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About The Village Guru

The Village Guru, Jeff O'Leary

My name is Jeff, and I think I’m doing my small part to change the Real Estate Industry.

Before I get into the whole changing the industry bit, let me introduce myself. I used to be regular guy who had a regular job. Now, I’m doing what I love, working twice as hard at it but having 5 times more fun…..but that wasn’t always the case.

Life Before Real Estate

Fresh out of University, I landed a “safe” and promising career in the automotive industry. At first I enjoyed the high pressure environment, the responsibility, and the ‘Key Performance Indicators’. What started off for the first 5 years as a ‘promising career’ slowly turned to repetition and boredom. I wasn’t happy and didn’t know what to do about it. I had just recently married my wife Stephanie, had a house, and plenty of friends- I was supposedly living the dream. Except that every Sunday I would waste my day dreading the thought of starting another work week.

Then it happened, the day that changed everything. I will always remember it because it was my 30th birthday. Just like many other work days, I came home tired and in a grumpy mood. After dinner I was so exhausted that I forgot that it was my birthday and went straight to bed. I didn’t even realize what I did until I woke up the next morning wondering why my wife was so upset. Is this what it had come to? Something had to change. That night, Steph and I had a big heart to heart talk. What did I want to do that would make me happy? I liked helping people, I liked being creative, I liked statistics and I liked working on projects. My wife already had a Home Staging business so I thought, why don’t I become a real estate agent? How hard could it be…

The Beginning

I soon found out that regardless of how smart you are, or how much knowledge you have, none of that matters in real estate if you can’t find enough clients. The problem for me was that I couldn’t stand the stereotypical way realtors are taught to find clients. I didn’t like cold calling, door knocking, handing out pumpkins, high pressure sales tactics or begging friends and family for business. Not that I had the money at the time but I thought (and still do) that billboards and bus shelter advertisements do nothing to sell a house and only feed over inflated egos. So all the ways that the ‘experts’ and the trainers told me to do things were off the table. There had to be a better way.

The Village Guru

With a relatively small list of clients, a mortgage to pay, a pregnant wife and child to support, I started doing what most of my colleagues thought was crazy- I started blogging. Writing about my opinions of real estate was the best way I could create a connection with people who were searching for truth in a Negative Reputation Industry. It was slow going and very simple at first, but every time I had free time, I wrote about what I knew.

Keeping Real Estate Real

Soon after I started blogging, I discovered that people were doing video blogs with flip cameras, and I was hooked. When I was a teenager, my friends and I would make movies with an old VHS camera. It was a lot of fun and it kept us busy and out of trouble. Ironically, when I told my childhood best friend about my idea, he suggested that I name the videos, “Keeping Real Estate Real!” And so it was. 

When I first started making videos for real estate I felt very awkward but I stuck with it, and after a while this thing called blogging started to take off. Traffic to my site was growing and my phone was ringing. Home buyers and sellers actually liked what I was saying. Today I have 3 websites and the Village Guru is one of the best real estate websites in Mississauga. It’s just a hunch, but I believe the reason I’ve been able to succeed in real estate is by doing the opposite of what everyone else is doing. When I talk about real estate I do it as a human being, I have an opinion and I tell it the way I see it. Exactly the way I would want my real estate agent to speak to me if I was a home buyer or seller.

One of my Old School Videos (Flip Camera)
I tend to keep these old ones hidden in the vault…  😉 

More Recent Video (Iphone 5s)
5 years makes a Huge difference!


Jeff O’Leary- The Real Estate Agent

For the last decade, I’ve spent my days helping buyers and sellers in Mississauga and the west GTA. I am an award winning real estate agent who is focused on changing the Negative Perception of my industry, from one of scripts and high pressure sales tactics to one of knowledge, integrity and service. I think helping people with one of the largest purchasing decisions they will ever make is a very noble profession, and I do take that seriously.

Professionally, I have been invited to speak and share my story at a number of key real estate industry events across Ontario and in the US including OREA Emerge, The Better Homes and Gardens Fusion Conference Las Vegas, Inman Connect Toronto, National Association of Realtors Conference Toronto, and ReBar Camp Toronto. I have been awarded the Outstanding Sales Achievement Award for sales for the past 5 years in a row and I consistently rank as one of the Top Real Estate agents in Canada for Better Homes and Gardens Real Estate Canada.

Jeff O’Leary- The Person

My favourite thing to do is to spend time with my wife Stephanie and 3 boys. When I’m not busy working, we are usually visiting friends and family, out exploring the local community or just hanging out. I also take an active interest in my local community; I am Community Director for the Rotary Club of Mississauga-Meadowvale and Chair of the Lake Wabukayne Stewardship Committee.

Changing the Real Estate Industry

So why do I think I’m doing my part to change the industry? By doing things just like this. By opening up and being more human. By focusing just as much on my clients lifestyle as the act of buying or selling a home. I don’t like the tried and tested old school sales method: promise the world, show very little, get the sale and move on. I’m not a fan of many common practices in my industry and I’m happy to voice my opinion on the matter.

I want to treat my clients the way I only WISH I was treated the first time I bought a home. Providing value, being honest, bringing expertise to the table and telling it the way it is. Being a Protector.

I have since learned that publicly sharing your opinion in this industry is risky because it opens yourself up to criticism from others who are simply looking to make a quick sale. Also, if you ever do start to share your opinion, you will soon find out that people don’t always agree with you. On the other hand what pleasantly surprised me is that when you do take a stand on what you believe, you will attract people that really like you because you are a real person. I think if more real estate agents started taking this approach over the ‘quick sale approach’ we would all be better off.

It took me only 7 years to get up the guts to write a real ‘about me’ and it feels kind of liberating, so if you made it this far, thank you.