Meet the New Boss
Boss vibes in the WH Press Room. Masculine energy. AI commodification. Espionage! How to pay for TikTok. Macaulay Culkin and Brenda Song do John and Yoko.
This week, a slightly nonlinear extrapolation of topics touched on in this week’s pod…
ON THE POD: Episode 119, Decentralized Work
The nature of work and careers is undergoing profound changes that are often obscured by debates over return-to-work mandates. This week we consider the rise of decentralized work that’s networked and elevates autonomy over outdated command and control approaches developed in a different century. Plus Deepseek’s cannonball into the Big Tech AI pool party.
Watch PvA on YouTube. Or listen on Apple | Spotify | other podcast platforms.
Out Friday AM.
The Influencer in Chief is metastasizing
TROY: I am not gonna take unnecessary pot shots at Karoline Leavitt looking like fascist Barbie. Her debut as youngest White House Press Secretary was impressive. It’s a tough job channelling boss Trump in front of a fretful, punch drunk press corps. Setting aside your affiliations, you gotta agree she commanded the room. The ordainment of a “new media” front row seat certainly caught my attention. As they did on the campaign trail, team Trump is itching to make room for “independent journalists, podcasters, social media influencers and content creators.”
As if tired ole media hasn’t been through enough, Leavitt added, “The Trump White House will speak to all media outlets and personalities, not just the legacy media who are seated in this room, because according to recent polling from Gallup, Americans’ trust in mass media has fallen to a record low.” You twits are not to be trusted! FWIW, the White House received 7500 applications in the first 24 hours.

One could interpret this as filling seats with flacks blindly loyal to the cause, amateurs unconstrained by the rigors of reporting and fact checking, etc. But I will be more open minded if for no other reason it will be fun to watch the shenanigans. Content! Heretofore, the press room had ritual and pecking order with national TV outlets, Reuters and AP securing top spots in front, receiving the lion share of air time. Leavitt fielded the first question from Axios, the second from Breitbart. Next time pole position may go to Libs of TikTok or @nonlibtake.
A topsy turvy press room mirrors a topsy turvy media world. The GOP press strategy is befuddling the left and accelerating change in a run down media ecosystem.

Also, useful reading from New York Mag… “The Cruel Kid’s Table” (“It’s Republican Coachella, and Donald Trump is our Beyoncé”).
BRIAN: The most important factor in taking a high-profile job is make sure the previous occupant was a stone-cold disaster. Leavitt can’t lose. Also, browbeating the press these days hardly takes much courage. The industry has no juice right now. Tina Brown gave a great interview describing how the media as being “a miserable, angst-ridden profession, where everybody sits there going on about ‘the business model’.” I feel seen.
Time to compete
BRIAN: I’ve been thinking more about Zuck’s masculine energy comment to Rogan. It was silly, of course. As we discussed, modern work is networked and requires a lot of collaboration skills more in tune with feminine energy.
What he was getting at is companies need to be more competitive or "aggressive" in his words to Joe Rogan. Making it gendered is dumb, but framing it around competition makes more sense. The underlying message from the tech’s rightward shift is that they let their companies get bloated and focused on tangential social issues. Leave aside these same profiles in courage were running these companies when they got bloated and focused on tangential social issues.
When you have monopolies, you can have luxury beliefs. Competition is what is needed, Emperor Zuck declares. This is ironic because Silicon Valley has avoided competition. Zuckerberg has been a master of that. He even bought an analytics service that would detect apps gaining traction so he could buy them before they threatened Facebook. Taking out instagram was a masterclass in avoiding competition. Much of the braying of the tech right against Lina Khan is about not wanting competition.
Well, competition doesn’t wait for an invitation. The Deepseek bombshell that a scrappy group of Chinese engineers built a comparable AI model with a fraction of the resources rattled markets and the oligarchs because it showed competition was not just coming, it was here.
And in the narcissism of small differences, the Chinese and Americans are good matches. America has been defined by competition. Any people formed by coming to a new land and conquering it are gonna have a competitive gene. I think that’s why Australians and South Africans are good at sports. The Chinese clearly love competing as they continue an overdue resurgence of one of the great civilizations of history. They have a chip on their shoulder, and export restrictions aren’t going to stop them from competing.
I have to say, although a member of Team USA, I find this admirable and impressive, more so than the ludicrous spectacle of OpenAI whining that Deepseek cheated by distilling OpenAI’s model that itself is built off “distilling” content of others without permission. Breathtaking shamelessness, even grading on a curve with this category.
I actually thought Trump had the right reaction. He called Deepseek a “wake up call.” Time to build is now time to compete.
And that brings me back to the masculine energy stuff. These companies are in the midst of getting fitter and more competitive. Google continues its cuts and is steamrolling over increasingly meek employee objections. The NYT reports that Meta employees are bringing tampons back to the men’s room. No walkouts like in 2020, when Zuckerberg skipped warning labels or taking down Trump posts about the George Floyd unrest. (Meta also agreed this week to pay Trump $25 million for kicking him off their platforms after the Jan. 6 riot at the Capitol. The inauguration spectacle was a power move by Trump but also by the oligarchs to their employees. Daddy’s home, I guess.
I wrote this week in The Rebooting about how publishers need to pick up on this and get more competitive. I try to fight the doomerism that always pervades this industry — really, I do — and learned helplessness is rarely a good strategy.
ALEX: The company is 2/3 male in an industry where meetings are dominated by war and sports analogies. I wonder if Zuck is now in the trenches setting up war rooms so he can rally the troops and create a game plan because DeepSeek has moved the goal post or whatever. There’s plenty of teenage boy energy at these companies.
I don’t think the lack of strong public response from employees is a sign of a cultural change but rather a combination of having less opportunities and more risk of retaliation. Sounds manly but mostly opportunistic as always. It follows Meta’s pattern of opportunistic pivots when things change. They’re exceptionally good at it and once again, scale and free cash flow really makes it hard to fail.
And maybe he’s learned that he’s more of a find the groove than make the groove guy. The last time they tried to set the agenda they changed their name and spent $45 billion to try and make us believe we’d spend our lives in the metaverse. Now, the pitch seems to be we should all be spending more time elbowing each other in the octagon.
TROY: I want to focus on the DeepSeek point a bit more. I love the irony of an AI company incensed that their IP is being ripped off by another callous AI aggregator. A Chinese one, no less.
That said, as Bloomberg’s Matt Levine points out, the case for IP appropriation with AI is not black and white. The AI brain is just reading our stuff and getting smart, just like humans do. It’s not the same as old fashioned IP theft. AI czar David Sacks and Sam Altman may paint this as nefarious Chinese espionage, but it seems a lot like standard silicon valley, gray-area, break-stuff startup tactics. The “distillation” process may violate some terms-of-service fine print, but this never stopped tech innovators before. Baby AI brains learning from grown up AI brains will become the new digital order.
DeepSeek is a wonderful kick in the ass for AI innovation. If it results in all of us having a limitless brain running locally on our phones and laptops as tireless, discrete servants, all the better (ps: How the fuck do you encapsulate all of the world’s knowledge locally on my laptop or phone. The idea is a little hard to fathom).
Turns out more AIs are on their way as the battle heats up in China. Kimi AI and Qwen AI are the next offerings to fret over. Both claim to be competitive with the latest OpenAI offerings. I tried Kimi. It’s another interesting alternative to web search with a nifty hybrid AI / search interface.
The battle for AI supremacy is far from over. The back and forth reminds me of early days of search when Yahoo!, Altavista, Lycos, Excite, Ask Jeeves, Hotbot (from Wired!) vied for supremacy. Google barged in with a better product and better execution. First you have to make a great product, then an even better way to monetize. LLMs are an ingredient, not the product itself.
What is clear is LLMs are commoditizing. Innovation will happen at the data, interface and device layer. Frontier model makers may find ways to protect the exquisite edges of knowledge capability but open source models will serve the majority of use cases. Costs will fall dramatically and consumers will reward good, respectful products.
That said, Zuck and team USA will not let China own the global LLM open source position. Game on.
ALEX: DeepSeek reminds us why constraints are so valuable to innovation. Many industrial powerhouses were built on constraints after World War II. Meanwhile, AI funding in the US represents the opposite approach, with billions upon billions literally set on fire to power the building of models that increasingly look likely to become commodities. It's hard to gauge what such an abundance of capital does to a company’s culture. Engineers being paid millions with infinite resources no longer tell the story of the underdog-in-a-garage that led to much of the technology we enjoy today.
So yes, it's likely a bubble, and yes, there's a ton of money being spent on things that in the long run might turn out to be terrible businesses — but that doesn't have to be a bad thing. The big expensive frontier models are likely partially what supported the creation of DeepSeek and will likely benefit a slew of scrappy companies trying to get a piece of the pie. OpenAI might try to complain about their billion-dollar LLMs being used to train DeepSeek's models, but as they've told everyone whose content was absorbed, the cat's out of the bag. ChatGPT was a huge milestone we reached much earlier than most thought, and some thought impossible. DeepSeek is another one of those. We thought we were starting to get a sense of the trajectory but once again, we’re surprised by what we can get computers to do.
Don’t get distracted by all the silly features you’re seeing jammed into software, hilarious hallucinations, or more OpenAI drama — these are hugely consequential advances that we haven’t truly started to make sense of. The spaceship is hovering over the White House, we just don’t know if it comes in peace.
Spending billions building LLMs might turn out like laying fiber when the internet was just getting started: very valuable to us all over time but a massive loss for the companies who actually made it happen. The fact that there is a gigantic AI bubble forming doesn't mean we won't benefit (or suffer) from it. There will be massive casualties over the next few years, and OpenAI might be one of them — or they might be able to keep raising billions on the promise they can deliver a god we can access from our phones.
ANONYMOUS BANKER
Trump, TikTok, and the $150 Billion Dance-Off
The M&A headlines have been dominated by two major stories this week: Trump’s executive orders and AI + DeepSeek (essay is a deep cut but worth it if you have an hour). Let’s focus on the delay in the TikTok ban.
In addition to delaying the ban, President Trump, as the dealmaker in chief, further leaned in by proposing a long-term solution for TikTok to continue to exist through new American ownership, including the US taxpayers owning “50% of the newco.”
Here’s what many journalists are missing with the TikTok deal. Parroting the math of the All-In Podcast’s latest episode (+Thomas Laffont from Coatue), a back-of-the-envelope calculation places TikTok’s valuation between $100-$150 billion. Various groups, including Elon Musk and MrBeast, have been rumored as potential bidders, but the mechanics of how a deal would be funded remain unclear.
The capital needed to acquire TikTok is significant, and there’s some precedent here with the Twitter take-private. Banks suffered mightily in the Twitter acquisition financing, and this situation has similar “history rhymes” vibes. It’s unlikely that large banks will step up to provide the necessary debt financing for most bidders (Microsoft, yes; Oracle, maybe), and it would be funky to tap the Middle East for capital when it’s supposed to be an American deal. Raising this scale of capital is extremely difficult.
This is where Trump’s desire for 50% ownership of TikTok to facilitate the deal becomes possible. While rare, government intervention in private markets isn’t unprecedented; it has happened at scale in times of financial crisis (e.g., the Great Depression, WWII, 2008, COVID) and also to spur investment and innovation in new areas like green energy. In these situations, the government was given ownership of private enterprises by providing financial backstops
So, playing this out, there are three potential M&A paths for a future TikTok deal:
Microsoft (maybe Altman jumps in as a partner with OpenAI) acquires TikTok with cash, new debt, and stock.
Another bidder group with a significant portion of the capital provided by the government acquires TikTok.
ByteDance spins out TikTok into a new publicly traded entity. A bidding group could still participate and take a meaningful stake to support the public float.
In all three scenarios, the US government could act as a funding mechanism (e.g., direct investment or loan guarantees), providing a path to US taxpayer ownership—maybe not 50%, but at least Trump will get a win with some ownership in the spun business or its new parent.
GOOD PRODUCT
Reinterpreting an icon
The first cover is an auspicious moment for any new magazine editor. In 1965 Helen Gurley Brown transformed a stodgy general interest magazine into the most talked about women’s mag in the country with this:
Modernizing a brand with Cosmo’s deep cultural history is tough, particularly with long-time Hearst brass, who rightfully worshiped Helen, looking over your shoulder.
This week Cosmo’s youngest EIC ever, 30 year old Willa Bennett, took a swing at what a new generation might want to see in the brand with the “Love Issue” featuring two grown up child stars, Macaulay Culkin and Brenda Song.
Great start. I love it. Congratulations Willa. Good product.
