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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.
93 Episodes
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Send us a text 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 practical yearly money calendar, a savings rule you won’t quit, and an investment routine that runs quietly in the background. Plus, they discuss why comparing your finances to friends or social media can hold you back, and why focusing on your own household, values, ...
Send us a text Why betting big on a single stock can backfire When 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, Josh and Steve break down the recent drama surrounding DroneShield, a company that surged from cents to dollars before plummeting to just a share. They unpack what really happened, including the timing of the CEO’s multimillion-dollar sell-off and a retracted compa...
Send us a text 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 Advisors in Tasmania to unpack the real costs of aged care, how Centrelink actually works, and the decisions families need to make when a parent or loved one can no longer live at home. They cover what most people get wrong, what fees to expect, how the family home is treate...
Send us a text Cash isn’t just for emergencies: How to make your money work harder Got cash sitting in your account doing nothing? In this episode of The Winner’s Playbook, Josh and Billy break down how to make your money work harder without taking unnecessary risks. They unpack how to structure your cash across offset accounts, high interest savers, term deposits, and even low-risk cash alternatives like Latrobe. You’ll learn how to build buffers for emergencies, save for big goals, avoid...
Send us a text 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 exactly what gearing is, how it works with both property and shares, and why some strategies amplify your upside while others come with serious traps. They cover key concepts like loan-to-value ratios, debt recycling, gearing inside super, and the difference betwe...
Send us a text Cutting insurance costs without cutting corners Home, 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 can I cut the cost without leaving myself exposed?" In this episode of The Winner’s Playbook, Josh and Billy break down the smart way to review your insurance without risking your future. From home and contents to life and income protection, they unpack...
Send us a text Coming home? What returning expats need to know about tax, super and money If 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 before and after you return, including tax residency rules, superannuation strategies, insurance cover, investing, estate planning and what to do with foreign income. They talk about real client stories, common mistakes, and how to avoid a nasty tax surpri...
Send us a text 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 superannuation balances. They explain how the policy has shifted, including the scrapping of the tax on unrealised gains, and what the new $3 million and $10 million thresholds actually mean in practice. You’ll also hear about smart strategies like contri...
Send us a text 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 Playbook, Billy and Steve break down why gold has surged, whether the hype is justified, and what Aussie investors need to consider before jumping in. They unpack why central banks are buying gold in bulk, how it compares to other asset classes, and why gold is se...
Send us a text Moving to Singapore? What Aussies need to know about tax, residency and expat life Thinking 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 than just hopping on a flight. In this episode of The Winner’s Playbook, Josh is joined by Tristan Perry, Managing Director of Tax and Accounting at RP Financial Private in Singapore. Tristan is an Aussie expat himself and a leading expert on Australian ...
Send us a text 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, it’s getting harder to tell what’s real and what’s a trap. In this episode of The Winner’s Playbook, Josh and Billy break down the scams they’ve seen firsthand, including stories from clients, friends and even their own families. They cover the ...
Send us a text 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 when a big chunk of money lands in your lap. They talk through how to set priorities, avoid emotional decisions, and structure your money in a way that actually pushes you forward in life. You’ll hear how to decide between paying down debt, inve...
Send us a text ETFs made simple: how to build a strong investing foundation ETFs 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 The Winner’s Playbook, Josh and Billy strip it right back and talk about how to keep investing simple using ETFs and index funds. They cover what ETFs actually are, why they’re a great way to get started, and how they compare to stock picking. You’ll hear r...
Send us a text The US insider takeaways every Aussie investor should know Billy’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 unpack what he learned and what it means for Australian investors. They dive into the rise of private assets like private equity, credit and infrastructure, and why the best companies are no longer going public. You'll hear why this is a game-changer ...
Send us a text What a good financial adviser should actually help you with There’s a lot more to financial advice than just picking a few shares or tweaking your super. In this episode of The Winner’s Playbook, Josh breaks down the eight core areas every solid financial plan should cover, no matter where you're at in life. He walks through what real holistic advice looks like, starting with your goals and then covering everything from superannuation, debt, tax, and investing, through to estat...
Send us a text New first home buyer rules are here. What you need to know Massive changes are coming for first home buyers, and they’re hitting sooner than expected. In this episode of The Winner’s Playbook, Josh and Billy break down exactly what’s changing from October 1, who qualifies, how much you can borrow, and the fine print you don’t want to overlook. They unpack the real impact of no income caps, boosted price limits (hello, $1.5 million in Sydney), and the scrapping of lenders mortga...
Send us a text Why rentvesting is the strategy more buyers are choosing now Can’t afford to buy where you want to live? You’re not alone. With property prices climbing fast in major cities, more Australians are turning to rentvesting, a strategy that lets you live where you love and still get on the property ladder. In this episode of The Winner’s Playbook, Billy and Carlo from Link Wealth Finance break down what rentvesting is, how it works, and whether it’s a smart move for your situat...
Send us a text Tax time rolls around, the refund hits your account… and for most people, it’s gone just as fast. In this episode of The Winner’s Playbook, Josh and Billy unpack why so many Aussies waste their tax refund and what smarter, more strategic moves you can make instead. They explain how the tax system really works, why that “bonus” isn’t a gift from the ATO, and how to shift your mindset so you actually do something useful with your refund. From common mistakes to hidden traps aroun...
Send us a text You don’t need a head start: how to build wealth from scratch Think you need rich parents to get ahead financially? Think again. In this episode of The Winner’s Playbook, Josh and Billy dive into what it really takes to build wealth when you’re starting from zero. No trust fund. No family handouts. Just hustle, clarity and the right mindset. They open up about the hidden advantages of doing it the hard way, how to avoid common traps like lifestyle creep and comparison, and why ...
Send us a text Why most budgets fail and what to do instead Budgets are one of the most common financial tools out there, but let’s be honest, most people can’t stick to them. In this episode of The Winner’s Playbook, Josh and Billy break down why traditional budgeting often fails and share practical, realistic alternatives that actually work in real life. They cover: The real reasons people give up on budgeting (and it’s not just because it’s boring)How to make a spending plan you’ll actuall...
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