Member Brief: Quibi and VC-Subsidized Media

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In March of 2009, Uber launched in San Francisco to great fanfare. At the time, the mobility company’s Chief Executive, Travis Kalanick, had a goal that seemed simple enough: first attract the higher rungs of society and then dominate the world by capturing marketshare. Except, to do so, he’d have to adjust the prices. Uber was too expensive for everyday users. Over the next decade, Uber would employ a tactic that has been popular throughout Silicon Valley circles — deploying hundreds of millions in venture capital to subsidize the cost of the product, which in Uber’s case is rides.

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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

Member Brief: SMS and The New Chaos

2PM-SMS

The moment that changed the music business happened insurgently, as they do. In 1998, when Shawn Fanning began working on Napster, the once-infamous file sharing platform, it was built on a borrowed laptop with little money and even less support. And then, in an act of serendipity, a pre-Facebook Sean Parker met Fanning in a hacker chat room. The two would go on to raise a quick $50,000, move to California, and settle in on the second floor of a bank.

Though networks of distributed files existed across the web, Napster’s focus on MP3 files (coupled with a relatively simple interface) pushed the service to 80 million registered users. The growth was seemingly instantaneous. The platform’s sweet spot: unreleased and hard-to-find music (such as studio recordings, concert bootlegs, and older songs). In a number of ways, Napster paved the way for today’s streaming economy.

There was no ramp up. There was no transition. It was like that famous shot from 2001: A Space Odyssey, when the prehistoric monkey throws a bone in the air and it turns into a spaceship. Napster was a ridiculous leap forward.

Alex Winter, Director of Downloaded

The disruption felt like the violent recoil of heavy artillery after a feather’s landing on the trigger. There was collateral damage on both sides of the barrel. The music industry was unprepared for a disruption that would cannibalize the physical retail of music. And Napster was unprepared for the litigation that would come. Chaos was created, whether intentional or not.

In a year’s time, billions in value was lost to Napster, a platform that was designed to market music into a public good. The whole of today’s streaming economy was born of this disruption. And while Napster was at the precipice of this shift from physical to digital, its key technologies are no longer relevant. The modern version of Napster lives on as a carbon copy of the economy that it would later influence: subscription-based streaming. It would be a retail innovation by Amazon that, when applied to digital media marketplace, would re-define a two hundred year old industry for a new millenium.

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File sharing’s (1999-2002) and Spotify’s (2008 – on) impact on CD sales| Source: RIAA

Fanning and Parker’s platform emerged at the end of an explosive decade for the music industry. There were healthy profits reaped by many labels and publishers, thanks to the maturing of the compact disc (CD) as a preferred medium. At $15 – $21 per unit, the music industry’s primary channel was an expensive one. In this way, Napster was a catalyst for market correction. Until that point, a consumer would have to purchase an entire CD to listen to the two or three songs that they preferred. Napster allowed for the ownership of individual tracks and, in turn, it devalued the sale of entire albums.

Joe Rogan recently hosted The Wu-Tang Clan’s Robert Fitzgerald “RZA” Diggs on Episode No. 1382 of his podcast. The host couldn’t have predicted that the most newsworthy snippet of the conversation would hinge on the technology of the 1990’s.

Napster comes right in and and takes all these songs where all these people who are waiting for their publishing checks are waiting for the economics to be created from music. Now, there’s no publishing check. All of the numbers have decreased because there’s no physical sell of the music to accumulate value.

Diggs would go on to explain that between 2000 – 2015, the loss in physical sales ultimately transformed the industry into one that we see today. There were few winners in music during that span. Of them: the iPod, the iPhone, Spotify, Beats By Dre, Live Nation, and Universal Music Group. Music was no longer the product for sale.

On Chaos Theory and Patent US5960411A

As eCommerce is a multi-dimensional consideration, a single theory may not be sufficient for the overall perspective views. […] However, the Chaos Theory is suitable for describing the customer decision making, especially the buying behaviours seems to be random in which the classical model of classical decision model cannot be described. [1]

The market would begin to mold around Napster’s influence. Platforms with similar architecture went live. That list included: Gnutella, Freenet, BearShare, Kazaa, LimeWire, AudioGalaxy, and Madster. It’s important to note that each of these platforms was disrupted by copyright litigation.

Flapping a butterfly’s wings over the Amazon could influence the storm in China. This is the basis of the Butterfly Effect, also known as deterministic chaos, a phenomenon where equations with little to no uncertainty yield uncertain outcomes. Chaos Theory is the mathematics that explains the butterfly wings’ theoretical influence over China’s weather patterns. In this analogy, there is a bit of irony.

Chaos Theory is a delicious contradiction – a science of predicting the behavior of “inherently unpredictable” systems. It is a mathematical toolkit that allows us to extract beautifully ordered structures from a sea of chaos. [2]

It was Apple’s CEO Steve Jobs who challenged conventional wisdom by questioning the value proposition of file sharing. For Jobs, piracy wasn’t the catalyst for Napster’s monumental growth and influence. Rather, the combination of ease and convenience was the deterministic chaos. Steve Jobs would recruit the help of Jeff Bezos and a now-famous Amazon patent to address the mathematics of buying behaviors. When the deal was announced between the two companies, Jobs levied a glowing endorsement of Bezos’ early technological advantage.

The Apple Store has been incredibly successful and now we’re taking it to the next level. Licensing Amazon.com’s 1-Click patent and trademark will allow us to offer our customers an even easier and faster online buying experience.

In September of 2000, Apple became the first company to license Amazon’s 1-Click patent (US5960411A) and trademark for use across Apple’s eCommerce properties. This innovation enabled Apple to store billing and shipping information, allowing customers to click their mouses once without any data input. To Jobs, this was the key to the industry’s music problem. By making conversion easy and ownership effortless, consumers would flock to legitimate sources of commerce. And he was right.

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From Amazon’s Early Patent

By 2003, the iTunes Music Store was outselling its next best competition by a margin of five to one. That competition was a legitimate version of Napster. Apple’s combination of iTunes and the iPod provided a seamless experience for conversion, management, and consumption. Apple understood that Amazon’s advantage wasn’t what it was selling, it was how it was selling. This influence would affect music and entertainment. iTunes was a precursor to 2005’s Pandora and 2008’s Spotify.  Apple’s 1-Click system of retail influenced a new style of movie consumption, one that would spawn companies like Netflix in 2010 – though streaming technologies hadn’t yet caught up to market demands.

Apple would become the only company to license Amazon’s technology. US Patent 5960411A would help Amazon to nearly two decades of unfettered growth. That patent would expire in 2017. By that year, nearly half of all online retail volume in America was completed through Amazon.com and its affiliates. Consumers are willing to set aside cost for ease of purchase. Amazon was the first to prove this; Apple may have been the second.

Chaos Theory Revisited

Others, including Amazon competitors, have already noticed the 1-Click patent’s expiration. Last year, a group of companies in the alliance known as the World Wide Web Consortium, including Apple, Facebook and American Express, started working on standards to implement one-click purchasing. Google is also reportedly working on a one-click payment solution. [3]

Amazon’s innovations influenced an unforeseen number of industry advancements. With 1-Click commerce in the public domain, new upstarts like Fast join technology’s giants in building independent solutions to bolster the adoption of frictionless commerce. Apple Pay has seen wide adoption. Shopify Pay was a star of the most recent holiday season, garnering praise from the vendors who benefited from frictionless payments. This dizzying pace of innovation is the result of a technology that’s been locked away about for nearly 20 years.

Until recently, Amazon’s patents prevented wide use. Amazon’s 1998 lawsuit against Barnes & Noble is a persisting example of why few companies test Bezos knack for IP litigation.

Amazon started using one-click technology in September 1997, but did not receive a patent for it until Sept. 28 this year. Barnesandnoble has offered “Express Lane,” its one-click checkout, since the spring of 1998. “The one-click feature is one of Amazon.com’s signature strategies for differentiating itself from the competition and building loyalty among its customers,” Amazon wrote in its complaint. [4]

In 2000, then-students Erik Brynjolfsson and Michael D. Smith identified this in a case study written for MIT’s Sloan School of Management. Pricing rationality matters less when ease-driven loyalty is at the forefront of the consumer’s mind.

A direct prediction of these models then is the retailer with the lowest prices should have the highest proportion of sales since it will get sales from all the informed consumers in addition to its “share” of the uninformed consumers. However, this prediction is not supported by our data. Amazon.com is the undisputed leader in online book sales, and yet is far from the leader in having lower prices. [5]

To this end, a solution for the reduction of bottom-funnel friction recently launched. And it may be the most fluid of them all. “Ten years ago today, I was packing boxes.” Gary Vaynerchuk will go on record as saying that he isn’t very smart. Don’t let him fool you. In 1998, at the onset of his early days of growing his family’s online business, his team built one of the first iterations of an automated cart abandonment recovery. Unfortunately, he didn’t file a patent for that process – a tool that is now common throughout cloud-based carts like Shopify, BigCommerce, Adobe, and SalesForce Commerce Cloud.

Polymathic Audio No. 3: Gary Vaynerchuk

In 1998, Wine Library was grossing nearly $3 million annually. By 2011, that figure inched toward $67 million in annual sales. Vaynerchuk didn’t accept any outside investment to get to that point, a remarkable note when you consider the constraints of cash flow-driven growth. That same year, he stepped down from the family business to build VaynerMedia. When Vaynerchuk and I spoke with 2PM for Polymathic, he relayed a recent story of his father reaching out to him and asking for him to come back to the Vaynerchuk family’s original business and course-correct a company that had halved in size since Gary’s departure. Deterministic chaos: the solution that Gary executed may end up becoming another proverbial butterfly over the Amazon.

2PM-SMS-Commerce

To solve the problem for Wine Library, Vaynerchuk recruited some help from his VaynerMedia team. The result was WineText, an SMS-based marketing and commerce channel. The user begins by signing up on the homepage, providing a few key details: name, address, phone number, and payment data. Like Amazon’s 1-Click system, WineText saves users’ credit cards with the help of Stripe. Powered by Twilio, Vaynerchuk and team can send a daily deal to the list at a cost of anywhere between $240 and $360 per text. According to Vaynerchuk, the SMS list of nearly 9,000 customers consistently outperforms Wine Library’s email list of 400,000 by a magnitude of 9x. And here’s why.

WineText opt-in grants Vaynerchuk access to your phone number. On occasion, a customer will receive an SMS prompt with a “high value wine offer.” Users have up to ten minutes to respond to the text with the number of bottles requested. That number of bottles is at your door within 48 hours of shipping. The top-of-funnel friction removes all bottom-funnel checkout thinking. It makes a commerce decision reflexive.

To accomplish this, WineText built a native checkout solution to account for Shopify’s native restrictions with respect to stored credit cards. For those who are interested, there is a way around it according to Postscript Co-Founder and President Alex Beller:

One way around this for more mainstream merchants who want to allow customers to buy in-message is using Postscript + Recharge + Shopify. Recharge allows for that sort of open access to credit cards of saved customers.

Beller added:

All brands should not jump on this bandwagon. However, any brand with subscriptions, natural reorder cycles, or drop strategies should lean in here. Engagement rates are too high to ignore.

As more retail operators become aware of the technology stack implemented by Vaynerchuk and team, WineText-like services will become more common. There are no patents to protect it. Amazon’s innovation indirectly impacted the streaming industry that exists today. Just as eCommerce patents changed music forever, you have to consider unrelated industries that will thrive with frictionless commerce.

Chaos Elsewhere

The Action Network, created by the Chernin Group in 2017, has an app where gamblers can track their bets across sportsbooks. It’s also using in-depth stats and analysis to draw in bettors, and has been striking content and other deals with companies like Yahoo Sports, Nascar, PointsBet, William Hill, and DraftKings, to expand its footprint. [6]

In a conversation with Action Network’s Darren Rovell, I mentioned how 1-Click technology could impact publisher-driven betting. Rovell remains skeptical that a media platform could vertically integrate in such a way. When asked if Action Network would ever facilitate live bets, the industry veteran responded:

Facilitate? Yes. Click on our platform and it clicks to a [sports] book. Or bet with a book and you can track the progress with us. But, as of now, it’s not in our best interest to be an operator.

But in the analogy of the butterfly’s flight over the Amazon, all signs point to the intersection of media, commerce, and legalized gambling as the next major disruption in consumer media. Platforms like Barstool Bets, theScore, FanDuel, Draft Kings, B/R Sports Odds, and others are positioning to move beyond informing wagers by partnering with sports books to facilitate end to end commerce. They’ll eventually want users to place bets, natively.

In the past, people would read articles or watch videos on these publishers’ properties that would inform the bets they make elsewhere. But with sports betting becoming more widely legal, publishers can close that gap — and turn this into a revenue stream for themselves. “Our whole philosophy is if we do it right and give people an opportunity to bet within theScore, they’re not going to go elsewhere,” said John Levy, CEO of theScore. [7]

Frictionless commerce will define the next ten years of mid-market, online retail in North America. As it does, savvy commerce architecture will find its way to other industries once again. Legalized gambling appears ripe for this sort of disruption. Publishers want to shorten the distance between “finding your line” and you acting on it. What was once an industry built on publishing data and insights will become one where users can act with one click of a button. If there is one thing that we’ve learned from Napster, Amazon, Apple, and the streaming economy: ease of use is the safest bet.

Research and Report by Web Smith | About 2PM