Member Brief: The Press Club

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There is a saying in the direct-to-consumer industry: “You may have sales, but you don’t have shelf space.” Now apply these same words to the evolving media industry. The Passion Economy monetized creation, but it has yet to democratize access to respect. As the rise of darlings like Substack and Clubhouse compete with traditional media, the question becomes: if you build a successful media business around your ideas, are you in the club?

Perhaps one day, when there are discussions on the future of newsletters and media, there will be less focus on homogenous voices and linear examination when there are evolved spaces that are examining the under-examined.

These are recent words from my friend Sherrell Dorsey, the trusted and accomplished Founder and CEO of independent publishing company and newsletter The Plug. Dorsey, Trapital’s Dan Runcie, and I met for the first time in April 2019 at a WordPress-hosted panel on the future of newsletter media. The conversation was optimistic and idealistic. At the time, Substack was just a few months old. The platform had yet to disrupt the legacy journalism industry by poaching some of its most marketable, independent talent. Alisha Ramos, who came up in the panel discussion along with Lean Luxe’s Paul Munford, had already built Girls Night In as a side project. It was clear to me that Ramos’s fledgling newsletter would become a serious journalism-driven business. Today, she runs GNI full-time.

Looking back, there was a level of irony that we didn’t consider at the time of the panel. We were in a conference room in Miami discussing the democratization of newsletter media at the 44th meeting of the National Association of Black Journalists (NABJ). In a way, this signaled that very little had changed. To accomplish what the three of us hoped to, we shouldn’t have needed to be there in the first place.

To understand the history of the NABJ is to recognize the 1968 Kerner Commission Report’s impact on today’s traditional media. The report also explains why the NABJ is still relevant. Commissioned by former Illinois Governor Otto Kerner under LBJ, the report cited how small a role people of color held in traditional media environments. The founding NABJ meeting was held seven years later at what is now the Marriott Wardman Park in Washington D.C. The goal of the annual conference was “to increase the presence of Black people in mainstream media”, with its mission statement taken from a jarring section of the report entitled “The Negro in the Media” (Page 212).

Specifically, newspapers should integrate Negroes and Negro activities into all parts of the paper, from the news, society and club pages to the comic strips. […] Any initial surprise at seeing a Negro selling a sponsor’s product will eventually fade into routine acceptance…

At the time, I knew nothing about the historical significance of where we stood or the richness of the NABJ’s history. This, even though the conference’s halls were filled with Jackie Robinson artifacts, callbacks to the era of the Kerner Commission, and living acolytes who bridged the time of then to now. I was just building a newsletter and as a pragmatist, I believed that if you built something well enough, everything else would take care of itself. That isn’t exactly true. The greater media ecosystem benefits from a flywheel of participation, collaboration, and fellowship, requiring a level of respect that, like shelf space, not every DTC brand or publisher has access to. Dorsey continued:

Part of the challenge here is that underrepresented founders and professionals are only asked to be in position to comment on minority status, challenges, and discrimination. And thus we aren’t asked to comment on the industry. Or business models. Or growth.

The passion economy monetized creation but it has not democratized access. This week, at a dinner on Miami Beach just 12 miles from where I first met Dorsey and Runcie two years ago, I sat taking notes as a major tech editor and I discussed the business of journalism. One comment of his stood out:

For the first time in media history, anyone can build their own respected and recognized publishing operation.

I had to object. There is a growing divide between revenue success and the fruits of credibility and recognition in the media industry. Legacy publishers will launch newsletters, digital communities, and other brand activations to compete against insurgent forms of knowledge-sharing while stating that a newsletter’s use of the same mechanisms preclude the industry from serious consideration as an industry peer. Every media company seems to want to build for the future without acknowledging those pioneering at the edges of it.

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I too would like to be asked about the future of business, and media.Not just about being Black. Or being a Black woman. Or when there is crisis and trauma in the atmosphere. Like my peers, I too have range.

A media founder can build a business by reporting on a niche without the pedigree of having begun one’s career at The Wall Street Journal or TechCrunch, or without the co-sign of The Chernin Group. But are they really in the Press Club? Dorsey’s efforts have placed her in an objectively elite class of independent creators. Her work is still being overshadowed.

There are a number of minority-led publications that are on-track to become sustainable enterprises with seven figures or more in annual recurring revenue. Based in London, Cryptonary, an independent media company that specializes in paid commentary and data on cryptocurrencies and blockchain technologies, is one of them. I spoke with founder Asad Saddique at length about the challenges that he’s faced, despite the extraordinary operational growth of the business itself. When Saddique explained the depth, quality, and success of his business to me, I was taken back by his following statement:

I just can’t seem to breakthrough, especially in America.

There aren’t many independent publishers with the same momentum and unfulfilled potential as Cryptonary, The Plug, Trapital, and others. And yet in each case these founders still feel the singeing heat of the firewall. Hours after my back-to-back meetings with an admired technology editor and Asad Saddique, I was up drafting thoughts on the evolution of independent media and the “shelf space” analogy that often defines the measure of industry respect one receives. Does Axios cover your work? Does CNBC attribute you? Does Forbes champion your growth? For independent media, this is our proverbial shelf space. And as I was up writing, a shift in thinking occured.

Last night, a great panel of 10 media operators, newsletter founders, and technologists discussed the future of newsletter media, including Ben Thompson, Dan Primack, Jessica Lessin, Polina Marinova, Sam Parr, and Substack’s Chris Best. There were a number of people that I admire who spoke that evening. Noticeably absent from the highly visible panel was Dorsey or any other of her peers of color.

As we close the one month set aside each year to champion the Black experience in America and its history, it is important to recognize that history is still being made. There is still an NABJ conference. And despite being an accomplished media founder and Columbia Journalism grad, Dorsey as well as others like her are reduced to contributing to conversations that should have long ended. It can make you feel like you are in the lagging present while our peers are plotting the future. When I asked Trapital’s Dan Runcie about his thoughts on listening to last night’s panel on the future of newsletters, he replied:

Some people don’t think about how that stage looks from the outside and what perspectives are missing. Especially on Clubhouse, an app that grew in large part thanks to Black creators.

The result will be a high profile call on stage to discuss the importance of respect, attribution, diversity, and belongingness. What this represents is more wasted time; more focus on the history and the present, instead of what’s to come and who will be a part of its fabric. The Kerner Report is 53 years old. The National Association of Black Journalists will be 46. The passion economy monetized creation and it can democratize access. There is room on the shelf; the internet is vast.

What Dorsey really wants to discuss is the future of the newsletter media industry. She has range, you know. So do the rest of us.

By Web Smith | Editor: Hilary Milnes | Art: Alex Remy | About 2PM

An Open Letter: On Community


Community building isn’t easy. This weekend, everything went wrong.

It started with a weird bug that was causing us a few problems. Here and there, a paying customer would write to ask “Why am I receiving a rejection email?”, or something similar. We would explain it away and change a setting to prevent it, but it kept happening. And then on Saturday at 3:15 a.m. EST, a deluge of angry, confused or sad emails bombarded my inbox.

Behind the scenes, the 2PM Inc. organization is seven people large. I am the only full-time worker, like Sahil Lavingia’s lean strategy at Gumroad. That’s not to slight our team, however: four contractors and two paid interns are incentivized and capable of doing great things with the time that they share with the company. The 2PM team is so talented and consistently productive that the company would have to be venture-backed to afford each of them. I am working to get to the point where cash flows can support them. They are the best at what they do. We scrappily do the work of many, three days per week. If memberships are low for one week, I can at times feel like I disappointed them. This weekend, I disappointed far more than my team.

Why am I being rejected from something that I didn’t apply to?

In that moment, your entire business rests in the balance. Dozens upon dozens of loyal members opted out of auto-renew, angry at the insult. One email reply was: “You’re dead to me.” Another member wrote: “A real polymath would be smart enough to turn off automated emails before deciding who they want in their stupid little club.” He would later reply: 

I should have given you the benefit of the doubt and instead I sent a mean email. Thanks for clarifying. I enjoy your work so I was extra sensitive.

They were not mad because they were interested in joining 2PM’s growing community but because the email itself was incredibly callous. The subject line read: “You’ve been rejected from Polymathic.” And in the body of the email: “A staff member rejected your account.” Neither were true. Our community software sent that email from its servers with our branding but without any of the following: our permission, copywriting, or basic understanding of how 2PM’s community works.

Discourse, an open source community software, sent thousands of emails that we didn’t author after an admitted API bug between their backend and Memberful’s membership and paywall software. I emailed their support but the office is closed on weekends. By that morning, I had to send an email addressing the issue. It would be the first time that I’d ever send an email of that sort. I moved as quickly as I could, hoping that the vast majority of those offended would see it.

No Title

The one and only ⁦@web⁩ wrote this for your swipe files. Put it under “how to apologize when something beyond your control goes wrong”. We’ve all been (or will be) there. Well done, Web.

Meanwhile, communication between 2PM and Discourse’s teams moved slowly back and forth through email. I tried to communicate the severity of the situation; they tried to communicate how inconsequential the trigger that caused the fallout was. It would be 20+ hours of synchronous communication before this stalemate broke.

By this morning, Jeff Atwood, the Co-Founder of Discourse, chimed in, perhaps the first sign of affirmation that our hosting company recognized the severity:

We’ll be happy to send out individual apology emails to all affected users, taking FULL responsibility for that erroneous email – because that was absolutely our fault! I can offer to personally send them signed Stack Overflow stickers, if that helps (not sure if your audience uses / knows Stack Overflow, but I was a co-founder). I will write these apology emails myself, and send them from my personal email account.

I chose to opt out of this email. For one, our members don’t need another email from Discourse – even if it does provide 2PM’s vindication. And unless they were willing to apologize for the copywriting and flaws that relinquish the control of their clients, I wasn’t interested in continuing the conversation.

What we’re building at Polymathic

Anyone who reads 2PM understands the value of deep generalism (or polymathy) as an educational pursuit. Each newsletter’s curations are broad and cross-disciplinary. The Polymathic community that we are building for members is the next step in this process. We encourage the sourcing of reports, data, and insights in economics to art history to the sciences or real estate. It is my belief that the study of broad subjects unlocks deeper knowledge of your own industry. I often share the obscure Henry Ford anecdote as an example:

Henry Ford’s great technological breakthrough didn’t come by way of his own Industry. He visited a Chicago meat packing plant, watched the disassembly process, and reverse engineered the idea for his factory’s manufacturing revolution.

It has been a slow build, sometimes just adding 4-7 people per month across a spectrum of professional and academic specialties. Each of these members share a desire to contribute and learn from the woman or man next to them. The goal is an ambitious one: Polymathic is to become a school of thought for thousands. One where any long-term Executive Member can one day join and contribute and learn. In short, there are no rejections. That simply defeats the damn point of everything that I’ve worked to build.

When you are bootstrapping a company like this, you make several trade offs. In an ideal scenario, I’d build my own community server instead of whitelisting another’s but for the stage that the company is in, the current stack makes sense. Our technology stack consists of a number of outsourced solutions: WordPress, Memberful, Mailchimp, Discourse to name a few. But you never expect those platforms to do you active harm. The act of Discourse sending that email cost 2PM nearly $70,000 in short term business. The persisting problem with Discourse’s API connection to Memberful (who’s been a wonderful partner) is currently hindering nearly $1 million in long-term revenue for our company with no promise that it will return. But the lessons learned are far more important than money lost.

Community building is not easy, even when your software is working for you. I have never valued the grace and perspective of the 2PM community more than I do today. What it taught me was the power of the benefit of the doubt. Many in the community were apologetic after receiving the email that clarified what happened. An even larger number of community members waited for justification before assuming the worst, assuring me that I had done enough good with 2PM to know that we’d never send an email like this. But the most critical takeaway is that nothing matters more than the collective that you build around your products. In one weekend, five years of hard work was threatened. It was the community that kept it together as technology failed them.

By Web Smith

Here is Discourse’s official apology.

Member Brief: The Lying Mall Owner

Every mall ownership group has to lie or the house of cards may fall. It's not the pandemic's fault that the mall bubble is bursting; it's been years in the making. We've all seen it. A verified Twitter personality records and posts a video of a busy American mall with the caption: "Retail is back – just look at it." Yes, just look at it.  A Dior store is in the backdrop. Three moms are pushing strollers, each donning variations of the latest season of Louis Vuitton handbags. If you can listen, you will hear a classical pianist playing in the background. This content is designed exclusively for Executive Members