Winston Diamond was born and raised in the beautiful Twin Island of Trinidad and Tobago. He had a very humble upbringing and came to the Lord Jesus in his mid-twenties. He's a husband, father of four and a Bespoke Tailor by profession. He has a background in fashion illustration and fashion design and had the great opportunity of learning the highest form of tailoring under the tutelage of Mr. Andrew Ramroop OBE, CMTT a master tailor and the first Trinibagonian to work and own a Bespoke Tailoring atelier on Savile Row.

Winston's mission is to be a catalyst for personal transformation and finding one's true purpose and passion for life by using tailoring as the tool and instrument in conveying biblical wisdom and the Lord's truth.

IG: winstonvdiamond ; imritailoringatelier

FB: winston v. diamond

Hi, I'm Angel.

This mission starts right in our home.

So for my wife and three sons, thank you for standing with us.

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God chose us to have a conversation with us, his creation.

Our prayer is that this listening space brings growth and transforms your life forever.

Yeah, definitely green.

We moved in the height of COVID, so.

Okay.

When COVID was starting, so that was really, really a challenge.

That's a story for another day.

How did you meet Jesus?

I met Jesus in my, I would say, mid-20s through a friend and, well, a friend that I grew up with.

I mean, we were just talking one day, engaging one another, and we were sharing his faith.

And of course, I questioned it a lot.

The background I grew up in with black consciousness and all that, you know, I questioned it a lot.

And he said something to me, and it impacted me and made me really think about what he was saying.

He explained how the Bible was, you know, put together and the amount of years it took for this Bible to come into fruition and the different authors that it had.

So he was telling me, you know, there's no way one white person wrote this Bible.

That was news to me.

It was very intriguing, and he encouraged me to come to church.

I didn't pay him any mind at that moment, but eventually I went to church.

And yeah, when they made the altar call, I just got this prompting on moving to step forward.

And as they say, the rest is history from there.

Have you been able to identify other times in your life when you've heard that same voice, similar to that prompting you received at that time?

There are many, many times.

Out of them, the one that kind of stood out the most was when I started fashion design at Caribbean Fashion Design of Trinidad and Tobago.

While doing the program, the diploma program, because fashion is something I was really into.

One of my classmates would mention a gentleman by the name of Andrew Roup, and he being a Trinidadian and being the first Trinidadian ensemble to rule in London, that was something that was news to me.

I was very, very much taken aback.

I was like, and I was asking him like, really, are you serious?

And I started to do a lot of research on him.

And it was just so, so intriguing that some, this individual from a little island in the Caribbean was a master tailor on Savile Row.

One of the, this is like the creme de la creme of tailoring.

So I decided and I made up my mind right there and then after doing all the research, because after my next step was to go on to do Haute Couture and I started to do research as to how to get to Paris to do that.

And from hearing what they were talking about and then doing research, I didn't even know bespoke tailoring was something.

I decided there and then, well, hey, this is the path I want to go down.

And then I started to delve into how can I get to London and actually study bespoke tailoring and then get an apprenticeship on Savile Row.

Mind you, at this time I was married already and with two children.

It was, I was still, I was still believing I could have done it.

And then when I started to do the calculation for a boot, for tuition and, you know, just living away from my family for, I believe it had been two to three years.

I just like, this is impossible.

So I just forget about it.

So, well, and you know, I said, well, if this is the path I really have to go down, then the Lord will make a way.

And that's all I said.

And I left it alone.

Years passed by and then my wife sent me a WhatsApp with a picture of the Daily Express, Trinidad Express.

And so when I opened the message, I saw the picture of Mr. Andrew Ramroop, Savile Row Bespoke Tailor, coming to Trinidad and Tobago to run a bespoke tailoring program for his locals, where he wants to train the, you know, some local tailors in bespoke tailoring.

That right there and then, I knew that was the Lord that, and I got prompted to, you know, whatever you have to do, sign up for the course and, and hopefully get through.

So I, so there was an initial, where you, an initial, where you could put your name down for the wait list, wait and listen.

And after that, they reached out to us and then they told us the cost to do the course.

And that, I really, really thought I wouldn't been able to do it, but we, we got, we, we found the money to get me in.

And I went to the interview, there were a lot of other people, people who had years experience in tailoring.

And I'm, I'm still green in it.

I, I just started to learn actual tailoring after I started, studied so, fashion design.

So I was really green in it.

And, and I met with him first time meeting in my life.

And, you know, how to interview was, it was very, very taxing on me because, you know, he was asking questions left and right, asking about tailoring, what I wanted to do.

What is my, what, what was my vision or what I want to become.

And at that age, you're young, you know, so you're still trying to figure out what is, would be a profession for the rest of your life.

And what year this is?

This is, this is in 2018.

Okay.

Yeah.

And so just to give more context, 20, it was 20, 2008 to 2012 is when I did fashion design.

So that shows you how far of a gap.

That was your primary source of income, the tailoring or, or not?

No, no, no, no, no.

I was, I was working otherwise.

I was working, I was employed with the, I believe was the Ministry of Social Development or was National Archives, one of those two.

So this is more on hobby level, technically at the point in time you pick up a hobby and you, you love it.

You want to make it into a career.

Yeah.

Thanks for sharing that.

All right.

Five years from today, what would you tell future you listening to this conversation five years from today?

I would tell myself to continue dreaming big.

Nothing's impossible because the Lord has shown you that nothing is impossible.

And to always remember that the life and the opportunity that stands before you is not only for you, but for everyone else that you would encounter and meet along the way, because those people impacted your life and you have impacted those people lives as well.

So always remain humble and it's not only about you.

One diamond, one ton of wins.

Winston Diamond.

It's been a pleasure.

My treasure.

Thank you for being what has inspired me to open a dongle.