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...
Pay down the mortgage or invest?
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Paying down debt, investing and the property market
With interest rates rising and property prices falling, is it better to pay down your mortgage or keep investing?
In this episode of The Winner’s Playbook, Josh and Billy unpack the trade-offs between paying down debt and investing, including how interest rates, tax deductions, offset accounts and investment returns can influence the decision.
They also discuss debt recycling, why a falling property market could create opportunities for families looking to up...
What happens after your TPD payout?
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A TPD payout is not the end of the process
A total and permanent disability claim can provide a major financial lifeline, but the payout is only the start of the next set of decisions.
In this solo episode of The Winner’s Playbook, Billy breaks down what people need to understand before and after making a TPD claim.
He explains how TPD insurance works, why claims can be complex, the difference between own occupation and any occupation definitions, and when it...
The right way to pass wealth to your kids
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Inheritance, super control and property tax traps
How much is too much to leave to your kids, and should you pass wealth on earlier rather than waiting until it becomes an inheritance?
In this episode of The Winner’s Playbook, Josh and Billy unpack inheritance planning, how much support to give adult children, and why timing can matter when it comes to helping the next generation.
They also discuss the government’s growing influence over superannuation, why more Australians are...
How commercial property actually works
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Commercial property, healthcare assets and social infrastructure
Commercial property is getting more attention, but it is a very different world to residential investing.
In this episode of The Winner’s Playbook, Josh is joined by Marcello Caspani-Muto, Director at CBRE, to unpack how commercial property works and what investors need to understand before stepping into the space.
Marcello specialises in the sale and leasing of healthcare and social infrastructure assets, including childcare, healthcare, aged care, retirement living and medical property.
They di...
Why Australians are looking offshore
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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, and what in...
Five client scenarios every investor should know
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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 inside super can be structured, and wh...
The tax traps business owners need to know
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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 registration, first-year cash flow tr...
Money myths Australians get wrong
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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
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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...
Why everyday investors deserve access to private markets
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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, infrastructure, unlisted assets, and the work involved in...
Why the Aussie share market is falling behind
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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.
They also discuss re...
Is property still a good investment after the budget?
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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 market.
Kev also...
How we would fix Australia’s tax system
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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, stamp duty risks, and the practi...
Investing for Your Kids: What Parents Need to Know
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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 in...
Is it much harder to build wealth today?
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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 comes to b...
Should you move your business offshore?
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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 cover tax residency, moving a...
How to scale without losing control of your business
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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 re...
Is early retirement actually overrated?
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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, vulnerable beneficiaries, business owners or...
Do employee shares create wealth or tax stress
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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 prices, mortgage stress, and wh...
What’s really happening in Australia’s property market right now?
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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 more than ever, why commercial prop...
This could be the biggest IPO the world has ever seen
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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 brea...
Most Property Investors Are Buying Blind (and What to Do Instead)
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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 getting more attention, how proposed Budget changes could impact investor...
The retirement trap nobody talks about
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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 yo...
The 2026 federal budget: What it really means for your money
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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, like the instant asset write-off, tax lo...
Rates, Inflation & Tax Changes: What Could Hit Your Plan
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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 carefully about buffers, debt and risk.
They also break down the latest on Division 296, possible Fe...
What it really means to be financially ready for retirement
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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 spending habits shape the answer.
They break it down practically, starting with your current expenses, future plans, and the in...
Money mistakes that can set you back in your 40s
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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 investing too late, overcommitting to the family home, and relying too heavily on a single asset. They also share smarter strategies for building long-term wealth, inclu...
Stop chasing trends, start controlling your strategy!
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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 oil price surges fuel inflation, and how small to medium businesses are feeling the pressure.
On investments, they cover gold a...
Is now a good time to buy property in 2026?
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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 isn’t moving evenly, with affordable areas in Perth, Brisbane, Adelaide and parts of Melbourne still seeing strong demand, while higher priced segments sl...
Trusts explained: how the wealthy legally pay less tax
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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 with long-term family planning. They also unpack different types of trusts, how distributions work, and some of the co...
The biggest mistake people make after a pay rise
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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 long-term wealth.
They also cover the things people often forget to review after a salary jump...
The retirement move most people don’t know about
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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 lost income, why your investment mix needs to change as you move into drawdown mode, and the tax opportunities available in th...
How your business cash could be losing value
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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 capital. They talk through paying yourself first, separating business money from personal wealth, and why smart investing is...
The silent killer of family business success
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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 actually looking for when it's time to pass the baton.
Baz shares what he’s seen work...
Getting insurance right: protection that actually pays
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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. They also break down how to structure policies inside or outside super, the real risks of default cover, and how to avoid getting caught with junk in...
Planning your kids’ school costs the smart way
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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 stories, the pros and cons of public vs private, and how education choices shape not just...
How Aussies can claim the UK state pension
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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 upcoming changes in April 2026 mean for anyone thinking of topping up their pension year...
How should you structure your business & investments for 2026?
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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 business owners can avoid costly mistakes.
They also dive into the concept of tax drag, a must-know for anyone tr...
2026 Is the Year Your Money Habits Finally Change!
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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, and decisions is what drives real prog...
Why DroneShield crashed and how to protect yourself from the same mistakes!
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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 company announcement that shook i...
