『How to Save Millions in Taxes When Selling Your Business with Vincenzo Villimena』のカバーアート

How to Save Millions in Taxes When Selling Your Business with Vincenzo Villimena

How to Save Millions in Taxes When Selling Your Business with Vincenzo Villimena

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Have you ever wondered how much of your business sale could be lost to taxes simply because of how the deal is structured? In this episode, I sit down with Vincenzo Villamena, better known as the Online Taxman, to uncover the tax strategies that can make a significant difference when buying or selling a business. We explore why planning ahead is one of the most valuable moves an entrepreneur can make. Vincenzo shares his journey from working in Big Four accounting and private equity to building an international tax advisory firm. He explains how different deal structures can dramatically affect the amount of money owners keep after a transaction. We also discuss why tax planning should begin long before a sale is on the horizon. Beyond business exits, we explore everyday tax advantages available to entrepreneurs, including retirement plans, accountable plans, depreciation strategies, and charitable giving. Vincenzo shares why he believes the tax code rewards those who plan proactively rather than reactively. If you're considering buying, selling, or scaling a business in the next few years, this episode offers valuable insights to help you keep more of what you earn. Quotes: "The biggest takeaway is planning. Too many people wait until they're already talking to a buyer, when they could have had far more options if they started planning a year earlier." Takeaways: Start Tax Planning 12–24 Months Before You Exit The biggest tax savings opportunities often happen long before a deal closes. Waiting until the last minute can eliminate valuable planning options. Deal Structure Can Save or Cost You Millions Whether a transaction is structured as an asset sale or stock sale can dramatically change the amount of taxes paid by both buyers and sellers. Episode Timeline: 0:00 – Podcast intro and guest introduction 1:48 – Vincenzo’s background and founding Online Taxman 3:40 – Asset sales, stock sales, and IP taxation 6:44 – Purchase price allocation and deal structure 11:47 – Due diligence tips for buyers 14:42 – Why pre-exit tax planning matters 18:42 – Common tax planning mistakes 20:50 – Working with Online Taxman 25:08 – E-commerce acquisitions and opportunities 27:42 – Everyday tax advantages for business owners 29:17 – Acquisition strategies in the AI era 29:51 – Advanced tax and charitable giving strategies 33:24 – Legacy, mentorship, and giving back 34:50 – Closing thoughts and next steps Conclusion:  This episode drives home that how you structure a deal matters just as much as what you’re selling or buying. With examples around IP-heavy businesses, foreign sellers, QSBS, and charitable trusts, Vincenzo shows that the US tax code quietly rewards those who plan 12–24 months ahead and punish those who treat taxes as an afterthought. Listeners walk away with a clearer understanding of asset vs stock sales, purchase price allocation, and how to use entities and trusts to keep more of their exit proceeds. Just as importantly, Vincenzo frames all of this within a bigger mission of mentorship and giving back, reminding us that tax efficiency is ultimately a tool to create freedom and impact. If you’re anywhere near an acquisition or exit, this conversation is your signal to get educated, get advice, and start pulling the right levers now rather than later. Links & Resources Online Taxman – Schedule a consultation: https://onlinetaxman.com Global Expat Advisors (Sister Brand): https://globalexpatadvisors.com Connect with Vincenzo Villamena on LinkedIn: https://linkedin.com/in/vincenzo-villamena-7055815/ Co-authored Book: US Taxes For Americans Abroad (with John Hamilton, CPA) Previous Podcast Appearance: Earmark Podcast – "How Expat Clients Can Legally Slash Their Tax Bill
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