This Week in Tech (TWiT 1061): Amy's Crazy Husband - Can One Build a Truly Anonymous Laptop?

Date: December 8, 2025
Host: Leo Laporte
Panel: Kathy Gellis (attorney, Techdirt), Amy Webb (futurist, CEO: Future Today Strategy Group), special guest Brian Wolfe (Amy’s “crazy” husband & privacy experimenter)

Episode Overview

This episode features a rich panel discussion on digital privacy, major legal battles impacting internet rights, the realities of user anonymity in a surveilled age, new tech regulation proposals, and shifts in Big Tech (notably at Apple and Meta). Highlight: Amy Webb’s husband, Brian Wolfe, gives a fast-paced, fascinating account of building a truly anonymous laptop—testing the limits of privacy in the digital age. The show also delves into cell phone bans for students, “return to office” mandates, and the fight for the future of entertainment with Netflix’s potential Warner Bros. acquisition.

Key Segments & Discussions

1. Panel Introductions & Broadway Success

• Kathy Gellis: Techdirt attorney, Supreme Court–admitted, active in DMCA/copyright cases.
• Amy Webb: Futurist, CEO, Broadway producer—recent success with “Chess” on Broadway discussed.
  Musical geek-out and Amy’s surprising investment story (04:18–05:59)
  • “I invested because I wanted this thing to have a shot, not to make money.” – Amy Webb (05:53)

2. Supreme Court: Cox vs. Sony Copyright Case (07:35–31:14)

Background:

• Sony (label) suing ISP (Cox) for not policing piracy by users
• Safe harbor debate: Is Cox responsible for repeat infringers on its network?
• Kathy wrote an amicus brief for Cox.

Main Points:

• Safe Harbor Differences – Takedown notice vs. conduit provider obligations (09:53)
• Secondary Liability – Can an ISP be forced to police users for copyright (14:06)?
  • “If Cox loses, the consequences…are really awful. Like, show-stoppingly bad.” – Kathy Gellis (23:47)
• Speech & Policy Issues – The panel covers Constitutional, First Amendment, and over-broad liability (17:58–18:33)
  • “People use the internet to connect and speak…and somehow we’re glossing over that.” – Kathy Gellis (18:03)
• VPNs & Anonymity as a Loophole? (25:32–29:36)
  • Panel raises how VPNs challenge enforcement and raise bigger free speech/intermediary questions.

Memorable Quote:

• "Justice Alito made the most sense in this entire oral argument." – Kathy, on the strange dynamics of Supreme Court copyright questions (13:22)

3. Tech Regulation Run Amok: Banning VPNs & Age Verification Creep (37:26–44:11)

• Emerging laws: Age verification now proposed for everything from porn to skin cream; VPN bans mooted as technical workaround to these laws.
• “Old school cases about restricting sales… extrapolated to the internet and lost their minds.” – Kathy (40:22)
• Practical and business pushback: “Everybody is aligned against more regulation because it hurts rather than helps.” – Amy Webb (43:23)

4. Epic Privacy Experiment: Building an Anonymous Laptop

Guest: Brian Wolfe (“Amy’s crazy husband”) — 44:13–54:32

Brian’s Project:

• Trigger: Amy wanted to watch the Tour de France with European commentary—led Brian down a rabbit hole into VPNs, privacy, and anonymous hardware.
• Steps:
  • Bought Mullvad VPN cards with cash at Best Buy, NO personal info (47:49)
  • Used public library WiFi, USB WiFi adapters for MAC address randomizing
  • Stripped OS, hardened browser (Firefox) for anti-tracking
  • Had security friends do a “penetration test” to check for de-anonymization leaks (50:00)
• Used ChatGPT to orchestrate (and learned its limits: “ChatGPT makes many, many mistakes very confidently.”)
• Result: Created a laptop not traceable back to him for normal adversaries (nation-states still a risk).

Quote:

• “It serves no general purpose at all… It was just a fun game of trying to separate out [identity].” – Brian (52:03)
• “Thanks to AI… but if I didn’t have the base knowledge, I’d have been lost.” – Brian (54:32)

5. Health Tech: Glasses to Prevent Nearsightedness, Synthetic Biology, and Kids’ Eye Health (63:02–75:25)

• FDA-approved Stellest lenses to slow myopia in children (63:05)
  • “You keep the center vision sharp, but you blur the peripheral… and it breaks that feedback loop.” – Brian Wolfe (65:52)
• Brief banter about Apple, Meta, VR/AR, and the future of health wearables.

6. Big Tech Shake-Ups: Apple & Meta (93:28–106:33)

• High-profile Apple departures (design, AI, legal, environmental heads)
  • Amy Webb: “End-of-year shakeups are pretty normal—the story isn’t at Apple, it’s at Meta.”
  • Meta is cutting Metaverse budget by 30%; moving focus to AI and AR glasses (especially after the relative success of Meta’s Ray-Ban smart glasses).
• Industry Trend Observations:
  • “There’s an entirely new tranche of AI-native devices coming to market… next 12-24 months.” – Amy Webb (105:29)
  • Ongoing privacy/utility trade-offs: “We’ve seen time and time again, people make noise about privacy, then get some value and say ‘well, that’s fine’.” – Leo (108:45)

7. Workplace & Society: Return-to-Office Mandates and Layoffs (118:17–128:37)

• RTO seen as pretext for attrition, especially favoring refresh of workforce over older/“tenured” employees.
  • Amy: “I think RTO is less about cost savings… much more about trying to get fresh minds in.” (119:14)
  • Kathy: “It’s a pretext for driving away older employees… [But] it’s not going to bring energy back to the company.” (121:54)

8. Entertainment: Netflix’s Warner Bros. Play – Kill or Reinvent Hollywood? (128:37–143:23)

• Netflix rumored to buy Warner Bros.; Hollywood speculation about motives (content consolidation vs. eliminating competition from theatrical releases).
• Consensus: It’s about consolidating content, not killing movies—the tech vs. content identity crisis at Netflix.
  • “If the North Star for the company is consolidating content… that does not give them a long term strategic advantage.” – Amy Webb (139:07)
  • “What Netflix likes… is content people have on in their house… and they’re not interested in content worth going to a movie theatre for.” – Kathy (137:38)

9. Society & Parenting: Student Cell Phone Bans, Social Media Withdrawal (152:27–157:45)

• Discussion around nation-scale smartphone/screen bans for students (Singapore, Australia, Florida) and their social/psychological fallout.
  • “I’m legitimately worried about the mental health of kids there and what they're about to go through…” – Amy Webb (157:41)
  • Screen withdrawal and the dangers/necessity of “boredom” for creativity and resilience

10. Fun & Oddities (159:06–162:27)

• “Robocop” statue finally rises in Detroit after 15 years (159:06)
• Fast Company studies show gesturing with your hands makes you look more competent on stage (160:04)
• Petition to force X (Twitter) to abandon its Twitter trademark after Elon’s rebrand to “X”; explained by Kathy (161:31)

Notable Quotes & Moments

• On intermediary liability: “To protect the intermediaries or you don’t get an Internet, including all the speech that it facilitates. That’s what these cases are about.” – Kathy (28:27)
• On age verification laws: “It’s just book banning Democrats can get behind.” – Kathy (41:55)
• On AI assistants and privacy: “We should be concerned about privacy, but I think the real value is going to outweigh that concern.” – Leo (109:51)
• On AI and public attitudes: “We’re headed toward a civil war over AI. There’s a massive schism—half the population is terrified, the other half is excited and using it every day.” – Leo (110:05)

Brian Wolfe’s Privacy Laptop Saga (44:13–54:32)

• “Can you build a laptop that’s, if not nation-state secure, at least not traced to you unless you really screw up?” – Leo
• “It was just a fun game…but I could never have done this without AI—even though it’s confidently wrong a lot.” – Brian

Timestamps for Key Segments

• Amy on Broadway, “Chess” history: 02:41–06:00
• Supreme Court Cox v. Sony Copyright Case: 07:35–31:14
• VPNs/Age Verification/Regulation Creep: 37:26–44:11
• Brian builds an anonymous laptop: 44:13–54:32
• FDA eye tech & synthetic biology: 63:02–75:25
• Apple/Meta big moves: 93:28–106:33
• Return to office culture wars: 118:17–128:37
• Netflix-Warner consolidation debate: 128:37–143:23
• Student phone bans & psychology: 152:27–157:45
• Robocop statue/Trademark/Jokes: 159:06–162:27

Closing Remarks & Plugs

• Amy Webb: New reports at Future Today Strategy Group; “Chess” is a smash on Broadway (167:30)
• Kathy Gellis: Support Techdirt—vital work for digital civil liberties; Techdirt coin commemorates Section 230 (169:08)
• Leo Laporte & Twit: Thanks listeners, call to join Club TWiT to support independent tech journalism

TL;DR

A must-listen deep dive on privacy, digital speech rights, ISPs’ responsibilities, and the limits of anonymity—with a hands-on journey into building a surveillance-resistant laptop, biting commentary on privacy laws, and big-picture strategic insights on tech policy, business, and parenting.

Notable segment: Brian Wolfe’s detailed (and surprisingly doable!) guide to crafting an untraceable laptop for plausible real-world anonymity—in an era when governments are moving to undermine both privacy tools and digital speech.

(All timestamps in MM:SS–HH:MM format refer to the unabridged podcast as transcribed above.)