low-quality content,” The Capital Forum’s Sara Morrison has this to say regarding the issue of paywalls (emphasis added):

Thanks to the rise of generative AI and the fall of social media-fueled, algorithmically-driven traffic, there’s a better case than ever to be made that at least some of your content should be behind a paywall…

That might mean paywalling everything, or it might mean a “freemium” model that balances the need to have some readers paying for their journalism with the reality that not all of them will.

Yes, there will be a lot of people who can’t or don’t want to pay for news. They’ll be getting it from the diminishing number of free news sites, the scraps that paywalled sites throw at nonpaying readers, and an exponentially growing pile of AI slop, misinformation, and “something I saw/heard on social media/Reddit/some guy’s podcast.”

The Art of the Humblebrag

I recognize we’re in an environment where the rules are fading and history is being either rewritten or erased entirely. But is paywalling everything the answer? Last March, I spoke briefly about this thorny topic during a livestream I had with “Gen-Z Historian”

Kahlil Greene

:

As I write this post, the Smithsonian’s National Museum of African American History and Culture is being purged by the Trump administration, even dismantling the exhibit featuring the Woolworth’s lunch counter sit-in from the 1960s.

But what value does information have if it’s locked behind a paywall? When the financial markets crash, should my thoughts be reserved for the few who can afford to pay? I refuse to accept the notion of truth as a commodity. I want my work be free to anyone who finds value in it.

Still, I think those who willing to lend their support deserve a perk or two. I’m sure that together, we can figure it out.

But for now, all I need are a few more champions.

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