This Week in Tech 1061: Amy's Crazy Husband

Date: December 8, 2025
Host: Leo Laporte
Guests: Kathy Gellis (Techdirt attorney), Amy Webb (futurist, CEO of Future Today Strategy Group), Brian Wolf (Amy's husband, guest appearance)

Episode Overview

This lively episode of This Week in Tech blends analysis of pivotal tech law, future tech trends, and real-world privacy experiments. Host Leo Laporte is joined by legal expert Kathy Gellis and noted futurist Amy Webb. Topics range from a critical Supreme Court copyright case to the futility of age verification laws, the rise (and regulatory threat) to VPNs, and personal privacy techniques—highlighted by Amy Webb’s “crazy husband” Brian’s experiment building an anonymous laptop. The group also discusses AI-native devices, AR's rocky future, shifts in big tech company leadership, hot topics in media mergers, and even the effectiveness of student smartphone bans.

Key Discussion Points & Insights

1. Broadway, "Chess," and Amy Webb’s Many Hats

00:41–7:30

• Amy Webb discusses her role as producer for the successful Broadway musical "Chess," delving into its Cold War origins, music pedigree (Tim Rice, ABBA’s Bjorn, Benny), and 37-year journey to a triumphant return.
• Leo reveals his chess enthusiasm:

  "I'm a huge fan of Broadway musicals for one thing, so I'm glad to hear it's a...huge success." (02:08, Laporte)

• Amy shares backstory:

  "A geopolitical musical...about the US vs USSR. Two troubled chess players...It's also somewhat a commentary on American capitalism and power." (04:20, Webb)

2. The Supreme Court and the Cox–Sony Copyright Case

07:35–33:20

What’s the Case?

• Sony (record label) sues Cox (ISP), demanding ISPs proactively terminate customers accused of copyright infringement ("pirates"), or risk massive liability.
• Kathy Gellis explains ISPs like Cox are not liable by default (under DMCA’s "safe harbor") but lose that protection if they don’t act against "repeat infringers."

Key Legal Issues

• The distinction between platforms storing infringing files (e.g., social media) and simple "conduit" ISPs.
• Whether handing over IP addresses is enough proof of infringement.
• Consequences: If Sony wins, ISPs could be forced to police Internet use, with ripple effects for privacy, free speech, and even electric utilities.

First Amendment Angle

• Gellis laments First Amendment concerns aren’t front and center:

  "I can't believe we may get another major copyright decision where the words First Amendment don't show up at all...we're just glossing over that as if it's not an element." (18:03, Gellis)

• Conservative justices—surprisingly—seem more attuned to the danger of Internet access bans as a punishment.
• Outcome could set a broad precedent for platform liability in US law.

3. Age Verification, VPNs, and Lawmakers "Losing Their Minds"

37:26–44:08

• Across US states, age verification laws now threaten not just access to porn, but skin cream, social media, diet products, and dating services.
• EFF and Techdirt: These laws force massive data collection, kill anonymity/ privacy, and are easily bypassed with VPNs—so some lawmakers are proposing VPN bans.
• Kathy’s critique:

  "They've extrapolated [child protections] to the Internet and lost their minds...they're also driving kids off of being online and access to all sorts of information which they have their own First Amendment rights to access." (41:14, Gellis)

• Amy’s insight: Real business incentives may clash with regulatory efforts, and privacy measures are often afterthoughts until forced by law.

4. Amy’s "Crazy Husband": DIY Anonymous Laptop

44:11–57:41

The Challenge

• Amy invites Brian Wolf, her husband (engineer/ophthalmologist), to explain his privacy experiment: Could he create a laptop with no identity trail?
• Motivated by a desire to stream the Tour de France with UK commentators(!), he escalates into a technical challenge worthy of hackers—and AI.

The Build Process

• No Microsoft/Apple/Google account; no credit cards.
• Buys a Mullvad VPN card with cash at Best Buy.
• Sets up machine in public libraries to avoid IP/ location trail.
• Uses USB WiFi dongle to spoof MAC address.
• Pen-tested with geek friends; confirms nearly untraceable.

Lessons Learned

• AI (ChatGPT) is powerful for "assistant programming," but confidently wrong if you’re not careful.

  "[ChatGPT] makes many, many mistakes very confidently." (46:50, Wolf)

• Leo:

  "I mean, it does beg the question, what the hell do you need that for?" (51:52, Laporte)

• Brian:

  "Nothing. It serves no general purpose at all...it was just a fun game." (52:03, Wolf)

Legal & Practical Risks

• Kathy: Technical solutions only go so far. Legal process (subpoenas, warrants) can break chains unless there’s real First Amendment protection of anonymous speech.

5. AI-Native Devices & The Coming Wearables Wave

104:35–109:51

• Leo and Amy discuss Meta’s Ray-Ban glasses, Apple’s shifting priorities, and the future of "AI-native" screenless devices (e.g., Humane pin, Rabbit R1).
• Amy:

  "There’s a tranche of devices coming to market next year...very much about AI continual recording...There is a lot of that coming...and as soon as those use cases start to pop up...I think people are going to care a lot less about privacy." (107:13, Webb)

• Kathy’s caveat:

  "Do not wear those if you go to speak to a lawyer—you'll waive your privilege." (108:45, Gellis)

• Leo predicts an "AI civil war" with privacy and pro/anti-AI factions.

6. Student Smartphones & Societal Impacts

152:27–157:45

• Singapore and Australia banning phones/social media for students—test scores have risen.
• Amy:

  "You have to literally turn in the phone...then pick it up on the way out of school."

• Predicts severe withdrawal for kids cut off suddenly, highlighting the need for mental health support amid digital detox.
• Discussion about the necessity of boredom for creativity and resilience in kids.

7. News Blitz: Media, Tech, and Leadership Shifts

Netflix & Warner Bros.

128:43–143:23

• Speculation on whether Netflix is trying to kill traditional movie studios by acquiring Warner Brothers or simply consolidating content.
• Amy:

  "It would be counter to the business interests...to then stop making it or restricting it in some way." (135:15, Webb)

• Kathy’s concern: Netflix content may become "friendly noise" instead of real art.

Tech C-Suite Departures (Apple/Meta)

93:28–101:13

• Multiple Apple execs (Alan Dye, Lisa Jackson, Kate Adams, John Janandrea) leaving; "what's going on at Apple?"
• Amy:

  "Executive movement among the executive ranks...happens all the time in every industry...To me this is a gigantic nothing burger."

• More interest in Meta's strategic flailing—Metaverse, AI, hardware, etc.

Amazon/Microsoft Layoffs & RTO Mandates

118:17–128:37

• Amy suggests RTO (Return to Office) mandates are a tactic for weeding out tenured/“sparkless” workers rather than about productivity or real estate.
• Kathy:

  "It's a bad thing. I think it's...a pretext for driving away older employees." (122:45, Gellis)

Notable Quotes & Memorable Moments

• On copyright, liability, and free speech:

  "If Cox loses, the consequences...for the Internet are really awful...show stoppingly bad, and in a way that nobody's grappling with." (23:47, Gellis)

• On the futility of banning tech:

  "They've extrapolated that to the Internet and lost their minds because...they're also driving kids off of being online and access to all sorts of information." (41:14, Gellis)

• On privacy and AI tools:

  "ChatGPT makes many, many mistakes very confidently." (46:50, Wolf)

• On anonymous speech:

  "Anonymous speech is lawful and...protected by the First Amendment...but there's not enough case law that has fully cemented that protection..." (56:21, Gellis)

• On shifting company strategies:

  "When you have a company that has 60,000 people...you get these like, systems-level problems...super hard to...untangle." (124:01, Webb)

• On AR glasses & AI wearables:

  “There’s an entirely other tranche of devices coming to market next year...very, very much about AI continual recording...I think people are going to care a lot less about privacy." (107:13, Webb)

• On children's digital dependency:

  "There is for real withdrawal and there are going to be kids who are suffering through that..." (155:33, Webb)

Fun, Silly, and Personal Moments

• Brian Wolf’s (Amy’s husband) anonymous laptop experiment, complete with public library hopping and pen-testing barbecues. (44:11–57:41)
• Eye health Q&A: FDA-approved Stellest glasses to slow myopia, the science behind how blur at the periphery can prevent nearsightedness. (63:05–72:00)
• Kathy’s claim to fame: >120 Huey Lewis and the News concerts attended, including in Mississippi and Japan. (146:21–146:39)
• Detroit’s RoboCop statue finally erected after 15 years. (158:15)
• Kathy’s comparison:

  "If they left it to Zaslav, [Warner Brothers would] be out of business anyway." (130:25, Gellis)

Timestamps for Important Segments

• Chess on Broadway / Music Backstory — 00:41–07:30
• SCOTUS Cox–Sony Copyright Case — 07:35–33:20
• Age Verification & VPN Bans — 37:26–44:08
• Brian Wolf’s Anonymous Laptop — 44:11–57:41
• AR Glasses & AI Devices — 104:35–109:51
• Smartphone Bans in Schools — 152:27–157:45
• Netflix–Warner, Media Mergers — 128:43–143:23
• Amazon/Microsoft Layoffs & RTO — 118:17–128:37
• Personal/Misc. (Tour de France, RoboCop statue) — 83:38–87:03, 158:15

Conclusion

This episode represents TWIT at its best: expert insight, accessible explanations of major tech policy, genuine personal stories, and a sense of fun. You’ll understand complex ongoing copyright/ISP litigation, come away with a nuanced view of the coming AI device revolution, and even learn to never bet against Brian Wolf when it comes to privacy or barbecued engineering.