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A host interviews Gabe Hogan, a tax attorney and former IRS revenue agent, about how IRS audits work, why high-profile taxpayers are treated as examples to drive compliance, and why taxpayers—not preparers—are usually on the hook for penalties and interest. Hogan describes IRS bureaucracy, outdated systems, staffing declines, and increased hiring of non-tax personnel, plus the growing use of AI models that flag more returns amid a shrinking workforce. He explains how returns are graded with DIF scores, how agents and managers triage audit “stacks,” and why clear categorization and attaching substantiation (e.g., cost segregation reports) can reduce audit risk. They discuss common self-prep and CPA errors (TurboTax, misclassification, NIIT on business exits), documentation needs, audit escalation paths (agent, manager, Appeals, tax court), and strategies like the Augusta Rule when properly documented.
00:00 Celebrity Audit Fear
00:50 Wild Deduction Stories
02:10 Meet Former IRS Insider
03:36 From Bulls to Tax Law
06:14 Credentials Alphabet Soup
13:09 Taxpayer Liability Reality
14:58 Why Not TurboTax
18:24 Augusta Rule Done Right
22:53 Breaking Up With Your CPA
25:20 How Audits Get Picked
27:13 DIF Scores Explained
29:42 Stacks Managers and Backlogs
33:59 Statutes and Audit Chess
35:28 Audit Negotiation Tactics
37:12 Audit Types And Escalation
40:19 IRS Fear And Compliance
42:14 Gray Area Tax Strategy
44:45 Substantiation And Materiality
51:23 Regional IRS Culture
54:25 Politics And IRS Slowdown
56:29 Guest Wrap And Contact
57:14 Deal Desk Pitch
01:00:11 Due Diligence Framework
01:02:46 Final Call To Action
Connect with me:
LinkedIn: https://www.linkedin.com/in/lanekawaoka/
Facebook: https://www.facebook.com/TheWealthElevator
Instagram: https://www.instagram.com/TheWealthElevator
Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016.
Check out our Top-50 Investing Podcast, The Wealth Elevator.
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