The Literary Obsessive

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The Literary Obsessive
The Literary Obsessive
8 Questions for... Marlon Weems

8 Questions for... Marlon Weems

The Journeyman

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Eleanor Anstruther
and
Marlon Weems
Jun 03, 2025
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The Literary Obsessive
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8 Questions for... Marlon Weems
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Cross-post from The Literary Obsessive
A few weeks ago (after one of my livestreams, I think), I answered a few question for The Literary Obsessive. I talk about how I started writing, why I chose Substack as my primary platform, and my thoughts on paywalls. -
Marlon Weems

empty chair in front of green number 8 sign
Photo by Claudio Schwarz on Unsplash

Storyteller. Ex Wall Street trader. Exploring the intersection of politics, the economy, and anti-Back racism.
Marlon Weems
writes The Journeyman.

1. Why Substack?

Before I took up writing, I worked in finance, mostly in trading. Like any profession, trading has a unique lingo. For example, a saying I use from time to time is, “In God we trust. Everyone else bring data.” I picked it up from working on a trading desk. When I think of Substack, I’m reminded of how traders might refer to a stock that is the best choice out of a group of sub-par options. We’d call a stock “the least dirty shirt. “We likened it to a situation where all your shirts are dirty, but you have to wear one of them. So you pick the one that’s the least dirty and wear it.

I started my newsletter about five years ago, but I was on Medium for years before that. When Notes launched, I left Twitter. I’ve built a wonderful community of subscribers and followers, and I like the functionality, but I have issues with several things. The lack of moderation is one example. Within 24 hours of Trump winning the election, someone called me the n-word here. Believe it or not, it was the first time that had ever happened to me online. I reported it, but nothing came of it. As far as I know, that person is still on the platform.

Other things concern me, but at the end of the day, for me, it’s the best choice out of lots of sub-optimal options. I suppose I could uproot everything and leave, but is there a better option? I don’t think so. So for now at least, it’s the least dirty shirt.

2. How long did it take you to find your groove?

When I left trading, I started writing as a subject matter expert for capital markets. I consulted for a research firm that Wall Street investment firms would hire to produce white papers, and if what they wanted was in my wheelhouse I’d write the report. I had a bit of a style in terms of my writing but it wasn’t fleshed out. When Covid hit, that business dried up and I started my newsletter. There were things I wanted to write about but I was worried about what some people might say. I think it took a couple of years for me to find my voice.

3. How has it changed you?

I’m not sure how much I’ve changed. I’m just a lot more comfortable revealing a part of myself that was there all along.

4. What mistakes have you made?

Not starting sooner is probably my biggest mistake. A former colleague told me I should start a newsletter over ten years ago. For years folks would tell me that I should write a book. I’m about 50,000 words into a memoir about my travels in finance. It’s about how I started the first Black-owned investment bank in Arkansas and ended up working on Wall Street. But I waited a lot longer than I should have to start it.

5. To pay or not to pay?

If we’re talking about paywalls, I’ve wrestled with this for a while. We’re in an era where misleading content is free. More often than not, reliable information is behind a paywall. My newsletter is opinion-based, but it’s backed up with receipts. I avoid paywalls to give readers access to factual information and data. But it’s an expensive way to do things this way.

In a perfect world, subscribers would pay without me having to force them to with a paywall. Not only because they recognize the value, but also to keep things free for everyone. Right now my content isn’t paywalled, but only a small fraction of my nearly 10,000 subscribers have decided to pay for my work. That has me wondering if I’ve made the right decision.

6. What artistic and technical choices have you made?

I’ve gotten into live streams. It’s a great way to collaborate with other creators and to get your thoughts out quickly. When I post the recorded version of the live stream, I also highlight written content that’s relevant to the video. It allows me to highlight written content that folks might have missed. I like it a lot, but I don’t think I’m very good at it yet.

7. What’s been the effect on your writing?

I’m a slow writer anyway so there hasn’t been much of an impact. On the other hand, live streams help fill the void between long-form posts, especially for subscribers who aren’t on Notes.

8. In it for the long haul?

I’ve been writing for over a decade, so absolutely yes. Anyway, at this stage of the game, I’m probably unsuitable for any other profession.

The Journeyman.
A newsletter focused on the intersection of American culture, politics, and growing up Black in the South.
By Marlon Weems
23

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The Literary Obsessive
The Literary Obsessive
8 Questions for... Marlon Weems
11
4
Share
A guest post by
Marlon Weems
Storyteller. Ex-Wall Street trader. I write about the intersection of politics, the economy, and anti-Black racism. Subscribe: @thejourneyman
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