Won't Fix

About Won't Fix

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.

Publisher

Rob Leathern

Category

business · news · technology

Language

en

Explicit

No

First episode

7 Apr 2026

Latest episode

3 Nov 2026

Latest episodes

20 episodes in the feed.

1. 

   3 Nov 2026

   Won't Fix Episode 20: With Jeff Dunn, COO of the Digital Trust Council

   Jeff Dunn is the COO of the nonprofit Digital Trust Council, and is a long-time trust & safety leader, advocate and mentor. He has been Hinge's VP, Trust & Safety and Chief Risk Officer, and spent 7+ years in Trust & Safety at Google, with earlier work at ICANN and Harvard on child protection, election integrity and platform operations. He co-founded the Trust & Safety Network, which provides free resources for the people who keep everyone safer online. Chapter Timestamps: 00:00 Introduction 5:01 Building a stronger and more consistent trust-and-safety community 8:44 Safety as a business-growth driver, not merely risk mitigation 13:53 Dating-app safety: moving beyond verification toward proactive prevention 16:42 How scammers behave on dating platforms and how product design can help 20:00 Cross-platform scams and the need for industry signal sharing 25:09 AI for online-to-offline safety—and the privacy trade-off 27:31 DoorDash example: obvious signals and the business value of trust 29:38 AI-enabled voice fraud, targeted impersonation, and media literacy 33:21 Location data: essential for safety but valuable to scammers 34:58 User reports, offline incidents, and human review on dating platforms 38:33 Regulation, transparency, and competing on measurable safety outcomes 44:24 Trust-and-safety careers: salary trends and the return of liberal-arts skill Resources & Links: Jeff Dunn (https://www.linkedin.com/in/jeffmdunn/ (https://www.linkedin.com/in/jeffmdunn/)) Digital Trust Council (https://digitaltrustcouncil.com (https://digitaltrustcouncil.com/)) Trust and Safety Network (https://www.linkedin.com/company/trust-safety-network/home/ (https://www.linkedin.com/company/trust-safety-network/home/) and https://trustsafety.net (https://trustsafety.net/)) Rob Leathern (https://www.linkedin.com/in/leathern/ (https://www.linkedin.com/in/leathern/))

2. 

   16 Oct 2026

   Won't Fix Episode 19: With Author Becky Holmes

   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/ (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 (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) (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 (https://x.com/deathtospinach?lang=en))

3. 

   9 Oct 2026

   Won't Fix Episode 18: With Jon Leibowitz Former Chairman, FTC

   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 Intro 2:33 FTC career and current work 4:03 Old scams, new technology, and the rise of AI-enabled fraud 5:30 From the “spam king” to large-scale online deception 6:51 Fraud supply chains, overseas actors, and cross-border enforcement 9:52 AI deepfakes and the persuasive power of modern scams 11:21 Affiliate marketing, robocalls, and weakened FTC monetary remedies 14:42 State attorneys general and platform cooperation 17:48 - Shared intelligence and the multi-provider nature of scams 18:23 AI fraud’s scale and fabricated “evidence” 20:33 Long-form fake media and recurring-subscription traps 23:39 Domain authentication and the failure of voluntary privacy standards 27:03 Reporting, independent evaluation, and regulatory balance 33:02 Trust in the internet and FTC rules against impersonation and fake reviews 34:53 Business verification and the trade-off between friction and safety 37:14 A $0 trial that becomes $34.90 per month 39:58 Closing: protecting reality while preserving innovation Resources & Links: Rob Leathern: (https://www.linkedin.com/in/leathern/ (https://www.linkedin.com/in/leathern/)) Jon Leibowitz: (https://www.linkedin.com/in/jon-leibowitz-14091679/ (https://www.linkedin.com/in/jon-leibowitz-14091679/)) Steve Martin scam video website: https://assist.saeculums.com/ (https://assist.saeculums.com/?site_id=68333464&tracking_id=9f674797e4e22b5785c24be23e56d069&sub1=9f674797e4e22b5785c24be23e56d069&sub5=7683012&utm_campaign=md%257CUS%257CPC%257C0908%257CA%257CN&utm_content=U.S.+Neurologists+Link+Early+Alzheimer%E2%80%99s+to+a+Food+Millions+Still+Eat+Daily&utm_term=33709434&cc4d76fdaf5=6630&a0v5la7bquf89=3b3e7508e49c6f602l3cr100mmks1syx&uy3ubftvh0u6o8=9f674797e4e22b5785c24be23e56d069&cusduxj27i=5551224&xnfrr0ncac=35212&zsmoi87pih9=tracenep.admaster.cc&lzzgnpz8d=2ce2e6e33746b4224011d22068a89c02&Q09ORklH=2) 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 (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 (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 (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-offers (https://www.ftc.gov/news-events/news/press-releases/2012/02/ftc-halts-deceptive-practices-marketer-who-collected-359-million-using-bogus-free-trial-offers) The 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/ (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-loss (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-loss) Central 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-charges (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-charges) AMG Capital Management v. FTC (SCOTUSblog case page): https://www.scotusblog.com/case-files/cases/amg-capital-management-llc-v-federal-trade-commission/ (https://www.scotusblog.com/case-files/cases/amg-capital-management-llc-v-federal-trade-commission/) — The ruling came down April 22, 2021, unanimously, holding that the FTC can't get restitution or disgorgement under Section 13(b). Impersonation Rule taking effect (FTC): https://ftc.gov/news-events/news/press-releases/2024/04/ftc-announces-impersonation-rule-goes-effect-today (https://ftc.gov/news-events/news/press-releases/2024/04/ftc-announces-impersonation-rule-goes-effect-today) — It lets the FTC go straight to federal court to get money back for victims and seek civil penalties. Fake reviews and testimonials rule (FTC, Aug 2024): https://www.ftc.gov/news-events/news/press-releases/2024/08/federal-trade-commission-announces-final-rule-banning-fake-reviews-testimonials (https://www.ftc.gov/news-events/news/press-releases/2024/08/federal-trade-commission-announces-final-rule-banning-fake-reviews-testimonials) — This directly covers fake celebrity testimonials and AI-generated reviews. Click-to-cancel vacated (law-firm explainer): https://www.fenwick.com/insights/publications/eighth-circuit-vacates-ftcs-click-to-cancel-rule (https://www.fenwick.com/insights/publications/eighth-circuit-vacates-ftcs-click-to-cancel-rule) — The Eighth Circuit struck it down on July 8, 2025 because the FTC skipped a required preliminary regulatory analysis. InfoHawk funding announcement: https://finance.yahoo.com/sectors/technology/articles/infohawk-raises-2-25m-pre-123400630.html (https://finance.yahoo.com/sectors/technology/articles/infohawk-raises-2-25m-pre-123400630.html)

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Apple Podcasts (US)

5.0 / 5

1 ratings

Spotify

5.0 / 5

5 ratings

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