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.

Was there wealth in your childhood?

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.

Did you receive pocket money?

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.

Have you faced financial challenges?

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.

How did your entrepreneur journey begin?

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.

Why switch from properties to pizzas?

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.

Any financial dramas?

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.

Where do you generate earnings now?

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.

Are you stricter with your funds?

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.

Any cherished purchases?

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.

So your money relationship has evolved?

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.

Is the Lebanon experiment part of that?

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.

What is your future financial direction?

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.