Swati Mylavarapu still remembers the $20 check she sent to Pete Buttigieg by snail-mail in 2010.

Now, a decade later, Mylavarapu is the national finance chair of Buttigieg’s presidential bid — and she’s spending 100,000 times as much on Democratic causes in 2020.

Mylavarapu and husband Matt Rogers, who founded Nest and sold it to Google for $3 billion, are planning to spend at least $2 million on politics this year, a sum that will catapult them into the ranks of the top Democratic donors in the country.

Each in their late 30s, Mylavarapu and Rogers epitomize a new class of rising power brokers in Silicon Valley in the age of Trump: politicized, extremely well-connected, and eager to spend their money now rather than later. They are rising to prominence as the prior generation of baby boomers — who grew just as rich in the tech boom of their time but hewed apolitical and more philanthropically conservative — are slowly passing the reins.

“I would love to see the billionaires of Silicon Valley spend at least as much on giving back as they do on their yachts”

But their emergence coincides with the beginning of an era of far greater skepticism toward tech. As part of this techlash, the public and politicians have begun reckoning with the power of big tech companies, where both Mylavarapu and Rogers worked and made much of their wealth.

Many have grown increasingly skeptical of the industry, of its leaders’ influence, and yes, of its money. Meanwhile, the art of raising big dollars for political candidates is noxious to parts of both the left and the right. And billionaires like Mike Bloomberg are on the back foot, forced to defend their fortunes, their charity, and their mere existence more than ever before.

So as Mylavarapu and Rogers expand their reach, they also must wrestle with questions of whether they should have so much influence in the first place.

Sitting in the airy, sun-soaked living room of their home in San Francisco’s Russian Hill neighborhood — where photo books of Barack Obama lie side by side with reads on Indian history, and around the corner from a wall-length mural painted by a family friend that mixes Hebrew lettering and ornate paintings of tigers — the couple explained their uneasy embrace of big-money politics.

“It’s absolutely something that weighs on me. We talk about it a lot,” says Rogers. “[Republicans are] using all the weapons possible to raise money and all the means necessary to get there. And if progressives are going to quibble around raising $2,800 here and there and doing a fundraiser at someone’s house, we’re going to lose again.”

Mylavarapu is more direct and offers the philanthropist’s standard defense during this peculiar moment: Is it better for tech’s elite to not donate their money at all?

“Don’t you feel like when people have benefited so tremendously by the opportunities that society has made available to them, don’t they have the responsibility to be doing more?” she asks. “Why wouldn’t we expect more of them to do more of that?”

The problem is that as of late, tech wealth is funding not just inoffensive programs like hospitals and perpetual charitable foundations, it is also paying to build catastrophic political apps like the one used in Iowa and vague, $10 billion efforts to try and combat climate change. And while Mylavarapu and Rogers are not the richest entrepreneurs or the most prominent figures in town, they must navigate these same tensions as they part with their fortune.

Mylavarapu flatly dismisses the notion that she is becoming a “power broker.” And indeed, she is one of many tech figures — from LinkedIn founder Reid Hoffman to venture capitalist Chris Sacca — who is responding to the election of Donald Trump by turning her wealth into political influence.

“It’s about the work. I didn’t start the Arena because I want to broker who ends up in Congress,” Mylavarapu says of the group, which trains first-time candidates, that she started after 2016. “I did it because we need to flip a whole bunch more seats.”

The $2 million Mylavarapu and Rogers plan to spend — more than twice than they’ve ever spent before in a given year — includes $500,000 to the Arena and $100,000 to Vote Vets, a super PAC that backs veteran candidates and which has been providing significant advertising support for Buttigieg this cycle. They plan to spend all of their money by July, hoping to inspire Silicon Valley donors to give their money now, when the millions can go further than they can in the fall since groups can budget more effectively.

Rogers, the more cutting (and less restrained) of the two, makes plain his frustration with these peers in Silicon Valley, who he sees as hoarding their incredible wealth. The billions of dollars sitting in donor-advised funds at the Silicon Valley Community Foundation, for instance, is “atrocious.”

“I would love to see the billionaires of Silicon Valley spend at least as much on giving back as they do on their yachts,” says Rogers. “It’s ridiculous.”

Mylavarapu is the more diplomatic one.

“It just seems like there’s a coming-of-age that we’re going through out here,” she says. “If Silicon Valley had hundreds of people like me and Matt, that would be money that was so well put to work. And that’s my hope out here.”

It used to be Rogers who was the higher-profile one in the couple, who first met at their Florida middle school. Rogers co-founded the home security company Nest with Tony Fadell, which they sold to Google in 2014. But the political work of Mylavarapu has elevated her to first-name status in the world of Silicon Valley politics as the wizard behind a dynamo candidate who has tapped tech’s riches with unexpected success.

Mylavarapu met Buttigieg in 2002 when the future presidential candidate, holding a clipboard, led a group of Mylavarapu and friends that knocked on doors in East Cambridge for the Democratic candidate for governor. The two activists, separated by a year at Harvard, grew much closer as fellow Rhodes Scholars at Oxford.

“We were two nerds in a sea of nerds that believed that more nerds should be very civically active,” Mylavarapu recalls.

They kept in touch as they built their careers in South Bend and Silicon Valley, with Mylavarapu offering advice on whether Buttigieg should move home from Chicago, and sending him that $20 check in the mail when Buttigieg made his first run for office in 2010. In the spring of 2018, Mylavarapu and Rogers visited Buttigieg’s Indiana home, and over breakfast in his living room, Buttigieg broached the idea of running for president. Rogers encouraged him to do it; Mylavarapu was more skeptical.

By that November, Buttigieg was on the phone telling them he was, indeed, doing it — and the Silicon Valley power couple offered to host one of his first fundraisers. That February, they struggled to convince 25 donors to show up in their living room.

Now, this couple has proven to be the tip of the spear of Buttigieg’s Silicon Valley offensive, responsible more than anyone else for the high-dollar relationships that other candidates say put Buttigieg in the pocket of Big Tech but have nevertheless powered his improbable campaign.

When Buttigieg visited Silicon Valley last week for two fundraisers, Mylavarapu and Rogers blasted out invitations to hundreds of their former colleagues, classmates, and new political friends, along with dozens of more personal notes to contacts who they knew might be curious about Buttigieg.

High-dollar fundraising demands this personal touch. And so that Monday, a few days before Buttigieg’s events with hundreds of Silicon Valley contributors, Mylavarapu and Susie Tompkins Buell, an older-guard mentor to Mylavarapu in political fundraising, hosted a more intimate event for about 15 big donors who were committed to other candidates, according to people familiar with the event. Mylavarapu made her pitch on behalf of her college friend.

These private get-togethers — the meeting was called a “Cultivation Event” — can conjure the image of the secret, smoke-filled rooms that Buttigieg’s rivals, who have strained to keep their distance from tech donors, have tried to cast as corrupt.

But when asked about her new influence and that of other tech donors, Mylavarapu thinks of her 19-month-old daughter asleep upstairs and then turns unapologetic.

“I don’t want the first president that she remembers to be Donald Trump — and it’s as simple as that,” she says. “Are we here to win this? Or not?”