The Billionaire Breakup

TL;DR

1. Reddit accuses Anthropic of stealing data to train Claude

2. Shareholders reject Warner Bros. Discovery CEO’s $52M payday

3. $2.4T ‘Big, Beautiful Bill’ sparks backlash

4. Big money is bailing on early-stage investing

Reddit Sues Anthropic Over AI Training Data

Reddit has filed a lawsuit against Anthropic, accusing the AI firm of illegally scraping its site over 100,000 times since mid-2024 to train its AI models. Unlike OpenAI and Google, which signed formal licensing deals with Reddit last year, Anthropic reportedly refused to enter an agreement.

Reddit’s 20-year warehouse of user-generated content is a gold mine for AI training: It’s authentic, organized by topic, ranked by a community-driven voting system, and growing fast. 

• As of January 2025, Reddit has 1.1 billion monthly unique users, a nearly 50% jump since 2022. In the second half of 2024, users posted nearly 6 billion pieces of content — a 12% increase from the first half of the year. 

Data licensing has become a lucrative business for Reddit, generating $130 million in 2024 — roughly 10% of its total revenue. The value of Reddit’s data will likely rise as the supply of high-quality language data continues to shrink.

Large language models like ChatGPT and Gemini have already consumed Wikipedia, nearly every published book, and much of the open internet. Each new model demands more data than the last, pushing the industry to chase a shrinking pool of fresh, human-generated content.

Relying on AI-generated text as a substitute creates a feedback loop of degradation. Researchers call it “model collapse.” In one study, a model trained on synthetic data hallucinated fake jack rabbit species when asked about 14th-century English architecture.

This reminds me of my first board meeting at The New York Times back in 2000. My big idea was to stop letting Google crawl our content for free, and start licensing it. I argued that we needed to present a unified front as publishers. At that point, search wasn’t yet the dominant force it is today, but the signs were already there.

The Times leadership wasn’t receptive. They were stuck in an advertising mindset and focused on driving traffic. Their response: Google was sending us traffic, so why would we shut that off? What no one did until recently was the actual math: They were making a dollar off our content, and we were making two cents. So I applaud how aggressive Reddit is. This is good news for the content community. 

The next step is coordination. They need to call every other content platform that’s being scraped and say, let’s come together. Let’s agree on an economic model where compensation is tied to how much content is being crawled and used.

I loved how aggressive the complaint was. The opening line reads, “Anthropic is a company that bills itself as the white knight of the AI industry. It is anything but.” 

It’s very sassy, but it’s the right thing to do, and I think that’s why the stock rose more than 6%. Wall Street recognizes that Reddit CEO Steve Huffman knows exactly what’s at stake here. He knows that he’s sitting on a literal oil field of AI training data, and if they let companies like Anthropic come in and start pillaging their data then they’re gonna be left for dead.

WBD Revenue and EBITDA Fall, Shareholders Balk at CEO Pay

Nearly 60% of Warner Bros. Discovery voting shareholders have rejected CEO David Zaslav’s $51.9 million 2024 pay package in a nonbinding “say on pay” vote. It's a sharp increase from last year, when 51% were in favor. Zaslav's pay won't change, but the vote represents a stunning rebuke of Zaslav's performance.

S&P 500 CEOs earned $17 million on average in 2024, up 10% from the prior year. Zaslav’s package was more than triple that. 

Since the WarnerMedia–Discovery merger, Zaslav has overseen a 60% drop in WBD’s stock price. If the 2024 compensation is paid out, he will have earned $141 million since becoming CEO.

His 2024 compensation included a cash bonus of nearly $24 million and more than $23 million in performance-based stock grants. The bonus structure was weighted 70% toward hitting financial targets — revenue, adjusted EBITDA, and subscribers — and 30% toward meeting strategic goals. Yet on 2 out of 3 of those metrics, the company underperformed:

• 2024 revenue fell 4% YoY.

• Adjusted EBITDA dropped 11%.

To be fair to Zaslav, WBD added 19 million new subscribers in 2024 — a nearly 20% increase YoY — and has paid down $21 billion of its original $55 billion in debt over the past three years. 

But shareholders aren’t in the clear yet. Last month, the company’s debt was downgraded to near-junk status after an S&P Global analyst projected that WBD’s EBITDA will remain flat for the next three years, driven by continued declines in linear TV.

This kind of compensation in the face of shareholder destruction and a credit downgrade is indefensible. It is not just poor oversight. It is a midlife crisis being funded by Warner Bros. Discovery shareholders. The board could have saved a fortune by buying Zaslav a canary yellow Corvette and telling him to crash it into a hair plug clinic.

Here’s the bigger learning for young people: Compensation is a function of proximity. The CEO makes the most money because the CEO has closest proximity to the decision-makers — the board. Your physical proximity to the decision-makers, the relationships you have with them, is directly correlated to your compensation as evidenced by the fact that you are 38% less likely to receive bonuses when you work remotely. 

So if you want to work remotely, just acknowledge that you will make less money. If you are an economic animal, get into the office. I was an economic animal. People would ask, What’s your purpose? What's your passion? Answer: I want to be a f*cking baller.

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Trump’s $2.4 Trillion Bill Faces Senate Showdown Amid Warnings of Deaths and Fiscal Irresponsibility

The “Big, Beautiful Bill” is running into resistance from all sides. While it narrowly passed the House, the Senate fight is heating up, fueled by rising backlash from Republicans, tech billionaires, and policy analysts alike.

According to the Congressional Budget Office, the bill would add $2.4 trillion to the deficit over the next decade. But it’s not just fiscal fallout. Researchers from the University of Pennsylvania and Yale warned the bill’s proposed cuts to Medicaid and nursing home funding could lead to 51,000 additional deaths per year.

The political pushback is growing:

• Elon Musk called the bill “a disgusting abomination” warning it would “bankrupt America.” His public feud with Trump escalated on Thursday after Musk claimed credit for Trump’s 2024 win, prompting Trump to respond, “Elon and I had a great relationship. I don’t know if we will anymore.” Tesla stock closed down more than 14%, erasing $150 billion in market capitalization. 

• Marjorie Taylor Greene pulled her support after discovering an AI regulation clause in the bill, saying, “I would have voted NO if I had known.” She has 16 federal staffers — you’d think at least one of them would’ve read the bill. 

Senate Republicans are also sounding alarms. Ron Johnson called the bill “completely unsustainable,” and Rand Paul said it “is the opposite of conservative.” 

It’s also not surprising, when you consider Trump’s fiscal track record. The national debt increased by nearly $8 trillion during Trump’s first term. It was the third-largest rise in the federal deficit, relative to the size of the economy, under any U.S. president, according to the Urban-Brookings Tax Policy Center. 

The bill now heads to the Senate under budget reconciliation, meaning it only needs 51 votes to pass. If amended, it must return to the House before heading to the president’s desk.

This is the breakup we’ve all been waiting for. Elon Musk called the bill a “pork-filled disgusting abomination,” which sounds more like a TGI Fridays appetizer than a policy critique. But let’s be real: I doubt he has read the bill. What likely set him off is that it cuts the EV subsidies that boost his businesses.

Still, his outburst has drawn attention to the deficit conversation, and that’s where things get more frustrating. The holdouts opposing this bill are positioning themselves as fiscal hawks, but their outrage is selectively applied. They’re focused on the deficit numbers but not on the human cost. Since the U.S. pulled back on foreign aid, as many as 136,000 babies have been born with HIV who didn’t need to be. This bill removes people from Medicaid and then makes it harder for them to buy coverage on the open market. That’s not fiscal responsibility — that’s neglect.

And still, no one in this so-called deficit debate is talking about raising revenues. If we want to reduce the deficit in any meaningful way, we have to be honest about the trade-offs. That means raising taxes on the wealthy, or cutting back on large-scale programs like defense and Social Security. But no one wants to say that out loud. So, instead, we get this sideshow — rage tweets, personal feuds, and performative austerity — instead of a serious conversation about how we fund the government.

One silver lining of this Mean Girls-for-middle-aged-men feud? It might push Musk and his substantial political war chest back toward the political center, or reduce his influence. On Thursday, he posted a poll on X asking: “Is it time to create a new political party in America that actually represents the 80% in the middle?” It got over 5 million responses, with over 80% voting yes. 

If Elon funds a third party, he’ll face a steep climb. Billionaire H. Ross Perot failed to win a single electoral vote in 1992, despite winning 19% of the popular vote.

One of the World’s Richest Funds Is Tapping Out of Startups

Early stage startups are losing a major backer. Temasek, Singapore’s $300 billion sovereign wealth fund and one of the world’s biggest investors, has cut its early-stage exposure by 88% since 2021. Investments dropped from $4.4 billion to just $509 million in 2024, with only $70 million so far this year. It started capping early-stage bets at 6% of its portfolio and shifting focus to pre-IPO opportunities with clearer exit visibility.

This retrenchment comes after Temasek had to write off hundreds of millions on failed startups, including the crypto company FTX. 

Temasek’s decision is part of a broader market movement away from early-stage investments. 

• Seed stage deals have declined 28% YoY.

• Valuations have moved the other way, hitting new record highs, as investors fight over a smaller pool of perceived winners. 

What’s behind the shift? Higher interest rates have raised the cost of capital and made safer investments more attractive. Limited partners are demanding liquidity, but exits are scarce with the IPO market stalled, and megafunds are inflating valuations and crowding out smaller players. Add global policy uncertainty, from tariffs to AI regulation, and high-risk bets start to look far less attractive. 

Pre-money valuation is the value of a company before a new investment; in other words, it’s what investors believe it’s worth. The post-money valuation is its value after the investment, including the new capital.

This is yet another example of how the old-versus-young dynamic keeps showing up in every conversation we have about markets. You have older, wealthier people who control most of the capital and the system itself, and they’re making decisions based on their preferences and risk tolerance. But those decisions have real consequences for younger people — whether it’s young investors trying to get in on new opportunities or young founders struggling to raise capital. Early-stage funding is down 40% over the past two years, and it’s largely because older investors are deciding it takes too long and isn’t worth the risk.

What this really highlights is how hard it is to be a new entrant in America today, across the board. It applies to young people trying to build wealth, to first-time politicians, and to early-stage founders who are now getting shut out of the venture capital ecosystem.

OK, but before you sprinkle cyanide on your avocado toast, the flip side of your argument is the following: The explosion in technology has made previously difficult parts of starting a business much easier.

When I started Red Envelope, it cost us $500,000 to build a website that I think would cost $3,000 to $5,000 right now. We had to buy servers! We rented my neighbor's garage in San Diego, and that was our warehouse. There was no Shopify, there was no cloud, there was no HubSpot figuring out marketing.

If you have a good idea, you can get from letters A to D for less money than before. While the financial markets might not be as frothy and access to capital might not be as promiscuous right now, young entrepreneurs do have a lot of agency. 

Once price increases from Trump’s steel tariffs start rippling through industries, affecting autos, homebuilders, etc., he will chicken out (again), and U.S. steel stocks will return to pre-tariff levels.

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