WAYFARER · A Conversation
Riana
with Romy Hawatt
Sveti Stefan · 6 movements · 20 questions
Dear Romy — answer in your own words and your own hours. Tap Answer on any question: WhatsApp opens with it ready. No order, no rush.
Prefer to speak? Voice notes are perfect — we’ll transcribe them for you, so there’s nothing to write.
I. THE MAN
Origins & compass
Q01 You first came to know this coastline as a young backpacker, years before Montenegro’s re-independence in 2006 — when almost no one could place it on a map. What did that young traveller see here that the markets would only understand decades later?
Q02 Your career runs more than forty years and crosses aviation, education, real estate and hospitality. If you stripped it all back to one thing, what is the instinct that has guided every decision?
Q03 You’re known for turning early-stage businesses into lasting ones. What is the real difference between a business that simply scales and a business that endures?
Q04 You hold a pilot’s licence and you’ve spent your life moving between Australia, Dubai, Europe and the Balkans. How has a life lived in the air and on the water shaped the way you read an opportunity?
Q05 Philanthropy — water in Kenya, orphanages, the Global Sustainability Network — sits at the centre of how you describe yourself, not at the edges. Where did that conviction first take hold?
II. THE BUILD
Riana Group & Airways
Q06 The Riana Group moves across aviation training, charter, property and fine dining. From the outside that can look diverse to the point of contradiction. What is the thread that ties it together for you?
Q07 Airways Aviation grew into the world’s largest privately owned pilot training group. What did you see in aviation training that others in the industry missed?
Q08 Before this chapter you built and scaled the SAE education model to students in dozens of countries. What did that first act teach you that you still apply today?
Q09 You’ve spoken about a chronic, decades-long shortage of pilots and skilled aviation professionals. How are you positioning the group for a demand curve most people can’t yet see?
Q10 You describe yourself as a seasoned negotiator with a history of transactions on an international scale. When you walk into a deal, what are you really looking for before anything is signed?
III. MONTENEGRO
The bet & the country
Q11 You were among the first foreign investors in Porto Montenegro, and you introduced and brokered its sale to the Investment Corporation of Dubai. Take us back to the moment you decided this place was worth a decade of your life.
Q12 You’ve called Montenegro one of the two best places in the world to build a business, alongside Dubai. For someone hearing that for the first time, how do you make the case?
Q13 You’ve argued that foreign investment is an opportunity rather than a threat — “if it is directed properly and used wisely.” Where is the line between investment that builds a country and investment that merely extracts from it?
Q14 Discover Montenegro recently opened a new chapter after a decade as the country’s pioneering destination company. Where do you want Montenegro to stand as a destination ten years from now — and what still has to happen to get there?
IV. RIANA
The vessel & the choice
Q15 Everything else you’ve built follows the logic of business — scale, returns, expansion. Riana feels like she follows a different logic entirely. What does she give you that the rest of the portfolio doesn’t?
Q16 She’s a 42-metre classic sailing yacht — wooden-hulled, built for elegance rather than spectacle. In an Adriatic full of larger and newer boats, why did this one feel right?
Q17 Riana is often called the most photographed and filmed yacht in the Adriatic, and she has hosted global gatherings. Has she become something larger than a boat — a kind of ambassador for the life you’ve built on this coast?
Q18 You’ve put Riana to work for charity auctions and brought people together aboard her around causes you care about. At what point does a private object become a public one?
V. SVETI STEFAN
Here, today
Q19 We’re speaking from Sveti Stefan — the same islet where Riana once took center stage at the Global Citizen Forum. What does this particular stretch of coast mean to you, and why does it feel like the right place for this conversation?
VI. THE LONG VIEW
Legacy
Q20 Forty years of building, and you keep circling back to this coastline for the next chapter. When you look at all of it together — the businesses, the boat, the philanthropy, Montenegro itself — what do you most want it to add up to?
More ways to answer
💬 Send everything in one WhatsApp
✉ Answer by email
The email opens with all 20 questions ready to type under.
Thank you, Romy. I’ll shape this with the care it deserves.
Gabriel Silveirado
Founder & Publisher · WAYFARER