How We’re Using AI to Solve the Tax Headache
Introduction
After two decades advising clients and building wealth solutions at Citi, Deutsche Bank, and Barclays, I grew used to the phrase: “Computer says no.” Whether I was filling out rigid travel logs as a C-suite banker or helping founders navigate the tax treatment of international equity packages, the process was always painfully manual, fragmented, and out of step with modern life.
The system wasn’t broken, but it was clearly outdated. The tax residency model most professionals still rely on today was designed for a world with borders, not for a generation that builds companies on planes, holds board meetings across three time zones, and raises families across continents.
Frustration Turned Into Function
Resident Tax was born out of this friction. I was manually tracking travel history across platforms while watching clients get blindsided by audits and penalties for years of unknowingly incorrect residency classification. What should be a straightforward calculation to define where someone is legally "resident" had become a compliance nightmare.
In many large firms, tracking this information is still a full-time job for someone, often a personal assistant managing calendar entries across jurisdictions. Entire workflows exist just to count days and get it right. It’s slow, error-prone, and expensive.
That’s how I saw an opportunity to build something better. Resident Tax automates residency tracking using GPS data, AI, and embedded global tax law - all within a simple and secure app. It generates real-time, audit-grade reports that help individuals and companies stay compliant without lifting a finger. For many of our clients, that means eliminating the need for several full-time staff. We’re saving them hundreds of hours and helping them avoid six-figure mistakes.
A Universal Pain Point
What’s striking is how universal the problem is. Whether I’m speaking with a law firm managing cross-border clients, a startup scaling remote teams, or a multinational relocating executives, the foundational question is always the same: Where is this person actually resident for tax purposes?
Once that compliance layer is solved, the next challenge emerges: optimization. That’s where our AI Auto-Pilot comes in, calculating personal tax liabilities, including income, capital gains, and inheritance tax, across multiple jurisdictions. We’re currently expanding the engine to handle corporate tax strategy as well, helping global entrepreneurs decide where to base their businesses, not just their lives.
The Hidden Rock of Compliance
The mismatch between locally enforced tax rules and globally mobile lifestyles is growing sharper by the year. Tax authorities are no longer playing catch-up. They’re quietly collecting entry-exit data, banking records, and offshore account details through frameworks like CRS and OECD directives. Clients are increasingly blindsided by penalties on unpaid taxes going back five or even ten years, often amounting to six-figure sums.
Having reliable, transparent, and legally robust day-counting records is now a prerequisite for any internationally mobile executive, founder, or family office. In this instance, Resident Tax doesn’t just help users stay compliant, but it also provides peace of mind in an increasingly high-stakes environment.
The Coming Storm
We’re entering an era where tax residency is becoming a highly politicized and strategically contested domain. As fiscal pressures mount, more governments are expected to explore citizenship-based taxation (CBT) models, echoing the U.S. approach under FATCA, to curb outbound mobility and retain taxing rights over their globally mobile citizens. Digital nomads, once a lightly regulated curiosity, will face mounting scrutiny, especially as they maintain ties to their country of origin.
At the same time, technology offers us a way forward. By building tools that make tax residency transparent and intelligent, we can protect individuals while helping regulators get the data they need. That’s why we’re working closely with experts at Multipolitan to expand our solutions for digital nomads, integrating tax strategy with visa and residency planning in a single system.
Global Architecture for a Global Client
We chose to build out of London, not only for its legal and financial pedigree, but because it remains a hub where culture, capital, and compliance converge. Our leadership and tech team are based there, while AI and cybersecurity teams sit across Barcelona, Amsterdam, and Munich. Our client service team operates from India, delivering real-time support to users in more than 80 countries.
This distributed structure mirrors the nature of our users: hedge fund managers, crypto founders, actors, academics, and retired bankers who live transnational lives. They need tools built for the way the world actually works, not the way tax codes think it does.
Privacy by Design
Our currency is professional trust, and privacy sits at the heart of everything we do. Given the highly sensitive nature of geolocation data, we made a deliberate architectural choice: Resident Tax has no backend server. App-generated data never leaves the user’s personal device or their secure iCloud/Google Drive storage. Nothing is transmitted, nothing is stored externally, ensuring 100% data privacy by design.
We’re fully registered with the UK Information Commission Office and compliant with GDPR, but beyond regulatory boxes, our architecture reflects a deeper belief: tax tech should empower users, not surveil them. In an age of growing digital exposure, our goal is to give individuals full control, complete transparency, and absolute confidence in the tools they use.
Where Tax Intelligence Is Headed
Ultimately, we don’t see ourselves as just a consumer-facing app. Resident Tax is building the infrastructure layer for international tax compliance, one that can embed within law firms, wealth managers, immigration consultancies, and fintech platforms. By handling 80% of the prep work (data collection, client Q&A, compliance analysis), we let human advisors do what they do best: make judgment calls and add strategic value.
We’re also pushing forward with new AI models that transform tax law into real-time, tailored outputs. Our Auto-Pilot calculates tax burdens across jurisdictions using Large Language Models (LLMs), but we’re now developing Large Relational Models (LRMs) to go even further, mimicking the decision logic of trained professionals.
The vision is simple: no more clunky PDFs, endless forms, or vague uncertainty about where you stand. From submitting W8-BEN forms in the U.S. to registering A1 forms in Europe, Resident Tax will soon be able to do it all - quickly, securely, and intelligently.
In the future, the truly global citizen won’t just need a second passport. They’ll need a second brain, and that’s what we’re building.
About the Author
Nikhil Chouguley is the founder of Resident Tax, a platform that simplifies tax residency compliance for frequent travelers. Previously, he was the Global Chief Operating Officer at Citibank, where he built and managed international teams, developed ESG data platforms, and drove innovation. A senior banker with a 23 years + career in European financial services, Nikhil is also active in industry working groups, public speaking, and advancing best practices in regulation, product development, and financial technology.
Introduction
After two decades advising clients and building wealth solutions at Citi, Deutsche Bank, and Barclays, I grew used to the phrase: “Computer says no.” Whether I was filling out rigid travel logs as a C-suite banker or helping founders navigate the tax treatment of international equity packages, the process was always painfully manual, fragmented, and out of step with modern life.
The system wasn’t broken, but it was clearly outdated. The tax residency model most professionals still rely on today was designed for a world with borders, not for a generation that builds companies on planes, holds board meetings across three time zones, and raises families across continents.
Frustration Turned Into Function
Resident Tax was born out of this friction. I was manually tracking travel history across platforms while watching clients get blindsided by audits and penalties for years of unknowingly incorrect residency classification. What should be a straightforward calculation to define where someone is legally "resident" had become a compliance nightmare.
In many large firms, tracking this information is still a full-time job for someone, often a personal assistant managing calendar entries across jurisdictions. Entire workflows exist just to count days and get it right. It’s slow, error-prone, and expensive.
That’s how I saw an opportunity to build something better. Resident Tax automates residency tracking using GPS data, AI, and embedded global tax law - all within a simple and secure app. It generates real-time, audit-grade reports that help individuals and companies stay compliant without lifting a finger. For many of our clients, that means eliminating the need for several full-time staff. We’re saving them hundreds of hours and helping them avoid six-figure mistakes.
A Universal Pain Point
What’s striking is how universal the problem is. Whether I’m speaking with a law firm managing cross-border clients, a startup scaling remote teams, or a multinational relocating executives, the foundational question is always the same: Where is this person actually resident for tax purposes?
Once that compliance layer is solved, the next challenge emerges: optimization. That’s where our AI Auto-Pilot comes in, calculating personal tax liabilities, including income, capital gains, and inheritance tax, across multiple jurisdictions. We’re currently expanding the engine to handle corporate tax strategy as well, helping global entrepreneurs decide where to base their businesses, not just their lives.
The Hidden Rock of Compliance
The mismatch between locally enforced tax rules and globally mobile lifestyles is growing sharper by the year. Tax authorities are no longer playing catch-up. They’re quietly collecting entry-exit data, banking records, and offshore account details through frameworks like CRS and OECD directives. Clients are increasingly blindsided by penalties on unpaid taxes going back five or even ten years, often amounting to six-figure sums.
Having reliable, transparent, and legally robust day-counting records is now a prerequisite for any internationally mobile executive, founder, or family office. In this instance, Resident Tax doesn’t just help users stay compliant, but it also provides peace of mind in an increasingly high-stakes environment.
The Coming Storm
We’re entering an era where tax residency is becoming a highly politicized and strategically contested domain. As fiscal pressures mount, more governments are expected to explore citizenship-based taxation (CBT) models, echoing the U.S. approach under FATCA, to curb outbound mobility and retain taxing rights over their globally mobile citizens. Digital nomads, once a lightly regulated curiosity, will face mounting scrutiny, especially as they maintain ties to their country of origin.
At the same time, technology offers us a way forward. By building tools that make tax residency transparent and intelligent, we can protect individuals while helping regulators get the data they need. That’s why we’re working closely with experts at Multipolitan to expand our solutions for digital nomads, integrating tax strategy with visa and residency planning in a single system.
Global Architecture for a Global Client
We chose to build out of London, not only for its legal and financial pedigree, but because it remains a hub where culture, capital, and compliance converge. Our leadership and tech team are based there, while AI and cybersecurity teams sit across Barcelona, Amsterdam, and Munich. Our client service team operates from India, delivering real-time support to users in more than 80 countries.
This distributed structure mirrors the nature of our users: hedge fund managers, crypto founders, actors, academics, and retired bankers who live transnational lives. They need tools built for the way the world actually works, not the way tax codes think it does.
Privacy by Design
Our currency is professional trust, and privacy sits at the heart of everything we do. Given the highly sensitive nature of geolocation data, we made a deliberate architectural choice: Resident Tax has no backend server. App-generated data never leaves the user’s personal device or their secure iCloud/Google Drive storage. Nothing is transmitted, nothing is stored externally, ensuring 100% data privacy by design.
We’re fully registered with the UK Information Commission Office and compliant with GDPR, but beyond regulatory boxes, our architecture reflects a deeper belief: tax tech should empower users, not surveil them. In an age of growing digital exposure, our goal is to give individuals full control, complete transparency, and absolute confidence in the tools they use.
Where Tax Intelligence Is Headed
Ultimately, we don’t see ourselves as just a consumer-facing app. Resident Tax is building the infrastructure layer for international tax compliance, one that can embed within law firms, wealth managers, immigration consultancies, and fintech platforms. By handling 80% of the prep work (data collection, client Q&A, compliance analysis), we let human advisors do what they do best: make judgment calls and add strategic value.
We’re also pushing forward with new AI models that transform tax law into real-time, tailored outputs. Our Auto-Pilot calculates tax burdens across jurisdictions using Large Language Models (LLMs), but we’re now developing Large Relational Models (LRMs) to go even further, mimicking the decision logic of trained professionals.
The vision is simple: no more clunky PDFs, endless forms, or vague uncertainty about where you stand. From submitting W8-BEN forms in the U.S. to registering A1 forms in Europe, Resident Tax will soon be able to do it all - quickly, securely, and intelligently.
In the future, the truly global citizen won’t just need a second passport. They’ll need a second brain, and that’s what we’re building.
About the Author
Nikhil Chouguley is the founder of Resident Tax, a platform that simplifies tax residency compliance for frequent travelers. Previously, he was the Global Chief Operating Officer at Citibank, where he built and managed international teams, developed ESG data platforms, and drove innovation. A senior banker with a 23 years + career in European financial services, Nikhil is also active in industry working groups, public speaking, and advancing best practices in regulation, product development, and financial technology.
Introduction
After two decades advising clients and building wealth solutions at Citi, Deutsche Bank, and Barclays, I grew used to the phrase: “Computer says no.” Whether I was filling out rigid travel logs as a C-suite banker or helping founders navigate the tax treatment of international equity packages, the process was always painfully manual, fragmented, and out of step with modern life.
The system wasn’t broken, but it was clearly outdated. The tax residency model most professionals still rely on today was designed for a world with borders, not for a generation that builds companies on planes, holds board meetings across three time zones, and raises families across continents.
Frustration Turned Into Function
Resident Tax was born out of this friction. I was manually tracking travel history across platforms while watching clients get blindsided by audits and penalties for years of unknowingly incorrect residency classification. What should be a straightforward calculation to define where someone is legally "resident" had become a compliance nightmare.
In many large firms, tracking this information is still a full-time job for someone, often a personal assistant managing calendar entries across jurisdictions. Entire workflows exist just to count days and get it right. It’s slow, error-prone, and expensive.
That’s how I saw an opportunity to build something better. Resident Tax automates residency tracking using GPS data, AI, and embedded global tax law - all within a simple and secure app. It generates real-time, audit-grade reports that help individuals and companies stay compliant without lifting a finger. For many of our clients, that means eliminating the need for several full-time staff. We’re saving them hundreds of hours and helping them avoid six-figure mistakes.
A Universal Pain Point
What’s striking is how universal the problem is. Whether I’m speaking with a law firm managing cross-border clients, a startup scaling remote teams, or a multinational relocating executives, the foundational question is always the same: Where is this person actually resident for tax purposes?
Once that compliance layer is solved, the next challenge emerges: optimization. That’s where our AI Auto-Pilot comes in, calculating personal tax liabilities, including income, capital gains, and inheritance tax, across multiple jurisdictions. We’re currently expanding the engine to handle corporate tax strategy as well, helping global entrepreneurs decide where to base their businesses, not just their lives.
The Hidden Rock of Compliance
The mismatch between locally enforced tax rules and globally mobile lifestyles is growing sharper by the year. Tax authorities are no longer playing catch-up. They’re quietly collecting entry-exit data, banking records, and offshore account details through frameworks like CRS and OECD directives. Clients are increasingly blindsided by penalties on unpaid taxes going back five or even ten years, often amounting to six-figure sums.
Having reliable, transparent, and legally robust day-counting records is now a prerequisite for any internationally mobile executive, founder, or family office. In this instance, Resident Tax doesn’t just help users stay compliant, but it also provides peace of mind in an increasingly high-stakes environment.
The Coming Storm
We’re entering an era where tax residency is becoming a highly politicized and strategically contested domain. As fiscal pressures mount, more governments are expected to explore citizenship-based taxation (CBT) models, echoing the U.S. approach under FATCA, to curb outbound mobility and retain taxing rights over their globally mobile citizens. Digital nomads, once a lightly regulated curiosity, will face mounting scrutiny, especially as they maintain ties to their country of origin.
At the same time, technology offers us a way forward. By building tools that make tax residency transparent and intelligent, we can protect individuals while helping regulators get the data they need. That’s why we’re working closely with experts at Multipolitan to expand our solutions for digital nomads, integrating tax strategy with visa and residency planning in a single system.
Global Architecture for a Global Client
We chose to build out of London, not only for its legal and financial pedigree, but because it remains a hub where culture, capital, and compliance converge. Our leadership and tech team are based there, while AI and cybersecurity teams sit across Barcelona, Amsterdam, and Munich. Our client service team operates from India, delivering real-time support to users in more than 80 countries.
This distributed structure mirrors the nature of our users: hedge fund managers, crypto founders, actors, academics, and retired bankers who live transnational lives. They need tools built for the way the world actually works, not the way tax codes think it does.
Privacy by Design
Our currency is professional trust, and privacy sits at the heart of everything we do. Given the highly sensitive nature of geolocation data, we made a deliberate architectural choice: Resident Tax has no backend server. App-generated data never leaves the user’s personal device or their secure iCloud/Google Drive storage. Nothing is transmitted, nothing is stored externally, ensuring 100% data privacy by design.
We’re fully registered with the UK Information Commission Office and compliant with GDPR, but beyond regulatory boxes, our architecture reflects a deeper belief: tax tech should empower users, not surveil them. In an age of growing digital exposure, our goal is to give individuals full control, complete transparency, and absolute confidence in the tools they use.
Where Tax Intelligence Is Headed
Ultimately, we don’t see ourselves as just a consumer-facing app. Resident Tax is building the infrastructure layer for international tax compliance, one that can embed within law firms, wealth managers, immigration consultancies, and fintech platforms. By handling 80% of the prep work (data collection, client Q&A, compliance analysis), we let human advisors do what they do best: make judgment calls and add strategic value.
We’re also pushing forward with new AI models that transform tax law into real-time, tailored outputs. Our Auto-Pilot calculates tax burdens across jurisdictions using Large Language Models (LLMs), but we’re now developing Large Relational Models (LRMs) to go even further, mimicking the decision logic of trained professionals.
The vision is simple: no more clunky PDFs, endless forms, or vague uncertainty about where you stand. From submitting W8-BEN forms in the U.S. to registering A1 forms in Europe, Resident Tax will soon be able to do it all - quickly, securely, and intelligently.
In the future, the truly global citizen won’t just need a second passport. They’ll need a second brain, and that’s what we’re building.
About the Author
Nikhil Chouguley is the founder of Resident Tax, a platform that simplifies tax residency compliance for frequent travelers. Previously, he was the Global Chief Operating Officer at Citibank, where he built and managed international teams, developed ESG data platforms, and drove innovation. A senior banker with a 23 years + career in European financial services, Nikhil is also active in industry working groups, public speaking, and advancing best practices in regulation, product development, and financial technology.
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