The Winner's Playbook

Send us Fan Mail Who has it harder when building wealth today? Is it harder for younger Australians to build wealth today, or are there more opportunities than ever before? In this episode of The Winner’s Playbook , Josh and Billy unpack the latest changes affecting self-managed super funds, including the government’s move to stop borrowing for residential property inside SMSFs. They also debate o...

Send us Fan Mail Moving offshore, tax residency and the expat opportunity With major tax changes being proposed in Australia, more business owners, investors and professionals are asking the same question: should I consider moving offshore? In this episode of The Winner’s Playbook , Josh is joined by Tristan Perry , Managing Director of Tax and Accounting at RP Financial Private, to unpack the rea...

Send us Fan Mail Business growth, bank debt and making better capital decisions Running a business is not just about growth. It is about knowing where to put your capital, when to take on debt, who to back, and how to make decisions that still make sense years from now. In this episode of The Winner’s Playbook , Billy is joined by Steve Sloane , Managing Director of Link Wealth, to talk through th...

Send us Fan Mail Testamentary trusts, direct shares and the retirement question Testamentary trusts are back in the spotlight after the government walked back part of its proposed trust tax changes, and it could matter for families thinking about estate planning, asset protection and passing wealth to the next generation. In this episode of The Winner’s Playbook , Josh and Billy break down what a...

Send us Fan Mail SpaceX, employee shares and the Melbourne property question SpaceX has listed, the share price has already jumped, and thousands of current and former employees have reportedly become millionaires on paper. In this episode of The Winner’s Playbook , Josh and Billy unpack what the SpaceX IPO means, how employee share plans and ESOP-style incentives work, and why having a clear plan...

Send us Fan Mail Negative gearing, rising rates and lazy bank deposits The property market is shifting, interest rates are back under pressure, and Australia’s big banks are sitting on billions in deposits paying everyday Australians almost nothing. In this episode of The Winner’s Playbook , Josh and Billy unpack how the latest proposed negative gearing changes could affect property investors, fir...

Send us Fan Mail SpaceX could be heading for one of the biggest IPOs in history, and even if you never buy the shares directly, there’s a good chance you could still end up exposed through your super, ETFs, managed funds or index funds. In this episode of The Winner’s Playbook , Josh and Billy unpack what happens when a private company like SpaceX becomes public, why investors are watching Elon Mu...

Send us Fan Mail Property investing looks simple... until you factor in cash flow, debt, tax, yield, location, structure, timing and suddenly it’s anything but. In this episode of The Winner’s Playbook , Josh sits down with Joey from Gameplan to break down what smart property investing really looks like in today’s market. They unpack rentvesting, buyer’s agents, apartments vs commercial property,...

Send us Fan Mail What makes a good retirement? In this episode of The Winner’s Playbook , Josh and Billy unpack what retirement really looks like beyond the numbers. They break down the four types of retirees, why a big super balance does not always equal a happy retirement, and how work, purpose, relationships, health and lifestyle all play a role. They also discuss why the best retirement plans...

Send us Fan Mail Think the Federal Budget won’t affect you? This one might be worth paying attention to. In this episode of The Winner's Playbook , Josh and Billy break down the biggest proposed changes from the latest Federal Budget, including negative gearing, capital gains tax, trusts and bucket companies. They explain what could change, who may be impacted, and why property investors, bus...

Send us Fan Mail Are interest rates about to bite again? In this episode of The Winner’s Playbook , Josh and Billy record from the new podcast studio for the first time and unpack some big money topics facing Australians right now. They discuss inflation, the possibility of higher interest rates, what rising rates could mean for mortgages, bonds and cash, plus why investors may need to think caref...

Send us Fan Mail How much is enough to retire and why the answer is never simple. What if the real challenge isn’t how much you have, but how you define “enough”? In this episode of The Winner’s Playbook, Josh and Billy unpack one of the biggest questions in personal finance: how much you actually need for retirement. They explain why there’s no universal number, and how your lifestyle, goals, and...

Send us Fan Mail Your 40s are where money either starts working for you… or you start working harder just to stay afloat. In this episode of The Winner’s Playbook, Josh and Billy break down the realities of this stage of life, where peak earning years meet peak expenses, from mortgages and family pressure to career demands and retirement planning.  They discuss the most common mistakes, including...

Send us Fan Mail In this episode of The Winner’s Playbook , Josh and Billy break down what’s really happening in global markets, from interest rates and inflation to oil, AI, Bitcoin, gold, and tech stocks.  They explain why short-term market moves are unpredictable and why trying to time them can cost investors. They also explore how higher rates impact households and businesses differently, why...

Send us Fan Mail What’s really happening in the 2026 property market, and should you buy now?  In this episode of The Winner’s Playbook , Billy is joined by buyer’s agent Kev Tran to unpack what’s really happening, from rising interest rates and borrowing power cuts to inflation, construction costs, and policy conversations around capital gains tax and negative gearing. They explain why the market...

Send us Fan Mail 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 actually is, how it works, and why people use them beyond just “saving tax.” The conversation dives into how trusts can create tax flexibility, protect assets, and help wi...

Send us Fan Mail 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 pay rise count. They talk about lifestyle creep, tax, super top-ups, debt reduction, company share schemes, and the small decisions that can have a big impact on your lo...

Send us Fan Mail 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 start accessing your super while still working, which can help you cut back your hours without cutting back your lifestyle. They talk through real examples, how to replace...

Send us Fan Mail 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 cash properly, how much the business actually needs as a buffer, and what to do with the rest so it is working towards your long-term goals instead of sitting there as lazy capita...

Send us Fan Mail Thinking of selling your business? Start here What 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 reasons businesses sell (or don’t). They go beyond the surface-level advice and dive deep into the psychology of letting go, why so many owners sabotage their exit, and what buyers are...

Send us Fan Mail 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 different types of cover including life, TPD, trauma and income protection, and explain what they actually do, who needs them, and how much is enough....

Send us Fan Mail 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 $400k+ elite private education, they explain how school fees can blow out fast and why most families don’t realise just how much they’ll spend over 13 years. They share personal sto...

Send us Fan Mail 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 it matters for Australians who have spent time working in the UK, even decades ago. They explain how the system works, how it compares to Australia’s age pension, and what the upcomi...

Send us Fan Mail  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 your wealth. From sole traders and companies to family trusts, superannuation, and investment bonds, they walk through how each structure works, when it makes sense to use them, and how...

Send us Fan Mail 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 fin...