Most solopreneurs spend zero time thinking about taxes until April 14th. Bobby Casey has spent decades thinking about almost nothing else, for his own businesses and for the hundreds of location-independent entrepreneurs he’s helped restructure, relocate, and legally stop overpaying.
Bobby has lived in 10 countries, started and sold companies across multiple continents, and currently runs two businesses: a high-end consulting practice for entrepreneurs with complex international structures, and Business Anywhere, a platform that automates the compliance and administrative backend of running a business.
In this episode, we discuss:
His own origin story. A near-fatal motorcycle crash led Bobby to a solo camping trip where he worked out exactly what he wanted his life to look like. The dartboard analogy he came up with that week (Lifestyle as the bullseye, business as one of the rings) is one of the clearest articulations of the Life-First Business philosophy we’ve heard from a guest.
The most expensive mistake nomadic solopreneurs make. Bobby shares the story of a Canadian client who spent 10 years outside Canada without restructuring her business, and ended up paying $5 million in taxes she didn’t legally owe. The fix existed from day one. She just didn’t know to ask.
The 183-day myth. Almost everyone in the digital nomad space believes that staying under 183 days in a country keeps you safe. Bobby has read the tax residency laws of roughly 140-150 countries. He says only one actually uses a clean 183-day rule. Every other country has its own criteria, and assuming otherwise is how people get caught.
What U.S. solopreneurs can actually do. The Foreign Earned Income Exclusion (Form 2555) allows qualifying Americans abroad to shield up to $130,000 of earned income from federal taxes. Yes, even if your clients are all in the U.S. Bobby explains how it works, who qualifies, and how to maximize it with a spouse.
The South Dakota move. One night’s stay. A mailing address. And you can move your driver’s license and your state tax residency, to a state with zero income tax. Bobby explains why this works for solopreneurs and why it doesn’t work for remote employees.
This is a rare episode: genuinely practical, not theoretical, from someone who has lived it in 10 countries and helped hundreds of others do the same.
Connect with Bobby:
Life First. Then Business.
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