Fork in the road

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In today’s members piece, I dig into an essential question for successful independent content creators: Do you build an institutional brand or stay solo? First some things that have caught my attention and point to how the media ecosystem is evolving. Sign up for TRB Pro for $20 a month.

Is “the media” in the U.S. now more right-leaning? The first White House press conference was meant as a symbolic shift in power with the introduction of seats for “new media,” only for Axios co-founder and longtime Washington journalist Mike Allen to occupy the chair. That said, the power of right-aligned publications like The Free Press and Daily Wire has risen, along with the explosion of alternative media and the manosphere, to the point that Allen’s fellow Axios co-founder Jim VandeHei believes that “the media ecosystem favors the right more than the left.” 

Deep Research and the parade of agents. This is the year of AI agents, as the action (and hyperventilation) moves from doing Q&As with chatbots to agents taking actions. They will be clunky initially, of course, but you can be sure they begin with information retrieval vs transactions. OpenAI’s newest agent, Deep Research, is a similar product to Google Gemini Advanced Deep Research. It can create research reports on requested topics. Already, Goldman Sachs CEO David Solomon believes AI can do 95% of an IPO filing that would take up the days and nights of nicely paid research analysts. Much of this points to AI tools moving upstream from cognitive manual labor to more substantive knowledge work. “These systems are already capable of performing work that once required teams of highly-paid experts or specialized consultancies,” Ethan Mollick writes in One Useful Thing. 

The AI Super Bowl. It might not rival the (in)famous dot-com Super Bowl, which starred the Pets.com sock puppet, but this year’s Super Bowl will see a parade of AI commercials. OpenAI scrounged up the $7 million per 30-second spot. The Super Bowl is the last area of traditional media that has not seen compression in ad rates. OpenAI’s foray makes sense as it becomes more of an apps company, and the action in AI finally moves from the infrastructure phase to actual usefulness. Imagine. It’s a unique marketing challenge since the technology has arrived with plenty of fear of everything from mass unemployment to ending the world. Much of that has been fanned by OpenAI and others with vested interest in AI being seen as the most consequential human advancement since fire. 

Musk’s X turnaround is working. Like his approach or not, Elon Musk delivers. After tanking Twitter’s business, he’s now turned it around to the point where it delivered $1.25 billion in EBITDA last year. Its value, however, is even greater than its cashflow, since Musk has used his ownership to expand his power (and therefore value in his companies) and used X as leverage to build his xAI company that’s been valued at $50 billion. The success will further validate the deep cuts Musk enacted and embolden the fast followers of Corporate America to continue slimming down their operations.

Lessons learned from alternative media. Last week, we held an online forum with Newsweek chief product officer Bharat Krishna and Viafoura CEO Mark Zohar to dig into the ways institutional media can compete with alternative media. One of the biggest ways: Take steps to shift the audience to participation See the replay. 

Adam Ryan, CEO of Workweek, weighed in on Tuesday’s “publishing’s original sin” piece with the perspective that media is still an influence game. Reach still matters, although it is hardly sufficient and only in the service of influence.

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The recent Semafor Media podcast had a conversation with Kara Swisher, who has built a tidy business around Kara Swisher. She and her partner Scott Galloway are shopping around their podcast, Pivot, and expecting a big pay day. 

She and Galloway are prime examples of independent content creators that face the choice of using their personal brands as leverage to build a bigger enterprise or continue down the lucrative path of staying mostly solo. Galloway has said Pivot alone generates $10 million in annual revenue. Swisher says she makes “many millions of dollars” a year. The costs are very low.

The fork in the road for these types of businesses built around individuals is whether to build out an institutional brand, with added costs and headaches but also bigger potential upside, or stay lean and  highly profitable without as much long-term equity value.

In the 20102, this choice was typically to build an institutional brand. This was the path that Swisher took with her All Things D partner Walt Mossberg when they split off from News Corp in 2014, raised money and launched Recode. That didn’t pan out, and perhaps the experience soured her on the prospect of doing it all over again. Running a company means more of your time and focus will be spent elsewhere. 

Bill Simmons was possibly the most successful at this path. He split from ESPN in 2015, and used his own star power to build The Ringer. The reach of his own podcast enabled him to push audiences to others in The Ringer cinematic universe. Critically, Simmons has proven to be a good judge of talent. Spotify’s  $200 million deal to buy The Ringer in 2020 was validation of this approach. 

Similarly, Dave Portnoy in many ways pioneered this approach by being the Main Character of the Barstool Cinematic Universe while assembling a supporting cast of characters that have produced several breakout stars like Pat McAfee, Big Cat and Alex Cooper. Barstool hasn’t kept all of them, but its hit record is testament also to Portnoy’s ability to attract talent. Barstool’s massive exit to Penn and Portnoy’s subsequent re-acquisition of the asset for $1 is a testament to his business acumen. That’s a rare combination. As Swisher noted, most journalists should stay put because they’re not about the far-from-glamorous aspects of the entrepreneurial life.

But this does not always pan out. Consider 538, which took a similar approach when Nate Silver left his perch at The New York Times in 2013. Silver hired a news team that would take his data-focused approach to politics and news and expand it. 538 never outgrew Silver’s shadow and floundered at ESPN and then ABC News before being gutted as Silver departed. Now, as a solo Substacker, I’d argue he’s more at home – and producing more interesting content, possibly because he's not spending as much time in corporate meetings. The Silver Bulletin has 271,000 subscribers on Substack.

There are many tradeoffs that face independent creators when deciding the direction they take after they achieve traction. Staying solo has tremendous financial leverage, as evidenced by Swisher’s bonanza. This is something of a turnabout. When selling Recode to Vox Media in 2015, Swisher pointed to the inability to compete with massive platforms. “Being a smaller fish is really hard,” she said.

The opposite is now true. Thanks to the maturation of platforms like YouTube, the emergence of Substack and the shift from institutional brands to individuals, being a smaller fish in media is safer. (Nothing is easy; this is media.)

Digital media has decentralized and intensely fragmented. In such an environment, the leverage of scale became mostly an albatross. The success of Substack has shown that staying solo and small has far more short-term leverage than adding tons of costs. I’m still somewhat surprised more breakout solo people haven’t built bigger teams. 

As Swisher told Semafor, much of that comes down to what people want to spend their time doing. I found it noteworthy that Kara noted the goal of having no employees. Building out teams and infrastructure requires a lot of time, energy and focus. She envies the Ben Thompson model: “He gets to do what he wants, and he makes a good living doing it.”

This approach is indicative of how these businesses are created by the people making the product as opposed to “operators.” The operator mindset and skillset goes to scaling and inevitably exits. I had a conversation recently with a successful operator who was surprised I hadn’t hired an editorial team, gone hard at events and basically replicated the Digiday model. That strikes me as both less exciting personally and unattractive to build the old models when the media ecosystem is changing so quickly.

The Free Press and The Ankler are somewhat exceptions by taking the throwback approach. Both have raised money and seen success as expanded enterprises that look a lot like regular institutional media brands with some alternative media fumes. The Free Press has emerged as a leading new brand in the political influence sector. The Ankler has expanded into covering the creator economy and taken the shape of a Hollywood trade, attempting to break the stranglehold Jay Penske has established on that market.

This approach sacrifices short-term leverage for long term value. Building a business around yourself means the business does not have much or any equity value. It can’t function without you. Mr. Beast goes to zero if something befalls Jimmy Donaldson. These businesses are not tradable assets. 

Instead, I suspect a middle ground will emerge. Swisher and Galloway have done a masterful job of linking with bigger companies to get access to their infrastructure and distribution channels while maintaining their autonomy, although they do not own the Pivot brand. Institutional media companies are more amenable to these kinds of partnerships where they sacrifice control since the leverage has swung toward individual talent.  

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