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 hit follow and join us for practical advice, honest insights and maybe even a few laughs along the way.
Episodes
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 bet...
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...
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 a...
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...
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 p...
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 protec...
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...
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...
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 b...
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 ...
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 opportuni...
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 d...
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, ...
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 o...
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 wh...
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 an...
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 wor...
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 co...
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...
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...
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