Memo: A Five Year Reflection

The writing of this memo shared a day with a podcast conversation with Bradley Tusk, the former campaign manager for Michael Bloomberg’s third mayoral campaign and political acolyte. Tusk is the co-founder and Managing Partner of Tusk Venture Partners, a New York venture capital firm that notes:

TVP invests in early-stage technology startups operating in heavily regulated markets, or creating new business models where no regulatory framework exists.

As I write this, one of the most substantive articles written about 2PM and its mission is just days old. Written by Sherrell Dorsey, Annaliese Griffin, and Rachel Jepsen: the essay encapsulates where 2PM is today.

One of the most compelling aspects of 2PM is the deft way Smith mingles deep data sets with historical narrative context, using thrice-weekly essays to explain not just what Americans are consuming, but how and why. He’s as much a sociologist as a trend forecaster. Smith has a way of moving seamlessly from retail and entrepreneurship, to access to capital and real estate, to the social forces, particularly race, that shape the market. A conversation with him might leap from retail square footage in the U.S. to Brown v. Board of Education to the current pandemic. Makes you understand why he chose the name “2PM” — “to polymaths.” [1]

The business of 2PM has long evolved since the first newsletter was mailed to a testing group of 12 (yes, twelve) friends in October of 2015. But this isn’t about the business of newsletters, this is about the content – itself. As the time and research devoted to publishing these letters increased over time (thanks to the growth in subscription revenue), so did the depth of discoveries made. This led to a slight revision of the company’s stance on matters of socio-economic and socio-political significance. I’ll explain.

The idea for 2PM came about while seated in the conference room of Gear Patrol, my former employer. There, I served as its head of eCommerce operations. Many of these commerce strategies were in place elsewhere: Hodinkee, Uncrate, and Barstool Sports already maintained robust commerce operations. At the time, I was taking a break for the world of direct-to-consumer brand development. By building online retail capabilities into the strategy at the now-Hearst owned publication, I was able to understand how media and commerce established a new playing field. But it was another revelation that set me off on this path.

2PM was designed to drill down on matters of digital industries.

The autumn of 2015 was a tumultuous one for American media. The upcoming Presidential election of 2016 meant that the vast majority of publishers found new angles to publish issues related to the game-changing election. As you know, it was an election that pitted the first-ever female nominee of a major party and a reality television star turned political firebrand. And every last publisher wanted in on the traffic. It was a field day for a lot of the venture-backed media companies who – like the New York Times – positioned the coverage to ride the wave of the most captivating elections in recent history.

Overheard in that very conference room, that day: “Is there an angle for us to cover this election?” No matter the area of interest, media sought to devote resources to topics in and around the arena of politics. The result was that industry-driven insights, stories, and reports grew harder and harder to find. Gear Patrol chose not to, but the idea was set. I found myself lagging in my work, unable to see the industry as a whole. I was tied to the minutiae and unable to guide the company’s next steps. The idea for my newsletter was born; I believed that by studying a cross section of industries, belief systems, and sciences – you would become better prepared to lead your own operation. 2PM was designed to drill down on matters of digital industries. To facilitate this format of curation, I avoided discussing matters that could be perceived as political. I wanted none of it.

On the eve of the beginning of the newsletter’s fifth year, a reader will be hard pressed to find references to party politics throughout 2PM’s archives. I am slow to explain developments by pointing to the happenings of news cycles, a skill that is aptly performed by Ben Thompson. But the essays have certainly evolved. There’s good reason that a former political operative like Bradley Tusk has taken an interest in writings like Sanitized Urbanization. Or why the landmark case on school desegregation Brown vs.The Board of Education is referenced by The Plug‘s Sherrell Dorsey in the context of the essay on the acceleration of malls: in The Ballad of Victor Gruen, I explained America’s journey to over-retail by pointing to the commercial tax incentives that succeeded this landmark decision. The United States saw one mall turn into 25 in just two years. In the decade that followed, 25 malls became 1,000. America’s resegregation was the culprit. Is that political? It shouldn’t be – it’s merely the correct analysis. A more recent example explores recent educational shifts and the potential of long-term impairment of our consumer economy.

The key to middle-class growth has been the pursuit of the aspirational American Dream. A family makes a good living, their children go to good schools, those students are afforded better experiences that provide a ladder to an even better life. Between 1945 and the close of the 1970s, this approach provided a virtuous cycle that served as the basis for the golden age in middle-class economics.[1]

While far from political in the contemporary sense, 2PM has not shied away from the impact of socio-politics on our industries, our realities, and the innovations that accelerates those trends or upends them altogether. What I have come to learn is that there is an incredible advantage to viewing today’s industries outside of the narrow scope that typically constrains their narratives. 2PM will always include the practical sciences of commerce. But the higher you are in leadership, the less that practical knowledge determines outcomes. There are always other forces to consider.

And with this revelation, yes, 2PM has evolved greatly from the first public issue [2] in March of 2016. By setting the expectation that I’d omit all mention of American politics, the readership suffered by way of incomplete data and shallower insights. The great literary giant Thomas Mann once quipped, “Everything is politics.” This is an over-simplification. Any decision that involves human nature can be perceived as politics. But relaying the role of policy, human nature, and the sociological impact of our history of decisions are far from political. Rather, those elements complete the context. They paint the entire picture.

I believe that this style better prepares the industrialist by shedding light on the past, contextualizing the present, and providing forecast to the future. The readers of 2PM, today, are much better prepared for it. Here’s to another five years and the discoveries that will come.

By Web Smith | Editor: Grace Clarke | About 2PM 

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Memo: The Public / Private Linear Play

They did what? I was sitting in the office with a small group of investors when the news crossed the wire: The Chernin Group completed a deal to sell a majority of Barstool Sports to Penn Gaming. The room was astonished. Chernin had taken an ill-advised chance in betting on the controversial media company in a 2016 deal that turned out to be one of the smartest private market media deals in recent history. The irony of the moment was that no one in traditional venture capital would have risked their limited partners’ capital on Dave Portnoy and his band of characters. But quietly, many investors wished they had. The Penn deal didn’t make sense to many in that room. Why so early?

A 2017 essay by investor, media personality, and author Anthony Pompliano opened with the assessment that “Barstool Sports is building the most valuable media company in the world.” Pompliano, who spent time assessing the startup’s role in sports media, concluded the essay with the following:

I just hope that [Portnoy] doesn’t get scared and sell the company too early because he can’t handle true greatness. [1]

It remains to be seen whether or not Chernin Group’s sale of Barstool, coming three years after this essay, was too early. But the result was one of the most fascinating turnarounds of a legacy retailer in recent history, and the data suggests that Chernin may have pioneered a strategy that others will soon follow. Just seven months prior, Chernin invested in niche media company MeatEater, Inc. This deal enabled CEO Kevin Sloan to accelerate his company’s linear commerce strategy. The press release made it simple: The deal marks a major milestone in MeatEater’s plans to expand from content to commerce and builds on the longstanding relationship between MeatEater founder Steven Rinella and the First Lite team.

Over the summer, The Chernin Group poured $50 million of additional capital into the franchise, of which it’s a majority stakeholder. That money was used, in part, to make MeatEater’s first acquisition. The company acquired First Lite over the summer, a technical apparel brand that it has partnered with for years. [2]

But the Penn Gaming deal is different. It’s a public deal, one where value could be quantifiable in ways that you don’t find in private markets.

The Public / Private Linear Play

The Chernin Group has mastered linear commerce. If you’ve built a great product, you will need an organic and impassioned audience. And for companies that possess a captive audience, they’ll need products and services to support them. The digital economy rewards the companies that operate along the line that separates media and commerce.

Led by media giant Peter Chernin and Jesse Jacobs, The Chernin Group (TCG) has never been a traditional private equity firm. According to Portnoy, TCG was the only offer in 2016. Scouted by firm executive Mike Kerns, TCG helped to evolve Barstool from a simple cash flow positive operation among friends to a sophisticated operation led by former Yahoo Vice President and AOL Chief Marketer Erika Nardini.

Technically, TCG did sell Barstool early. But not too early. Given the company’s suitor, it didn’t seem that the Los Angeles-based investors seemed worried about the hasty timing. What they may have recognized is that Barstool’s value would create a wealth that even Penn Gaming couldn’t have predicted. With upside remaining (TCG still owns a stake in Barstool) and newly acquired stock in Penn Gaming – a publicly traded casino holding company – TCG created a unicorn asset out of a sports blog.

In finalizing this deal, TCG established a blueprint for a public/private linear commerce maneuver that we will see more of. Meanwhile, Penn’s stronger competitors are pursuing traditional partnerships to accomplish the same. This week, MGM announced a deal with actor, comedian, and musician Jamie Foxx in what traditional industrialists cited as a savvy move for the larger casino and hotel operator.

On Tuesday, BetMGM announced that Foxx agreed to star in their new advertising campaign, centered upon the invented claim that it’s the King of Sportsbooks. Possibly adopting from Budweiser’s “King of Beers” or maybe borrowing from their lion symbol meaning king of the jungle. Whatever the case, having Jamie Foxx on board will certainly get people’s attention and command respect.[3]

The BetMGM sportsbook is reflective of the shift towards gambling legalization, democratized for the internet commerce age by digital innovators like DraftKings and FanDuel. Many disagree with MGM’s insistence that Foxx’s impact will accomplish for the joint venture of MGM Resorts and GVC Holdings what Barstool accomplished for Penn Gaming.

No Title

I have bad news for BetMGM: Betters don’t care what Jamie Foxx things about sports gambling.They care what @stoolpresidente has to say. They care what @PatMcAfeeShow has to say. This will go down as an absolutely incredible waste of money. https://t.co/wJTr1B6dMv

Unlike MGM Resorts (which grossed $12.9 billion in 2019), you’ve likely never heard of Penn Gaming or a number of its institutions. With over 18,700 employees and a footprint across the Midwest and South, Penn Gaming owns and operates five raceways and casinos. In 2019, revenue exceeded $5.1 billion with an operating income of $500 million. The acquisition of Barstool Sports is at least partly responsible for taking the company’s market capitalization from a 1x multiple of top line revenue to a 2.5x multiple during one of the most unfortunate periods for sports in recent history. Penn Gaming revenue for the quarter ending on June 30 was $306 million, a 76.91% YoY decline. With the pandemic shutting down college and professional sports seasons, it was Barstool’s content factory that propped up the stock of a company starved for operational income from legalized vices.

At nearly 55 years old, Penn Gaming acquired a loyal audience and a digital-first future that will position it against the likes of DraftKings, FanDuel, and initiatives by William Hill, Fox Bet, BetRivers, PointsBet, and the aforementioned BetMGM. With the launch of Barstool Sportsbook in Pennsylvania, early signs pointed to its potential. The app led all others in sports betting downloads. Bank of America’s Shaun Kelley noted:

Our initial impressions are positive given the app’s ease of use and leverage of the Barstool brand to create a unique interactive experience. We think the app targets more of a casual bettor than competitors.

And this is where the value of Penn Gaming’s bet on Barstool Sports (and The Chernin Group’s bet on Penn Gaming) come into focus. As the legalization of sports betting continues to convert casual fans into gamblers, it will happen on a channel that Barstool is exceedingly better at than Penn Gaming’s competitors: the internet. But this $6.6 billion value add is more than a strategy for the gambling industry or sports as a whole.

The public/private linear play is the acquisition of an audience for a commerce-based company or the acquisition of a product for an audience-based company. We will see more of it as the Barstool Sports acquisition has proven that non-adjacent, private market acquisitions can have significant market moving power. The linear commerce strategy is not reserved for direct to consumer brands or influencer content. Even the oldest institutions can employ the strategy against their larger competitors. Penn Gaming has proven that. And in doing so, they’ve successfully hedged for a future that may become more digital than their industry is ready for.

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