Callaghan O’Connor

Callaghan O’Connor is a Victoria, British Columbia native who returned to his hometown to pursue a career in real estate. Born and raised in Victoria, Callaghan excelled at hockey and rugby from a young age and played WHL Junior A hockey after high school. He earned a degree in sports management and business, and after running several businesses during his time at university, he interned for the Vancouver Canucks and the BC Lions.

However, rather than sports, Callaghan O’Connor found his calling in real estate. He focused on commercial real estate for five years in Vancouver before moving back to his hometown of Victoria, where he could pursue his passion for interior and landscape design by shifting his focus to residential properties. In just a few short years, he built a very successful luxury/high-end real estate business. Callaghan now lives in Victoria, which he sees as a great place to raise his kids.

Where did the idea for your career come from?

I saw an opportunity for young blood to bring new ideas and competition into the marketplace. I’ve been following the real estate market in Victoria for the last ten years, and I could see that we were becoming one of the strongest real estate markets in the world. I saw that as the perfect environment for me to come in, because I’m passionate not just about home design, but also about my hometown of Victoria. It was the right time for us to enter the market with new ideas and new technology, and use that to our advantage to gain a foothold in the market.

What does your typical day look like and how do you make it productive?

I’m on a fairly consistent routine. I wake up at 5:30, make coffee, then hit my desk for about 45 minutes. During that time I’m doing research, looking at the markets and at new listings and sales, and following up on emails. Then I draft up my day. I make a list of things I need to accomplish and people I need to connect with and follow up with. That sets my day up. That first hour of the day, before anyone else in the house is awake, really sets the tone for my whole day.

My son wakes up at 6:30. I spend about half an hour reading and hanging out with him, then head to breakfast. At 8 o’clock I’ll get an hour of workout in, and then I will sit in my infrared sauna for about half an hour, doing more research and connecting with clients all the while.

By 10 o’clock, I’m in the office working. I like to get most of my work done before lunch, because I’m out and about in the afternoons. Appointments, showings, driving around to look at real estate – I mostly spend my afternoons on the road.

After I get off work, we usually have an early dinner, and then it’s family time for the evening.

How do you bring ideas to life?

I do my best thinking when I spend time alone, whether that’s first thing in the morning or at night, once the household has quieted down. When I think of something, the first step is to write it down. Once I have the idea down, I then have to consider the surrounding factors – what’s needed to bring the idea to life. Technology, evidence, resources, and connections. There are so many moving parts involved in taking an idea and actually bringing it to life, and that’s the hard part. Not coming up with the idea, but figuring out how to bring that idea to market and then following through on that. It takes time.

What’s one trend that excites you?

The trend toward working from home has been important for where I work and live. Normally, Oak Bay in Victoria hasn’t been a strong market for work. Now, with what’s happening with this shift, we’re seeing a lot more young entrepreneurs and innovators coming into Victoria and setting up home offices, and it’s actually helped to build a stronger, more vibrant community. We’re seeing a huge shift in day-to-day life here in Victoria. It’s been exciting to see, as we’re trending up as a desirable place to both live and work. It’s a trend that has really helped our business, and I think it has helped the people and families here as well.

What is one habit of yours that makes you more productive as an entrepreneur?

Taking the little things that contribute to your health, wealth, and happiness, and making sure that they add up. How you spend your day is how you spend your life. For me, that involves sleep, fasting, exercise, and eating well. It also involves focusing on family connections, and I include my friends in that as well. Take a few hours of the day to be present with your family. When you take care of these things each day, you can go to sleep peacefully. And when you sleep peacefully, you wake up bright and early, energetic and ready to go.

What advice would you give your younger self?

Nothing is as bad as it seems, and nothing is as good as it seems. Never struggle, and never settle. Try to be as consistent as possible, and realize that there will be ups and downs. It’s about how you manage that. If you can stay calm during trials and tribulations, that will really set you apart.

Tell us something that’s true that almost nobody agrees with you on.

When people look at major life events, ones that make them feel small, they often tend to curl up or shrink into themselves. I think it’s important to stand tall and proud in those moments, even when you feel inferior or you feel shunned. You have to find the light at the end of the day. There’s always a silver lining, no matter how bad something is.

I think people can handle far more than they give themselves credit for. No matter what you’re going through, there’s an opportunity to uplift someone else. And when you uplift someone else, it can bring you out of some dark times too.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

This goes back to routine and habits. It’s about doing all the small things right, to build a strong foundation. Having a solid routine every day has set me up for success. Having a game plan and goals keeps you in line. You’ve got your short-term and your long-term goals, and you look at them at the beginning of every day or every month. If you stay on track and stick to your plans, you’d be amazed at what you can accomplish.

What is one strategy that has helped you grow your business?

One side of growing my business has really just been getting out of my comfort zone. Connecting with people, calling people out of the blue, knocking on doors, and so on. Creating opportunities where none was there before. In order to do that, you really do need to get out of your comfort zone. There will be times when you’ll be shunned. Doors will be closed on you, and phones will be hung up on you. But if you continue to do that every day, the wins, both small and large, will add up. Over time, it’s huge, but you can’t do it without getting out of your comfort zone.

What is one failure you had as an entrepreneur, and how did you overcome it?

Any entrepreneurial pursuit has its challenges. There are ebbs and flows to business, and the marketplace is always shifting and changing. There will be good quarters and bad quarters. Victoria is a resilient marketplace, but there are times when the phones aren’t ringing and transactions aren’t coming through.

Take those slower times as an opportunity. Those times represent extra time to research, to learn, and to build, instead of just running on the hamster wheel when things are busy. Take a step back, re-evaluate your business, integrate new technologies, and implement new ideas. Use that time to learn and grow and be innovative. You’ve got to continually innovate and change and build your business.

What is one business idea that you’re willing to give away to our readers?

I’m really into health, eating well, and ‘biohacking’. I’m really into these new technologies around longevity, staying healthy, and staying fit and young. For me, food has been huge for that. Every morning, I’ll have hot lemon water with ginger. Now, it might sound silly, but it takes time to peel the ginger, squeeze the lemon, and boil the water. Sometimes you’re busy and you just don’t have time for all of that. You don’t have time to grab something healthy.

So, an idea I had is for packets that are essentially ginger, lemon, and cayenne, on the go. You can have the packets in your car or in your office, so when you’re looking for a quick boost, you can just throw the packet in a cup of cold or hot water. I was going to call it “R&R”. The idea is raw, organic food, on the go.

What is the best $100 you recently spent? What and why?

My moleskin books. I must have over 50 in my office here. For the last ten years, every day when I set my day up, I go to my moleskin book and I set out my goals, my tasks, my chores, plans I want to execute, and what I have planned for the day. I have these things on my computer too, of course, but I like writing it down where I can read it from something tangible in my hands.

What is one piece of software or a web service that helps you be productive?

Google Calendar is really important, both for my work life and my personal life. It keeps me organized, and it’s accessible via any device I have around, whether that’s my phone or my laptop.

What is the one book that you recommend our community should read and why?

I like Grit by Angela Duckworth. If you’ve got grit, you can really get through anything. Nowadays, lots of things can be thrown at you and catch you off guard, but I’m a firm believer that if you’ve got grit, you can be great. The world can be tough and life can be tough, but if you can get up every morning, put your socks on, and show up, I think it sets you apart.

What is your favorite quote?

“Not every great man is a good father, but every good father is a great man.”

Key Learnings:

• A good idea is merely the first step on the path to success.
• Make sure all the little things in your day add up to something big.
• Your health and wellbeing are important factors in your path to success.
• Sometimes success means getting out of your comfort zone.
• Don’t waste the slow times – that extra time is a great opening to improve your business.