The Winner's Playbook

Send us Fan Mail 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...

Send us Fan Mail 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 liv...

Send us Fan Mail 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 altern...

Send us Fan Mail 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 ke...

Send us Fan Mail 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...

Send us Fan Mail 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 foreig...

Send us Fan Mail 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...

Send us Fan Mail 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 w...

Send us Fan Mail 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 Fi...

Send us Fan Mail 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...

Send us Fan Mail 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 t...

Send us Fan Mail 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 actual...

Send us Fan Mail 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 infrastruct...

Send us Fan Mail 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 wit...

Send us Fan Mail 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 i...

Send us Fan Mail 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 Fina...

Send us Fan Mail 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 mind...

Send us Fan Mail 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 advantag...

Send us Fan Mail 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 gi...

Send us Fan Mail Talking to your parents about money, wills & what comes next In this episode of The Winner’s Playbook, Josh is joined by Carlo, a Senior Mortgage Brokers from Link Wealth Finance, for a conversation that many avoid but absolutely need to have: how to talk to your parents about money, wills, aged care and estate planning. It’s not about being morbid. It’s about making sure your...

Send us Fan Mail If you're in Australia on a visa, you might be wondering what you can and can't do with your money. The rules can feel like a minefield, but there are smart ways to make progress if you know how to play it. In this episode, Billy sits down with financial adviser Fei Kong to unpack what non-residents need to know about investing, saving and building a future in Australia....

Send us Fan Mail Thinking about changing careers but worried about the money side of it? In this episode, Josh and Billy break down how to make a career change without blowing up your finances. They cover what to expect if you’re taking a pay cut, how to prepare for it, and the smart moves you can make to stay afloat while starting over. They share personal stories, practical tips on budgeting, bu...

Send us Fan Mail No one likes thinking about what happens when they die, but sorting it out now can save your family a world of stress later. In this episode, Josh and Billy break down everything you need to know about estate planning. They cover wills, superannuation, life insurance, and the tax traps most people don’t even know exist. You’ll learn how super, and insurance payouts actually work,...

Send us Fan Mail Combining finances with your partner can be a game-changer or a total mess if you’re not on the same page. In this episode, Billy and Steve break down the real-world pros and cons of combining money in a relationship. They talk through common setups couples use (from full joint accounts to hybrid models), why shared goals matter and the red flags to watch for in each other’s money...

Send us Fan Mail With Division 296 set to kick in from July, Aussies with over $3 million in super could be hit with a new tax, and for some, that bill could run into the millions. In this episode of The Winner’s Playbook, Josh and Billy break down how Division 296 works, who it affects, and why it’s causing such a stir. They unpack the real-life case of a self-managed super fund holding over $1.7...