It's tempting to view Roger McNamee as both a visionary venture capitalist and someone who cashed out in middle age to indulge his rock-'n'-roll fantasies and rail at the Man—who, until just recently, was him.

"I feel most days like Cassandra, you know?" McNamee says, comparing himself to the character in Greek myth cursed to speak true prophecies but never be believed.

McNamee, now 63, discovered an early aptitude for investing in tech stocks. He moved to California's Silicon Valley from Baltimore in 1991 and sank money into Google, Yelp and dozens of others. Among his biggest winners: investments in Facebook in 2009 and 2010. Three years earlier, McNamee advised founder Mark Zuckerberg not to sell his company to Yahoo! for $1 billion. It was good advice. A 2012 initial public offering valued Facebook at $104 billion.

Now Facebook has no bigger critic than McNamee.

He saw the light, he says, in 2016, when he watched false political advertising on the platform fan the flames of Trumpism and Brexit. He emailed CEO Mark Zuckerberg and chief operating officer Sheryl Sandberg and warned that Facebook had enabled things that were "truly horrible."

They brushed him off, and McNamee's inner bomb-thrower emerged.

"The values of these companies conflict with the Enlightenment values on which this country was founded," McNamee said in an interview with WW.

McNamee has been on a jihad since, speaking and pitching his new book, Zucked: Waking Up to the Facebook Catastrophe. He will have more things to say when he speaks in Portland at WW's TechfestNW on April 2 and 3.

At the close of the Roaring 1990s, McNamee started a second firm, Silver Lake Partners, in 1999 to hunt bigger game in a crash he saw coming. Sure enough, the tech bubble burst in 2000, and Silver Lake went shopping. Then, in 2004, he founded Elevation Partners with Bono, lead singer for U2. It was through Elevation that McNamee invested in Facebook.

Guys like Zuckerberg and Uber founder Travis Kalanick aren't necessarily sinister, McNamee says. They were just brought up wrong.

"These guys were raised at a time when most parents told their children they were exceptional, particularly white children," McNamee says. "And they came into a business environment that had been deregulated to the point where there were, more or less, no rules. Smart people were encouraged to grab what they could get."

For a (very) rich hippie who is otherwise cheerful, McNamee can get dark. He suspects the Trump administration may be cooking the numbers to make the economy look better than it is. "Why not?" he says. "They're cooking everything else."

McNamee sees a scary alliance between Zuckerberg and Trump. Zuckerberg, McNamee says, considers Trump his best protection against Democratic presidential candidate Elizabeth Warren, who has vowed to break up Facebook if she becomes president.

He frets about Google, too, particularly what the company, now called Alphabet Inc., is doing with its Sidewalk Labs subsidiary in Toronto. The local government there has given Sidewalk near carte blanche to develop 12 acres of derelict waterfront. On paper, the project looks fantastic: Sidewalk plans to spend $1 billion to build thousands of apartments and shops, all connected with free Wi-Fi, snow-melting bike lanes and sidewalks, light rail, and self-driving cars.

The part that freaks out McNamee is a plan to install sensors to gather "urban data," as Sidewalk calls it, on traffic, pedestrian volume, and even usage of park benches. Sidewalk says that information will be used to better plan new parts of the neighborhood and improve old ones. McNamee and others say it will create an Orwellian surveillance state.

"If you were going to pick one place to win the battle, that's it," McNamee says. "They're going after control of municipal services."

Alphabet is a for-profit company, and it will monetize Sidewalk Labs somehow, McNamee says. The question is how. The rest of Alphabet's business is built on collecting personal data and using it to tailor ads users will click on. Sidewalk's sensors will produce a trove of that data, and Alphabet will use it to further manipulate our behavior, McNamee says.

So, how does big tech's Cassandra stay sane and happy in these troubled times? Music. McNamee's a lifelong musician, playing dozens of shows a year in two bands. One of them, Full Moonalice, often plays Portland. The group's biggest hit is "It's 4:20 Somewhere." In one Full Moonalice song, he croons the title, "Am I High?" The answer, despite Trump, Brexit and the digital surveillance state, is, clearly, yes.

GO: TechfestNW is at Portland State University's Viking Pavilion, 930 SW Hall St., techfestnw.com. Thursday-Friday, April 2-3. Visit the website for tickets.