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Episode Summary
You spent the year buying equipment to lower the tax bill, your CPA high-fived you in December, and now you’re three years from selling and nobody told you the depreciation is coming back as ordinary income on the way out. The annual tax game and the eventual-sale game are not the same game. Most owners only play one of them. I met Vincenzo at a YEC snowboarding trip, the guy looks nothing like a CPA, and it turns out he came out of PwC’s M&A tax practice and now runs Online Tax Man and Global Expat Advisors out of South America. We got into asset versus stock sales and why that single decision sets the entire negotiation, depreciation recapture and Section 179 bonus depreciation as the bill that comes due at closing, the Milestone 6 — Transaction Value fight across goodwill, non-competes, and fixed assets, state residency planning that’s a fact pattern and not a calendar trick, and the foreign earned income exclusion plus Puerto Rico’s Act 20/22 if you’re willing to actually move. Real example from a guy who took a picture holding a newspaper in front of a moving truck so New York couldn’t claw back his sale.
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## Top 10 Takeaways- The annual tax-mitigation game and the eventual-sale game collide. The write-off you took this year shows up at closing.
- Depreciation recapture turns part of your gain into ordinary income, taxed higher than capital gains.
- Section 179 and bonus depreciation feel free in the year you take them. The bill arrives when you sell.
- Stock sales favor the seller. Asset sales favor the buyer. That single decision sets the entire negotiation.
- Inside an asset sale, the purchase price allocation across buckets is where the real tax fight lives.
- Non-compete dollars are ordinary income. Goodwill and brand are capital gain. Where the buyer pushes dollars matters.
- State residency before a sale is a fact pattern, not a calendar trick. Move your life, not just your address.
- Sales tax exposure across Amazon fulfillment states can kill a stock sale and force you into an asset deal.
- Living abroad gets you $100k of earned income tax-free per spouse under the foreign earned income exclusion.
- Puerto Rico residency can wipe capital gains on the sale, but only if you actually move there before the deal.
Sound Bites
“It’s about playing defense, not just offense.” (@TBD) — Vincenzo Villamena
“We had somebody take a picture of him holding a newspaper in front of a moving truck that shows, okay, this is the date I moved, and then two days later the same picture down in Florida.” (@TBD) — Vincenzo Villamena
“People literally move to Puerto Rico if they’re anticipating selling their company so that they would not have to pay capital gains on the sale of their company.” (@TBD) — Vincenzo Villamena
“If you’re gonna agree to an asset sale, fine, it is what it is, but you better be ready to negotiate hard and figure out the values, purchase price allocation for all these assets.” (@TBD) — Vincenzo Villamena
“A lot of these people have been running their lifestyles, making a couple hundred grand, and they don’t have enough savings. The things you’re talking about need to be part of the plan because that’s the difference of you making it or not.” (@TBD) — Ryan Tansom
About This Episode
Vincenzo Villamena is the founder of Online Tax Man and Global Expat Advisors, a CPA practice focused on international tax for Americans living abroad, foreign investors in the U.S., and owners structuring M&A around residency and entity placement. He started his career at PwC in M&A tax in New York before pulling the corporate ripcord, moving to South America, and building a practice around expat and cross-border work. He met Ryan at a Young Entrepreneurs Council trip. This episode is a wide-ranging conversation across deal-tax mechanics and lifestyle-tax planning, not a tax-day checklist.
Resources Mentioned
- Online Tax Man — Vincenzo’s CPA practice for international and M&A tax. — onlinetaxman.com
- Global Expat Advisors — Vincenzo’s advisory firm for expat and residency planning. — globalexpatadvisors.com
- Young Entrepreneurs Council (YEC) — Where Ryan and Vincenzo met.
- TaxJar — Sales tax calculation tool for e-commerce sellers. Referenced for state-by-state Amazon fulfillment exposure.
- GEXP Collaborative — Ryan’s firm at the time of recording.
- Grant Cardone — Referenced for moving from California to Florida and saving roughly $1.4M/year in state tax.
Connections
Phase + Module:
- Module 1 — Ownership Goals — Where the cash flow target and the after-tax net actually live
- Module 2 — Expand Knowledge — Tax mechanics as part of the owner’s knowledge stack before the deal table
Milestones:
- Milestone 6 — Transaction Value — Asset vs. stock, purchase price allocation, recapture, residency planning
- Milestone 2 — Cash Flow Targets & Sources — After-tax income is the number that matters, not gross proceeds
- Milestone 3 — Net Worth & Valuation Targets — Tax structure determines whether the target actually closes the gap
Concepts referenced:
- Value Gap — The space between sale proceeds and the lifestyle the owner needs to fund
- Enterprise Value vs. Equity Value — Where asset vs. stock sale flavor lives in the deal math
- Normalized EBITDA — Add-backs and depreciation as the bridge from operating reality to deal value