Stop Overpaying Taxes: The Real Rules for Location-Independent Solopreneurs

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In this episode of The Aspiring Solopreneur, Carly Ries and Joe Rando sit down with Bobby Casey, a serial entrepreneur who has lived in 10 countries, built and sold companies globally, and now helps location-independent solopreneurs structure their businesses for maximum freedom and minimum tax liability. Bobby shares his own life-first business origin story (a near-fatal motorcycle crash that led him to redesign his entire life around what he actually wanted), and how that experience shaped his dartboard analogy: your lifestyle is the bullseye, and your business is just one of the rings around it. From the foreign earned income exclusion to South Dakota residency strategies, this episode is a practical guide for solopreneurs who want to work from anywhere without leaving money on the table.

EPISODE KEY POINTS

• Most solopreneurs build their business first and try to fit their life around it. Bobby's near-death experience taught him to flip that order: design the life you want, then build the business to serve it.
• The biggest mistake location-independent solopreneurs make is not restructuring their business properly before going nomadic. One Canadian client paid $5 million in unnecessary taxes over 10 years by not getting advice early.
• The 183-day tax residency rule is a myth. Only one country (Ukraine) actually uses it as a clean cutoff. Every other country has its own set of criteria, many of which have nothing to do with how many days you're physically present.
• U.S.-based solopreneurs working abroad can exclude up to $130,000 in earned income from federal taxes using the Foreign Earned Income Exclusion (Form 2555), and this applies even if all your clients are in the U.S.
• South Dakota is a practical option for U.S.-based digital nomads to establish state residency in a no-income-tax state, with just a one-night stay and a mailing address required.

EPISODE FAQs

Do I need to restructure my business if I'm just spending a month abroad? No. If you're testing the waters with a short stay, treat it as a long vacation and keep everything as-is. Restructuring only becomes necessary when you're committing to a fully nomadic lifestyle or leaving your home country long-term.

What is the Foreign Earned Income Exclusion and do I qualify as a solopreneur? The Foreign Earned Income Exclusion (FEIE) allows qualifying Americans living abroad to exclude up to $130,000 of earned income from federal taxes. You qualify based on your personal status as a U.S. person living abroad, not based on where your clients are or where your LLC is registered. If you're a solopreneur with a U.S.-based LLC and U.S. clients, you can still qualify.

Is it true that staying under 183 days in a country keeps you from becoming a tax resident there? This is one of the most common myths in the digital nomad space. The 183-day rule is not a universal standard. Only Ukraine uses it cleanly. Most countries determine tax residency based on factors like where your primary home is, where your family is, and where your economic interests are centered. You need to research each country individually, or work with someone who has.

Can I really move my state residency to South Dakota to avoid state income tax? Yes, if you're a solopreneur. South Dakota allows you to establish residency with a one-night stay and a mailing address. It does not work for employees with remote jobs, as South Dakota has cracked down on that specifically. But for self-employed solopreneurs, it remains a viable strategy.

Where can I learn more about Bobby's work? Bobby runs two businesses: Global Wealth Protection (globalwealthprotection.com), a consulting firm for location-independent entrepreneurs with international income and asset structures, and Business Anywhere (businessanywhere.io), a platform that handles company formation, registered agent services, virtual mailboxes, bookkeeping, compliance, and more, built specifically for entrepreneurs who want the tedious backend of business handled.

Connect with Bobby:

• Global Wealth Protection: globalwealthprotection.com
• Business Anywhere: businessanywhere.io

Life First. Then Business.