Cover of Won't Fix

Won't Fix

Won't Fix

By: Rob Leathern
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From the founders of InfoHawk: conversations about AI-driven deception, abuse and scams, and why they’re so hard to stop. In software engineering, “won’t fix” describes a bug by acknowledging the issue but intentionally leaving it unsolved because addressing it is too costly, risky, or not worth the trade-offs. Hear from the practitioners fighting phishing, deepfakes and bots, and learn about the broken systems and misaligned incentives that keep us all vulnerable.Copyright 2026 Rob Leathern Economics Leadership Management & Leadership Politics & Government
Episodes
  • Won't Fix Episode 19: With Author Becky Holmes

    Won't Fix Episode 19: With Author Becky Holmes
    16 Oct 2026

    Somewhere out there, Keanu Reeves is desperately in love with you. So is Jason Statham. And a brave peacekeeping soldier who just needs a few gift cards to get home.

    Of course, none of them are real. Keanu Reeves isn’t even on social media. But that hasn’t stopped scammers from impersonating him again and again.

    My guest today has had more of these online romances than anyone alive. Becky Holmes joined Twitter during lockdown, started stringing scammers along for laughs, and built a following of more than a hundred thousand people under the name Death to Spinach. Then victims began reaching out, people who’d lost their savings, their friendships, and sometimes far more. And the joke turned into a mission.

    Her book, Keanu Reeves Is Not in Love With You: The Murky World of Online Romance Fraud, is laugh-out-loud funny and heartbreaking, often on the same page. It takes on the scammers, the scripts and the shame that keeps victims silent. Her follow-up, The Future of Fraud, came out this spring.

    Chapter Timestamps:

    00:00 Intro

    2:37 Why Keanu Reeves and other celebrities are impersonated

    4:16 How celebrity fraudsters persuade victims to send money

    8:28 Scam-baiting, scripted responses, and an absurd Brad Pitt exchange

    12:14 Platform responsibility and the UK reimbursement debate

    14:56 Victim stories: financial ruin, isolation, and secrecy

    19:02 Changing the language around fraud victims

    21:23 Male victims, sextortion, and underreporting

    23:28 The harm caused by stolen identities and images

    27:12 Scam networks as a professional industry

    Resources & Links:

    Rob Leathern (https://www.linkedin.com/in/leathern/)

    Keanu Reeves Is Not in Love With You: The Murky World of Online Romance Fraud

    (https://www.amazon.com/dp/B0D7SHMNB4)

    The Future of Fraud (https://www.amazon.com/Future-Fraud-FUTURES-Becky-Holmes-ebook/dp/B0FJD3WBJR/ref=books_amazonstores_desktop_nis_default)

    Becky Holmes on X (https://x.com/deathtospinach?lang=en)
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    42 min
  • Won't Fix Episode 18: With Jon Leibowitz Former Chairman, FTC

    Won't Fix Episode 18: With Jon Leibowitz Former Chairman, FTC
    9 Oct 2026
    My guest Jon Leibowitz spent nearly a decade at the Federal Trade Commission, and four years running it — as Chairman from 2009 to 2013, right through the wreckage of the financial crisis.During Jon’s chairmanship (March 2009 to February 2013), the FTC's enforcement centered on "last dollar" frauds preying on Recession-battered consumers: coordinated national sweeps against mortgage-rescue and foreclosure-relief scams (leading to the 2010 MARS Rule banning advance fees), and a landmark $108 million settlement with Countrywide over mishandling struggling borrowers. It hit deceptive marketers hard — the roughly $359 million Jesse Willms "free trial" negative-option case, a $163 million scareware judgment against fake-virus-pop-up operators, the 2011 fake-news-site sweep over bogus acai-berry weight-loss claims and phony Oprah and Rachael Ray endorsements, and a 2012 international crackdown on India-based tech-support scam boiler rooms.On the robocall front, it brought cases like the Cash Grant Institute and the auto-warranty scheme (the telemarketer who surrendered his Mercedes) and launched the public Robocall Challenge contest. Beyond fraud, his FTC also built the agency's modern privacy agenda — landmark settlements with Google and Facebook and a record $22.5 million penalty against Google over Safari tracking — and stayed active on antitrust and competition alongside all of it.After the FTC, he went into private practice at Davis Polk, testified before Congress more times than he can probably count, and today he chairs the National Consumers League — one of the oldest consumer advocacy groups in the country.But here's what makes this conversation timely. The scams he chased fifteen years ago never died. They got faster, cheaper, and — thanks to AI — a whole lot more convincing.Chapter Timestamps:00:00 Intro2:33 FTC career and current work4:03 Old scams, new technology, and the rise of AI-enabled fraud5:30 From the “spam king” to large-scale online deception6:51 Fraud supply chains, overseas actors, and cross-border enforcement9:52 AI deepfakes and the persuasive power of modern scams11:21 Affiliate marketing, robocalls, and weakened FTC monetary remedies14:42 State attorneys general and platform cooperation17:48 - Shared intelligence and the multi-provider nature of scams18:23 AI fraud’s scale and fabricated “evidence”20:33 Long-form fake media and recurring-subscription traps23:39 Domain authentication and the failure of voluntary privacy standards27:03 Reporting, independent evaluation, and regulatory balance33:02 Trust in the internet and FTC rules against impersonation and fake reviews34:53 Business verification and the trade-off between friction and safety37:14 A $0 trial that becomes $34.90 per month39:58 Closing: protecting reality while preserving innovationResources & Links:Rob Leathern: (https://www.linkedin.com/in/leathern/)Jon Leibowitz: (https://www.linkedin.com/in/jon-leibowitz-14091679/)Steve Martin scam video website: https://assist.saeculums.com/ Cases from Jon's era:Sanford Wallace "Spam King" (CD-ROM tray) — FTC release: https://search.ftc.gov/news-events/news/press-releases/2004/10/ftc-cracks-down-spyware-operation — The FTC's 2004 complaint describes spyware that popped open CD-ROM trays and then flashed a "FINAL WARNING!!" pushing paid fixes. Nice follow-up detail: a court later ordered Wallace to give up $4,089,500, from selling the "fix" at roughly $30 a copy.Scareware $163M judgment (Kristy Ross): https://www.ftc.gov/node/47528 — Useful context for listeners: a co-defendant and his father had to give up $8.2 million under a 2011 settlement, which is a good contrast with the giant headline number.2012 international tech-support crackdown: https://www.ftc.gov/news-events/news/press-releases/2012/10/ftc-halts-massive-tech-support-scams — This is the press conference Jon describes; one of the six operations found victims by buying Google ads that appeared when people searched for their computer company's support number, which echoes your toll-free-number point.Jesse Willms $359M settlement: https://www.ftc.gov/news-events/news/press-releases/2012/02/ftc-halts-deceptive-practices-marketer-who-collected-359-million-using-bogus-free-trial-offersThe Atlantic, "The Dark Lord of the Internet" (Willms profile, 2014): https://www.theatlantic.com/magazine/archive/2014/01/the-dark-lord-of-the-internet/355726/Fake news sites / acai sweep (2011): https://www.ftc.gov/news-events/news/press-releases/2011/04/ftc-seeks-halt-10-operators-fake-news-sites-making-deceptive-claims-about-acai-berry-weight-lossCentral Coast Nutraceuticals (fake Oprah / Rachael Ray endorsements): https://www.ftc.gov/news-events/news/press-releases/2012/01/internet-marketers-acai-berry-weight-loss-pills-colon-cleansers-pay-15-million-settle-ftc-chargesAMG Capital Management v. FTC (SCOTUSblog case page): https://www.scotusblog.com/case-files/cases/...
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    41 min
  • Won't Fix Episode 17: With Dave Willner, Co-Founder of Zentropi

    Won't Fix Episode 17: With Dave Willner, Co-Founder of Zentropi
    25 Sep 2026

    My guest today is Dave Willner, cofounder of Zentropi and a fixture in the Trust and Safety world.

    In 2008, he was a young Facebook employee who sat down to replace a one-page list of banned content — it said, roughly, no Hitler and no naked people — with the first real set of community standards the internet had ever seen. The rules he wrote are still the foundation of how Meta governs content shared by billions of people.

    He went on to build community policy at Airbnb, and then joined OpenAI in early 2022, before ChatGPT existed, to figure out how to stop an image generator from producing bad things.

    Now he's co-founded a company called Zentropi, with Samidh Chakrabarti, which is built on the idea that moderation at scale was never actually impossible — we just didn't have the right tools.

    In This Episode:

    Human moderation suffers from high turnover, trauma, and inconsistent judgment—problems small, tailored language models solve by strictly enforcing written rules.

    Specialized small models can run circles around massive frontier models on speed and cost, making real-time classification financially viable.

    Written policies and labeled datasets are two sides of the same coin; when an AI disagrees with a human label, it usually exposes a vague policy rather than a model error. Running moderation models locally on your own servers cuts per-check costs, dodges European privacy paperwork, and keeps user data in-house.

    Bad actors are using AI to scale exploits at high speeds, forcing safety teams to adopt AI defenses immediately just to keep up.

    A single global moderation rule doesn't work—dating apps, teen platforms, and social feeds require custom enforcement thresholds based on their specific risks.

    Using the same LLM to draft a policy, generate test cases, and grade itself creates lazy evaluation loops that hide major safety blind spots.

    Giving open-weights AI tools to volunteer moderators on Reddit or Discord lets small teams govern massive communities without burning out.

    Chapter Timestamps:

    00:00 Intro

    3:21 Dave Willner’s trust-and-safety background and the origins of Zentropi

    7:04 Zentropi’s specialized moderation models and policy-optimization tools

    11:15 Why human moderation is inconsistent and difficult to measure

    15:45 The limits of human judgment and the case for automated moderation

    21:09 Imperfect language, model precision, and faster adaptation to abuse

    24:43 Shared moderation infrastructure versus platform-specific policies

    28:46 Why small specialized models can outperform larger general models operationally

    32:26 Local deployment, privacy, and trust-and-safety resource constraints

    34:16 Customer economics and real-time video moderation

    38:09 The danger of “slop” policies and weak AI evaluations

    44:10 AI moderation as a tool for decentralized community governance

    47:06 The adversarial threat landscape and urgency of AI-enabled defense

    Resources & Links:

    Zentropi (https://zentropi.ai/)

    Dave Willner (https://www.linkedin.com/in/davewillner/)

    Rob Leathern (https://www.linkedin.com/in/leathern/)
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    53 min
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