“One Dream at a Time”: 10 On The Weekend with Hiran Chohan

"The human desire for security, freedom, opportunity, and the ability to protect one's family, are far more powerful than any political headwind"
IMI
• Amman

10 On The Weekend is a weekly (-ish) feature in IMI, the concept of which is simple: Each time, we ask the same ten questions of a different IMI Pro, letting readers get to know the interviewee on a more personal and informal level than they might during the ordinary course of business.

Our guest this week is Hiran Chohan, Managing Director of Windsor Capital Management

How do you spend your weekends?

Weekends are family time first and foremost. With two daughters, there’s always something going on, whether that’s the usual domestic rhythm of family life or just being present and enjoying time together.

I also make sure I get to the gym; it’s non-negotiable for me in terms of keeping a clear head. And then there’s football! I’m a Manchester United supporter, have been my whole life, as my father followed them before me.

What makes it extra special now is that my eldest daughter has caught the United bug, too. There’s something really wonderful about sharing that passion across three generations.

banner

On a good weekend, United wins, and everyone’s happy. On a bad weekend, well, we’ve had plenty of practice dealing with those as well.

What are your top three business goals this year?

First, to continue building Windsor’s reputation as a genuine family office, one that clients trust with the full picture of their wealth, their lives, and their legacy, not just a single transaction.

Second, to deepen our relationships in the markets where we are already strong such as Africa and expand meaningfully into new ones, particularly across the US and Asia, where demand for integrated wealth and mobility solutions is growing rapidly.

Third, and perhaps most importantly, to keep raising the bar on the client experience. In a sector where everyone claims to be bespoke, I want Windsor actually to be bespoke and for our clients to feel that difference every single time.

What’s your biggest business concern right now?

The increasingly restrictive stance that governments around the world are taking towards global mobility. We are seeing more barriers, more complexity, and more political resistance to the very concept of freedom of movement, and that concerns me, not just commercially, but philosophically.

banner

Mobility is not a privilege reserved for the ultra-wealthy; it is a fundamental enabler of opportunity, security, and human potential. What strikes me, however, is the paradox at the heart of this trend; the more governments restrict it, the more essential it becomes.

When pathways narrow, the value of expert guidance grows. Clients who might once have considered their options at leisure are now planning with far greater urgency and far greater care.

So while the regulatory headwinds are real, they have also sharpened Windsor’s purpose because in a more complex world, the need for a trusted, knowledgeable partner becomes not a luxury, but a necessity.

Which book is on your nightstand right now?

I’ll be honest, I’m not a big reader in the traditional sense, and I think there’s something refreshing about admitting that.

What I am is a committed listener. I spend a lot of time with podcasts, particularly anything touching on science, space, and big-picture thinking.

Joe Rogan and Neil deGrasse Tyson are regular companions. There is something about conversations on the universe, physics, and human potential that I find genuinely energising.

When you spend your days thinking about wealth structures and jurisdictions, it’s good for the soul to zoom out and contemplate something rather larger.

How and when did you first get into the investment migration industry?

My background is in financial services and wealth management, and for a long time, that was the whole picture, helping clients build, protect, and grow their wealth.

What became increasingly clear, working with high-net-worth individuals and families, was that wealth alone was never really the whole conversation. People wanted options! They wanted freedom of movement, security for their families, and the ability to structure their lives across borders.

Investment migration was the natural extension of everything I was already doing. Windsor grew out of that realisation that the most valuable thing we could offer clients wasn’t a single product, but a genuinely joined-up service around every dimension of their financial and personal lives.

What was your proudest moment as a service provider?

It is difficult to distil twenty years of work into a single moment, and perhaps that is the most honest answer I can give.

What fills me with the greatest pride is not any one transaction or outcome, but the relationships that have endured across time and across generations. I have clients whose families I have been part of for two decades. I was there in the early days when we were structuring their wealth and planning their futures. I watched their children come into the world.

And now, those same children are adults, building their own lives, and Windsor is helping them structure their own wealth in turn. That continuity, being genuinely trusted by a family not just once, but across a lifetime and beyond, is something that no deal or approval letter could ever replicate.

Which investment migration market development has surprised you the most in the last year?

If I am being honest, it is the sheer resilience of the industry itself. There has been no shortage of headwinds, growing political pressure to close programmes, the removal of visa-free access for certain passport holders, and an increasingly hostile narrative in parts of the mainstream media.

Many predicted, not unreasonably, that the cumulative weight of that pressure would cause significant damage to the sector. And yet here we are. Demand has not collapsed, clients have not retreated; if anything, the appetite for mobility solutions has intensified.

What that tells me is that the fundamental drivers of this industry, the human desire for security, freedom, opportunity, and the ability to protect one’s family, are far more powerful than any political headwind. This reinforces my conviction that what we do at Windsor matters.

If you could go ten years back in time, what business decision would you change?

I would have started Windsor sooner. The instinct to build something truly independent, a firm that could wrap around the client rather than fitting the client around the firm, was always there.

But like most people, I spent time in structures that weren’t quite right before committing fully to the vision. The journey was valuable, absolutely. But the destination was always going to be this.

What investment migration industry personality do you most admire?

Henry Fan, without question. What he has built at Globevisa is genuinely remarkable. Growing from a two-person start-up into the world’s largest investment migration consultancy is amazing. The scale alone is impressive, but what I find truly admirable is the thinking behind it.

His so-called “supermarket model”, the idea that every client should be able to find a solution tailored to their specific circumstances rather than being pushed towards whatever a firm happens to sell, perfectly reflects a philosophy I deeply respect.

If all goes according to plan, what will you be doing five years from now?

I hope Windsor will be recognised as one of the most trusted family office firms operating across our key markets, a firm that clients come to not for a single service, but for a relationship that spans generations.

On a personal level, I hope to have more time on the weekends where United are genuinely challenging for titles rather than just hoping for a top four finish. One dream at a time!

How prepared are you for sudden geopolitical shifts?

Find out where you're exposed — and what to do about it — in 3 minutes. From freedom of movement and backup jurisdictions to economic independence and asset spread.

Check your Sovereignty Score now and get a personalized action plan.

Check My Sovereign Score
Sovereign Score gauge showing 81 of 100
Visa-free access world map
Sovereignty radar chart across 10 pillars
Pillar breakdown showing 10 sovereignty dimensions

Have a question?