The Winner's Playbook

Episode

• 
  Why Australians are looking offshore 16.09.2026 44mnt

  Send us Fan Mail Tax havens, private credit and super access More Australians are starting to think seriously about tax, residency and where their money is actually being invested. In this episode of The Winner’s Playbook, Josh and Billy unpack tax havens, special visas and why some Australians are looking at countries like Singapore, Dubai, Hong Kong, New Zealand, Italy, Greece and Portugal. They also discuss private credit, how it works, why it has become a growing investment asset class, a...
• 
  Five client scenarios every investor should know 08.09.2026 36mnt

  Send us Fan Mail Property, TPD payouts and real client strategy Sometimes the best way to understand financial advice is through real client scenarios. In this episode of The Winner’s Playbook, Josh and Billy unpack five client situations they have worked through recently, covering property decisions, insurance claims, expat investing, super strategies and building wealth in your 50s. They discuss why selling an underperforming property too early can be a costly mistake, how a TPD payout insi...
• 
  The tax traps business owners need to know 01.09.2026 36mnt

  Send us Fan Mail Business structures, GST traps and Div 7A loans Starting a business is exciting, but getting the structure wrong early can create expensive problems later. In this episode of The Winner’s Playbook, Josh is joined by Adam Jacobson, Accounting Principal at Link Wealth Accounting, to unpack what business owners need to understand when setting up and running through a company, trust or both. They discuss asset protection, company tax rates, family trusts, directorship risks, GST ...
• 
  Money myths Australians get wrong 19.08.2026 35mnt

  Send us Fan Mail Money myths, super and smarter wealth decisions Is financial advice really too expensive, or is the bigger risk making poor decisions without it? In this episode of The Winner’s Playbook, Billy is joined by Steve Sloane, Founder and Managing Director of Link Wealth, to unpack five common money myths that can affect how people build, protect and structure wealth. They discuss the cost and value of financial advice, whether young people should be putting more into super, and wh...
• 
  The hidden death tax within super 12.08.2026 43mnt

  Send us Fan Mail Super death tax, TPD payouts and the age pension problem Superannuation can be one of the most tax-effective ways to build wealth, but many people do not realise there can still be tax waiting inside their super when they pass away. In this episode of The Winner’s Playbook, Josh and Billy unpack the hidden super death tax, how taxable and tax-free components work, and why beneficiary nominations matter more than most people think. They also discuss withdrawal and re-contribut...
• 
  Why everyday investors deserve access to private markets 05.08.2026 30mnt

  Send us Fan Mail Private markets, business pressure and managing a big lump sum Private markets are usually reserved for the wealthiest investors, large super funds and institutions, but should everyday investors have better access? In this episode of The Winner’s Playbook, Billy is joined by Steve Sloane, Founder and Managing Director of Link Wealth, to unpack what private markets actually are and why access has traditionally been limited. They discuss private equity, private credit, infrast...
• 
  Why the Aussie share market is falling behind 29.07.2026 41mnt

  Send us Fan Mail Market moves, redundancies and building a personal brand The Australian share market has lagged behind the US, tech has continued to dominate globally, and investors are being reminded why diversification still matters. In this episode of The Winner’s Playbook, Josh and Billy unpack what has been happening across the Australian and global share markets, including the role of AI, tech stocks, index funds, active managers and why chasing the latest market trend can be risky. Th...
• 
  Is property still a good investment after the budget? 21.07.2026 49mnt

  Send us Fan Mail Property investing after the Budget Property investing is changing, but that does not mean the opportunity has disappeared. In this episode of The Winner’s Playbook, Josh is joined by Kev Tran from KTG Property Advisory to unpack where the property market could be heading after the latest Budget changes. They discuss SMSF property changes, negative gearing, supply and demand, Melbourne’s potential opportunity, and why property selection matters more than ever in the current m...
• 
  How we would fix Australia’s tax system 17.07.2026 36mnt

  Send us Fan Mail Trust changes, tax reform and what Australia should fix Australia’s tax system is changing, and family trusts are now firmly in the spotlight. In this episode of The Winner’s Playbook, Josh and Billy unpack the latest details around the government’s proposed trust changes, what structures may be excluded, and why business owners need to start thinking carefully before making any major restructuring decisions. They also discuss rollover relief, companies, franking credits, sta...
• 
  Investing for Your Kids: What Parents Need to Know 14.07.2026 26mnt

  Send us Fan Mail Investing for your kids without getting the structure wrong Investing for your kids sounds simple, but once you start looking at tax, account structures, ownership and what happens when they turn 18, it can get complicated quickly. In this solo episode of The Winner’s Playbook, Josh breaks down what parents need to understand before investing for a child under the age of 18. He explains how minor tax rates work, why savings accounts may not always be the best option, and how ...
• 
  Is it much harder to build wealth today? 09.07.2026 54mnt

  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 one of the biggest money questions in Australia right now: who really had it harder when it come...
• 
  Should you move your business offshore? 02.07.2026 52mnt

  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 realities of becoming an expat and what Australians need to understand before making the move. They co...
• 
  How to scale without losing control of your business 29.06.2026 33mnt

  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 the realities of building and scaling a business. They unpack the record short bet against Australi...
• 
  Is early retirement actually overrated? 25.06.2026 42mnt

  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 testamentary trust is, how it works, and why it can be useful for families with children, vulnerab...
• 
  Do employee shares create wealth or tax stress 18.06.2026 40mnt

  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 around vested shares, tax and concentration risk matters. They also look at Melbourne property pr...
• 
  What’s really happening in Australia’s property market right now? 11.06.2026 37mnt

  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, first home buyers, renters and borrowing capacity. They also break down why yield and income matter m...
• 
  This could be the biggest IPO the world has ever seen 02.06.2026 37mnt

  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 Musk so closely, and how a major listing could flow through global markets. They also break down t...
• 
  Most Property Investors Are Buying Blind (and What to Do Instead) 26.05.2026 56mnt

  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, and the most common mistakes investors keep making. They also explore why commercial property is...
• 
  The retirement trap nobody talks about 19.05.2026 40mnt

  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 are flexible, how to avoid feeling lost once work slows down, and why building a life you actua...
• 
  The 2026 federal budget: What it really means for your money 13.05.2026 43mnt

  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, business owners and retirees should be watching closely. They also talk through some of the smaller wins, ...