Money & Me: 'I was a crazy spender and had two Ferraris and a Bentley'

Former airline steward Alessandro D’Ubaldo is a serial entrepreneur who owned a pioneering property letting business and a classic car sales portal and also traded cigars before launching UAE dining brands 800Pizza, Pisanity and Cluckers. Born in Italy, Mr D’Ubaldo served in the navy, worked in a London hotel, then joined the aviation industry, which landed him in Dubai. He invested funds from his pre-Airbnb short-term rentals company and property deals to create 800Pizza, establishing 12 branches before a significant exit last year. Mr D’Ubaldo, 47, also has e-commerce investments, including apparel platform Asos. Currently pondering his next business opportunity, Mr D’Ubaldo divides his time between Dubai’s Damac Hills and a Beirut hillside penthouse with his wife and children, aged 9, 11 and 14. My mother had an office job and my father was in the police; their example was to work hard for your money. It was a middle class (family) where there wasn’t an abundance, but my sister and I were looked after very well. We lived in a rough neighbourhood close to central Rome that didn’t develop, until I left for military service. The general take on life in the area was, “don’t dare to dream”. My spirit has always been entrepreneurial (but) I was being directed towards something safe and secure, and not towards investing. My parents would give me jobs at home — cleaning windows, my father's bicycles, vacuuming — there’s no way they would give me money for doing nothing. We try to do the same with our children, which is harder because times have changed. My first job, I was 14 and washing cars in a car wash at the weekend and in summer. It was good enough money for me. The idea was to do a military career, to be a navy pilot or seal. I was into travelling and had a one-way ticket to London with Ethiopian Airlines, the cheapest flight. I had very little, no idea how to manage my money and within a week had almost run out. My standard of living started at a hotel, then a hostel, then a bed space, and survival. I’d have been 19. Then I got a break at a Sheraton hotel in Knightsbridge as a waiter's assistant and experienced things I never knew existed. After a year or so, I secured a cabin crew job in Milan, a stepping stone to joining Emirates in 1999. I had a passion for classic cars and saw this Cadillac 1975 Eldorado for sale in the UK. I flew there and shipped it to the UAE. I built a portal with classic cars for sale and had people listing from the US because they got exposed to the Gulf. This was my first business, but revenue was small. I had friends who had properties, were renting to tourists and I started assisting with managing them. I built a network and eventually a website to manage and advertise properties. We ended up managing so many, my wife also left Emirates so we were both working in the company. The business grew very fast. I got my first Ferrari, which was the dream for me, at 29. No one else is doing this, no Airbnb, but eventually we had competitors. I also bought and sold properties like everyone was doing in 2007, but got to a point where I worried this real estate [boom] was too good to be true. Two years later, the bubble burst and we shut down. I wanted to diversify; around that time, there was nobody serving proper wood-fired Italian pizza. Everything I got into just happened to work well. There was definitely a good degree of luck. There was this one-bedroom apartment in Downtown Dubai I bought a week before the bubble burst, for Dh2.5 million; seven years later we sold at Dh800,000. That hurt. Another was a property I thought I bought in Egypt. I was defrauded with fake documents. The development was introduced to me by a friend I trusted, but who was also swindled. I got about 70 per cent back. We own a villa in Dubai that we have arranged as a luxury Airbnb, the place we were living in. I have a small team on the ground. We did short-term rentals for a living … it was exciting to go back on those footsteps. It’s convenient because we make use of the property ourselves and have our home available when we need it. I am motivated by fear and ambition. It is a good thing for me to be worried because that is when I do my due diligence and analyse properly. I have had cash flow for many years. Now, I am in a position new to me; I have got nothing to do and have no cash flow, except for our Airbnb, which is performing extremely well but still not enough for me. So, what am I going to do? How am I going to make use of this [800Pizza sale] capital? It is losing value at the rate of inflation, which is tremendous. It is one of those problems most people would like to have. As a young man getting his first Ferrari, a 612 Scaglietti … I thought that was the accomplishment of a lifetime. In hindsight, you realise that is just a purchase, entertainment. It is a bit like a holiday, you can spend a fortune and you are left with the experience and emotions. Financially, there is no value in buying a Ferrari unless it is a collectible investment. At some point, we bought a house for the family, a different level of maturity. Because of responsibilities … had I been single, no children, I would probably still be buying Ferraris. But you must have financial stability to ensure your family has food and shelter, safety, education. If the money is not there, I cannot sleep, I don’t feel safe. I have to be careful. We have done some crazy spending in the past; I had two Ferraris and a Bentley. That was unsustainable, because the business went through a cycle, people started leaving the UAE, the customer base decreased. We had to adjust our lifestyle, a hard process to go through. My evolution is happening as we speak. We sold 800Pizza, a 100 per cent equity acquisition. Until I decide what to do, we have a standard of living I want to sustain and Lebanon allows me to keep overheads very low. If I stayed [full-time] in Dubai, I’m going to burn through capital. I learnt that a lot of people [entrepreneurs] have been through this stage, where they get worried about the future, what to do next after many years of 24/7 engagement. I thought I could be OK doing nothing, until my brain started seeing opportunities. I need to be engaged daily and rewarded daily. Retirement won’t work for me in the sense of sitting, doing nothing. Challenge is a component that I need; as well as engagement and financial stability.

Money & Me: 'I was a crazy spender and had two Ferraris and a Bentley'

Entrepreneur Alessandro D'Ubaldo says his relationship with money has evolved and financial stability is now more important