
Episode #151
151 | The Future of Tax Strategy: AI, the IRS, and What Entrepreneurs Need to Know
Should entrepreneurs trust AI with their tax strategy, or is that a risk too big to take? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Ricky Lavigna, a CPA and the founder of TaxFyle, to separate the hype from the reality of AI in tax filing. Lavigna started his career at PricewaterhouseCoopers before founding TaxFyle in 2015, and today serves on the IRS's Electronic Tax Administration Advisory Committee (ETAC), giving him a rare, inside perspective on how both the private sector and the federal government are approaching the future of tax technology. Throughout the conversation, Lonergan and Lavigna dig into what AI can realistically do for tax preparation today, why human accountability remains essential even as accuracy improves, and how the IRS itself is deploying AI to close a tax gap worth tens of billions of dollars. The episode also tackles the difference between legitimate tax strategy and the kind of aggressive tax gimmicks that can land entrepreneurs in serious trouble, along with a practical framework for thinking through which tax moves require IRS guidance versus real investment versus sophisticated entity structuring. Entrepreneurs and financial advisors alike will walk away with a sharper understanding of where AI genuinely adds value in tax planning, and where it falls dangerously short. Key Takeaways: AI is highly accurate at document reading, calculations, and data aggregation, but remains fundamentally predictive in nature and cannot be wholly relied upon for tax filing decisions The IRS's known tax gap sits at roughly $90 billion or more, and the agency is leaning on AI to reconcile 1099s and flag discrepancies amid staffing shortages Accountability, meaning a licensed professional with "skin in the game," remains the key differentiator between AI-assisted tax prep and simply outsourcing to AI or offshore labor Tax strategy exists on a spectrum: from IRS-guided moves requiring no investment (like optimizing the QBI deduction), to moves requiring capital (401(k)s, SEP IRAs, cash balance plans), to advanced strategies that combine multiple sections of the tax code Documentation is increasingly critical as AI makes it easier for the IRS to flag returns for review, particularly around gray-area claims like real estate professional status The line between smart tax strategy and tax gimmicks matters, since not every deduction an AI surfaces is one an entrepreneur should actually take Financial advisory and tax preparation are converging, as entrepreneurs increasingly want one trusted partner managing tax, investment, and wealth strategy together Learn More About Ricky: TaxFyle Resources: Visit vitalwealth.com/resources to download FREE resources Follow on Instagram at https://www.instagram.com/vitalwealthstrategies Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ Credits: Sponsored by Vital Wealth Music by Cephas Audio, video, research and copywriting by Victoria O'Brien






