The Tax Mistakes That Are Costing Expats in Thailand More Than They Know | Bobby Casey

What started as a conversation about Thailand's shifting tax environment with Bobby Casey turned into a full operational teardown of the most expensive structural mistakes location-independent entrepreneurs make. We cover the collapse of Hong Kong and Singapore as go-to nomad jurisdictions, why a Wyoming LLC is the correct default structure for non-US founders doing business in Thailand (and why most Americans set it up in a way that destroys their own privacy), the HoldCo structure that saves a $300K earner roughly $25,000 a year in self-employment tax, the bonafide residency test that most Americans living abroad have never heard of, and why California has a specific tax trap that follows you across borders even if you haven't set foot in the state in five years. If you are building a business while living or traveling in Southeast Asia, this is the conversation I wish existed when I first arrived in Bangkok in 2012.

This video was NOT sponsored.

About the Guest:
Bobby Casey is the founder of Business Anywhere, an online platform serving location-independent entrepreneurs who need company registration, registered agent services, virtual mailboxes, banking solutions, bookkeeping, and tax consulting all in one place. He has built one of the most recognized compliance and tax optimization platforms in the digital nomad space, with a client base spanning dozens of countries and a content library of over 2,000 specialist articles. His practice focuses almost exclusively on the tax and structural realities of operating across multiple jurisdictions, and he has personally guided clients through some of the most complex cross-border compliance situations in the industry.
https://businessanywhere.io

About the Host:
I'm Scott Pressimone, a Fractional Country Director and strategist with over a decade of executive experience on the ground in Bangkok. I help foreign capital, founders, and CEOs bridge the gap between Western expectations and Thai operational realities.
https://www.scottpressimone.com/

Chapters:
00:00 Introduction
03:00 Thailand's Tax Crackdown
06:14 Residency vs. Tax Residency
08:06 Scott's Permanent Residency Story
09:30 Stop Taking Advice From Facebook
13:01 The Compliance Gray Scale
14:44 Portugal, US LLCs and Tax Treaties
17:03 Why Hong Kong and Singapore Are Dead
22:05 The Seven-Figure Bank Account Trap
24:02 Why a Wyoming LLC Wins
26:19 When Simple Is Better
27:48 The $300K American in Thailand
31:49 The DIY LLC Privacy Mistake
35:53 The HoldCo That Saves $25K a Year
38:23 The German Nomad Simple Setup
42:19 Why Paying Thai Tax Matters
43:25 The California Tax Trap
44:48 The Bona Fide Residency Test
51:13 Final Mistakes and Oh Shit Moments
57:37 How to Find Bobby Casey