Agent David Highland: On 21 years in real estate, and the hardest thing he's ever done

David Highland grew up in Cronulla surfing its beach’s famous waves. Now at the helm of Highland, the third-generation real estate agent has been in the industry for more than 20 years, and is embracing the changing property world. Despite the pace, this managing director has managed to keep his feet firmly on the ground. He is married with two children.

Did you surf as a youngster?

Being born in Cronulla, I enjoyed all sorts of water sports, from surfing, to fishing, to sailing. I even played water polo at my old school, The Scots College.

How did you get into real estate?

We had a family relationship with a real estate office in Randwick. My first leasing role began when I was 18, at The Spot. I moved into sales at 21. I’m 39 this year and have been in real estate for 21 years.

What made you think you wanted to go into real estate?

I wasn’t incredibly academic at school, I just didn’t have the aptitude for study, I was more of a practical thinker. Real estate was appealing, obviously, because of my family background, but also because it’s an industry where there’s no limit to what you can achieve – there’s no ceiling.

Any regrets about not taking a gap year and travelling after school?

I’ve travelled a lot over the years with my wife, but that came later. I made the sacrifices early on, and so didn’t go to London with all my friends. But I think my decision paid off long term. Are there any regrets? Sure, but my career path was always fairly clear in what I wanted to achieve. I haven’t got there yet, but I haven’t changed direction at any point.

What’s this job taught you about people?

Everybody is wired differently, and so there’s no cookie cutter way of managing people.

Outside of real estate what do you consider to be your biggest achievement?

I have a healthy and happy daughter and son, and a happy wife. That’s a great achievement.

Your agency has also been a big supporter of the Sydney Children’s Hospital?

The children’s hospital resonates with our values and we are proud of the $1.4 million we have raised over four years at our Blue Lunches. We are in a privileged position where we can pool our resources and reach out to the community for a worthwhile cause.

The hardest thing you’ve ever done?

We’ve been through some tough times in business and, emotionally, that’s probably been the toughest. You learn from your mistakes, and come out the other end better.

Your most memorable sale and why?

Selling my grandmother’s Cronulla beachfront home five year ago. It was a house that had been in the family for 40 years. I ended up selling it to a friend of mine, who has renovated it for his five young kids, and they are now enjoying it.

If you could live anywhere in the world?

Cronulla, where I live now. I have lots of friends and family locally, and I love the fabulous lifestyle.

Your guilty pleasure?

A good pinot.