How Andrew Henderson Inspired My Move To The Caribbean
Andrew Henderson, Founder at Nomad Capitalist, has been pivotal in my journey toward global mobility. Embodying the ethos of "go where you're treated best," Henderson's insights and strategies have profoundly shaped my approach to building wealth and personal freedom. Shared through his YouTube channel and live conferences around the world, his expertise in navigating the intricate world of international tax laws, citizenship by investment, and investment opportunities has established him as a leader in the field and provided a guiding framework for thousands of successful entrepreneurs and investors.
Boating in the Caribbean is a Dream I’m Had Since Childhood
This article dives into how Andrew Henderson helped me transition from traditional self-imposed boundaries to a life of diversified wealth and freedom in the Caribbean. He also inspired me to start my own real estate and investment migration firm, Offshore Freedom especially focused on the Caribbean region.
Who Is Andrew Henderson of Nomad Capitalist?
My journey towards a global lifestyle took a pivotal turn when I encountered Andrew Henderson, the founder of Nomad Capitalist. Through his guidance, I found a path and a gateway to personal freedom outside the bounds of my familiar Canadian surroundings. His in-depth knowledge and unwavering commitment to the ideals of a borderless life propelled me to take the leap and relocate to Antigua and Barbuda, a tropical paradise in the Caribbean where I could expand my real estate investments and grow my knowledge and experience.
Andrew Henderson at Nomad Capitalist Live, September 2022
Andrew Henderson's articles and the content that he releases weekly have given me an understanding of the Nomad Capitalist philosophy. It's not about simply moving from one place to another; it's about strategically positioning oneself in an environment that optimizes personal growth and financial opportunities. Andrew's expertise in harnessing the potential of diverse markets and his intricate knowledge of international law concerning residence and citizenship assured me that my decision to leave Canada and live a global lifestyle was correct.
The concept of Citizenship by Investment, which I learnt from Andrew Henderson’s YouTube videos, was particularly interesting and opened my mind to global mobility. As an investor, I loved the idea of having a diverse passport and residence portfolio and owning homes worldwide where I would spend time at my leisure. Who wouldn’t want the freedom to travel, reside, and do business with the added benefit of lower taxes? And this is all in a setting I proudly call home in the Caribbean.
Andrew's strategic, borderless living vision resonated with my aspirations and goals. His expert insights and attention to detail in the content he produces fundamentally altered the trajectory of my investments and international presence. The expertise and profound personal approach the Nomad Capitalist team offers isn't just impressive; it's transformative for investors and entrepreneurs looking to live a life with more freedom.
How Andrew Henderson Motivated Me to Leave Canada
Leaving Canada was the Hardest Decision I Ever Made
Shared His Personal Journey to Find Freedom
When I came across Andrew Henderson's story, I opened my eyes to a new perspective on life and personal freedom. He'd done what many only dream of: living by the five magic words, "Go where you're treated best." His personal journey was a bit more intense then mine, cutting ties with the United States and renouncing his citizenship. He created a life across various global destinations before anybody else, and that resonated deeply with me. This wasn't just a fairytale; it was Andrew Henderson's real-life story, infused with the ethos of Nomad Capitalist. The more I learned about his ventures, from multiple citizenships to international business foundations, the more I felt inspired to chart a similar path.
Provided Free Advice
Amidst my quest for change, I was especially grateful for the freely shared knowledge and how-tos from Andrew Henderson and the Nomad Capitalist team's YouTube channel. The immense library of articles, videos, and podcasts offered insights into the complexities of global taxation, immigration, citizenship by investment and everything in between. Unlike many advisors who retain their best tips behind a paywall, Andrew laid his advice out in the open. This generosity laid the groundwork for my decision to seek a new life in Antigua and Barbuda—a country and region that is becoming synonymous with growth and potential.
Sent Me down a Rabbit Hole
Absorbing this rich stream of content, I spiralled down a rabbit hole of leaving Canada, becoming a non-resident for tax purposes, and relocating to the Caribbean. With every piece of content, whether from the Nomad Capitalist's website or Andrew Henderson's book and interviews, I felt the pull towards an unbounded, sovereign life. Andrew Henderson's Nomad Capitalist philosophy didn't just hint at the possibilities; it propelled me to action and paved the way for my relocation to the Caribbean. I embraced that life is dynamic and recognising the right time to make bold moves is key to truly thriving globally. Looking at my LinkedIn profile over the past five years is a testament to this transformation — a narrative of ambition, taking bold risks, and an extreme example of lifestyle by design. This was especially catalysed by the Nomad Capitalist blueprint.
Andrew Henderson's own experiences and the Nomad Capitalist platform were instrumental in my migration from Canada to Antigua and Barbuda. His ethos of living freely, without boundaries, has fundamentally altered my approach to personal and financial sovereignty.
My Own Journey to Financial Freedom
My Career in Sales Management
My career in sales management honed my skills in negotiation, strategic planning, and client relations. I thrived on driving revenue growth and forging strong teams, yet I always knew a traditional corporate ladder wasn't my destined path. I craved independence and the freedom to make my life decisions based on my own terms rather than being tethered to one location or a single market's economic fluctuations. This concept and mantra has been the driving force behind my real estate investment strategy in Canada for the past decade, and is propelling new business initiatives in the Caribbean region.
Building Wealth Through Real Estate Investment
I was lucky to discover my calling early on in life when a good friend and my landlord at the time introduced me to the world of real estate investing. I was 24 then, and this individual pushed me to purchase my first home and offered to match my downpayment. This helped me enter the Greater Toronto Area housing market in 2010, a few years earlier. I didn’t understand this then, but the timing was excellent. Less than a year later, I purchased another home, my first rental property in Hamilton, Ontario. In 2014, I quit my career in sales management and became a full-time real estate investor. By 2019, I built a $15M portfolio of multi-family, mixed-use and small commercial assets, all in the downtown Hamilton core that I independently owned and managed.
Discovering the Offshore World and Living Tax Free
The pivotal turn in my personal and professional life came when I stumbled upon the concept of becoming a non-resident of Canada for tax purposes. I had a family member at the time that was living in Malaysia. I didn’t understand why until he explained that by living in Malaysia full-time and securing residency by investment through their MM2H program, his worldwide income was no longer subject to taxation. As a 29-year-old entrepreneur, this was mind-blowing. It was a concept that resonated with me on a profound level: the power to legally reduce my tax obligations while embracing a global lifestyle. The teachings of Andrew Henderson and Nomad Capitalist added to this and gave me the tools that eventually take action almost 6 years later.
Living in Malaysia with Family in 2017
Pairing this concept of offshore living, global mobility, and international real estate investment made sense as my next big career and lifestyle move. After many years of research, planning, and considering several options worldwide, I concluded that certain Caribbean nations—notably smaller islands like Antigua and Barbuda with tax and citizenship programs—offered compelling investment options and lifestyle benefits. Compared to other regions in the world, I saw the Caribbean as undervalued, underappreciated, and uniquely positioned to benefit from the emerging trend of remote work and perpetual travel. This is especially true for Canadians, Americans, and Brits looking for a winter escape.
Becoming a Non-Resident of Canada
The decision to become a non-resident of Canada was a significant but necessary step in my quest for global mobility and financial sovereignty as I continued to build wealth. Leaving a country you have called home for 35 years was one of the hardest decisions I had even made. Moving to the Caribbean was exciting, but selling everything I owned and leaving friends and family behind was emotionally difficult. But, this strategic move wasn't about renouncing ties to my homeland but rather expanding my horizons and securing the best possible lifestyle and financial advantages for myself.
After comparing many different options worldwide and within the Caribbean region, I concluded that Antigua and Barbuda’s Citizenship by Investment program provided an ideal gateway to a new level of personal freedom and investment potential. Embracing Andrew Henderson's ethos of going where I'm treated best, my migration to Antigua and Barbuda materialized into a life beyond my expectations—full of growth, freedom, and opportunity.
Living and Investing Tax-Free in the Caribbean
Stunning Beaches in Antigua and Barbuda
My Home Base in Antigua and Barbuda
Inspired by Andrew Henderson's philosophy, I made the pivotal decision to relocate from Canada to Antigua and Barbuda. These learned concepts propelled my interest in a jurisdiction that beautifully marries personal growth with financial strategy. Antigua and Barbuda became my chosen hub in the Caribbean, where I could develop my business interests in Caribbean real estate and relish in an enviable lifestyle. Here, I am afforded the luxury of zero capital gains tax, zero inheritance tax, and competitive corporate tax structures, all while residing in a place that most days felt like a perpetual holiday.
How Have the Last 3 Years Been
The past three years have had no shortage of challenges and difficulties, but it has also been transformative. I’ve grown my network in the Caribbean exponentially and spent thousands of hours learning and researching investment and business opportunities. The move was more than just a financial calculation—it has been a holistic change. The community, the climate, and the incredible potential investment opportunities I've been exposed to have reinforced the decision to move and uproot my life.
Opportunities I See in the Caribbean Right Now
Real estate in the Caribbean is starting to heat up, and the opportunities for affluent families, investors and entrepreneurs are endless. I've observed a sharp uptick in demand for luxury properties, particularly from non-residents and expatriates in some of the smaller emerging markets. Countries like Antigua and Barbuda that offer Citizenship by Investment Programs have become especially attractive, drawing in high-net-worth individuals looking for mobility and privacy. Diversifying my portfolio within the Caribbean region will continue to help me identify pockets of potential across the islands, most notably in eco-tourism and sustainable developments that cater to the growing trend of environmentally conscious living.
If I Could Do It All Over Again, What Would I Have Done Differently?
Reflecting on my journey, weighing the 'what ifs' is imperative. If I could retrace my steps, would I have done it again? Although hindsight is 20/20, I should have paid a firm like Nomad Capitalist early on to guide me through the exit from Canada. This would have actually saved me hundreds of thousands of dollars and allowed me to spend more time on my core business. Making a move based on Andrew Henderson's insights sooner rather than later might have allowed me to capitalize on the upswing in market trends and establish myself in the Caribbean earlier. Nonetheless, it's never about regret but optimizing the present with an eye to a brighter future.
Conclusion
Enjoying the Sunset in Antigua and Barbuda
Embracing Andrew Henderson's Nomad Capitalist philosophy has transformed my life. I've experienced firsthand the benefits of strategic international living and investing, and I am grateful for all of the people who have helped me along the way. My journey to Antigua and Barbuda and the Caribbean community opened doors to financial freedom and personal growth that were once just dreams. I'm living proof that you can “go where you're treated best” with guidance and a bold approach to global opportunities. Whether for asset protection, tax optimization, buying your dream home, or a better quality of life, this new global lifestyle might be the key to unlocking a world of potential.
Bio
International Real Estate Investor and Entrepreneur. Founder @Offshore Freedom | Host of the @CaribbeanRealEstatePodcast
We help successful investors and entrepreneurs live and invest tax-free in the Caribbean and buy real estate internationally.
Schedule a consultation with Dan Merriam, and let him help you design the life of your dreams and achieve Offshore Freedom™. Ask questions and get answers about the Caribbean, tax planning, banking, international real estate, second residencies, citizenship by investment and lifestyle design,
Writer in Tax Reduction, International Tax Planning, Travel, Golden Visa, Second Residence, Real Estate Investing, Andrew Henderson, Nomad Capitalist Live, Invest Asian, MM2H, Malaysia, Thailand, Caribbean, Citizenship By Investment, Global Mobility, Technology, Asset Management, Lifestyle Planning, Company Formation, Offshore Banking, Asset Protection, Technology, Entrepreneurship
