Compliance into the Weeds

By Tom FoxBusiness News Business News Management

Compliance into the Weeds episodes

September 10, 2025Fracht - The Bonkers Sanctions Case
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 a subject more fully. Looking for some hard-hitting insights on compliance? Look no further than Compliance into the Weeds! In this episode, Tom Fox and Matt Kelly discuss a recent OFAC enforcement action against a Swiss-domiciled freight forwarding company, Fracht.
The case stands out for its complexity, involving a single, high-value transaction that exposed the company to significant sanctions risk through dealings with both Venezuelan and Iranian entities. Tom and Matt break down the compliance failures, the role of senior management, and the extensive remediation steps taken post-incident. This episode offers actionable lessons for compliance professionals on supply chain due diligence, the importance of compliance involvement in urgent deals, and the consequences of sidelining compliance functions.
Key highlights:
OFAC Enforcement Details

Anatomy of the Transaction

Third- and Fourth-Party Risks

Senior Management Involvement

Compliance Failures & Supply Chain Visibility

Remediation & Consequence Management
Key Takeaways for Compliance Professionals:
Always involve compliance in high-value, urgent transactions.

Ensure robust due diligence for all counterparties, including third- and fourth-party risks.

Senior management must be accountable for compliance failures.

Remediation should include policy updates, staff training, and ongoing oversight.
Resources:
Matt on 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 for podcast excellence.

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25 min
September 03, 2025Examining the Impact of Reducing Middle Management on Corporate Culture
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 a subject more fully. Seeking insightful perspectives on compliance? Look no further than Compliance into the Weeds! In this episode, Tom Fox and Matt Kelly discuss the implications of reducing the number of middle managers in corporate America.
Kelly’s blog post, inspired by a Wall Street Journal article, serves as the foundation for a broader discussion on how the reduction of managers impacts corporate culture, employee dynamics, and compliance programs. They explore the reasons behind this trend, such as the desire for agility or cost-cutting, and its effects on communication, institutional knowledge, and the role of compliance officers. They also explore potential solutions, including the use of AI, enhanced training, and adaptive compliance strategies, to mitigate the risks associated with fewer middle managers.
Key highlights:
Corporate America’s Managerial Shift

Implications for Corporate Culture

AI and Compliance Solutions

Institutional Knowledge and Risks

Compliance Takeaways and Final Thoughts
Resources:
Matt on 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 for podcast excellence.

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24 min
August 27, 2025Unpacking the University of Michigan Football Scandal: Compliance and Consequences
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 a subject more fully. Seeking insightful perspectives on compliance? Look no further than Compliance into the Weeds! In this episode, Tom Fox and Matt Kelly discuss the recent University of Michigan football scandal.
They draw parallels to the infamous 2017 Houston Astros sign-stealing incident and examine the numerous compliance failures within Michigan’s football program. Highlighted issues include impermissible scouting, leadership failures by Jim Harbaugh, marginalization of the compliance function, and the NCAA’s ineffective enforcement. The conversation highlights crucial lessons for corporate compliance, emphasizing the importance of documentation, intern training, cooperation in investigations, and maintaining robust enforcement actions.
Key highlights:
Michigan Football Scandal Overview

Impermissible Scouting and Violations

Leadership Failures and Compliance Issues

NCAA’s Toothless Enforcement

Comparisons to Corporate Compliance

Lessons for Compliance Officers
Ed. Note: Tom Fox has written a 5-part blog post series on the UM Cheating Scandal. It will be posted each day this week. You can view the full series on his blog, the FCPA Compliance and Ethics Blog.
Resources :
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.

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28 min
August 20, 2025The Dark Side of AI in Employee Training
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 a subject 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 emerging concerns surrounding AI, particularly ChatGPT, in the realm of employee training.
Their discussion centers on the potential use of AI, specifically ChatGPT’s newest ‘Agent Mode’, to administer compliance training courses on behalf of employees, which could potentially enable them to cheat. They debate the implications of this capability, touching on the historical context of cheating, the effectiveness of current training methods, and the need for new internal controls and strategies to adapt to these technological advancements. They also contemplate the future of training, potentially evolving into AI-driven bots that provide on-the-spot, micro-learning modules. The episode encourages compliance officers to thoroughly vet their training vendors to ensure measures are in place to prevent AI-enabled cheating.
Key highlights:
The Dark Side of AI in Compliance Training

AI’s Impact on Employee Training

AI’s Role in Training and Compliance

Future of AI in Corporate Training

Challenges and Considerations
Resources:
Matt Kelly 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 a Davey, Communicator, and W3 Awards for podcast excellence.

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28 min
August 13, 2025Two Cyber Security Cases for the Compliance Professional
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 a subject 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 recent enforcement actions under the False Claims Act (FCA) related to cybersecurity failures by government contractors.
They analyze two significant cases: Illumina, a medical device maker, and Aero Turbine, a contractor for the US Air Force. The conversation highlights the importance of ‘security by design’ in product development and the growing scrutiny on compliance practices, especially for smaller companies. The discussion emphasizes the need for robust cybersecurity measures and the challenges faced by organizations in meeting regulatory requirements.
Key highlights:
False Claims Act Cases Overview

Illumina Case Analysis

Aero Turbine Case Insights

Compliance Challenges for Smaller Companies
Resources:
Matt Kelly 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 a Davey, Communicator, and W3 Awards for podcast excellence.

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28 min
August 06, 2025A Deep Dive into Cadence Design Systems' Export Control Violations
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 a subject 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 the recent enforcement action against Cadence Design Systems for export control violations.
They explore the company’s illegal sales of sensitive technology to a Chinese university connected to the Chinese military, resulting in $140 million in penalties and a three-year probation. The conversation delves into topics like weak subsidiary governance, challenges in monitoring Chinese subsidiaries, and the complexities of conducting investigations in China. They also reflect on the broader implications for U.S. companies operating in China and the intractable risks involved.
Key highlights:
Cadence Design Systems Case Overview

Subsidiary Governance Issues

Details of the Misconduct

Resolution and Penalties

Challenges in Compliance and Monitoring

Complexities of Doing Business in China
Resources
Matt Kelly 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 a Davey, Communicator, and W3 Awards for podcast excellence.

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24 min
July 23, 2025Sanctions Compliance Failures: Lessons from Harman International and Interactive Brokers
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 a subject more fully. Seeking insightful perspectives on compliance? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss two recent OFAC enforcement actions involving Harman International and Interactive Brokers and the lessons they provide for compliance professionals.
Tom and Matt delve into the facts of both cases, finding under-resourced sanctions compliance programs in both companies. They highlight key issues, including inadequate personnel, misconfigured compliance tools, and a failure to conduct proper risk assessments. Despite self-disclosure and cooperation, both companies faced significant fines and were required to implement extensive remediation measures. The discussion highlights the growing importance of robust sanctions compliance programs in mitigating risks and preventing enforcement actions.
Key highlights:
Sanctions Enforcement Cases Overview

Harman International’s Compliance Failures

Interactive Brokers’ Compliance Issues

Lessons and Final Thoughts
Resources:
Matt Kelly 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 for podcast excellence.

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27 min
July 16, 2025Agentic Misalignment and AI Ethics: Analyzing AI Behavior Under Pressure
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 a subject more fully. Seeking insightful perspectives on compliance? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss a recent Anthropic report that highlights “agentic misalignment in AI systems.”
The discussion addresses the unsettling, independent, and unethical behaviors exhibited by AI systems in extreme scenarios. The conversation explores the implications for corporate risk management, AI governance, and compliance, drawing parallels between AI behavior and human behavior using concepts such as the fraud triangle. The episode also explores how traditional anti-fraud mechanisms may be adapted for monitoring AI agents while reflecting on lessons from science fiction portrayals of AI ethics and risks.
Key highlights:
AI’s Unethical Behaviors

Comparing AI to Human Behavior

Fraud Triangle, the Anti-Fraud Triangle, and AI

Science Fiction Parallels
Resources:
Matt Kelly 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 for podcast excellence.

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29 min
July 03, 2025Boeing’s New Safety Initiatives and Compliance Reforms
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 a subject more fully. Are you seeking insightful perspectives on compliance? Look no further than Compliance into the Weeds! In this episode of Compliance into the Weeds, Tom Fox and Matt Kelly discuss Boeing’s recent safety initiatives and reforms, as outlined in their annual aerospace safety report.
They explore Boeing’s efforts to improve its speak-up culture, internal reporting systems, and the introduction of an expansive Safety Champions Program. The episode explores the procedural changes Boeing has implemented, including the handling of third-party reports and increased transparency for employees. Additionally, they examine the challenges and necessities of manager training in fostering an ethical corporate culture. The conversation concludes with insights on the recent Federal District Court hearing regarding Boeing’s non-prosecution agreement and the implications for transparency and accountability.
Key highlights:
Speak Up Culture Enhancements

Ambassador Program Expansion

Manager Training and Corporate Culture

Court Hearing on Boeing’s Non-Prosecution Agreement
Resources:
Matt Kelly 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.

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21 min
June 18, 2025The COSO Governance Framework
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 a subject more fully. Are you seeking insightful perspectives 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 recently released COSO Corporate Governance Framework.
Tom and Matt take a deep dive into the new COSO Corporate Governance Framework draft. They discuss the importance of public comment on the draft, which is open until July 11, and explore the framework’s six key components. The framework aims to provide discipline in achieving good governance within organizations, covering areas such as strategy, culture, human resources, and resilience. Kelly highlights the significance of culture in compliance and the role of information quality in the future, providing practical tips on implementing and testing the framework. The episode highlights the importance of this framework for various stakeholders, encouraging practitioners to review and provide feedback on the draft.
Key highlights:
Overview of COSO’s Draft Corporate Governance Framework

The Six Objectives of the Framework

Importance of Culture in Compliance

Principles and Points of Focus

Resilience in Corporate Governance
Resources:
Matt Kelly 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.

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26 min

About Compliance into the Weeds

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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…