No. 343: From Audiences to Communities

2PM-Opener

An open letter to creators. By now, there are hundreds, if not thousands, of viable membership-based newsletters. And that’s a great thing – an unequivocal advantage for creators and consumers alike. Of those thousands, a number of them serve as sources of original ideas, news, and analyses that are incredibly valuable to professional ecosystems. It’s the synthesis of these ideas that has the greatest potential impact. If education is priceless, we are entering a new era of value creation. Imagine an Enlightenment-era coffeehouse.

There are newsletters run by operators who publish original ideas. There are meaningful letters that curate the ideas of of others. Some of them report on the news and others categorize and comment on industry developments. Often, reports that have been written by one person are refined by others. And frequently enough, mainstream outlets like The Wall Street Journal or CNBC will pick up on original concepts and make them their own. Like a coffee shop, this is a valuable form of information synthesis.

John Dowell is a professor at Michigan State University. Over his nearly 40-year career, he’s taught English, Sociology, and Anthropology. His course on the introduction of synthesis explains:

A synthesis is a written discussion that draws on one or more sources. It follows that your ability to write synthesis depends on your ability to infer relationships among sources – essays, articles, fiction, and also non-written sources, such as lectures, interviews, observations. This process is nothing new for you, since you infer relationships all the time – say, between something you’ve read in the newspaper and something you’ve seen for yourself, or between the teaching styles of your favorite and least favorite instructors.

In the Age of Enlightenment (1715-1789), a European could gain entry into a coffeehouse by buying a drink. But the drink was just the price of admission, the conversation was the attraction. It wasn’t solely the conversations on matters of sociology, economics, and law that drove the age forward. Sometimes, patrons would overhear concepts that would fill gaps in their own thinking. Other conversations would solidify pivotal ideas, directly or indirectly.

Coffeehouse Inspiration

It was a coffeehouse conversation that I had in November of 2015 that struck me as one of the most important professional discussions that I’ve had. The discussion was on the mechanics of community and the need for tools that could maximize serendipity. On an idle day in late 2015, I began planning the launch of what I then called 2PM Links. I paid for a service called Goodbits and launched the landing page for the site. After a week or so of pushing the idea of 2PM on Twitter, I confirmed that the first letter would publish to twelve whole readers. I’d go on to publish five days per week for 180 business days straight.

On paper: 2PM Links would be one part original concepts and one part data and narrative synthesis, a curation of developments that would tell a story. The emails themselves would allow for 1:1 dialogue. The most engaged readers would write in explaining how they recognized microtrends and larger movements. Others would explain methods for synthesizing each letter for maximum effect. On occasion, I’d read an email from an early subscriber explaining how a cluster of articles over several weeks helped them to plan their company’s next steps. For nearly two years, those letters would help sustain the motivation to maintain operational consistency.

Reach vs. Depth

To build something that was designed to grow slowly, I maintained paying roles at established companies. However, at the time that I started the publication, I was between media jobs. Having managed or led eCommerce at two digital media publishers, I learned a tremendous amount from two vastly different styles of conversion-based (read: affiliate) publishing.


Company A built a hyper-targeted funnel, honing in on a specific (affluent) consumer. There, direct traffic was high and SEO was a secondary funnel. Brand was most important. This company would rely on it. Company B built a system that would rely upon SEO and topic interest, not the clout of the platform itself. For B, reader loyalty was secondary to SEO discovery. Visitors clicked through to read about a topic that they stumbled upon. If A was a funnel, it would be short and wide. Trust was built over time. For A, the readership would be driven by loyalty to the platform. Meanwhile, the B funnel captured new people by optimizing articles for topical keywords. Its funnel would be longer with a number of entry points throughout. Those entry points would also serve as exit opportunities. Churn was higher.

The result:

  • Company A: smaller audience, higher loyalty, higher conversion rate. 1.8 million to 2.2 million MAU. Product segment: modern luxury.
  • Company B: lower loyalty, lower conversion rate, larger audience. 6-7 million MAU. Product segment: accessible luxury down to daily deals.

A and B continue to operate successful media brands with disparate objectives. As they say, there’s more than one way to skin the proverbial cat.


To prove out the long term viability of the newsletter, I allotted 180 letters to figure things out. As things progressed, 2PM took on more and more characteristics of Company A. After reaching number 180, this identity influenced the next steps. Once I reached Letter No. 180, there would be three options:

  1. move forward and publish No. 181
  2. shutter the letter
  3. replatform and build a company

The choice was option number three. In my seven pages of scribbled plans, I agreed that I’d emphasize depth over reach. I’d maintain an emphasis on the “A” version of media. To do so, I emphasized a paid subscriber model. And then a data / advisory model. And later, an executive community. These initiatives would allow me to reinvest revenues into improved services, design, content development, and greater overall access.

From Audience to Community

Over a matter of two weeks between December 2017 and January 2018, I replatformed from Goodbits to Mailchimp, designing around a Memberful integration. I invested in branding and design. I coded much of v1 of the site in my free time. And later I’d import some 240 editions of 2PM to the WordPress site, one by one. In March of 2018, after two months of testing, 2PM’s first membership launched to the Monday Letter’s subscribers.

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How 2PM works. | About 

In this way, 2PM’s system became somewhat of a funnel. Around 10% of all subscribers become Executive Members. And, upon invitation, a percentage of Executive Members opt in for direct communication with like-minded executives across a number of digital industries.

2PM’s community of Executive Members, Polymathic was inspired by two separate thoughts.

  • The forum is designed to help talented executives develop new core competencies by: (a) identifying blind spots and (b) learning from leaders who’ve mastered those pursuits.
  • When I arrived at the latest Code Commerce, I recall four great conversations within my first hour at the venue. These conversations were with Jason Del Rey, Alex Taussig, Marc Lore, and Jen Rubio.
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Executive Member Dinner: SF (December)

To attend Recode’s two-day event, tickets range from $2,000 to $4,000. Pricing serves a valuable function, in this respect. There, everyone that you talk to is likely to leave a valuable impression. The events tend to attract high level operators. Between the keynote speeches at these key events, few conversations are wasted and most every extracurricular interaction adds professional value. As such, the event isn’t the only product. The community of attendees provide an additional value. The Polymathic Forum is designed to resemble digital hallways of top conferences like Sundance, PopTech, Google’s Solve for X, or FOO Camp. As the numbers grow, so does the strength of the venue.

From hosting 15-25 Executive Members at our monthly roundtables to building out 2PM’s Polymathic, the shift from audience to community has provided serendipity in ways that were previously unimaginable. Subscription revenue becomes the key variable here. Paid memberships provide a level of opportunity that advertising-driven platforms cannot. For a practical example, consider the difference between fast food restaurants and four star establishments.

There are generally two types of restaurants. One chain advertises “billions served”. This emphasizes the company’s KPIs: reach, volume, and satisfaction by the masses. But what if you aren’t trying to reach the masses? The second type of restaurant stands on the quality of the food and service in addition to the inviting atmosphere for conversation. In the latter environment, serendipity is more likely to be found. It’s emblematic of a shift from prioritizing audience (reach) to prioritizing community (depth). 

Andy McIllwain, a senior marketing manager for GoDaddy, had an interesting thought on the growth of the newsletter industry and the shift from audience to community. In a short series of tweets, he explains:

The 2010s were about radically open social media platforms – a gigantic, unmanageable mess. The next ten years? The pendulum swings back to niche communities of interest and purpose.

McIllwain goes on:

Community revenue models: Direct sponsorship, tiered membership fees, affiliate commissions, and paid experiences (events, retreats). Brands need to get in on this. It’s the flip from audience to community.

Though membership-driven newsletters existed prior to Substack, the concept of paywalled community was popularized as the A16Z-backed platform’s popularity has grown. Like a table at your favorite dining establishment, the food is only a portion of the attraction in these environments, when executed appropriately. The other is the ambiance and the environment. For 2PM, the idea of community is taken one step further. Executive Membership unlocks legitimate opportunities for serendipity. Ten times per year, we invite our paying members to a complimentary dinner in one of the major markets (New York, Los Angeles, Chicago, Austin, and Boston).

In this way: gated, media-driven communities have become the antidote to the noise of digital commonplaces. You’ll see this in publications like: Trapital, Petition, Off The Chain, Stratechery, and Thing Testing. In each instance, each media founder works tirelessly to provide value for their paying members. A membership is a vote for the future in addition to the present. There is more room for businesses like these. And these projects often begin with simple strategies around original ideas. The hope is that more newsletters launch and more communities form around. We should encourage involvement and competition. This is how ideas take shape. The ecosystem, as a whole, is the coffeehouse of today. This isn’t just the future of media, it’s emblematic of a greater shift as humanity adopts digital-first culture as its own.

Read the No. 343 letter here.

Report by Web Smith | Edited by Carolyn Penner | About 2PM

No. 337: Stick To Sports

For as long as there has been athletic competition, there has been a narrative that permeates from the field of play. Gladiators of Rome were commonly first-generation slaves, bought and sold at the whim of their owners – the sporting promoters of their day. Like today’s gladiator sports, cruelty was a part of the spectacle. And the minds of the time contrasted in their approval or disapproval of their era’s proudest spectacle. Great minds like Seneca disapproved of the competition. Marcus Aurelius once abolished a tax on gladiator-based taxes and commerce; he wanted nothing to do with the capitalism of it all. And still, he couldn’t resist hosting lavish games from time to time. The spectacle of cruelty was insatiable to the average man and the great one – alike.

As it was, as it will always be. Sports was never without its social commentary. Jesse Owens’ olympic showing wasn’t just impressive because of the speed of his feet; he beat the myth of German superiority with a foot race. Jackie Robinson wasn’t just a baseball player, he was remembered as a hero. That was the narrative that was formed about the man, even while his involvement lacked the popular sentiment that it is awarded today. Janet Guthrie was a media fixture, not just because of her precedent off of the track but because of her accomplishments on it. Before Danica Patrick, there was her. And with a little more support from sponsors and officials, she could have accomplished much more.

Since when has sports been about athletic accomplishment alone?

On a November evening after the Baltimore Ravens’ decisive victory against the undefeated New England Patriots, ESPN National NFL Writer Kevin Seifert made a statement with a simple tweet. He listed three quarterbacks, each of whom are considered candidates to win the league’s coveted most valuable player award. The quarterbacks that Seifert listed: Russell Wilson, Deshaun Watson, and Lamar Jackson are what veteran industry analysts would call: unconventional, mobile, dual-threat. However, they’re more than that. In each case, whether these quarterbacks pass or rush, they lead from the front. More than anything else, that’s their common thread.

Kevin Seifert on Twitter

If we’re doing the MVP now, I’m going: 1. Russell Wilson 2. Deshaun Watson 3. Lamar Jackson

Here is a selection of quarterbacks drafted before 2019’s MVP candidates: Ryan Tannehill, Brandon Weeden, Brock Osweiler, Mitchell Trubisky, Baker Mayfield, Sam Darnold, Josh Allen, and Josh Rosen. To the casual observer, this thought may as well be morse code. So consider the following: the National Football League has never had three African-American quarterbacks in the front running for most valuable player. And certainly not in an era of the sport’s greatest quarterbacks, namely Tom Brady and Aaron Rodgers. We’re still in a period of firsts in this 150 year old sport. Brigham Young University started their first African-American quarterback in the year 2019. The sentiments of the 1950’s still linger. So what Seifert was doing was making a statement without controversy. To the untrained eye, it was merely the fact of the matter. But to those who understand the historical significance, it was a dog whistle of sorts.

“If you ask me is there a false narrative out there, I will tell you ESPN being a political organization is false,” he said. “I will tell you I have been very, very clear with employees here that it is not our jobs to cover politics, purely.” [1]

But even with the mandate by new ESPN President Jimmy Pitaro, Seifert found a way to toe the proverbial line. Wilson, the 75th pick of the 2012 draft is now the highest paid quarterback in the league. Bears quarterback Mitchell Trubisky was drafted before Watson. And Ravens quarterback Lamar Jackson was publicly and privately coaxed to convert to wide receiver by many in the media. He didn’t fit the image. His chorus of detractors included former Indianapolis Colts GM Bill Polian [2].

After this historic game, Bleacher Report took a muted approach as to avoid the conversation altogether. In the NFL, running backs don’t win MVP over transcendent quarterbacks. In the last 20 years, just four have won. Sixteen quarterbacks have been selected in that time. Just the same, here was their take:

And [Jackson] a clear MVP candidate. This game firmly planted him in that discussion, along with Panthers running back Christian McCaffrey, Seahawks quarterback Russell Wilson and Texans quarterback Deshaun Watson.[3]

Meanwhile, at Deadspin, the two lead stories are written by a generic “Deadspin.” A sign that no one is behind the wheel. The reports were merely a collection of embedded tweets. There’s one on the Ravens surprise victory. The one where the quarterback (that should have played receiver) trounced the greatest of all time. As the two shook hands upon leaving the field of play – battered and bruised – Jackson uttered “You’re the GOAT.” As if Brady needed a reminder. The other Deadspin “story” featured the Cleveland Browns latest off-the-field issue.

The only report with any personality was written by Karu F. Daniels of The Root, another property of G/O Media. It was repurposed into Deadspin content. One can only wonder what Deadspin would have written about a unique moment in the sport’s vaunted history. But the site is currently a shell of its former self. The staff quit en masse after being told to by G/O Media management to “stick to sports.” A common refrain in today’s corporate media.

G/O Media is the product of Great Hill Partners’ acquisition of the former Gizmodo Media Group. The all-equity transaction was facilitated with Jim Spanfeller, best known for his leadership at Forbes.com. Perhaps, it’s his lack of experience in sports media that permitted such a fatal miscalculation.

The Irony of The “Stick to Sports” Mandate

Google Search interest for “Stick to Sports” peaks in September 2017

On its merits, the nature of the phrase is divisive. When ESPN’s Rachel Nichols spoke out in September of 2017, the peak of its interest, she raised questions around the hypocrisy of it. It was around that time when J.J. Watt was rightly praised for raising $20 million for hurricane relief while other athletes faced pushback for highlighting other extracurricular causes – most often around social justice issues. With the current state of American politics at a relative boiling point, the separation of societal politics and corporate entertainment have never been more difficult to parse. ESPN found ways around its “stick to sports” mandate by elevating intelligent and nuanced figures like Pablo Torre, Stephen A. Smith, Max Kellerman,and Bomani Jones. Deadspin wasn’t as forward thinking and they ultimately paid for that.

“Stick to sports” is, of course, a fault line in 2019’s culture wars. [4]

But as the state of our political machine continues to polarize Americans, the mandate becomes harder and harder to follow. Yet, it becomes more important to disobey. In fact, at some point, the mandate becomes bad business. This is especially true for digital media where Deadspin rival and The Chernin Group-owned Barstool Sports has thrived by using sports as a platform to enter adjacent conversations. And I am using the word “adjacent” liberally here. Several of the top stories on Barstool Sports currently include an Instagram influencer questioning his history syllabus, a feature on the “Watchmen” series, and a woman that tattooed her eyeballs.

The banner of Barstool’s homepage features a link to the media group’s famed Chicks podcast. And all of this is to say, it seems to be working for Barstool. This includes its cozy relationship with Fox News, including regular appearances by founder Dave Portnoy on Tucker Carlson. And this isn’t an argument against their approach. Rather, it was an acknowledgment that Barstool Sports has thus far succeeded by understanding the property’s psychographic. The Chernin Group seems to have avoided the stick to sports conversation with CEO Erika Nardini.

Ringer, Deadspin, B/R, Barstool and Psychographics

Consumer psychology involves the interest in lifestyle, behavior, and habit. It’s an encompassing measure that considers our idiosyncrasies, our temperament, and even our subtle personality traits. These are the variables that influence our behavior as consumers. Psychographic segmentation is the analysis of a consumer cohort’s lifestyle with the intent to create a detailed profile.

The Ringer is jovial and care-free. Bleacher Report is dead-pan with the occasionally dry humor. Barstool is edgy and offensive as a strategy. And so was Deadspin.

While largely focused on sports, Deadspin for years had delved into a broad range of topics in a voice that was sometimes rude, often funny and always conversational. On Tuesday, the site’s top editor, Barry Petchesky, was fired after refusing to go along with the order. The departures shocked fans of the site, which put a new spin on sports coverage for a generation of digital natives. But they were the result of a long buildup of resentment between the journalists and their new bosses, according to interviews with 13 current and former employees of Deadspin and G/O Media.[5]

Nov 4: Barstool’s Homepage

For Deadspin, the majority of their sensationalism involved topics that were completely unrelated to sports in substance, this report isn’t necessarily about the history of those articles. Bill Simmons’ The Ringer shares a similar narrative with Barstool. On the homepage, you’ll find stories about Mr. Robot, Jeopardy, AppleTV+, and The Watchmen. Bleacher Report contrasts the three. The publication leans heavily towards strict sports coverage, a methodology that works for them. But even B/R featured an epic story on Colin Kaepernick written by Rembert Browne. And most recently – a story about Jared Lorenzen, the former Kentucky quarterback who died prematurely. Which brings me to the point: where do you draw the line when your publication covers sports? Collegiate and professional sports represent a layer of American life, not the totality of it. Sports is merely a dimension, not the whole.

No Code and The Business Case FOr: Stick To Sports

OM on Twitter

Let me rewrite this tweet from Jason. 1/ Deadspin writers are immensely talented and have a huge following. They have a lot of goodwill at present and as a result they should Marshall their collective resources and start a new publication. Let’s call it SpunOut. https://t.co/161I1HkInj

The editors and writers who resigned from Deadspin had a basis for their frustration. Sticking to sports is a nearly impossible proposition in today’s media. Given how rare it is to see a media company stick to their original charter, it’s understandable that Deadspin’s former employees saw the charge for what it really was: a euphemism for staying away from covering athletes who’ve immersed themselves in left-leaning causes.

But we’re in an ever-expansive era of digital media. Companies are rewarded for reaching. Complex Media is developing television shows and consulting third parties on commerce and audience development. Barstool Sports has a podcast starring two employees who discuss their friendship and sex lives, and Bleacher Report successfully collaborated on soccer kits with top hip hop artists.

Whatever happens moving forward, the Deadspin that was is no longer. It was one machine of a blog with nearly 30 million monthly visits and a penchant for engaging and re-engaging their loyal readers, many who’d visit the site multiple times per day. But it begs the question, if Deadspin was still Deadspin, what might they have written of Kevin Seifert’s idea? How would it have covered a tweet that should have been more than inconsequential. It’s doubtful that Deadspin may have told the story in the same ways that Barstool, Bleacher Report, ESPN, and The Ringer relayed theirs. To those platforms, the MVP race was not a story at all. But take it from NFL veteran and commentator Cris Collinsworth. As the Ravens led the Patriots, with the crowd in disbelief, Collinsworth quipped:

We’re going to be able to point to quarterbacks in the NFL that got a chance because of this night.

But in 2019, for many digital publishers, that’s too loaded of a statement. But many understood what it meant. And that understanding is part of the story too. The market has a need and the opportunity rests on the journalists who decide to forge their own paths. It’s only right that Deadspin alumni launches a Substack with the call sign of their mandate: Stick to Sports. Used ironically,  of course, as one last jab at the man they called an herb. The publication would almost instantly lead the Substack board.

With that model, Deadspin’s former writers and editors would have the freedom to do it the right way. Anyone who’s ever played the game knows that sports doesn’t end when you step off of the field of play. A sport is America’s pastime, it’s the most watched television event, it’s the most expensive event ticket, it’s the basis of a nation’s network of country and athletic clubs. Across America, hotels are built solely to support a thriving youth sports cultures of areas that would otherwise be barren without its expensive field complexes. Young people wear jerseys and the shoes of sporting legends. And adults bet and cry and yell and travel to watch their teams. It’s the irrationality of it all that reminds us that sticking to sports is an impossible task. And media should reflect that impossibility. Seifert knew the significance of his tweet, America should have known it too.

Report by Web Smith | About 2PM

Member Brief: Substack and Local News

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The New York Times did something extraordinary.  The legacy publisher pivoted from a legacy publisher to the media playbook suited for this era of technology and hyperconnectivity. The New York Times (NYT) traded the past for the future by leveraging the present. In 2015, the United States of America was in the midst of one of the most divisive political campaigns in recent memory. The New York Times used this moment like a brand marketer uses a major sporting event or a Hollywood awards show. It became a part of the story and redefined legacy media in the process.

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