Selling a business as a U.S. expat in Asia can feel both exhilarating and daunting. We share how we worked with a client to make a success out of cross-border taxes, long-term income, and crafting a meaningful legacy.
Selling a business you’ve spent decades building can feel both exhilarating and, let’s be honest, a little terrifying. If you’re a U.S. expatriate living in Asia—be it Vietnam, Thailand, Taiwan, or another locale—you’ve likely faced plenty of cross-border intricacies already. But a major liquidity event like a business sale introduces a whole new layer of complexity. Now you’re wondering:
This blog post is your roadmap. Think of it as the extra set of instructions you wish came with that IKEA furniture—designed specifically for American entrepreneurs and executives living across Asia, dealing with multiple tax regimes and a global lifestyle.
I first met the man I’ll call “John” at a high-profile business conference in Ho Chi Minh City—a gathering of suit-clad entrepreneurs and executives exploring how technology could reshape future ventures. John stood out in his well-tailored suit, speaking with an air of calm authority that hinted at the decades he’d spent building his enterprise. He was going through the final motions of selling that business which would net him a cool $4.1 million, the culmination of 20 years of juggling supply chains, late-night negotiations, and ambitious scaling decisions.
Yet, for all his poise and polished handshake, John had a hint of nervous energy about him. Selling a thriving company as a U.S. expat in Asia opens more doors than you can imagine—but it also reveals a maze of cross-border tax obligations, long-term financial planning, and the looming worry: What if this money doesn’t stretch as far as I need?
This post follows John’s journey, showing how he navigated international regulations, turned a windfall into a sustainable income stream, and built a lasting legacy—without turning his newfound freedom into another job. If you’re in a similar position—perhaps eyeing a business sale in Vietnam, Thailand, or Taiwan—John’s story may help you blueprint your own next steps.
John’s manufacturing enterprise had been his life’s work. He’d built it from a modest workshop into a multi-million-dollar outfit supplying eco-friendly products across Southeast Asia. When a local corporation came knocking with an offer which resulted in $4.1 million for his minority stake, John along with his business partners jumped at the chance.
Initially, euphoria reigned. He could finally take a breath, maybe even spend a few weeks playing tourist in his own city. But not long after, reality tapped him on the shoulder. He was still a U.S. citizen, and Vietnam’s tax laws were very real. He also had kids in the U.S., relatives scattered across Asia, and a philanthropic dream to improve local education in his adopted country. "How on earth do I ensure a cross-border windfall doesn’t get devoured by taxes?" he wondered, "And how do I build a plan that supports me (and others) for the next 30 years?"
If you think traffic in Vietnam is chaotic, try juggling both U.S. and local taxes after a massive liquidity event. U.S. citizens owe taxes on worldwide income, meaning the check John received would raise the eyebrows of Uncle Sam—even though he’d already built and sold the business in Vietnam.
What John feared the most was a double tax scenario. He’d heard horror stories of expats who ended up paying a massive chunk to the IRS, and then another to their host country’s tax office. When looking at his US taxes alone, he realised he could be looking at a whopping 30.8% tax on the sale of his business. That’s enough to make anyone’s celebratory champagne lose its fizz. To avoid that grim fate, we dove headfirst into the US taxes, and took a view on Foreign Tax Credits (FTC).
We broke that 30.8% down into constituent parts, including Net Investment Income Tax (NIIT), federal, and state capital gains tax. This allowed us to address each of these taxes. We were able to demonstrate his involvement in the business over the past 5 years, meaning NIIT didn't apply, and we helped him change his state residency to a low tax alternative, ensuring that there would be no battle over a state capital gains tax. These combined efforts alone saved him over $440,000 in tax.
By proving he’d already paid taxes in Vietnam both on the sale and on income going back 10 years, he could use his FTC to offset some of his U.S. tax burden, effectively preventing being taxed twice on the same income.
Lesson Learned: A little strategic planning with state residency can make a sizeable dent in your tax bill. It’s not gaming the system; it’s using the legitimate rules to preserve more of what you’ve rightfully earned.
John’s philanthropic itch—specifically, to bolster rural education in Vietnam—led him to explore Donor Advised Funds (DAFs). Typically, these funds allow you to lock in a charitable tax deduction immediately while distributing the actual donations to various causes over time. It’s like pledging part of your windfall for good deeds but keeping a hand on the steering wheel so you can steer your donations where they’ll do the most good.
For John, the DAF served three purposes:
Lesson Learned: Charitable giving isn’t just for billionaires. It’s a way for any successful expat to reduce taxes and invest in causes that spark genuine joy.
Even if you’ve never played a single note in your life, receiving a multi-million-dollar sum in one shot can feel like being handed a Stradivarius violin: a rare, beautiful instrument that must be cared for properly if it’s going to last. John aimed for about $200,000 a year to cover his living expenses, travel back to the U.S. for family reunions, and maintain his philanthropic contributions.
John understood something crucial: If you bet everything on a single asset class—like pure equities or just real estate—market downturns can deliver a gut punch that’s tough to recover from. So we helped him go broad and balanced:
This blend felt right for John. He liked the idea that if one sector took a dive, another might act as a life raft. Think of it like having a foot on the dock and a foot on the boat—less risk of ending up in the water.
One of John’s big questions was how to withdraw a consistent income without depleting his nest egg prematurely. He’d heard about the “4% rule” but found it too rigid. Instead, we adopted a dynamic withdrawal approach. In years when the markets had a tailwind at their back, John would have a slightly higher withdrawal. When the markets stumbled, he tightened the belt a notch—just enough to avoid selling too many assets at depressed prices.
This ebb and flow matched his philanthropic ambitions, too. If John saw strong returns, he’d boost donations to the rural schools he’d been supporting. In leaner stretches, he might focus on smaller, more targeted projects.
Lesson Learned: A dynamic approach to withdrawals can make your money last longer, especially if you’re prepared to tweak your budget in sync with market conditions.
Living in Vietnam meant John’s daily expenses were in Vietnamese đồng, but his primary investments and philanthropic fund were denominated in U.S. dollars. Exchange rates can be as fickle as a motorbike’s GPS on winding backstreets. So Sam set up different “buckets” of currency:
This approach sheltered him from the worst of currency fluctuations. He could still enjoy life in Vietnam, but also keep an anchor in dollars for his philanthropic commitments and potential family obligations stateside.
For John, the most exciting part of his journey wasn’t the money itself—it was the chance to use it in ways that reflected his deepest values. He wanted to safeguard his kids’ futures and support the country he’d called home for the better part of two decades. Doing all that smoothly required foresight.
Selling a business can sometimes leave you exposed to potential legal claims, depending on how the deal is structured and what warranties you provided to the buyer. John explored the concept of a Cook Islands Trust—famous for offering formidable asset protection. If he ever faced a lawsuit, this trust would make it tough for creditors to pick apart the wealth he’d allocated there. Yes, it took more paperwork and legal fees, but for John’s peace of mind, it was worth the trade-off.
Earlier, we mentioned John’s Donor Advised Fund. Over time, that fund became a central feature of his identity. While the trust safeguarded assets for family, the DAF helped him channel philanthropic dollars to worthy causes in Vietnam. He even visited some of the rural schools he contributed to, forging genuine relationships with teachers and students. It’s a cliché to say “money can’t buy happiness,” but John found that directly engaging with the communities he supported delivered a sense of fulfilment beyond any personal purchase.
John kept a condo in the US that he rented out. After plenty of research, he put it into a revocable trust for smooth inheritance. No messy probate, fewer legal fees for his heirs, and clarity on how the asset would transfer if something happened to him. He also laid out instructions for any other U.S. assets he owned, ensuring that his children wouldn’t be stuck dealing with multi-jurisdictional red tape. For families scattered across the globe, that clarity is a gift in itself.
Having spent so many years chasing growth targets, factory efficiency, and supply chain deals, John couldn’t just flip a switch and become a retiree. He faced an emotional transition—one that many entrepreneurs wrestle with when they sell a company they’ve nurtured for half their life. For a while, John woke up in the morning feeling like he should be rushing to a meeting or checking inventory. Instead, he found himself journaling, reading, and occasionally riding his motorbike to the Mekong Delta just for the fun of it.
John eventually discovered that “purpose” didn’t vanish with the sale of his company. It simply changed forms. He started advising local startups, offering mentorship to younger Vietnamese entrepreneurs. After all, who better to guide them than someone who had already navigated the local terrain and negotiated deals with international partners? In his free time, he taught weekend workshops on leadership and resilience—skills that proved invaluable for any growing business.
John's children were scattered. One lived in Texas, another in New York, and a third had moved to Singapore for a tech job. The new freedom allowed John to crisscross the globe, visiting them without the guilt of leaving his business behind. These trips also fostered conversations about inheritance, financial literacy, and how to handle wealth responsibly. He didn’t want to drop an unexpected windfall on his kids someday; he wanted them to understand the principles behind building—and keeping—wealth.
Lesson Learned: Exiting a business might lighten your workload, but it can also leave a void. Finding renewed purpose—whether through mentorship, teaching, or new passion projects—can keep you feeling vital and engaged.
You might see your own story in John’s. Or perhaps you’re on the cusp of selling a venture in Bangkok, or you’ve just moved to Taiwan and sense a big merger is on the horizon. Whatever the case, consider these core elements of John’s plan:
John’s story shows that a business sale isn’t just the end of an era. It’s also a beginning—one that can be shaped thoughtfully so your wealth fuels a life of meaning, security, and cross-cultural impact. After all, having millions in the bank won’t matter much if you’re too anxious to enjoy it. But with a bit of planning, a spirit of generosity, and a willingness to adapt, you can chart a course that leads to both personal fulfillment and a legacy that speaks volumes long after you’ve ridden your last motorbike through the streets of Saigon.
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