Today’s conversation: Kristin Heitman, CRO of The Associated Press, discusses how the AP’s model is shifting from primarily licensing to news publishers to tech companies. Apple | Spotify
On PvA: We unpacked Sam Altman’s code-red moment, the deal-guy takeover of tech and politics, and Troy’s case that the only thing that matters in media now is leverage. Apple | Spotify | YouTube
TRB Backchannel: I’m adding an option to receive SMS updates from me. These will be limited to 3-4 a day and focused on what I’m hearing and seeing, as well as weekly requests for input as I craft my stories and prepare for conversations. I’m doing this through Subtext, and the part I like most is that this is interactive but not like a group text. I’ll be responding to as many texts as I can. Upgrade to TRB Pro
AI is rewriting the rules of content discovery
Search traffic is falling, visibility is shrinking, and publishers are being forced to rethink how audiences find and engage with their content. Navigating the AI Traffic Cliff: The Publisher Playbook is your guide for adapting to this new reality. Built for publishing executives, audience strategists, and revenue leaders, this guide unpacks how AI-driven search, content summarization, and recommendation engines are reshaping the media ecosystem—and how smart publishers are responding.
The Associated Press is increasingly a content supplier to tech
The AP is quietly becoming a core supplier to the AI economy. I talk with Kristin Heitman, the Associated Press CRO, about how a 178-year-old cooperative built on serving newspapers is pivoting to a business where newspapers now account for under 10 percent of revenue and tech companies already make up 15–20 percent, with that share expected to double over the next few years. We get into how AP prices its data, why recency has become the new battleground, the long-tail demand from companies building their own models, and what this shift signals for the future of licensing across the media industry.
Newsweek is making the move to beehiiv
Why is an industry leader like Newsweek migrating their newsletter program to beehiiv? Let’s get it straight from the source: "We needed to be able to run newsletters as its own business within Newsweek, and a platform like beehiiv gives us more capabilities and opportunities to monetize those newsletters," said Bharat Krish, Chief Product Officer at Newsweek.
beehiiv’s ecosystem of tools is core to their ambitious growth plans, as they look to scale their flagship Bulletin newsletter while launching new subscriptions. Krish added, "I'm excited about partnering with a team that's tech-first and has an entrepreneurial mindset." Keep an eye out for Newsweek’s partnership with beehiiv launching in mid-December, and learn more about working with beehiiv here.
Deal Guys
This is the golden age of deal guys.
A lawyer and consummate Deal Guy, David Zaslav will go on the Deal Guy Rushmore for his maneuvering the Warner Bros “assets” into a position where it’s in the midst of a political tug of war between Netflix and Paramount, with no less than the Deal Guy in Chief as arbiter.
The hostile bid was to be expected from Larry and David Ellison, a father-and-son Deal Guy duo. Larry has positioned himself as a main beneficiary of the AI gold rush by cutting the kinds of picks and shovels deals that Deal Guys always do in manias. The experience of the Dot Com days are weirdly relevant again with the echoes of that time of Deal Guys who flooded Silicon Valley to cut roundtrip deals that gave dot-com businesses the appearance of growth by trading revenue.
In Silicon Valley’s narrative, the end of the dot-com bubble flushed out the Deal Guys. Of course, the Deal Guys never truly go away. They just go into waiting for the next burst of entrepreneurial enthusiasm.
We are wired to worship the entrepreneur, who made something from nothing, particularly the builder archetype that Elon Musk represents. Deal Guys are not that. Zaslav’s place on the Deal Guy Rushmore notwithstanding, Deal Guys are not culturally awarded the same kind of laurels as builders. That’s appropriate. Life is full of tradeoffs. Deal Guys tend to get fabulously wealthy by extracting fees and financializing assets.
In the makers vs takers matrix, Deal Guys are on the taker side. Anonymous Banker, who is a Deal Guy, noted to me that part of the problem of Deal Guys is the value created is opaque. Did Zaslav steer Warner Bros to this outcome because he’s just that good as dealmaker, or was he mostly the beneficiary of a happy set of circumstances? The answer is likely yes. Deal Guys understand you make enough bets, some are going to generate fabulous returns, and you’ll just focus on those as proof of your derring do and ignore all the other duds.
So Deal Guys deserve their due. AI to date has been as much about deals as it is about tech. Silicon Valley has spent the past week huffing and puffing at The New York Times for daring to question the ethics of its embedded Deal Guy in the White House, David Sacks. The argument is it’s better to have a Valley Deal Guy to oversee policies like the sale of advanced chips to China than a run of the mill DC lawyer or, God forbid, an accomplished academic.
Deal Guys are market participants but frequently not principals. Venture capitalists are consummate Deal Guys. Some have made things in the past, but increasingly many skip that step and go from being a product manager to dealmaker. They need to know the market, the forces shaping it, and the players in it. Deal Guys are frequently in the services business.
(To be clear, Deal Guy isn’t gendered; it just sounds better than Dealmaker or Deal Person.)
Needless to say, this administration is run by a particular type of Deal Guy: New York City Real Estate Deal Guy. Trump fancies himself a builder but is truly a Deal Guy. His feral instinct gravitates to leverage. And so it’s no surprise that when the Ellisons urged him to intervene prior to the Netflix offer on their behalf that Trump demurred. Why not let the show play out? This just means more drama, tension and, yes, dealmaking.
Deal Guys are easy targets. Zaslav’s oversized compensation has long made him a source of derision.
Like them or not, Deal Guys are necessary for well functioning markets. Troy reminds me they’re “artists” of sorts. I’m not going that far, but they’re needed participants because markets always have opacity that must be instrumentalized. In marketplaces, value tends to accrue at the dealmaking layer. Art Basel is not for artists.
The downside of the ascent of Deal Guys is that inevitably makers are losers. Hollywood makers don’t have many good choices in this situation. Netflix is hostile to key parts of the Hollywood model, with notably little nostalgia for theater windowing and unions, while Paramount positions itself as a champion of creatives but also carries the baggage of being regime-aligned. The deal leaves CNN in flux, as it has been for years now.
Media reporters love Deal Guys. The prospect of a drawn-out dealmaker fight is like a stimulus package for media reporters. Candid text messages between Deal Guys – typos are a flex – are a welcome respite from more Olivia Nuzzi revelations.
A drawn-out battle will also carry a whiff of nostalgia for the days of swashbuckling media Deal Guys like John Malone, Gerry Levin, Barry Diller and Ted Turner. That level of media Deal Guy is fading. David Ellison is a nepobaby Deal Guy who brings his dad to negotiations. I can’t see any of the Highwaymen doing that. It’s the Deal Guy equivalent of those viral stories of Gen Z bringing their moms to job interviews.
OpenAI is fascinating character in the AI drama. Sam Altman is a classic Deal Guy. He’s maniacally cutting deals left and right for compute. He managed to squeeze in a joint venture with Thrive Holdings to build vertical AI services and to explore a sidequest of taking his quarrel with Elon Musk to space. His dealmaking rubs many the wrong way. See Elon Musk frequently calling him a snake and how he’s alienated many of the key technical employees who actually built ChatGPT.
The problem with the dealmaking ethos is it isn’t the same as the builder ethos. And Altman’s Code Red means a return to focusing on the building part. OpenAI has lost its technical advantage to Google, and is faced with Google’s disproportionate distribution advantage. Time to Build, Sam; the deals can wait.
Meanwhile, large publishers are looking to their own Deal Guys to wring as much as possible from AI companies. The sting of the wholesale theft of content to build these engines will not go away, but in the meantimes, there’s at least Perplexity to sue. This week, The New York Times joined other publishers in suing publishers favorite boogeyman, notorious for finding ways around efforts to block its crawlers. But let’s be real: Perplexity is also an easy target.
Publishers are in dealmaking mode and deep down they want a deal with OpenAI. Think about it: They see Open AI Deal Guy in Chief Sam Altman making outlandish commitments for compute, so why not wet their beaks? And with Google, the tough guy act only goes so far. Give Google’s Deal Guys credit. They made sure Google didn’t create different crawlers for search and AI, giving publishers no choice but to allow it to continue to slurp their content. They can’t turn off traffic from Google. This kind of brazen use of market dominance would be harder to pull off without a government of dealmakers that are disinclined to intervene, particularly on behalf of the so-called Enemies of the People.
Meta is the latest tech company to cut licensing deals with large publishers. The devil is in the details of these deals. The optimistic scenario is that we will continue to see model parity as models commoditize. That, and the explosion of the kind of app layer, creates the demand for content differentiation. On the consumer side, there will be a marketing advantage to being the model with access to the most important information brands. This is an insider game, of course. The small-scale publisher does not have a Deal Guy with a line to these companies.
Deal Guys will also pick over distressed media. The SEO glue factory will continue operating in 2026, as these “assets” are aggregated and wrung for value. The logic of these deals is never to build new value by standing up an events franchise or new expressions of IP, it’s to cut the making costs and wring value from the carcass. It’s important for Deal Guys not to be sentimental. A civilian sees an asset like AOL as irrelevant in 2025, a Deal Guy sees an annuity of free cash flow and a stable business of selling old people antivirus software they don’t need and likely will never even use when they call customer services to change their AOL password.
I’d argue a healthier media ecosystem and overall society would be for Deal Guys to have less influence. Musk is not without his sins, but there’s a clarity in his advice to build things. There’s a palpable feeling that the West is losing to China. The Economist now doesn’t ask if China will take over a sector; it wonders which it will swamp next. One root cause: The decisionmakers in China are far more likely to be engineers than lawyers (original deal guys) as in the American system
The future of media will not be shaped but not written by Deal Guys. The dealmaking is premised on value discovery, not on creating new value. That will be done, as it always is, on the edges by those who will make new forms of media that create new value.
I like to be a sponsorship Deal Guys, so get in touch to discuss how The Rebooting partners with brands like EX.CO and Beehiiv. See how The Rebooting works with partners.