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

Is your business exit on the horizon, and have you already decided that some of your wealth will one day go to causes you care about? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan, founder of Vital Wealth and advisor to high-level entrepreneurs, sits down with Phoenix Hafen, Director of Advisor Solutions at UI Charitable. UI Charitable manages more than $550 million in donor-advised funds for high-net-worth individuals and families. Together they break down why cash is the least tax-efficient asset you can give, and how entrepreneurs can donate appreciated stock, private business interests, real estate, and even venture fund stakes to a donor-advised fund to avoid capital gains tax and capture a charitable deduction.

Pat and Phoenix walk through the real mechanics of charitable planning before a liquidity event. They cover why the IRS wants the deal “still at risk” when you give, how qualified appraisals work, the AGI deduction limits that can catch donors off guard, and when a private foundation makes more sense than a donor-advised fund. Phoenix also shares a creative example of a venture investor who turned illiquid LP interests into a charitable deduction, and he explains how families use donor-advised funds to bring the next generation into philanthropy. If you’re charitably minded and expecting a significant sale in the next few years, this episode shows you how to give more intentionally and more tax-efficiently. For more on tax strategy and wealth building, visit vitalwealth.com/resources, and send your own questions for future episodes to vitalwealth.com/questions.

Key Takeaways

• Never donate cash. Appreciated assets with large capital gains are usually the most tax-efficient gifts.
• Donate appreciated stock and use the cash you would have given to buy it back. You keep your exposure and reset your cost basis.
• Almost anything that can be appraised can go into a donor-advised fund, including private business interests, real estate, precious metals, and LP interests.
• Give before the sale, not after. The IRS wants the deal to still be at risk when you make the gift.
• For a charitable gift, you want the appraisal as high as possible, the opposite of estate planning, where you often seek discounts.
• AGI limits apply to charitable deductions, but unused deductions can carry forward up to five years.
• A donor-advised fund fits most donors. A private foundation is mainly needed to pay staff or give grants directly to individuals.
• Measure charitable impact by outcomes, not outputs.

Resources to Link

• UI Charitable: uicharitable.org

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