How this young professional gained confidence as a property investor

Jack Henderson started building his property portfolio at the young age of 18, and three years later, he has successfully acquired two properties and is now well on his way to buying his third property—but not without having to face challenges and make sacrifices along the way.

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Unlike other young budding property investors, Jack did not have to worry so much about his first deposit after he decided to leave school at Year 10 and spend years working in his father’s construction firm.

“[The fact that] I could go broke, that didn't even cross my mind,” he said.

However, standing on the same field as an 18-year-old first-time buyer with seasoned property investors who have already successfully built massive portfolios through the years proved to be unnerving for him.

According to Jack: “The big thing ... especially with the Asian suburbs, I was an 18-year-old kid walking into these places and [there are] all these agents … and I was asking questions … [and] I was really nervous.”


“[I thought], ‘Look at these people in their suits and driving their Mercedes Benz out [at] the front.’ I thought, ‘What am I?’ and that's honestly how they looked at me, too ... like, ‘What are you doing here?’ ” he added.

 Despite finding himself in a tough situation, he continued to look through around 50 properties every weekend for over six months. Jack only started to find his confidence when he met a buyer’s agent who would also become his mentor.

The young investor shared: “I bought my first property through Dean Power in Bondi … We got along really well [and] he helped me a lot, too, because, you know, I'm buying my first property [and] I was nervous, to say the least.”

Soon enough, Dean also took on the role as Jack’s property manager. “We got along really well, and then, I just said … ‘I'll give the management to you’ and it hasn't been vacant for a week,” Jack said.

Aside from taking inspiration from his mentor, Jack also dedicated himself to getting good education through several means.

According to him: “I did [a] lot of research, too … If I went through a property on Saturday, I'd have my list of what I went through and then I'd go home and I'd look [at]”

“In the side door of my car, I had about 40 pamphlets in there and I'd get them out when I got home and I'd look through them all … [scribble on them to remember],” he added.

A mere year and a half following his first purchase in Coogee, which is a $720,000 two-bedroom unit, he took advantage of the “market steaming ahead” and bought his second investment property in Maroubra. On top of these, he has also already acquired pre-approval for another investment, which he plans to buy in Newcastle.

Right Property Group’s Steve Waters and Victor Kumar believes that Jack’s example is worth emulating, especially for the younger generation.

Steve said: “Just to be in at 18, without any real people holding your hand or [any formal] education, so to speak, I think that's such feat … And ... to go again … for the third time up in Newcastle … It’s awesome.”

Jack’s advice to young budding property investors: You will have to make sacrifices, like passing on going out or traveling for a while, but all these will be worth it in the long run. Moreover, don’t be afraid to make mistakes because it won’t define your journey—after all, you don’t know what you don’t know unless you actually jump in and start learning from your own experiences.

According to Jack: “They say, ‘You're missing out on a lot of things [and] you're going to regret all this,’ but I don't think that.”

“[Looking back], when I was 18 ... I've been out with buyers’ agents and I had lunch with them and met all these awesome people in property and doing this podcast—I'd have never thought that would happen, [so] I want to keep buying, [I] want to keep doing stuff with my money.

“I look in ten years’ time when they're trying to get into the property market and they're wives have [babies … Meanwhile, I’ve been holding my properties for several cycles] … The goal is not to be retired [too] old,” he concluded.


Tune in to Phil Tarrant’s portfolio update on The Smart Property Investment Show to know more about the benefits buying in bulk, the purchases fundamentality for the portfolio, and the opportunities it will bring as a hub for economic growth and development.


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