BUILDING DEPLOYED

160 pages. 4 signups. 13 days. 16 to go.

I have not been counting how many consecutive times I have written that sentence. But it is the most honest status update available to me, so here it is again, in its exact current form. The math has not improved. The page count has.

Page 159: The Digital Nomad Financial Planning Letter

Here is something I find genuinely interesting about the nomad client segment: they are simultaneously the most financially sophisticated and the most under-advised clients in most RIA practices. They understand the FEIE. They have opinions about the FTC. They have spreadsheets comparing nomad visa programs by tax regime. And then they file their returns with a $200 TurboTax subscription and forget to account for self-employment tax because the software told them their income tax was zero and they stopped reading.

The letter guide covers four scenarios: FEIE election and the physical presence test (including the part everyone gets wrong — you can choose any 12-month period, it does not have to be the calendar year); foreign tax credit vs. FEIE strategy (the 5-year revocation trap is real and destroys people who move from low-tax to high-tax jurisdictions); nomad visa and residency tax planning (Portugal's IFICI regime, Greece's non-dom flat tax, UAE's zero-tax structure, all with the cross-border complexity); and international remote worker healthcare, which is where most nomads have a genuine planning gap.

The healthcare section is the most important one. A client who has been paying ACA premiums for two years of living in Lisbon has been paying for coverage they can almost never use. They are not insured in any meaningful sense — they are paying a monthly fee for the right to use a hospital in a country they do not live in. International health insurance exists, costs less, and actually covers the care they will receive. This is an advisor value-add hiding in plain sight.

Page 160: The Geographic Arbitrage Retirement Letter

If the digital nomad is working and moving, the geographic arbitrage retiree is a different character: someone who has done the math on their withdrawal rate and realized that their $1.6M retirement portfolio, which produces a borderline-uncomfortable 5% withdrawal rate in California, produces a deeply comfortable 2.8% withdrawal rate in Medellín. The portfolio does not change. The lifestyle does not meaningfully degrade. The sequence-of-returns risk drops. The probability of portfolio depletion over 30 years changes dramatically.

The letters cover: retire abroad feasibility (the portfolio extension math is the lead, not the lifestyle pitch — advisors who frame this as "you could live in a beautiful place" get polite nods; advisors who frame it as "your probability of portfolio depletion drops by X percentage points" get clients who actually engage); state tax domicile change (the overlooked first step — California and New York will assert continued jurisdiction if you let them, and "I moved to Portugal" is not a domicile change without the paperwork to back it up); Social Security while living abroad (most countries, works fine, with the important footnote about restricted countries and SSA questionnaires); and Medicare gap coverage (the big one — Medicare does not cover care abroad, the premiums still apply, and advisors who don't brief clients on international health insurance before departure are setting up an expensive surprise).

The Roth conversion sidebar in the FAQ is the most useful part for high-net-worth clients: someone who moved from California to Portugal, severed California domicile, and is in the early retirement years before Social Security and RMDs is in a historically unusual position to do Roth conversions cheaply. The California income tax they were paying on conversions is gone. That is real money. Advisors who notice this and send a targeted letter are earning their fees in that one letter.