They flattered him. They shared their troubles. They criticized his opposition. They emphasized common enemies.
The change in strategy speaks to what business leaders learned during the first Trump presidency and illustrates how they have adapted their approach before Trump returns to the White House.
Believing that his political positions are fluid and his actions are often transactional, they are forging direct relationships they hope will benefit their businesses.
In his first term, Trump criticized tech companies for manipulating coverage of him on their platforms and opposing his agenda. He was punitive with those he considered antagonists.
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In one instance, Amazon accused Trump of pressuring the Pentagon to cancel a cloud computing contract with the company because its founder, Jeff Bezos, owned The Washington Post. But Trump heaped praise on Cook, CEO of Apple. He liked that Cook called him directly to discuss business and economic issues. Such direct engagement helped Apple avoid tariffs on many of its products, even as the Trump administration cracked down on other companies that were manufacturing in China.
This time, tech CEOs have been following Cook’s playbook. Zuckerberg, CEO of Meta, spoke to Trump after an attempted assassination in July. Pichai, Google’s CEO, told Trump that his campaign stop at a McDonald’s restaurant was one of the biggest things ever on Google.
And Andy Jassy, CEO of Amazon, introduced himself with a phone call, while Bezos, his predecessor, called Trump to praise his resilience after the July shooting.
The executives never offered a public endorsement, but after Trump’s victory Tuesday, they feted him with congratulations on the social platform X. Cook, who was typically the last of his peers to weigh in on hot-button issues during the previous Trump administration, offered the final word, saying: “Congratulations President Trump on your victory! We look forward to engaging with you and your administration.”
Jeffrey Sonnenfeld, a Yale management professor who has advised executives and Trump over the years, said the direct outreach and quiet wooing of Trump were “the right thing” to do, noting the executives’ responsibility to shareholders to have a relationship with whoever is in the White House.
“They were building a rapport,” he said. “And that’s the right way to do it — establish personal eye contact and get a foundation for the future.”
Meta and Google declined to comment, while Amazon and Apple didn’t respond to requests for comment. Some of the details of their CEOs’ outreach were shared by Trump during several podcasts and an interview with New York magazine. Others were reported previously by The New York Times and The Washington Post.
The tech titans’ private outreach to Trump has contrasted with the public embrace by Elon Musk, CEO of Tesla, and many of Silicon Valley’s chatterbox venture capitalists.
Musk hit the campaign trail for Trump in Pennsylvania and turned his personal feed on X into a Trump-advocacy channel, while venture capitalists donated generously to Trump’s campaign in hopes his administration would be more friendly to their pet causes — crypto, antitrust and taxes — than President Joe Biden’s has been.
These prominent investors were ebullient on social media Wednesday morning. When Musk posted that America’s “nation of builders” would soon be “free to build,” Marc Andreessen, a prominent investor who donated to Trump’s campaign, responded with his catchphrase, “It’s time to build,” with an American flag emoji.
In reaching out to Trump, tech executives were doing more than hedging their bets before a tossup election. They were also laying the groundwork for improved relations between Silicon Valley and Washington.
The relationship between some of the tech leaders and the president quickly deteriorated after that 2016 Trump Tower meeting. Just weeks into Trump’s presidency, some of them criticized his executive order temporarily blocking immigration from seven Muslim-majority countries. Sergey Brin, one of the co-founders of Google, was spotted at a protest against the measure at San Francisco’s airport.
Silicon Valley’s revolt sowed tension with the Trump administration. The fraught relations continued when Biden took office in 2021.
The Biden administration put tech on its heels with aggressive antitrust action and a crackdown on mergers and acquisitions. Over the past four years, the Justice Department and Federal Trade Commission have filed antitrust lawsuits against Amazon, Apple, Meta and Alphabet, the parent company of Google. The cases have threatened their businesses, especially Google, which was ruled a monopolist.
The FTC has also cracked down on mergers and acquisitions and announced an inquiry into investments by tech giants in artificial intelligence startups. The agency’s scrutiny has been criticized by venture capitalists and others for slowing deals in Silicon Valley and stymieing traditional opportunities for big companies to grow.
Trump has said the leaders of those companies have expressed a readiness to turn the page on such regulatory headaches. He has been receptive to their appeals, listening sympathetically as Cook complained to him on a call last month about European regulators.
“I’m not going to let them take advantage of our companies,” Trump recalled telling Cook, during a podcast interview last month. “That won’t be happening.”
Trump has also voiced skepticism about the possibility that the government might break up Google, saying he considered it a bulwark against China’s technology ambitions.
Though the president-elect has criticized the company over the years for how its algorithm ranks news articles about him, he expressed concern that weakening the company could be dangerous at a time of international tech competition.
Those softer regulatory positions have lifted hopes across Silicon Valley that Trump might replace Lina Khan, the chair of the Federal Trade Commission, who has sought to block mergers, and Gary Gensler, the Securities and Exchange Commission chief, who has antagonized the crypto industry.
Khan’s term has expired, and Trump will have to decide whether to keep her. She has won accolades from Vice President-elect JD Vance, who has praised her for being willing to go after big tech companies. But his views will be only one of many entertained by Trump, who has a history of courting competing opinions on issues before making final decisions.
By directly engaging with Trump, tech executives are increasing their chances of convincing him what action to take and possibly influence Khan’s replacement, said Adam Kovacevich, CEO of Chamber of Progress, a tech policy group that is backed by companies including Amazon and Apple.
“We know he’s susceptible to the last person in his ear,” Kovacevich said. “His style of management hasn’t changed, but he may be more knowledgeable about what to prioritize.”
