49 Secrets of an Elite Matchmaker
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About this ebook
Trudy Gilbert is the wise and with-it big sister you wish you had – full of great dating advice, a wealth of entertaining stories and she’ll tell you like it is. As owner and founder of Elite Introductions, a dating agency for executives and entrepreneurs, Trudy is known as Australia’s Millionaire Matchmaker. She has introduced thousands of successful singles and knows what makes a perfect match.
"Trudy Gilbert has a little black book to die for. As the founder of Elite Introductions, Gilbert offers a matchmaking service for millionaires and corporate high-flyers." Business Review Weekly
“Anyone can bring people together, but there’s a skill to doing it well.” Australian Women’s Weekly
"Trudy Gilbert is something of an expert on executive love matches." Sydney Morning Herald
"The Millionaire Matchmaker...Trudy Gilbert may be able to find your match." Wealth Creator
Trudy Gilbert
Trudy Gilbert is the wise and with-it big sister you wish you had – full of great dating advice, a wealth of entertaining stories and she’ll tell you like it is. As owner and founder of Elite Introductions, a dating agency for executives and entrepreneurs, Trudy is known as Australia’s Millionaire Matchmaker. She has introduced thousands of successful singles and knows what makes a perfect match. "Trudy Gilbert has a little black book to die for. As the founder of Elite Introductions, Gilbert offers a matchmaking service for millionaires and corporate high-flyers." Business Review Weekly “Anyone can bring people together, but there’s a skill to doing it well.” Australian Women’s Weekly "Trudy Gilbert is something of an expert on executive love matches." Sydney Morning Herald "The Millionaire Matchmaker...Trudy Gilbert may be able to find your match." Wealth Creator
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49 Secrets of an Elite Matchmaker - Trudy Gilbert
Chapter One
Why a Matchmaker?
If you’d told me at a young age that I was going to become a successful matchmaker, I would’ve been the first one to laugh out loud. A Matchmaker? Seriously? Did that even exist as a profession? Believe me when I say this was not something I sought out. Matchmaking found me .
It isn’t your everyday profession, seriously, but looking back over the last nine years, I can honestly say that I can’t imagine having done anything else. Bringing two people together and changing their lives for the better is the most wonderful feeling. Knowing that I’ve helped thousands of people find love is richly rewarding indeed.
Where it all began
Let’s look back at when it all began. At 16 I was fortunate enough to take a two-month study trip to Israel. It was the adventure of a lifetime… we rode camels, slept in the desert in a Bedouin tent, worked in a Kibbutz and did military training. We travelled, studied, made friends and had amazing life-changing experiences. On my return, I introduced my new friend Mark, to my close school friend Veronica. Even though I’d only known them separately, under totally different circumstances, I had this sixth sense — a unique knowing, really — that they would just click. I was always good at reading people and knowing what made them tick.
It turned out I was right! The pair started dating almost straight away. At the time, I thought that was so cool. Awesome even. I was genuinely happy for my friend and got a real buzz out of seeing two people find each other. But don’t misunderstand me. I had no light bulb moment here. I did not suddenly wake up the next morning and think: I want to be a matchmaker . Life continued as normal.
When friends and family started asking me about my post-graduation plans in my last year of high school, like many 17 year olds, I just felt lost. I didn’t have the faintest idea of what I wanted to do. A Doctor? A Lawyer? Something in marketing? So many options! How to choose? Still, amidst the sea of possibilities and indecision, I did actually have an answer when posed with THE question. I want to be a Managing Director
, I’d say with my head held high. It was pretty bizarre as I had no idea where this was coming from. What’s more, I didn’t really know what a Managing Director did. I was going around making this rather arrogant statement without understanding its true meaning. When people asked me: A Managing Director of what?
I never knew how to respond. What I did know, however, was that I wanted to be the boss; the decision maker. It seems clear now that one thing was for sure; whatever I was going to do, I was going to be a business owner.
To understand where this certainty came from, we need to look at my family. My dad was a sales agent in the rag trade and a very good one. He was well-dressed, charming, down-to-earth and fun. You could tell he loved what he did. I saw my dad work hard and he was well rewarded for his efforts. I know that I’m very lucky to have grown up in a loving, supporting and inspiring environment. My parents were always encouraging; they gave me the confidence to achieve anything I set my mind to. We had a wonderful family life with regular overseas holidays, trips to the theatre and lots of socializing with friends.
Raised as an only child, I often enjoyed the company of my parent’s friends. I found it fascinating to observe adult camaraderie. I’d watch their social behaviour and, without knowing it (from a rather young age), I began to analyze their exchanges. Soon I discovered there was much to learn from these subtle interactions, communication styles, long-form discussions on sophisticated topics and their body language. It became truly captivating.
I remember one day, when I was about 10 years old, I went to work with my Dad. We drove around and visited five of his clients, showing a range of clothing to each one. Throughout the day I noticed something each client had in common: They all truly enjoyed seeing my dad, welcoming him like a close friend. He would joke with them; ask after their families and how business had been, what was selling and how he could help them to further increase sales with the new range he had to offer. As I recall, he received orders from every single client that day. When we returned home, my Mum asked me how it had gone and I remember saying: Dad does business with his friends.
At that time I thought having your own business was amazing — you had fun, had complete freedom, a great lifestyle and your clients were your friends. This was the reason I was so keen to tell people I wanted to be a Managing Director!
When high school finished, I went to university. Being a Managing Director could wait until I had a Bachelor’s Degree, I thought. I enjoyed university and graduated with a Bachelor of Arts; majoring in Social Science and Psychology. I still wasn’t sure which area I’d end up in, but I was fascinated with these subjects and knew they would be useful in the future.
After working for a few years, I decided to travel and live abroad. I had made up my mind that I wanted to live in Italy — which is exactly what I did. So I sold my car, packed my bags and flew to Rome. I enrolled in a language school in Florence for three months and allora ... had the time of my life! I was 23 and living in one of the most exquisite and romantic cities in the world. I started dating a tall, dark and handsome Italian man, with a keen eye for fitted jeans and checked shirts. His name was Simone, (pronounced Si-moe-ney), which just happens to be my middle name – so of course at 23, I thought this was kismet. How Rome- antic, right? I lived in an apartment with five other students - two girls from Denmark, a girl from Germany, an American and a guy from Belgium. We all became the best of friends, and if you’ve seen the film The Spanish Apartment , that’s exactly what my first six months in Italy were like.
My living arrangements were like a multi-cultural wonderland, but after a while my exciting lifestyle resulted in a depleted savings account. I needed a job. And fast. I’d worked as a waitress back in Sydney, but I was terrible at it (nor did I enjoy it), so further brainstorming was required. A lot of foreigners were working as au pairs for Italian families, but I heard the families didn’t pay well and you had limited freedom. This wouldn’t work for me either. Then a friend told me about becoming an English Teacher. It was easy to get work and you could earn extra cash by teaching private students on the side. Intrigued by this idea, I went ahead and landed a job teaching at a language school. I was paid about 15 euro an hour, which was pretty good at the time (22 AUD). Soon, I’d made friends with the other Teachers and found some private students. La vita e bella!
Then, an exciting opportunity came my way that changed things forever. A fellow teacher was working for a Registered Training Organization (RTO) and they needed more English Teachers to run courses. They were paying an amazing 35 euro an hour! The only catch was I needed a car so I could drive to the companies that were outside the city centre. No problem; a friend was leaving Florence and she left me her car. Perfetto ! Amazingly, everything fell into place.
By this time, I was sharing a flat with my boyfriend and I was earning enough from my private students to survive, with a bit of spending money left over. Since my business with individual students was going so well, I decided I could save the money I was earning from the company work. Brilliant! Life was great! I would zip around the Florentine suburbs in my little Fiat, teaching English to employees of La Perla, Gucci and Armani, and the perks from my connections at these luxury fashion houses weren’t bad either. My boyfriend certainly enjoyed the La Perla lingerie. Anyway, my good fortune continued; I began making enough money to enjoy a great lifestyle as well as save some to send home.
A few months later, I had yet another amazing opportunity. I discovered that the training organization was paying me only 25% of what they were charging the company. My brain kicked into gear and