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My property to shares transition strategy (made easy)

August 22, 2026

759Years of Freedom Created

Like many Aussies, I started out building wealth through property.

But I later realised that shares are generally a much simpler and easier way to generate a solid income to live off.

The problem was, I didn’t know how to switch a big portfolio from one asset class into another, while somehow being able to live off it at at the same time while also making it easy, controllable, and low risk.

I couldn’t find anyone who’d done it. So I built my own strategy. And it’s worked fantastically well over the last 10 years.

This week’s article unpacks that in detail, including:

— The different ways to turn property equity into income (including strategies that do not include shares)
— How the strategy works in practice (and how it covers risks)
— Whether to keep any property
— Which property to sell first
— How much property equity you need to make this work

Read: My Property to Shares Transition Strategy (Simplified)​


​STRONG MONEY PODCAST

Imagine trying to help people become financially independent.

Then one day, you get told that what you’re doing is bad for people, for yourself, and for society.

This actually happened to me a while ago. The angry emailer brought up some interesting discussion points that I had fun shredding to pieces. I think you’ll enjoy!

Listen here on Spotify, Apple, or on the website

Read the article version 
here


​AUSSIE FIRE PODCAST

We recently did an episode about moving overseas with your wealth. Safe to say, since the budget this topic has generated quite a lot of interest.

But there’s a TON of things to know tax wise before you do it. So we brought on Brett Evans from Atlas Wealth to explain how the income/asset/tax side of things works in practice (he’s been doing it for decades).

There’s also some very interesting info about the main residence exemption, the ATO rules, and where people get it wrong.

Listen now on 
Spotify,Apple or on YouTube


​​​THOUGHTS OF THE WEEK​

“I’d be bored without work, FI is not for me.” The same people can’t wait for the weekend. If they could snap their fingers and have $2m, they would. Their real objection is against the effort, action, and perceived difficulty involved – not the outcome.

“The true price of anything is the amount of life you give in exchange for it.” – Henry David Thoreau

The most common thing I hear from people who are FI yet hesitant about leaving work is that it’s hard to quit a job that pays well. They get hooked on seeing the numbers go up, and feeling safe. When I ask about their job… “it’s ok I guess.” You’re trading YOUR LIFE away for ‘ok’?!?!


​MORTGAGE QUESTIONS

I’m planning to have my mortgage broker come on the Aussie FIRE pod to answer all of your prickly and unusual mortgage and home loan related questions (stuff that Hayden and I probably don’t know the answer to).

If you’ve got anything you’ve been wondering about loans, bank policies, borrowing strategy etc please reply to this email. I’ll make a big list of topics/questions and see how we go!


​RECENT INTERVIEW

This week I was on the Get Rich Slow Club podcast.

We actually did a 2-part interview. The first part goes back to the very beginning – where my desire for freedom came from and how it all began.

I talk about what it was like trying to learn all this stuff back before the FIRE community was even a thing, who helped me understand the share market, unpacking the math behind property, and why I don’t see any of this FI stuff as sacrifice.

Listen on Spotify, Apple, or on YouTube.

My new book on semi-retirement, transitioning to freedom and learning to enjoy your wealth is out now. Learn more here or at the links below.

Audiobook on

spotifyaudible

Paperback & Kindle

amazon
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