The Weekend
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May 30, 2026 |
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| Welcome, Weekenders! In this newsletter: |
| • The Big Read: Can OpenAI’s revenue chief catch Anthropic in enterprise tech? |
| • Plus, Recommendations—our weekly pop culture picks: “Deep Cover: The Family Man,” “1873” and “Legends” |
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| On Tuesday, I dropped in at JPMorgan Chase’s glitzy new Midtown headquarters for a confab on national security, a sector that has become an investment pillar for the banking giant. While the event encompassed other areas like energy and supply chain infrastructure, defense tech was really the star of the show. Venture and private equity investors packed the room to hear about the booming field of dual-use startups, which sell to both commercial and government clients. It’s an area that not too long ago drew skepticism from much of Silicon Valley. |
| The defense sector and Silicon Valley aren’t strangers to each other. The modern U.S. tech industry arguably owes its existence to the military’s decades-old investments in semiconductors and early internet efforts. Still, the venture industry has had limited success breaking into the insular world of defense contracting, long dominated by names like Lockheed Martin, Booz Allen and RTX (formerly Raytheon)—until the last few years, at least. |
| Outside the AI labs, the buzziest Silicon Valley companies are actually clustered in places like Southern California and Texas, where startups like Anduril, Saronic Technologies and Shield AI are turning defense-spending paradigms on their head. Palantir, which went public in 2020, has already dwarfed the market cap of its more venerable defense competitors. |
| The shift in power from lumbering contractors to startups backed by venture capital and private equity was on clear display at the off-the-record JPMorgan event last week. Investors mingled with operators between sessions featuring firms like In-Q-Tel, an independent venture firm created by the CIA, as well as a panel hosted by John China, JPMorgan’s head of innovation economy, on the corporate venture strategy of Lockheed Martin, Booz Allen and RTX. (Even the incumbents are coming to the private capital party.) |
| Everyone had dollar signs flashing in their eyes. The event was convened to celebrate the new edition of the NatSec100, a list of the top private national security companies created by the nonprofit Silicon Valley Defense Group and now in its fourth edition. |
| The report detailed a sea change in defense spending under the administration of President Donald Trump. Changes in the complex rules around how government agencies dole out contracts, as well as the dire need for new supplies created by the U.S.’s ballooning wars, have created the ideal environment for relative newcomers like Anduril, whose valuation has spiked to over $60 billion. Companies on the list saw a 2.5 times increase in federal spending commitments from 2023 to 2025, though that still represents just 0.5% of spending from the Department of War’s total budget, showing the vast expanse of green space that lies ahead. |
| The money is showing up in force. A total of nearly $40 billion in investments poured into the NatSec100 companies in 2025 (excluding OpenAI, which appears in 12th place on the list). But will that trend last? |
| Not too long ago, many venture firms stayed away from companies like Anduril. For some, their distaste stemmed from ideological concerns about funding war machines. For others, it was because they were skittish about financing companies with such a fickle customer base. As Trump agencies announce one multibillion-dollar contract after another for tech companies, Silicon Valley is returning to its defense roots. Now investors have to hope the government gravy train lasts beyond the next two years.—Leo Schwartz (leo.schwartz@theinformation.com) |
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| The Big Read |
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| OpenAI’s new chief revenue officer, Denise Dresser, is on a quest to convince enterprises to buy its products. Can she help it catch up with Anthropic? |
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| Listening: “Deep Cover: The Family Man” |
| Jake Halpern, host of “Deep Cover: The Family Man,” isn’t so much a multihyphenate as he is a multimultihyphenate. Halpern is a veteran print journalist, having first made his bones as a fact checker (quaint!) at The New Republic. He has also written a number of nonfiction books and a pair of young adult novels, including a bestseller, “Nightfall.” And in 2018, he and illustrator Michael Sloan won a Pulitzer Prize for a comic about refugees serialized in The New York Times. |
| Halpern has also been an NPR contributor, and lately, he has put his talent behind the mic to different use with “Deep Cover,” a series about people who’ve led double lives. The latest season looks at the exploits of the Boonie Hat Bandit, a prodigious Missouri bank robber in the 2000s who studiously maintained his image as a blue-collar dad. |
| As a guy who has lived many varied lives himself, Halpern obviously finds great interest in how we compartmentalize ourselves. Sometimes it wins a person a Pulitzer. In other instances, it fuels a crime spree.—Abram Brown |
| Reading: “1873” |
| When a book decides to take its title from a single year in history, that definitely conveys a certain sense about those 365 days: A lot happened. Such is certainly the case with 1873, a year marked by financial maelstroms across the world, with the ripple effects felt into the next century. |
| “1873” is an exquisitely compiled account of the year’s drama, crafted with great care by Liaquat Ahmed, who won a Pulitzer Prize for another intricate history: “Lords of Finance,” an examination of the bankers involved in the Great Depression. As Ahmed emphasizes, 1873 involved no single great calamity but rather a “cascading chain” of medium-size ones that fed “upon each other as financial chaos in one corner of the globe successively contaminated other parts of the world.” In Vienna, the stock exchange lost nearly half its value in a day, the result of a “collective madness” among speculators; in America, a spate of bank failures produced a stock market rout, forcing the New York Stock Exchange to close for 10 days. |
| Together, a maelstrom formed, intensifying when some countries tried to ignore the problems and others bumbled their responses. In the U.S., a sour economy weakened the Republican party and rejuvenated the Democrats, giving rise to the Jim Crow South. The Ottoman Empire and Egypt both defaulted, upending the Middle East; in Egypt’s case, its credit woes led to British occupation. And in Europe, the downturn inflamed populist sentiment and antisemitic feeling, much of it directed at the Rothschild family, which appeared throughout the period’s twists and turns.—A.B. |
| Watching: “Legends” |
| In law enforcement terms, a legend is a backstory—the personal details that help an undercover officer fill out their assumed persona. Legends abound in “Legends,” an energetic Netflix series about a ragtag group of U.K. customs officers who take on a much bigger challenge than checking suitcases: halting the flow of heroin into early ’90s Britain. |
| The show, which is loosely based on real events, comes from Neil Forsyth, who had success recently with “The Gold,” a tale of Thatcher-era gold thieves. He populates “Legends” with characters who feel familiar, misfits longing for greater purpose, banded together by Don (Steve Coogan), a weary veteran of covert ops who’d been hoping for a few quiet years before retirement. His squad includes document wonk Erin (Jasmine Blackborow) and a trio of field agents: Kate (Hayley Squires) and Bailey (Aml Ameen), who get sent to Liverpool to hunt down English traffickers. Meantime Guy (Tom Burke, the “Furiosa: A Mad Max Saga” love interest) investigates Turks in London. |
| The outcome of their operations ultimately comes down to how well they can pass off their legends as the honest truth, Don tells his group, framing the stakes in stark terms: “When legends don’t work, people die.” Yeah, Don’s intense about work. I imagine he’d never mute his Slack notifications.—A.B. |
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