

Compliance into the Weeds
Tom Fox
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.
Episodes
Mentioned books

Oct 28, 2026 • 21min
Anthropic’s Board Structure - What Does it Mean for Compliance
The award-winning Compliance into the Weeds is the only weekly podcast that takes a deep dive into a compliance-related topic, literally going into the weeds to explore it fully. Looking for hard-hitting compliance insights? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss Anthropic’s S-1 registration statement for a forthcoming IPO, focusing on what it reveals about corporate governance and risk oversight rather than financials.
Kelly notes Anthropic has a seven-member board with three insiders (CEO Dario Amodei, Daniela Amodei, and CFO Christina Rao) and four outsiders, operating through four committees: audit, compensation, nominating/governance, and a safety and risk committee tasked with AI safety, security, and broader legal/regulatory/compliance risks. They question whether a two-member safety and risk committee, chaired by Novartis CEO Vas Narasimhan and joined by Christopher Liddell, has sufficient capacity, and note that the committee has an undisclosed written charter. They also flag uncertainties about Anthropic’s internal compliance/risk leadership and reporting filters, potential amended filings, and a five-member long-term benefit trust (one seat vacant) with influence over nominating outside directors.
Key highlights:
Anthropic IPO S-1 overview
Board size and committees
Risk committee staffing questions
CEOs talking about AI risks
More filings and disclosure gaps
Resources:
Matt in Radical Compliance
Tom
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A multi-award-winning podcast, Compliance into the Weeds, was recently named one of the Top 25 Regulatory Compliance Podcasts, Top 10 Business Law Podcasts, and Top 12 Risk Management Podcasts. Compliance into the Weeds has been awarded a Davey, Communicator, and W3 Award, all for podcast excellence. Learn more about your ad choices. Visit megaphone.fm/adchoices

Oct 21, 2026 • 28min
Bank of America’s $1.2B AML Breakdown: Too Big to Remediate?
The award-winning Compliance into the Weeds is the only weekly podcast that dives deep into compliance-related topics, going into the weeds to uncover hard-hitting compliance insights. Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss the recent OCC and Federal Reserve enforcement actions against BAO for $1.2bn.
The enforcement action against Bank of America (with OCC, FinCEN, OFAC, and others) was for BOA’s failure to maintain an effective Bank Secrecy Act/AML program, including flawed transaction monitoring that led to inadequate suspicious activity reporting, weak customer due diligence, and deficient sanctions screening, sometimes with law enforcement flagging issues to the bank rather than the reverse.
They place this alongside recent actions against UBS, American Express, and a New York DFS fine of SEB, arguing recurring failures stem from poor transaction analysis. Kelly ties Bank of America’s problems to its homegrown “Event Processor” system, launched in 2010, which critics say uses arbitrary risk-scoring thresholds and lacks recalibration, compounded by insufficient staffing and management support. They highlight governance and accountability concerns, including unresolved findings from a 2024 OCC order, questions about board oversight of compliance, and doubts that fines alone will drive lasting remediation.
Key highlights:
BofA Fine Breakdown
What Went Wrong in AML
How the Tech Failed
Leadership and Culture Accountability
Fixing It People and Oversight
Risk Assessments and Too Big to Remediate
Resources:
Matt in Radical Compliance
Tom in the FCPA Compliance Report
Tom
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A multi-award-winning podcast, Compliance into the Weeds was most recently honored as one of the Top 25 Regulatory Compliance Podcasts, the Top 10 Business Law Podcasts, and the Top 12 Risk Management Podcasts. Compliance into the Weeds has been awarded a Davey, Communicator, and W3 Award, all for podcast excellence. Learn more about your ad choices. Visit megaphone.fm/adchoices

Oct 14, 2026 • 21min
Amex AML Enforcement: Credit Card Risk, SAR Failures, and Board Accountability
The award-winning Compliance into the Weeds is the only weekly podcast that takes a deep dive into compliance topics, literally going into the weeds. Looking for hard-hitting compliance insights? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss the recent OCC and Federal Reserve enforcement actions against American Express.
The penalties included a $350 million civil penalty, cease-and-desist orders, and extensive compliance obligations tied to weaknesses in customer due diligence, suspicious activity reporting, staffing, and risk assessment. Tom highlighted that Amex processed billions of transactions, many ordinary credit-card transactions, showing banks must know all customers, not just high-dollar activity, and noted regulators’ broader pattern of similar actions across the industry as financial innovation outpaced compliance investment.
Matt noted that regulators depend on SARs as critical inputs for broader enforcement “mosaics,” explaining why SAR failures draw intense scrutiny. The orders’ notable feature is direct board involvement, requiring a board-level compliance committee and action plan to hold management accountable, with a strong focus on end-to-end documentation and evidence trails; they see no facts suggesting the egregious, employee-involved criminality seen in TD Bank.
Key highlights:
Industry Pattern and Root Causes
Innovation as Compliance Risk
Board Oversight Mandates
Why SARs Matter
DOJ Risk and TD Bank Comparison
Disjointed Compliance and Fixes
Resources:
Tom in the FCPA Compliance Report, Part 1 and Part 2
Tom
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A multi-award-winning podcast, Compliance into the Weeds, was recently named one of the Top 25 Regulatory Compliance Podcasts, Top 10 Business Law Podcasts, and Top 12 Risk Management Podcasts. Compliance into the Weeds has been awarded a Davey, Communicator, and W3 Award, all for podcast excellence. Learn more about your ad choices. Visit megaphone.fm/adchoices

7 snips
Oct 7, 2026 • 25min
New Fraud Section Guidelines
The DOJ’s new fraud priorities put companies on notice. The discussion explores ten prosecution factors, how small incidents can reveal systemic weaknesses, and risks spanning business lines, supply chains, immigration, and political exposure. It also covers voluntary disclosure, whistleblower incentives, board engagement, and the continuing role of compliance evaluations and corporate enforcement.

Sep 30, 2026 • 22min
Southern Glazer’s NPA: How Remediation and ECCP Alignment Drove a Favorable Settlement
The award-winning Compliance into the Weeds is the only weekly podcast that takes a deep dive into compliance-related topics, literally going into the weeds to explore a subject in greater depth. Looking for hard-hitting compliance insights? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss the Southern Glazer NPA.
The Southern Glazer Wine and Spirits’ non-prosecution agreement is a rare example where prosecutors credited compliance program remediation, rather than self-disclosure or extensive cooperation, as central to a favorable outcome. Southern Glazer, the largest US liquor distributor, faced a major California kickback and bribery scheme involving five former employees, fabricated records, sham agreements, and luxury benefits to retailers and others, along with alleged tax impacts. The company resolved the matter with a $12.5 million payment and a two-year NPA requiring the CEO and CCO to certify program effectiveness. Tom and Matt review how the NPA affirms DOJ’s Evaluation of Corporate Compliance Programs as still relevant and detail remediation steps: major headcount and budget increases, upgraded compliance leadership, audits of marketing spend, enhanced training, strengthened third-party controls and AP payment blocks, outside reviews, and tone-at-the-top messaging.
Key highlights:
Southern Glazer Case Setup
Industry Risks and Scheme
ECCP Guidance Still Matters
Program Overhaul Timeline
Concrete Remediation Metrics
DOJ Signals Under Trump Era
Resources:
Matt in Radical Compliance
Tom
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A multi-award-winning podcast, Compliance into the Weeds was most recently honored as one of the Top 25 Regulatory Compliance Podcasts, a Top 10 Business Law Podcast, and a Top 12 Risk Management Podcast. Compliance into the Weeds has received Davey, Communicator, and W3 Awards, all for podcast excellence. Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 23, 2026 • 21min
Whistleblower Resolution Delays Is Justice Denied
The award-winning Compliance into the Weeds is the only weekly podcast that takes a deep dive into compliance-related topics, literally going into the weeds to explore a subject in greater depth. Looking for hard-hitting compliance insights? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss a GAO audit of the Department of Homeland Security’s whistleblower retaliation program.
They use it as a case study for corporate compliance officers. DHS employees can report internally via the Office of Inspector General hotline or externally to the Office of Special Counsel. However, the GAO review focused on DHS’s internal process, where the OIG’s Whistleblower Protection Division (eight investigators) investigates retaliation and, if substantiated, sends cases to the Office of the Secretary and ultimately the DHS Secretary for corrective action. Although targets are six months for investigation and 30 days for secretarial action, GAO found investigations averaged 3.2 years (some up to six) amid rising complaint volumes, turnover, and evidence-gathering challenges. Meanwhile, none of the 11 substantiated cases were decided within 30 days because of missing written procedures and no designated accountable official—showing how delayed resolution erodes reporting culture and “institutional justice.”
Key highlights:
Why the GAO Report Matters
DHS Whistleblower Program Structure
Timeline Expectations vs. Reality
Compliance Lessons and GAO Value
Resources:
Matt in Radical Compliance
Tom
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Facebook
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Twitter
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A multi-award-winning podcast, Compliance into the Weeds was most recently honored as one of the Top 25 Regulatory Compliance Podcasts, a Top 10 Business Law Podcast, and a Top 12 Risk Management Podcast. Compliance into the Weeds has received Davey, Communicator, and W3 Awards, all for podcast excellence. Learn more about your ad choices. Visit megaphone.fm/adchoices

Sep 16, 2026 • 28min
Governing Agentic AI: DFS Cyber Risk Assessments, EU AI Act Accountability, and the Inventory Problem
The award-winning Compliance into the Weeds is the only weekly podcast that takes a deep dive into compliance-related topics, literally going into the weeds to explore them fully and uncover hard-hitting compliance insights. Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss the growing compliance and cybersecurity challenges posed by agentic AI.
They focus on New York Department of Financial Services (DFS) guidance on cybersecurity risk assessments and a European survey Kelly cites. They argue DFS’s rule, requiring annual or as-needed reassessments after significant technology and threat changes and maintaining an accurate IT asset inventory, implicitly compels organizations to identify and track AI agents, even though agents are not mentioned. Kelly cites a Veeam Software survey of 1,000+ European executives reporting limited visibility into employee-created autonomous AI workflows and AI interactions with sensitive data, complicating EU AI Act requirements for human accountability. The conversation compares potential governance models to Sarbanes-Oxley sub-certifications and enterprise software management, questions whether CISOs can certify compliance amid decentralized agent creation, and notes potential enforcement avenues and the risks of industry self-regulation.
Key highlights:
Why DFS Guidance Matters
Risk Assessments Meet Agents
Accountability Under EU AI Act
SOX Style Governance Model
Enforcement and Self-Regulation
Resources:
Matt in Radical Compliance (2 posts)
Tom
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A multi-award-winning podcast, Compliance into the Weeds was most recently honored as one of the Top 25 Regulatory Compliance Podcasts, a Top 10 Business Law Podcasts, and a Top 12 Risk Management Podcasts. Compliance into the Weeds has received Davey, Communicator, and W3 Awards, all for podcast excellence. Learn more about your ad choices. Visit megaphone.fm/adchoices

9 snips
Sep 9, 2026 • 34min
Clippers Salary-Cap Circumvention: Sham Endorsements, Contract Red Flags, and Compliance Lessons
An NBA salary-cap scandal unfolds through sham endorsements, vague contracts, unusual counterparties, and a paper trail of incriminating emails. The discussion examines how roughly $18 million in extra compensation allegedly reached Kawhi Leonard, why repeated violations raised tone-at-the-top concerns, and what fines, suspensions, lost draft picks, and stronger contract oversight mean for compliance in professional sports.

Sep 2, 2026 • 22min
Broken Execution in Day-to-Day Compliance Operations – The BAE Enforcement Action
The award-winning Compliance into the Weeds is the only weekly podcast that takes a deep dive into compliance-related topics, literally going into the weeds to explore a subject in greater depth. Looking for some hard-hitting insights on compliance? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss the recent BAE export control enforcement action.
Matt views the BAE export control enforcement action as a strong example of how ITAR compliance failures often stem from routine breakdowns in day-to-day operations rather than dramatic smuggling schemes. He notes that BAE’s U.S. subsidiary sent technical information and services overseas without proper licenses, including to China and even some allied countries, showing that export controls apply to both data and services, not just physical weapons. Kelly argues that the case reveals common compliance weaknesses such as poor training, unclear procedures, weak system warnings, and employee turnover that can leave staff unsure of the rules. His broader point is that companies in export-controlled industries must maintain current licenses and build strong, monitored compliance programs because governments will continue using export controls as an important geopolitical tool.
Key highlights:
ITAR data shipments trigger BAE’s $36 million penalty
Broken execution in day-to-day compliance operations
Export-control warnings before sensitive file transmission
Missing Red-Flag Prompts in Export Control System
Self-Disclosed, Cooperated, Remediated, Monitored by Another Name
Resources:
Matt in Radical Compliance
Tom
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A multi-award-winning podcast, Compliance into the Weeds was most recently honored as one of the Top 25 Regulatory Compliance Podcasts, a Top 10 Business Law Podcast, and a Top 12 Risk Management Podcast. Compliance into the Weeds has been conferred the Davey, Communicator, and W3 Awards, all for podcast excellence. Learn more about your ad choices. Visit megaphone.fm/adchoices

Aug 26, 2026 • 25min
AI for Compliance: Lessons from Teaching Cohorts
The award-winning Compliance into the Weeds is the only weekly podcast that takes a deep dive into compliance-related topics, literally going into the weeds to explore them more fully. Looking for some hard-hitting insights on compliance? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss Kelly’s collaboration with Ethena to run short, paid online AI classes for compliance professionals.
Since May, there has been an excellent AI training for compliance professionals, covering vibe coding, content/video generation, and data analytics with hands-on exercises using dummy or public data. Kelly says his biggest takeaway has been how much AI education is still needed and that many compliance teams are only scratching the surface, despite fears that “everyone else” is further along. They review common tools but emphasize that success depends more on the inputs and outputs, data readiness, clear use cases, and acting on results than on which model is chosen. They also address governance, security, privacy, maintenance, technical debt, costs and token budgets, and the need to involve compliance, which often leads to AI governance. The episode ends with reflections on Dolly Parton’s leadership and a story about her retaining rights to the hit song “I Will Always Love You.”
Key highlights:
AI Class Overview
AI Skills Gap Reality Check
Good Enough to Start
AI Angst and Cost Questions
Why Compliance Should Lead AI Governance
Dolly Parton Tribute
Resources
Matt in Radical Compliance
Tom
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A multi-award-winning podcast, Compliance into the Weeds was most recently honored as one of the Top 25 Regulatory Compliance Podcasts, a Top 10 Business Law Podcast, and a Top 12 Risk Management Podcast. Compliance into the Weeds has received Davey, Communicator, and W3 Awards, all for podcast excellence. Learn more about your ad choices. Visit megaphone.fm/adchoices


