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Property Investing Lessons from 31-Year-Old Millionaire Ali Rolleston

Property Investing Lessons from 31-Year-Old Millionaire Ali Rolleston

After hitting millionaire status at 31 years old, one property investor is now helping others do the same. Learn more about her journey and discover top property investing tips.

Ali Rolleston started investing in property as the Great Financial Crisis unfolded around her.

She was 15 years old at the time. And as you can expect, all her friends told her it was a bad idea. 

But no one’s thinking that now. 

After all, Ali was able to prove her doubters wrong. Despite the seemingly questionable timing of her entry into property investing, she was able to leverage the situation.

…And she became a millionaire by 31. 

Incredible as her journey might have been, it doesn’t mean everything went perfectly well. For starters, Ali admits she was terrified with every step she took as a newbie property investor. 

Fortunately, she had guidance from her mother who’s been investing in the Australian property for 50 years. Her mother gave her the knowledge and courage she needed to continue investing even when the odds didn’t seem to be in her favour. 

And just like Ali in the past, you might be sitting there right now, terrified to get started in property investing. Or perhaps you’ve started small and are terrified to take bigger steps forward. 

Now, you can quit worrying. 

Because in this article, we’ll pass on the lessons Ali learned from her mum… as well as the ones she learned in her own investing journey. Hopefully, these lessons will also give you the courage and the knowledge you need to trudge on. 

So, keep reading!

The 3 Property Investing Lessons

Going into property investing, Ali had a pretty simple goal: 

To be a millionaire in her 30s. 

A simple goal, indeed… But nowhere near easy. 

And here are the four lessons that made this dream a reality for Ali: 

Lesson #1: Don’t Let Anyone Scare You Off From Investing

As mentioned earlier, Ali started investing right smack in the middle of the Great Financial Crisis. She’d been saving up her allowance, her Christmas money, and any other income she got from working odd jobs so she could finally start investing. 

But one of her friends warned her about the severity of the big housing crisis… And it got her thinking:

“Oh my gosh, what am I doing?”
“This is my life savings.”
“What if I lose it all?”

And that’s when Ali’s mum sat her down and gave her her first lesson in property investing. Her mum said:

“It’s all good, Ali. We’ve done our research. You know what you’re doing, so don’t let anyone scare you off from doing it.”

That was all Ali needed to pull the trigger on her first investment: a $302K property in Sydney. She got equity on that property, so she bought another. 

And another. 

And another. 

Until she became a millionaire. 

And then, not even her most skeptical friends could doubt what she was doing! 

None of that would have happened if Ali let the media – or her well-meaning friends – scare her off from investing. 

Lesson #2: Play the Property Game to Fully Understand It

One of the first questions Ali asked her mother when she started gaining interest in property investing was:

“How do you make money in this industry?”

And her mum said: 

“Well, you buy at bottom prices and sell when they peak.”

Understandably, Ali was underwhelmed. After all, she already knew that. In fact, hundreds of thousands of people already know that. So, the question on her mind was:

“If that’s really all there is to it, why isn’t everybody earning millions in property?”

And that’s when her mum told her: 

“Knowing something in theory is different from knowing how to do it in real life.”

So, in order to fully understand what it takes to make millions in property, you’ve got to dip your toes in the game. There’s only so much you can learn from books, tutorials, and seminars. 

Lesson #3: Have an Investing Community You Can Trust

Now, here’s a hard pill to swallow: 

Not every newbie investor will be lucky enough to have a mum like Ali. 

We don’t all have relatives who are experienced and well-versed in property investing. For most of us, we have no other choice but to seek out that guidance ourselves.  

So, find people who will be supportive of your journey. People who will help you drown out the noise and the negativity. And those who can share with you valuable tips and advice on how to make it as a property investor. 

Remember: having an investing community you can trust is crucial for your success.  

3 Tips Ali Wants to Give Her 19-Year-Old Self

Here’s a question I asked Ali:

“With almost every decision working in her favour, is there anything she would have done differently?”

She said yes. 

In fact, Ali shared that there are three things she would have done at the start of her property investing journey if she only knew what she knows now:

  1. Trust her mum’s guidance more
  2. Have faith
  3. Buy more

See, Ali believes she could have been more aggressive in her early property investing years. 

While she did make some bold moves that made people around her equally nervous and impressed… she realised now that she could have done more.

If only she had trusted her mum’s guidance a bit more, had faith in what she knew, and bought more properties at the start… she could have been a millionaire much earlier. 

That said, being a millionaire at 31 is certainly a feat! 

…A feat that you could match or even surpass if you take to heart the lessons you’ve learned from this article. 

Take the Road to Millionaire Status


Have faith. 

Buy more.

These are lessons Ali learned the hard way – and now, you don’t have to. You don’t have to look back at this moment 10 years from now and wish you’d have been more aggressive. 

Instead, you can implement Ali’s learnings now so you won’t have any regrets later. 

And if you’re unsure where to start, well, this article has shared with you the lessons that made Ali a millionaire at 31. All you have to do is follow those lessons… 

…And you’d be set for success.

Keen to explore your own property strategy?