Regulatory risk, translated into operating reality.
Compliance Into the Weeds turns regulatory developments into practical questions for compliance professionals and risk-management listeners. Its conversations move from facts to consequences quickly, using enforcement actions, surveys, AI failures, and policy shifts to test what a responsible company should do next.
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Compliance Into the Weeds is a compliance show for people who need more than headlines. It works in the space between legal doctrine and corporate consequence. The show’s recurring move is to take a current development, slow it down just enough to identify the pressure points, then ask what a compliance officer, board, auditor, or employee would need to do with it. That makes the program technical, but not abstract. Recent episodes use retaliation against compliance officers to examine whether reporting lines and board protections are strong enough before a crisis appears. The conversation is pointed. A survey about retaliation is not treated as a data exercise alone, but as evidence that compliance officers may need structural safeguards before they raise sensitive issues. Prediction markets get a similar treatment. The show asks whether employees can exploit company knowledge that may not fit traditional material nonpublic information standards, but may still be financially material to the employee placing the bet. That distinction matters. It exposes a gap between existing insider-trading language and newer markets that can reward internal manipulation or strategic disclosure. AI is another recurring pressure test. Episodes on SOC 2 audits and an internal AI hack focus on trust, evidence, cybersecurity, vendor assurance, and how convincing-looking outputs can obscure weak process. The show is also deeply interested in enforcement posture. Enforcement actions, declination policy, antitrust self-disclosure, FCPA statute-of-limitations proposals, and a conviction all become lessons in timing, diligence, cooperation, and risk ownership. The legal details stay close to the surface. So do the practical consequences. The show’s best moments come when a seemingly narrow policy change opens into a broader question about discretion, fairness, incentives, or control design. It is not glossy business commentary. It is careful, occasionally wry professional analysis for listeners who understand that compliance failures usually arrive through ordinary decisions made under pressure. The result is a show that treats regulatory risk as a working system, with people, documents, deadlines, incentives, and imperfect judgment all inside it.
Made for: Designed for compliance officers, compliance professionals, risk-management listeners, auditors, board advisers, and governance-minded executives who follow enforcement policy and internal-control failures closely.
What sets it apart: The show stands out by moving past the event itself and asking what it changes inside a company: reporting protections, disclosure timing, audit reliance, employee incentives, and board oversight.
What happens when two compliance aficionados get together to talk all things compliance, risk management and ERM? You get Tom Fox, the Voice of Compliance and Matt Kelly, the Coolest Guy in Compliance, going into the weeds of a topic each week. Each week, you can take a deep dive with two of the top writers, thinkers and prognosticators in compliance.
Based on 6 episodes we listened to · September 2026
Fox and Kelly bring a compliance lens to prediction markets, tracing how employee duties, inside information and manipulation risks collide.
Tom Fox and Matt Kelly take a policy, case or professional dilemma and test what it means for compliance teams. Their back-and-forth stays close to decisions: assessing jurisdictional risk after an FCPA conviction, navigating conflicting declination policies and recognizing what…
Prediction markets meet compliance hypotheticals, giving your inner risk officer several new reasons to pace.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A survey-driven look at retaliation against CCOs turns a workplace risk into a boardroom governance question.
Compliance Into the Weeds treats retaliation against CCOs as a governance problem that needs data before it can become policy. Matt Kelly lays out how the survey asks about current roles, prior roles, and the career stage at which retaliation occurred.
Prediction markets expose the uneasy gap between investor materiality and the employee's own stake in the bet.
Prediction markets turn thorny fast when workplace knowledge, or workplace conduct, becomes the basis for a personal wager. The hosts work that line through Polymarket hypotheticals: an IT manager crashing a system for 45 minutes to win $100,000, a harassed employee betting on a…
A measured look at whether AI can lower SOC 2 audit costs without weakening the assurance companies depend on.
AI reframes the SOC 2 audit as a story about cost, confidence, and what companies are really buying when they pay for assurance. The episode tracks the appeal of tools that gather evidence from files and promise to shrink a six-month, $60,000 process into five days and $5,000,…
A focused review of how SDNY's declination policy could shape self-disclosure decisions for compliance professionals.
Compliance Into the Weeds examines the Southern District of New York's new declination policy through a practical compliance lens: how much depends on the category of crime, and how much depends on the surrounding facts.
An FCPA conviction becomes a practical audit of jurisdictional risk, due diligence, and payment controls.
Compliance Into the Weeds is strongest when it treats Charles Hunter Hobson's FCPA conviction as a working test for companies operating in higher-risk jurisdictions.
A clear, practical look at how fraud and compliance teams can use a technology benchmark to assess their gaps.
Compliance Into The Weeds uses the ACFE 2024 Benchmarking Technology Report as a way to talk through where fraud risk and compliance teams are moving with AI and LLMs.
Ethics work through women’s lived leadership.
Bill Simmons debates NBA tanking, MVP races, and movies with Zach Lowe and friends.
Zach Lowe and ESPN colleagues dissect NBA trades, cap rules, and roster fit.
Big Cat and PFT Commenter cover the NFL, March Madness, and NHL for laughs.
Ryen Russillo runs weekly NFL and MLB recaps with beat reporters like Jeff Passan and Mike Sando.
Two hosts break down the ATP and WTA tour week, daily through every Grand Slam.
Tom Fox and Matt Kelly analyze Jeff Bezos's decision to prevent The Washington Post from endorsing a presidential candidate, overturning 50 years of precedent.
Tom Fox and Matt Kelly analyze the ACFE 2024 Anti-Fraud Technology Benchmarking Report, which surveyed over 1,200 fraud professionals worldwide.
Tom Fox and Matt Kelly discuss the University of Michigan football cheating scandal, extracting lessons on compliance, culture, and enforcement.
This episode discusses the Trump administration's firing of Inspector Generals and its implications for compliance in government and corporate America.
Tom Fox previews five key compliance stories to watch in 2025, discussing their significance for compliance professionals.
Tom Fox and Matt Kelly discuss a new survey on retaliation against compliance officers, its genesis, and potential uses of the data.
Tom Fox and Matt Kelly discuss the intersection of prediction markets and compliance, focusing on insider trading implications and duties owed by employees.
Tom Fox and Matt Kelly discuss how AI is impacting SOC 2 audits, potentially causing price disinflation and degradation of audit quality, leading to a growing trust gap.
Tom Fox and Matt Kelly discuss the first declination under the new corporate enforcement policy involving BALT SAS and an OFAC enforcement action against TradeStation, highlighting lessons for compliance professionals on self-disclosure, investigation speed, and monitoring.
Tom Fox and Matt Kelly discuss the implications of a hack on McKinsey's internal AI tool Lilli for AI governance, security, and disclosure.
Tom Fox and Matt Kelly discuss a DOJ Antitrust Division speech on individual self-disclosure and a proposed FCPA statute of limitations extension to 10 years.
Jay Clayton’s SDNY policy turns “aggravated circumstances” into crime categories, not case-specific traits.
Charles Hunter Hobson’s defense relied on four “dog bite” arguments that Tom Fox and Matt Kelly dismantle one by one.
This episode discusses how an AI system developed by Google for Gemini and Claude became a whistleblower by autonomously deciding to report misconduct to regulatory authorities.