Life After Business

How to Play Defense - Tax Tips and Tricks to Net More $$

My guest today is a CPA named Vincenzo Villamena. Vincenzo began his financial career in New York and decided to move to South America for a change of pace. He is the founder of Online Taxman and Global Expat Advisors. He specializes in M&A (merger and acquisition) and international tax services. We discuss how moving to lower tax brackets can save you tons of money on the sale of your company. The catch is, you have to jump through the hoops to keep your previous state off your back. Vincenzo shares what some of the benefits of living abroad are for former business owners and why it isn’t an overnight process. We also explore the pros and cons of asset sales and stock sales. If you are a business owner and have considered moving to “greener pastures” after you sell your company, Vincenzo may have a strategy that will work for you.

What you will learn:

  • Vincenzo’s life in New York.
  • Why he moved to South America.
  • His specialty in international tax services and international investing.
  • How a long-term plan can improve your tax situation.
  • Depreciation recapture, what is it?
  • What is the 179 Strategy?
  • The changes the new U.S. tax codes have made to the 179.
  • The differences between an asset sale and a stock sale.
  • The main sorting buckets for assets.
  • The things you need to consider when designing a deal structure.
  • Why a “fact pattern” is important when you move from states or countries.
  • The issues that come up with e-commerce deals.
  • When an international move a good idea?
  • The Foreign Earned Income Exclusion.
  • The Puerto Rico strategy.
  • How to reach Vincenzo.


I mention an accelerator program with GEXP Collaborative during this episode. Our first event should be in August with more on the way. If you are interested in the accelerator program, then you can reach out to me at or LinkedIn. We also have a page on the website with more information.

Links and Resources:

GEXP Collaborative
GEXP Accelerator Program
Global Expat Advisors
Online Taxman

About Vincenzo:

Vincenzo Villamena, CPA, is the founder of Global Expat Advisors and Online Taxman, specializing in offshore structuring and US tax for international corporations and individuals. Prior to starting his own firms, Vincenzo served as a partner at 4 Corners Inc., where he advised high net worth individuals in private equity investing and tax matters. Vincenzo worked in audit, tax and valuation during his time with PricewaterhouseCoopers, involved in Fortune 100 audit engagements and M&A transactions, giving him the knowledge to perform analysis in valuation, corporate finance, and technical accounting issues. He has both a Masters of Accounting and Bachelors of Business Administration with distinction from the University of Michigan’s Stephen M Ross School of Business.

Brought to you by Ryan Tansom of Life After Business