Tax Enforcement Insights, Crypto, and the Future of IRS Investigations
Explore IRS Criminal Investigation trends and crypto compliance with former IRS Chief Jim Lee
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Go inside the world of tax enforcement with former IRS Criminal Investigation Chief Jim Lee, now Head of Global Policy at Chainalysis. In this exclusive session, Jim joins Anomaly CPA co-founders Greg O’Brien and John Malone to share what’s really happening behind the scenes: from IRS CI’s latest case data and crypto tax cases to how Chainalysis is shaping digital asset compliance. This is a must-attend if you're a business owner, investor, or advisor navigating the future of taxes, enforcement, and crypto regulation. Plus, hear about some of the largest criminal takedowns in US history from the man in charge!
Tuesday, June 24, 2025
@2:00PM EST
Client Exclusive
Exclusive to Anomaly clients + 1 friend
Your Guest Speaker:
Jim Lee
Former Chief, IRS Criminal Investigation Division | Head of Global Policy & Government Affairs, Chainalysis
Your Host:
Greg O'Brien
Award-winning CPA specializing in complex tax planning and virtual CFO
Your Host:
John Malone
Award-winning certified Tax Coach, Attorney, and Business Advisor
IRS Criminal Investigation plays a pivotal role in protecting the integrity of the U.S. tax system and no one knows that better than Jim Lee, the chief law enforcement officer for tax for years. In this webinar, Jim will walk through the mission of IRS Criminal, how to stay clear of criminal tax issues, and a few wild standout cases from his time as Chief of the IRS’ criminal division.
He’ll also discuss his transition to Chainalysis and how his team now works with public and private sectors to advance financial transparency in the crypto space.
We’ll then dive into real-world crypto tax investigations, both illicit and legal sources, including IRS enforcement wins and Chainalysis case support. Whether you're involved in digital assets, tax advisory, or financial compliance, this session will help you better understand how crypto tax enforcement is evolving and what it means for the future of tax planning and compliance.
REGISTER MY SPOTWhat You Will Learn On This Live Training Event:
What IRS Criminal Investigation does and why it matters now more than ever
Key IRS CI enforcement trends and what business owners need to know about criminal tax matters
Real examples of criminal tax cases, including those involving digital assets
Why Chainalysis is central to crypto compliance and how it supports investigations
What legal crypto users and investors should know to stay compliant
As Seen On:
About the Guest:
Jim Lee
Guest
Jim Lee is the former Chief of the IRS Criminal Investigation Division, where he oversaw some of the agency’s most high-profile fraud and tax evasion cases. Now serving as Head of Global Policy and Government Affairs at Chainalysis, he brings deep expertise in digital asset compliance, financial crime, and enforcement trends. His experience offers a rare behind-the-scenes look at how the IRS is approaching crypto, AI-driven audits, and tax enforcement in 2025 and beyond.
About the Hosts:
Greg O'Brien
Host
Greg O'Brien is an award winning CPA specializing in complex tax planning and virtual CFO services for startups, entrepreneurs and high growth individuals. A leader in finding creative solutions to today's complex tax and business environment.
As the only Certified Tax Strategist in Massachusetts, licensed by the American Institute of Certified Tax Planners, he specializes in using advanced tax reduction strategies to help business owners and individuals with complex situations reduce their overall tax burden.
John Malone
Host
John is a multi-faceted advisor with a passion for working with entrepreneurial clients and early stage businesses as they navigate complex tax and financial issues. John understands that your business and life are intertwined, requiring a management strategy that considers the right now in conjunction with your company's financial longevity and wellbeing.
John’s focus is on his client’s future, which is centered around proactive and advanced tax planning. John is a Certified Tax Coach as designated by the American Institute of Certified Tax Planner. With this background, he aims to provide innovative solutions to the ever-changing tax landscape. John is also an Attorney that has been recognized as a “Rising Star” each year from 2018 through 2021 by the Massachusetts Super Lawyers Magazine.Â
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Hosted by Greg O’Brien, John Malone and Special Guest Jim Lee
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