From a throne-like leather chair in the lobby of D.C.’s luxurious Waldorf Astoria on Wednesday, I watched billionaires field pitches from litigation-plagued founders, Trump administration officials widen their eyes at offerings from up-and-coming defense contractors, and lobbyists scheme to squeeze money from all the “America First” energy. 

In short, it was the perfect place for a journalist to eavesdrop. 

I was supposed to be a block away, where other media members were covering the Winning the AI Race summit hosted by the “All-In” podcast. There, the Silicon Valley A-list, including Nvidia’s Jensen Huang and Advanced Micro Devices CEO Lisa Su, celebrated President Donald Trump’s AI executive orders, which demanded that the country fast-track building data centers and become the dominant nation in the technology. The president, who signed the orders that night, made an appearance at the event. 

“America is the country that started the AI race,” Trump said from a gilded stage at Mellon Auditorium. “I’m here today to declare that America is going to win it.” 

I had been invited to the summit. Then, around a week after my colleague Rya Jetha and I published a story on “All-In” cohost and Trump AI and crypto czar David Sacks, the organizers disinvited me, citing a lack of space.

But while tech leaders were speaking in shimmering platitudes during panel sessions, they were undoubtedly saving their real feelings — and dealmaking — for off the stage. So I camped out a block away from the summit at the Waldorf Astoria bar, where billionaires, founders, and Trump‑world power brokers gathered to toast the country’s AI future (and figure out how to profit from it).  

Boy, was I right. 

At around 6 p.m., five employees of one of the country’s largest commercial real estate firms sat down on teal velvet couches to my left and began a public strategy huddle on how best to monetize Trump’s America First initiatives. 

The firm, which works with a range of blue-chip defense contractors, had decided it needed to win over the new wave of U.S. defense and hardware startups; i.e., the next generation of the military-industrial complex. It’s a sector that Trump donors like Marc Andreessen and Ben Horowitz have been flooding with money. 

Among the ideas from the brainstorming session: make a killing by sourcing unused land for data centers; maintain flexibility with payment structure, since startups throw fits over high fees; and, if cards are played right, new defense customers would benefit the company’s institutional defense customers too. 

The defense giants “want to know ‘what are we seeing from the really innovative companies?’” one of the employees said. 

On the couch to my right, a prediction market founder, wearing blue-tinted sunglasses indoors, pitched the billionaire owner of a financial services company. “The Trump admin’s been good for us,” the founder bragged, before admitting that his company was embroiled in a bunch of pesky lawsuits. 

He boasted about landing deals with sports leagues to launch prediction markets for games, but players can bet on themselves. “I don’t even know how you would discover it,” the billionaire countered. The founder assured him the company would use AI to track the players. The billionaire didn’t seem convinced of the technology, or that the lawsuits were really all that harmless. 

They ended the meeting with some classic rich-guy small talk: $20,000 sports tickets, whether the billionaire would buy eBay, their deep-rooted anxieties about Alexandria Ocasio-Cortez. The founder lowered his tone as he discussed the idea that AOC might run for president. “If she wins,” the founder sighed, “we’re all done.” 

Later, a defense-tech startup founder pitched a member of the Trump administration at the table directly in front of me. They laughed about startups that refuse to sell weapons — “they’re crazy,” the founder said — and both agreed that Trump is good for business. The business, by the way, is killing. 

“Trump knows there’s no ceiling to what he can do,” the defense tech founder said, as the government official nodded profusely. 

As the night went on, more people flooded into the hotel, and the vibes got looser, with the help of libations. Two men ordered the hotel’s fanciest gin, kept in a locked glass box and illuminated with fluorescent blue lights. To access the bottle, the staff handed each man a tiny key to the box, and they fiddled with the lock for several minutes. It seemed like an awfully expensive humiliation ritual, but to each their own. 

For many, the hotel was just the pregame. The real party was 15 minutes away at The Ned, a members-only club where Christian Garrett, investor at 137 Ventures, was throwing the summit’s official after-party, and guests like OpenAI COO Brad Lightcap, Meta’s Alexandr Wang, and Sen. Rick Scott, R-Fla., were reportedly on the invite list. Around 8 p.m., I left the Waldorf with my husband to go on a romantic stroll — and rope him into more eavesdropping. 

When we reached The Ned, the road was lined with black Escalades and wiry men in backpacks. A classic tech party. We took a seat on some stone steps and watched as investors and founders spilled out. Two men complained about a mystery founder who has been using company-chartered jets for personal use (if you know who this is, shoot me an email!); another pair of investors joked about an acquaintance who suggested dining at a pricey three-Michelin-star restaurant. 

I quickly noticed that my husband and I weren’t alone. There was a young woman in running clothes who had been limbering up for 30 minutes. Every time someone left the party, she grabbed her phone and slyly took a picture. A fellow snooping journalist, I thought gleefully.  

I gave her a wave and was about to ask what outlet she was with, but she shot me dagger eyes and went back to stretching. That’s when it occurred to me: Nothing says you’ve arrived in Washington quite like having spies loitering outside your after-party.

We stayed for a few minutes, observing the partygoers. The mood was largely celebratory. After all, the day had brought Big Tech nearly everything it wanted from Trump: a commitment to building data centers and slashing AI regulation. 

But amid the smiles and backslapping, I remembered a happy hour I had attended the night before, hosted by a pro-tech think tank. 

I was sipping Diet Coke at a rooftop bar overlooking the Washington Monument as I chatted with an administration member whose job is to help guide the government’s use of AI. I peppered the person with questions: Does Sacks have real political power? What are the DOGE boys doing without daddy Elon?   

They just shook their head. “I don’t know,” they said. “If I ask about anything outside of my direct purview, I get fired.” 

“That sounds like an unpleasant way to work,” I replied.

“It is,” they sighed, staring into their drink.