The Left-Wing Tech Investor Running For Governor

Ben Jealous slips into the driver's seat. It's a tight fit (he's a towering 6 feet, 4 inches with broad shoulders) and he takes off his blazer in the most peculiar of ways: by grabbing the collar and pulling it over his head, as though it were a sweater.

"I gotta move quickly," he says.

That could be the tag line for his life. Just 44 years old, Jealous has already racked up quite a few distinctions.

He was: the student activist kicked out of Columbia University for protest, and then awarded a prestigious Rhodes scholarship to study at Oxford; the community organizer in Mississippi who then became a journalist in that state; the youngest-ever president of the NAACP, the historic African-American civil rights organization (a life goal he accomplished far earlier than he had expected); and then, in another unexpected turn of events, a venture capitalist in Silicon Valley.

Now, Jealous is trying to make the single biggest change of his eclectic career — from outsider to insider — as he runs for governor of Maryland. The campaign will test the Democratic Party's ability to reinvent itself — and the technology sector's role in populist politics.

NPR spent two days on the campaign trail with Jealous.

Day 1 started, but didn't end, in a predictable place. Jealous, who is best-known in this very blue state as an African-American civil rights leader, stood at the dais of a black church in West Baltimore.

It was Sunday morning, a little after 10. Kids in the projects across the street — the same projects his mom grew up in — had recently told him they wished they didn't have to walk by dead bodies on the way to school.

"We are not here for the Crucifixion," Jealous preached. "We are here for the Resurrection."

By 8 p.m., he was working to recruit a very different part of the base: Trump voters. Specifically, Trump voter Billy Andrews. Weeks earlier, the two had met at a campaign event for single-payer health care.

While the issue may be dead in the nation's capital, Jealous is pushing for it at the state level. Andrews wants that. He owns a car dealership and says skyrocketing premiums will kill his business.

Jealous asks Andrews to help recruit others, to which the Trump voter responds: "Around here on the Eastern Shore, the president of the NAACP comes up and that does kind of scare people. I'm being real."

The hesitation doesn't turn Jealous off. It draws him in. His hazel eyes light up. "Get some folks who are just kind of curious," he prods. "What, Billy Andrews has been hanging out with the president of NAACP? That sounds different!"

Jealous' dad is white. His mom is black. And this bizarre moment is happening — despite the race wars tearing America apart — because the gubernatorial candidate believes the choice between white working class and minority voter is a false choice. If you address rising inequality, Jealous says, you can win both; and Bernie Sanders — whose popularity has increased since the 2016 election — is proof of that.

Jealous was one of Sanders' earliest supporters. Both men are left wing. But to call Jealous a Berniecrat would be to overlook a key fact: While Sanders trashes capitalism, the gubernatorial hopeful believes the market can solve many problems far more effectively than protest can. That's why, in 2013, he went from civil rights to Silicon Valley.

It's not a familiar storyline, although it did start with a walk on the beach. Jealous was at Martha's Vineyard — the small island where the rich retreat — visiting tech guru Mitch Kapor, the founder of Lotus (the 1980s spreadsheet-maker).

Jealous was ready to leave the NAACP, which, many say, he had managed to stabilize. It was in financial shambles when he arrived. Like past chiefs, he raised millions from big banks on behalf of the nonprofit (including during the financial crisis). Unlike others, he used the Internet to grow online engagement from 200,000 to more than 2 million and increase the donor base nearly tenfold.

"Ben did a huge turnaround job," Kapor says. "Seeing opportunities where others don't — that's an investment skill."

Kapor introduced Jealous to the hidden world of tech investment with a simple example: LendUp, a startup that is an alternative to payday lending. Poor people can borrow and, as they repay, their interest rates go down. A lightbulb went off for Jealous, as Kapor recalls it: "He told me, 'You guys have made more progress in a year or two than we've made in a decade.' "

Jealous soon joined Kapor Capital and became a partner. The boutique Silicon Valley firm does "impact investing" — putting money into tech startups that purport a social mission, not just a profit motive.

Kapor is one of the powerful liberal investors who are regularly courted by Democrats to write big checks. He says Jealous' connection to Silicon Valley "puts him on the leading edge of progressives. Progressives need a positive image for how to grow the economy. It can't just be about distribution."

It's unclear how much Silicon Valley's message (not just money) will touch Maryland voters.

On Day 2 with NPR, Jealous goes from a student protest against the Trump administration straight into meetings at a tech incubator run by Johns Hopkins University. As a "mentor in residence," he is searching for startups he can back in fields like education, biotech and cybersecurity.

One by one, millennials come to seek advice: Will a teachers union open doors for a startup that wants to sell online accounting software to public schools? Will chicken plant workers use a new app that provides carpal tunnel therapy by tracking hand movements? Would the mayor of Los Angeles (a friend of Jealous') be interested in small, portable air quality monitors that look like mousetraps?

Jealous readily opens up his massive Rolodex. He's at home mixing business and progressive causes. "It's just a new path up the same mountain," he says.

At this stage in the campaign, technology is more a side hustle for Jealous than a stump speech.

Political scientist and pollster Mileah Kromer says that could change.

While tech jobs may not resonate equally among all communities, she says, "Maryland is one of the most college-educated states in the nation. A tech platform could be particularly popular with upper-class college-educated voters."

Jealous says if he wins, he'll bring Silicon Valley to Maryland. It's a big if. He faces a crowded Democratic primary, and a very popular Republican incumbent.

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