Ep. 21- Tax Structuring & Diligence in SMB M&A | Sean Smith & Roman Basi

In this episode, Sean Smith, Managing Partner at Search Fund Ventures and founder of the SMB Investor Network, sits down with Roman Basi, Managing Partner of Basi & Basi, Attorneys & CPAs. Roman brings nearly three decades of experience advising on mergers, acquisitions, and tax structuring. Together, they break down the critical aspects of tax diligence in SMB transactions — from entity selection (C-Corp, S-Corp, LLC) to advanced structuring tools like QSBS (Section 1202), F Reorganizations, 338(h)(10) elections, and personal goodwill strategies. Key discussion points include: - Why tax diligence is essential in SMB acquisitions - The risks of bad S-Corps and how to avoid them - How to mitigate post-close tax liabilities - Strategies to minimize double taxation - Structuring to maximize value for buyers and sellers - Insights on the new tax bill and its impact on investors This conversation is a must-watch for investors, operators, and advisors navigating the SMB acquisition ecosystem. 👉 Subscribe for more interviews with SMB dealmakers and experts. 👉 Share your thoughts in the comments below — what tax diligence questions do you want answered? Connect with Roman Basi & Sean Smith: - The Center for Financial, Legal & Tax Planning, P.C.– https://www.taxplanning.com/ - Roman Basi LinkedIn - https://www.linkedin.com/in/roman-basi-/ - Sean Smith LinkedIn - https://www.linkedin.com/in/sean-smith-47ab2a70/ - SMB Investor Network – https://www.smbinvestornetwork.com/ #SMBInvesting #SearchFunds #MergersAndAcquisitions #TaxDiligence #DealStructuring #PrivateEquity #SMBInvestorNetwork #QSBS #SBDebtAndEquity #RomanBasi