The Rebooting Show

Stagwell CEO Mark Penn is a veteran of politics. In this discussion, he examines how shifting audience behaviors and trust patterns are reshaping where Americans get their news. The conversation delves into the thorny challenges of advertising on news content and why brand safety concerns are usually overblown. Penn outlines how news organizations can build sustainable businesses by adopting lessons from political campaigns, while warning that chasing ideological audiences risks further eroding media's broader cultural influence.

AI-powered search engines have clawed a foothold in the critical search market that controls distribution on the open web. Media management consuling firm Activate estimates 15 million people are using these answer engines rather than Google, which is adding AI summarization to its results. By 2028, Activate expects that to rise to 36 million. The open question is whether publishers can stem this tide.

Michael Wolf, the CEO of Activate, sees a fundamental shift in the search market, as generative AI can currently handle about 40% of searches as an open web discovery tool. He expects the rest of searches will follow suit over the next five years as the fundamental nature of the open web changes. This will lead to search becoming the front end to what Wolf calls "gated web discovery" and eventually "discovery-led transactions."

Blockworks CEO Jason Yanowitz discusses how Blockworks has evolved the company from an events business to podcast network to news provider to becoming a data and information play with media, events and franchises feeding the core data and research business. This kind of shift is hard to pull off. Among the issues we discuss:

1. Using podcasts for broad reach and affinity
2. News as a credibility driver
3. Pulling back on B2C events to focus on B2B
4. Using media to drive “negative CAC” for information services
5. Implementing a “house of brands” strategy

Defector Media, the sports and culture publication launched four years ago by former Deadspin writers, is an example of the mixed picture for the future of the media business. On the plus side, it is a profitable, employee-owned publication with 42,500 paying subscribers supporting a $4.6 million business. At the same time, the company saw revenue growth drop to 2.2% from 18% last year and 16% in 2022.

Defector's Jasper Wang joined me to discuss Defector’s plans to expand its ad revenue, the inevitable challenges of fast decisionmaking in an employee-owned business, the “lean stack” approach of outsourcing as many publishing and corporate functions as possible, and the growth of its Normal Gossip podcast and diversification of Defector’s audience.

I was joined by Reid DeRamus to discuss the strategic and tactical decisions that go into building an independent media business. We discuss everything from choosing a business model, using the leverage of individual reputation, the value of consistency and authenticity, the mistake of over-reliance on optimization techniques, and the challenge of growth as tried-and-true methods wane in efficacy.

In this Spotlight episode, Josh Brandau, CEO of The Rebooting partner Nota, discusses how AI can be a critical tool for newsrooms in a more-with-less era. osh is a publishing veteran having been CRO and CMO at the Los Angeles Times. That informed his decision to create Nota since like other publishers he saw legacy media struggling to adopt technologies that underpin sustainable businesses. 

We discuss the inefficiencies inherent in a lot of newsrooms that end up taking scarce resources away from the actual news reporting, and how tasks like versioning, content optimization, SEO and tagging can be sped along with an AI assist.

We also take a big picture view of where journalism goes in an AI world, licensing as a growing revenue source and how AI could create other new revenue streams as publishers inevitably move beyond efficiency and begin to create new products that improve the customer experience.

Fitt Insider, a media brand for the fitness and wellness industry, is a good example of the type of media brand that hits on many of the current trends in the industry:

• Niche. The fitness and broader wellness industry is a growing area that will only expand.
• B2B.  The most robust media models are B2B or targeting influential audiences with similar approaches.
• Direct. Fitt relies on podcasts for engagement and its 100,000 email subscriber list for audience data and a direct connection. 
• Organic. Too many newsletters are growth hacked. Fitt Insider has traded slower growth for a quality list that has open rates near 75%.
• Expertise. Fitt Insider’s founders, Anthony and Joe Venare, are fitness industry experts, having owned gyms and invested in the space.
• Media flywheel. The best media models tend to make most of their money in media-adjacent areas. For Fitt, this is through its recruiting and consulting arms.

Anthony Vennare joined me on The Rebooting Show to break down the Fitt Insider model, and how he views media more expansively. That’s led him to forgo the typical ads and marketing heavy approaches to monetization. 

This week, I was joined by one of my favorite media entrepreneurs, Adam White. Adam has built Front Office Sports from a college project to the $10 million in revenue mark, with backing from Jeff Zucker's Redbird IMI.

Some of the topics we covered:

• Why investing in creative strategy is critical to break through with big brands.
• The “faces and franchises” approach.
• The limits of built-if-sold projects.
• The decision to put off subscriptions.

Adam Mendelsohn operates at the nexus of sports, media, business and culture. Adam is a longtime advisor to LeBron James and his business partner Maverick Carter. He’s a communications advisor to many athletes and companies. And he’s recently rolled out his own sports platform, OffBall, which is something of a throwback to a pre-algorithmic era where Drudge report and other curators reigned supreme.

We discussed:

• The genesis and vision behind OffBall, a new sports media venture
• The long-term impact of "The Decision" on sports media and athlete communications
• The shift towards human curation in content discovery
• The evolving landscape of sports journalism and brand partnerships
• The rise of women's sports and international leagues in the U.S. market
• The importance of storytelling and character development in sports media

This week marks an important moment in the history of digital advertising as the U.S. Department of Justice presses its case that Google is a monopolist in ad tech. 

The seeds of this case were planted in 2007, when Google bought DoubleClick, a critical piece of internet advertising infrastructure that was widely used by advertisers and publishers in running ad campaigns. With DoubleClick in the fold, Google methodically grew to dominate all phases of digital advertising by piecing together a full stack solution for ad tech, supplying the tools used to both buy and sell ads as well as the exchange used for transacting. And Google was the biggest source of demand for the exchange. The go-to comparison of this situation is if Goldman Sachs owned the New York Stock Exchange.

On this week’s episode of The Rebooting Show, I spoke to Ari Paparo, a former DoubleClick executive and ad tech veteran who now runs Marketecture. Ari, in addition to being the funniest person in ad tech, knows the history. We go back in time to when the Google-DoubleClick deal took place, just as programmatic advertising was becoming a reality, and get into the weeds about why controlling the plumbing of digital advertising created an unavoidable set of misaligned incentives.