The Winner's Playbook
The Winner’s Playbook is your go-to podcast for real talk about money, careers, success and the challenges along the way.
Hosted by financial advisers Josh and Billy, we break down the financial world in a way that’s clear, relatable and actually enjoyable to listen to.
Whether you’re trying to grow your wealth, make smarter money moves, level up your career, or just figure out what success looks like for you, we’ve got you covered.
No boring lectures, no complicated jargon - just straight-up conversations that help you win in life and money.
New episodes drop every week, so hit follow and join us for practical advice, honest insights and maybe even a few laughs along the way.
Episodes
102 episodes
Trusts explained: how the wealthy legally pay less tax
What is a trust… and do you actually need one?In this episode of The Winner's Playbook, Billy sits down with Adam from Link Wealth Accounting to break down trusts in plain English. They cover what a trust ac...
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Episode 102
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50:02
The biggest mistake people make after a pay rise
Getting a pay rise should feel like a win, but for a lot of people, the extra money disappears faster than expected.In this episode of The Winner's Playbook, Josh and Billy break down how to actually make a ...
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Episode 101
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24:43
The retirement move most people don’t know about
Thinking about slowing down… but not ready to fully retire?In this episode of The Winner's Playbook, Josh and Billy break down how a Transition to Retirement strategy actually works. From age 60, you can sta...
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Episode 100
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24:47
How your business cash could be losing value
Business owners often sit on big cash balances because it feels safe, but over time inflation quietly does the damage. In this episode of The Winner’s Playbook, Josh and Billy unpack how to think about ...
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Episode 99
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40:04
The silent killer of family business success
Thinking of selling your business? Start hereWhat actually makes a business sellable? In this episode of The Winner’s Playbook, Billy sits down with business mentor Baz Gardner to unpack the real reas...
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Episode 98
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56:58
Getting insurance right: protection that actually pays
Insurance isn't exciting. But losing everything is.In this episode, Josh and Billy keep it real about personal insurance and why it’s one of the most important (and misunderstood) parts of your financial plan. They unpack the diff...
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Episode 97
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54:28
Planning your kids’ school costs the smart way
Thinking about private school? This one’s for you.In this episode of The Winner’s Playbook, Josh and Billy break down the real cost of education and how to plan for it. From $100k Catholic schools to ...
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Episode 96
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41:58
How Aussies can claim the UK state pension
Have you lived or worked in the UK? You could be entitled to thousands in extra pension payments for life.In this episode of The Winner’s Playbook, Josh and Billy unpack the UK state pension and why i...
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Episode 95
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34:50
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How should you structure your business & investments for 2026?
Thinking about growing your wealth smarter and faster this year? In this episode of The Winner's Playbook, Josh and Billy break down how different tax structures can either boost or drag on...
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Episode 94
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39:39
2026 Is the Year Your Money Habits Finally Change!
Most people have good money intentions, but few turn them into habits that last. In this episode of The Winner’s Playbook, Josh and Billy break down simple financial systems you can actually stick to.They cover a practica...
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Episode 93
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38:20
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Why DroneShield crashed and how to protect yourself from the same mistakes!
Why betting big on a single stock can backfireWhen a single stock skyrockets, it’s easy to get caught up in the hype. But what happens when it all comes crashing down? In this episode of The Winner’s Playbook
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Episode 92
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26:11
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Confused About Aged Care? Listen Up
Aged care isn’t something most people want to think about, but when the time comes, families are often caught off guard. In this episode of The Winner’s Playbook, Billy is joined by Daniel McCarthy from Sky Advi...
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Episode 91
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36:35
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Stop parking cash in the wrong place, start earning more without extra risk!
Cash isn’t just for emergencies: How to make your money work harderGot cash sitting in your account doing nothing? In this episode of The Winner’s Playbook, Josh and Billy break down how to make your...
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Episode 90
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32:29
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How Aussies are using debt to build wealth (without going broke)
Gearing: how to use debt to grow your wealth (without blowing it all up)Gearing sounds risky, but done right, it can fast-track your path to wealth. In this episode of The Winner’s Playbook, Josh and Billy break down exac...
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Episode 89
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37:24
Are you paying too much for insurance? Here’s how to fix it
Cutting insurance costs without cutting cornersHome, car, health, life, trauma, income protection... insurance is one of those things you need but hate paying for. And with premiums on the rise, a lot of people are asking, "How ca...
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Episode 88
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37:39
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Moving back to Australia? Don’t fall for these expat financial traps
Coming home? What returning expats need to know about tax, super and moneyIf you’re an Aussie moving back after a stint overseas, this episode is your essential money checklist. Josh and Billy dive into what you need to know befor...
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Episode 87
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31:25
What do the new Super changes mean for you?
Confused about what the new super tax changes really mean?In this episode of The Winner’s Playbook, Josh and Billy unpack the latest changes to the controversial Division 296 tax and what they mean for Australians with large supe...
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Episode 86
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36:18
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The Truth About Investing in Gold (What Most People Miss)
Gold just hit record highs… but is it too late to buy?The price of gold just smashed through an all-time high, and suddenly everyone wants in. But is this a smart move or classic FOMO?In this episode of The Winner’s ...
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Episode 85
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23:25
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What every Aussie should know before moving to Singapore
Moving to Singapore? What Aussies need to know about tax, residency and expat lifeThinking about making the move to Singapore? Whether it is for a career opportunity, lifestyle change, or lower taxes, there is a lot more to it tha...
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Episode 84
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49:20
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This is how scammers know exactly how to hook us
𝗪𝗼𝘂𝗹𝗱 𝘆𝗼𝘂 𝗳𝗮𝗹𝗹 𝗳𝗼𝗿 𝗮 𝘀𝗰𝗮𝗺? 𝗛𝗲𝗿𝗲’𝘀 𝗵𝗼𝘄 𝘁𝗼 𝘀𝗽𝗼𝘁 𝗼𝗻𝗲 𝗯𝗲𝗳𝗼𝗿𝗲 𝗶𝘁’𝘀 𝘁𝗼𝗼 𝗹𝗮𝘁𝗲! Scams and hacks are getting more sophisticated every day. From phishing texts and deepfake video calls to fake investment platforms and remote access attacks, i...
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Episode 83
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24:08
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Sold a car, got a bonus, or an inheritance? Here’s the smart play.
Sold a car? Got a bonus? Received an inheritance? A sudden lump sum can be a massive opportunity, but if you don’t have a clear plan, it’s easy to waste it or make the wrong moves.In this episode, Josh and Billy break down what to do wh...
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Episode 82
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24:47
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The ETF cheat sheet that makes investing simple
ETFs made simple: how to build a strong investing foundationETFs have become one of the easiest and most effective ways to start investing, but with thousands to choose from, it can get overwhelming fast. In this episode of Th...
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Episode 81
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33:22
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The US advice model vs Australia: here’s what we do better
The US insider takeaways every Aussie investor should knowBilly’s just back from a whirlwind trip through Harvard, MIT, New York and LA, meeting with some of the biggest fund managers in the world. In this episode, Josh and Billy ...
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Episode 80
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33:23
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