When Pete Buttigieg joined Facebook as a Harvard undergrad in 2004, he was the 287th user registered on the site. The social network’s founders were friends of friends, and it felt like an insular message board for Harvard classmates, he remembered in an interview in San Francisco last week.

“I don’t think any of us could have guessed what implications that technology would have in the long run,” Buttigieg said.

Fifteen years and 2.4 billion users later, as Facebook wrestles with cascading scandals over data privacy, misinformation and election meddling on its platform, Buttigieg has become one of several presidential contenders calling for tougher regulation of the company and Silicon Valley’s other biggest tech firms.

The debate over Facebook’s future took on new resonance last week as one of the company’s co-founders, Chris Hughes, published a New York Times op-ed calling for the tech giant to be broken up. Buttigieg said Hughes, his former Harvard classmate, “made a very convincing case” that no company “should have the type of power that… these tech companies have.”

But unlike Sen. Elizabeth Warren, he hasn’t endorsed breaking up the tech giants, instead suggesting “a spectrum” of regulation that could include fines, blocking new mergers or splitting up companies. That’s attracted criticism from some on the left who want the candidates to take a strong stance on issues of corporate power.

Buttigieg’s vaguer position comes as the 37-year-old mayor of South Bend, Indiana, has courted support from Silicon Valley, attending a packed schedule of fundraisers around the Valley and San Francisco on Friday.

In the first three months of 2019, Buttigieg received at least $27,250 in donations from employees of Facebook, Google, Apple and Amazon, the fifth-highest total among the Democrats running for president. Hughes also gave him $2,700 (while donating to several other 2020 Democrats as well). Meanwhile, his campaign has spent about $181,000 on Facebook ads, less than a fifth of the amount spent by Sens. Kamala Harris or Warren.

“Here in the Bay Area, we’ve been waiting for a new generation that is going to redefine politics, and I think Pete’s going to do it,” said Adam Hundt, a tech worker who met Buttigieg in college and co-hosted one of his fundraisers. “Tech is all about change, and the way Pete has an open mind and embraces change makes him a natural fit.”

Buttigieg was two years ahead of Facebook founder Mark Zuckerberg at the Ivy League school, and was a senior when Zuckerberg, Hughes and their co-founders launched the site from a dorm room. Buttigieg’s account is the 287th on the network (although a few of those before him were created as tests) — if you go to facebook.com/287 while signed into Facebook, the Harvard grad’s original page, which he still updates, will pop up.

At the time, following his friends on Facebook felt like “a curiosity,” and an improvement over services like MySpace, Friendster or AIM, Buttigieg said. In recent years, he’s used his page to share photos from his deployment to Afghanistan in the Navy Reserve and post pictures and videos of life in South Bend. (He has separate pages for his presidential campaign and mayor’s office.)

When Zuckerberg embarked on a cross-country trip to see more of the U.S. in 2017 — attracting rumors about his own presidential ambitions — he stopped by South Bend to meet with Buttigieg, connected by a mutual Harvard friend. The mayor drove the tech mogul on a tour of the city, as Zuckerberg streamed live video from his cell phone on the dashboard of Buttigieg’s car.

Zuckerberg and Buttigieg stayed in touch, and they last spoke earlier this year, his campaign said.

As Buttigieg explained to Zuckerberg on the tour, he’s also worked to attract tech investment to his Rust Belt hometown, helping open a data center on the site of an abandoned Studebaker plant and transforming other old factories into glassy work spaces for startups.

“What they’ve done to revitalize the city is pretty remarkable,” marveled Matt Rogers, the co-founder of the smart home company Nest and an investor who’s been to the city multiple times at the mayor’s invitation. “You go out to dinner in South Bend and the streets are full of millennials, and there are great restaurants that feel like you’re in San Francisco.”

Rogers, who’s hosted fundraisers for Buttigieg, said he found the candidate to be “literate, fluent and deeply knowledgeable” about tech issues.

Buttigieg has suggested that that tech know-how is missing in D.C. He criticized the congressional hearings featuring Zuckerberg and other tech executives last year, which he called “political theater where very little actually got achieved.”

“What we saw was a spectacle of people in charge of regulating a very powerful force demonstrating that they had no concept of what it was they were in charge of overseeing — which is incredibly dangerous,” Buttigieg said, arguing that political leaders “need some kind of literacy in these technologies, what they mean and more importantly what they can do, in order to regulate properly.”

“This is not necessarily an age thing, although I think it helps to have grown up with these technologies at your fingertips,” he added.

Meanwhile, Buttigieg has toed the line between criticizing tech companies and voicing a more sympathetic perspective.

He said Friday that “a lot of people here in the tech sector still have a David mentality when they’ve increasingly turned into Goliath.” But he added that he believes tech companies are making policy decisions “perhaps, not necessarily with bad intentions,” and said he was struck by how many of Silicon Valley’s executives have “become very introspective” and are “really reflecting on what they wrought.”

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Kamala Harris favors look at breaking up Facebook That more diplomatic approach — and Buttigieg’s avoidance so far of calling for breaking up companies like Facebook — “has been a personal sigh of relief for a lot of people in the tech industry,” said Jacob Helberg, a tech policy advisor who’s hosted fundraisers for the candidate.

While most of the other top Democrats are also playing coy on the issue, Buttigieg’s refusal to be pinned down has frustrated tech critics who see it as a defining debate in the party.

“He is going for Silicon Valley money and he wants to express some nod to the problems but he doesn’t want to offend anyone powerful,” said Matt Stoller, a fellow at the Open Markets Institute and an advocate of splitting up the tech giants. “Take a position.”

WHAT OTHER DEMOCRATIC CANDIDATES SAY ABOUT BREAKING UP BIG TECH COMPANIES

Support it:

Sen. Elizabeth Warren: “Today’s big tech companies have too much power — too much power over our economy, our society, and our democracy. They’ve bulldozed competition, used our private information for profit, and tilted the playing field against everyone else… That’s why my administration will make big, structural changes to the tech sector to promote more competition — including breaking up Amazon, Facebook, and Google.”

Rep. Tulsi Gabbard: “Absolute power corrupts absolutely. I agree with Senator Warren on the need to break up big tech companies like Facebook, Google, Amazon. Will be introducing similar legislation in U.S. House.”

On the fence:

Former Vice President Joe Biden: Breaking up Facebook is “something we should take a really hard look at,” he told the Associated Press, saying Warren “has a very strong case to be made.”

Sen. Kamala Harris: “We have to seriously take a look at that… [Facebook] is essentially a utility that has gone unregulated. And as far as I’m concerned, that’s got to stop.”

Sen. Bernie Sanders: “We are living in an era of monopolies that dominate every aspect of our lives — including our government. It’s time to take that power back.”

Voiced concerns about it:

Sen. Cory Booker: “I don’t think that a president should be running around pointing at companies and saying breaking them up without any kind of process here. It’s not me and my own personal opinion about going after folks. That sounds more like a Donald Trump thing to say, ‘I’m going to break up you guys.’”

Former Rep. Beto O’Rourke: “I’m not sure if having five more Facebooks — if you broke up Facebook into five component parts, or any of these other large social media or technology companies — makes as much sense as regulating them.”