Now playing on Otherppl, a conversation with Roger McNamee. His new book, Zucked: Waking Up to the Facebook Catastrophe, is a New York Times bestseller, available from Penguin Press.

McNamee has been a Silicon Valley investor for 35 years. He co-founded successful funds in venture, crossover and private equity. His most recent fund, Elevation, included U2’s Bono as a co-founder. He holds a B.A. from Yale University and an M.B.A. from the Tuck School of Business at Dartmouth College. Roger plays bass and guitar in the bands Moonalice and Doobie Decibel System and is the author of The New Normal and The Moonalice Legend: Posters and Words, Volumes 1-9. He has served as a technical advisor for seasons two through five of HBO’s “Silicon Valley” series and was also responsible for raising the money that created the Wikimedia Foundation.

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Last Halloween, I’d asked a few Nervous Breakdown contributors to share their favorite terrifying movie scenes, and D. R. Haney was among them with his contribution from Rouben Mamoulian’s 1931 Dr. Jekyll and Mr. Hyde. I, on the other hand, had picked the tunnel scene from Willy Wonka, which I explain so you understand why I like collaborating with Duke. My brain grows three sizes bigger by association. He’s like a cinematic moral compass for which true north is James Dean. And this year for Halloween, Duke and I decided to discuss the classic tale that produced another old-school Hollywood icon.

Jeff Selingo’s new book, College Unbound: The Future of Higher Education and What It Means for Students (New Harvest, 2013), finds the editor at large for the Chronicle of Higher Education articulating the challenges to contemporary higher education. He also explores possible new directions for a future in which learning may well be unbundled from many of its traditional structures.

I interviewed Selingo and published a short version of our conversation at the Huffington Post under the title “When the Jobs of Tomorrow Don’t Exist Today: Jeff Selingo on College, Liberal Arts, and the Possible Future.” Here, I let the conversation expand to its full flowering, and then move at its close to issues of contemporary publishing.

Years ago, when she was around my current age, my mother went to Mexico and was robbed.  She had just been granted American citizenship, so it was very important that she was able to find her papers.  The story has been passed down to me since puberty, as a word of caution for a woman entering the world: freedom is a risk.

Digital native is a term coined by writer Marc Prensky, one I discovered, along with its counterpart, digital immigrant, in New York Times tech reporter Nick Bilton’s excellent book about media and technology, I Live in the Future & Here’s How It Works. According to Wikipedia, “A digital native is a person who was born during or after the general introduction of digital technology, and through interacting with digital technology from an early age, has a greater understanding of its concepts,” while “A digital immigrant is an individual who was born before the existence of digital technology and adopted it to some extent later in life.” According to my understanding, a digital native is someone for whom the use of digital technology is innate and natural, who never had a moment when they learned, say, what the internet was. Not so for me; I’m pure digital immigrant.

The internet is changing my name,
eliminating the apostrophe like some
cyber Ellis Island. I am attached to

my apostrophe, the “of the” of my father
and all his drunken Irish forebears, a gentle
breathy caesura before learning from whence
I came.

And then there’s the apostrophe itself, the South Dakota
of the semicolon, the most unassuming cousin
in the punctuation family portrait,
hair-combed neatly in the first row,
so often misused in plurality when all
it really wants to do is possess.

O the clock, of my father, dead now
ten years and without a grandson that bears
his name. Back in ’59, the year he shipped out
for Okinawa, there had to be a bad
key on the Smith Corona for the apostrophe
to be abandoned, and the typer never scolded
you for using an “invalid character.”

If I decide to the fly the 2,000 miles
to my father’s grave I’ll enter our name in
the appropriate field. All the wasted years, all
the whiskey drunk will come with me and when
I land I’ll hope despite one missing speck
that I am still his son.

I am sick of the fucking internet. I’m not supposed to say this because I am a child of technology. When I was 12, my big brother got us on AOL. He was in a chat room for fans of the Allman Brothers Band and introduced me to all these people. As they all said hi to me, I felt shivers running up and down my spine. I was so excited I couldn’t stop moving.

Chat rooms felt like a dark closet full of strangers, outrageously intimate. I liked to engage in religious debates the most. I also wanted a boyfriend but found teen chat rooms annoying. I would stay home when the neighborhood kids went out to play because I didn’t like them and preferred to talk to strangers on the internet. I mailed my cheer-leading pictures to a boy in New Orleans who may or may not have been a real person.

I hang out with real geeks because I wish I was one of them. I am uncool in the non-hipster way of being uncool. As in, I’m too awkward to get along with normal people but I don’t know any programming languages. I taught myself HTML once upon a time and thought I was pretty badass, but I couldn’t stay afloat once CSS came on the scene. I know how to crimp a Cat 5 cable, and I can put together a PC. I married my husband because I thought it was hot when he wrote code.

Every now and then I get this need to be well informed about the world, and I go on a news binge. Last week, it was a combination of Norway, Lulzsec, the debt ceiling and Google News Badges. Those badges don’t update properly. The thing says I read 5 articles about Norway, so I started reading a lot of articles on different topics. Then I read like 20 on Anonymous, but it wouldn’t update. I have a bronze Norway badge. I am disappoint.

Although it damn near made me kill myself over the weekend (only a slight exaggeration), I go back to Google News on Monday like an addict looking for inspiration. There are people out there breaking the law and pissing people off and making a difference in a way I can never do. It’s totally possible that the things they’re doing all completely wrong. I’m not convinced anyone is doing anything that’s not completely wrong.

I am a project manager. I am a rule follower. I respect authority.

Every few months, I decide I’m not really a writer. I am angry that I went to college and even more so that I went to grad school. I wish someone had told me how worthless it was. I’m not saying it wasn’t fun or that I didn’t meet lovely people and learn some stuff, but look, I discovered yoga at age 16, and I knew I wanted to teach yoga at age 17, yet I dropped that idea and went to college because that seemed like the appropriate thing to do. I am so tired of the appropriate thing.

If I had followed my instinct, I would have a career by now.

I try to tell myself this is my dharma, that karma put me here. I tell myself I’m here to learn something, and I’m working extra hard to learn it as fast as possible so I can get the fuck out of this cubicle and start doing what I wanted to do all along. Did I really need all those student loans to have this realization, karma? I am $32k in the hole for a degree I will never use.

I don’t mean to be such a downer about it. I mean, I can use a semicolon like nobody’s business, but I rarely do because most of the time it’s pretentious. I fucking love run-on sentences.

I’m tired of buying things. I hate things. I hate stuff. I hate clutter. It’s not just the laptops littering the living room but also the server racks down the hall from my bedroom, and also the ones in the basement, and the miscellaneous cables scattered around the technological wasteland that is my house. It’s also the unwashed underwear, the piles of recycling, the perpetually half done renovation projects, the stacks of unread books and magazines on the floor and dust bunnies, my god the dust bunnies. And furthermore, it’s Twitter and Facebook and Google + and Google Reader and Google News and my two blogs, one of them disused. It’s also IRC and GChat and once upon a time AIM and ICQ. It’s also Skype and Ventrillo and Stickam and Daily Booth and Youtube.

There is a BMW being born on my behalf and a loan check to prove it. I feel like a teen mom except I’m not a teenager, not a mom, and not a reality TV star, but my life does have that familiar ring of this is not really- this- this- this is not really happening…

You bet your life it is.

I am often afraid that if I said what I really thought about the world, I would be burned at the stake. Maybe I should just make peace with that. After all, this flame proof suit will not last forever. Maybe sometimes it’s better to douse yourself in gasoline and go for the fucking glory.

Maybe I should be a little less dramatic.

They tell me I’m better on the Internet. Funnier on Facebook, more oomph than “IRL.” I’m not sure how to feel about this. I suppose my avatar is something of an improvement, a jovially connected version of myself, my greatest hits, quickest comebacks, and most “likeable” observations. Version 2.0 as Zadie Smith says in her controversial essay, “Generation Why?”

Successful Hollywood films have an overwhelmingly ballsy, brassy and over the top obsession with the hero’s journey. While many people point to the cheap and easy way Disney films use the same formulaic music scores and elements of “imagination” from one film to the next, less has been said to criticize this same pattern in Hollywood movies aimed at adults. Perhaps this is because we are pretty comfortable with this motif. When The Social Network was first released, many critics marveled at how the director was able to make a film that was ostensibly about computer programming interesting and fun. In reality, this was done using the same formula used for any successful Hollywood movie. We were given booze and boobs, and a bunch of geeky college students suddenly transform into warring tribes, both on campus and in the courtroom.

I chatted with Jennifer Egan the day after a tornado touched down not far from the author’s Brooklyn neighborhood. Rushing to get home from the subway, she took shelter under scaffolding, watched the sky turn green, and later described the feeling as a “unique weather event,” a term one could use to describe each of her books: Egan is known for her versatility, whether she’s writing about the collision of identity, pop culture, and technology in the National Book Award–nominated Look at Me, or renovating the Gothic novel in The Keep.

A couple of weeks ago, I wrote a short piece for The New Yorker’s Book Bench blog about Kobo, the eBook reader competing with Amazon’s Kindle. For the story, I attended a Kobo company party and noted that the Kobo team seemed to be starkly divided between those who came from publishing or marketing backgrounds and the tech people whose skills actually power the innovative device. Or, as I called them in the piece, “the nerds.”

A despairing friend called late one night to say that he was looking at a photo of himself as a toddler holding his father’s rifle.

“I have an appointment with that rifle,” he told me. “I’ve always known I was going to end my life with it.”

He’s fine now, thank God, but his remark brought to mind a journal entry I made as a teenager, in which I said that I was sure I was going to kill myself one day; it was only a matter of how and when.