Beyond the Return: Ricky Lavina on Rebuilding Tax Prep for the AI Era

We’re talking with a CPA who left the billable-hour world to rethink how tax prep gets done. Ricky Lavina is the co-founder and CEO of TaxFyle, an AI-powered tax preparation and planning platform built for financial advisors, fintech companies and fractional CFOs. A former PwC accountant and University of Miami graduate, Ricky sits on the IRS’s Electronic Tax Administration Advisory Committee. He’s been named one of CPA Practice Advisor’s 20 Under 40 Top Influencers and one of the South Florida Business Journal’s 40 Under 40. Host Mike Manganillo sits down with Ricky to talk about the shortage of CPAs that inspired TaxFyle in 2015, and what more than a decade as a first-time tech founder has taught him about investors, rejection and staying power. Ricky explains why RIAs were the hardest market to crack, and why he believes tax belongs in the same place as the rest of a client’s financial plan. He also shares why “human-in-the-loop” AI matters when the stakes are someone’s tax return. They also get into what to look at before year-end, and how Ricky stays human while running a 40-person team in Miami with four kids at home, the youngest just four months old. Because Beyond the Balance is about more than the numbers. Topics covered: • Going from a PwC CPA to a first-time tech founder • The CPA shortage, and why AI alone can’t solve it • Why RIAs are the hardest market to crack, and why it matters to their clients • Human-in-the-loop AI and the future of tax prep • What to review before Q4: side businesses, S corp elections, depreciation timing and extensions • Four kids, a growing team, and why you can’t burn the candle at both ends TradeWinds LLC is an investment advisor registered under the Investment Advisers Act of 1940. The information presented is general in nature and is not designed to address your investment objectives, financial situation, or particular needs. Prior to making any investment decision, you should assess or seek advice from a professional regarding whether any particular transaction is relevant or appropriate to your individual circumstances. Although taken from reliable sources, TradeWinds cannot guarantee the accuracy of information received from third parties. The opinions expressed are those of TradeWinds and may not come to pass.