One Dream at a Time: an interview with Hiran Chohan from Windsor Capital Management — 10 questions on weekends, goals, and investment migration

“10 On The Weekend” is IMI’s weekly (sometimes slightly freer) feature. The idea is simple: each edition asks ten identical questions to another IMI expert, so readers get to know the guest beyond boardroom conversations.

This time, our guest is Hiran Chohan, Managing Director at Windsor Capital Management.

How do you spend your weekends?

First and foremost, with my family. I have two daughters, and weekends are always full—sometimes it’s the familiar family rhythm, and sometimes it’s simply the chance to be together and truly enjoy those shared moments.

Another non-negotiable is the gym. For me, it’s “no discussion” because it keeps my mind clear. And of course, football. I’ve supported Manchester United for as long as I can remember—a tradition passed down from my father, who followed the club even before I did.

What’s especially great right now is that my older daughter has caught the “United bug,” too. It’s genuinely surprising to share the same passion across three generations.

The perfect weekend is when “United” wins and everyone’s happy. If not… we’ve already built up plenty of practice in how to handle those matches with class.

Three main business goals for this year

First, to keep strengthening Windsor’s reputation as a true family office—one trusted to see the full picture: not only individual transactions, but clients’ wealth as a whole, their day-to-day lives, and the legacy they’re building.

Second, to deepen relationships in markets where we’re already strong, including Africa, while expanding more meaningfully into new regions—especially the United States and Asia. Demand for integrated wealth and mobility solutions is growing quickly there.

Third (and maybe most important), to raise the bar on the quality of the client experience. People in the industry say “personalized,” but I want Windsor to be genuinely bespoke—and for clients to feel it, again and again.

What worries you most about the business right now?

I’m concerned about how much governments around the world are tightening their stance on global mobility. We’re seeing more barriers, more complexity, and more political resistance to the very idea of freedom of movement.

Mobility isn’t a privilege reserved only for the ultra-wealthy. It’s a fundamental driver of opportunity, safety, and human potential. But there’s a paradox in this trend: the more states restrict mobility, the more necessary it becomes.

When “corridors” of opportunity narrow, the value of expert guidance rises. Clients who used to be able to consider options without much urgency now plan solutions much faster—and with much more care.

Yes, regulatory constraints are a real challenge. But they also sharpen our mission: in a more complicated world, the need for a trusted partner with deep knowledge isn’t a luxury—it’s a requirement.

What book is currently on your bedside table?

To be honest, I’m not the kind of person who reads a lot in the classic sense—and there’s something refreshing about admitting that.

I’m more of a “listener.” I spend a lot of time with podcasts—especially those connected to science, space, and thinking at the scale of big ideas.

I keep running into Joe Rogan and Neil deGrasse Tyson. I genuinely get energized by how these conversations explore the universe, physics, and human potential.

When you think day after day about capital structures, jurisdictions, and legal practice, it’s useful to “switch off” from the details and zoom out—toward what matters more than any checklist.

How and when did you first get into investment migration?

My professional foundation is finance and wealth management. For a long time, that was the whole story: helping clients build, protect, and grow their wealth.

But over time, it became clear that for HNW clients and families, money isn’t the entire picture. They need options. They need freedom of movement, safety for their loved ones, and the ability to shape their lives across borders.

Investment migration became a natural extension of what I was already doing. Windsor grew out of a key insight: the most valuable thing we can offer clients isn’t a single product—it’s a truly connected, end-to-end service that takes every dimension of their financial and personal life into account.

What moment makes you most proud as a service provider?

It’s hard to fit twenty years of work into one “most of all” moment. And maybe the most honest answer is this: I’m proud not just of a single outcome.

What inspires me most is the relationships that last over time and carry through generations. I have clients whose families we’ve supported for two decades. I was there from the beginning—when we formed their capital and planned the future. I’ve watched their children grow up.

And today those same children are adults building their own plans—while Windsor helps them again in how to structure wealth. That continuity—where trust isn’t a one-off, but stretches across a lifetime and beyond—isn’t something you can replicate with any single transaction or letter of approval.

What development in the investment migration market over the past year surprised you the most?

To be direct, I was surprised by the industry’s resilience. Pressure is increasing: the political push to close programs is strengthening, some passports are losing visa-free access, and in certain segments mainstream media is shaping an increasingly hard-edged narrative.

Many expected (and that was reasonable) that the combined effect of this pressure would hit the sector hard. But what we’re seeing is the opposite: demand hasn’t disappeared, and clients haven’t “backed off.” If anything, appetite for mobility solutions has grown even stronger.

For me, this confirms something important: the industry’s core drivers—people’s desire for safety, freedom, opportunity, and family protection—are stronger than any political headwind. So I’m once again convinced that what we do at Windsor truly matters.

If you could go back 10 years, what business decision would you change?

I would start Windsor earlier. The instinct within the company was always to build a truly independent business—one that “wraps around” the client and tailors solutions to them, rather than forcing the client to fit the structure of the business.

But like many people, I had phases where I worked in formats that didn’t fully match the future vision. The journey was valuable—absolutely. But the destination was always the same: where we’ve arrived today.

Which “personality” in the investment migration industry do you respect most?

Without question, Henry Fan. What he has done at Globevisa is truly impressive. The company grew from a two-person startup into one of the world’s largest investment migration advisory platforms—and that’s remarkable.

Scale alone is already worthy of respect. But what I especially appreciate is the logic the whole approach is built on. His so-called “supermarket model” means the client should have access to solutions that fit their situation—not be pushed toward what a specific company happens to sell.

This philosophy aligns completely with what I value deeply.

Where will you be in five years if everything goes according to plan?

I hope Windsor will be recognized as one of the most trusted family offices in our key markets—a company clients come to not for a one-time service, but for relationships that continue between generations.

And personally, I’m dreaming of calmer weekends—where Manchester United is really fighting for titles, not just “hoping” to finish in the top four. One dream at a time!

If you’re considering investment migration to secure a more stable financial and family future, it’s crucial to rely on real experience and a clear strategy. In Hiran Chohan’s interview, the main idea is that value comes not from one-off transactions, but from a whole-picture approach to wealth and legacy — the same principle applies to Golden Visa solutions. Want to find out which path fits your goals, timeline, and risk profile? Reach out for a consultation via digital-nomad.gr/en/goldenvisa.

Our Telegram channel about various types of Greek residence permits, digital nomad programs, and the Greek Golden Visa: @digitalnomadgr