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
130 episodes
What happens after your TPD payout?
A TPD payout is not the end of the processA 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 Winn...
The right way to pass wealth to your kids
Inheritance, super control and property tax trapsHow 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 P...
How commercial property actually works
Commercial property, healthcare assets and social infrastructureCommercial property is getting more attention, but it is a very different world to residential investing.In this episode of The Winner’s Playbook, Josh ...
Why Australians are looking offshore
Tax havens, private credit and super accessMore 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, ...
Five client scenarios every investor should know
Property, TPD payouts and real client strategySometimes the best way to understand financial advice is through real client scenarios.In this episode of The Winner’s Playbook, Josh and Billy unp...
The tax traps business owners need to know
Business structures, GST traps and Div 7A loansStarting a business is exciting, but getting the structure wrong early can create expensive problems later.In this episode of The Winner’s Playbook, Josh...
Money myths Australians get wrong
Money myths, super and smarter wealth decisionsIs 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 joine...
The hidden death tax within super
Super death tax, TPD payouts and the age pension problemSuperannuation 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...
Why everyday investors deserve access to private markets
Private markets, business pressure and managing a big lump sumPrivate markets are usually reserved for the wealthiest investors, large super funds and institutions, but should everyday investors have better access?In this e...
Why the Aussie share market is falling behind
Market moves, redundancies and building a personal brandThe Australian share market has lagged behind the US, tech has continued to dominate globally, and investors are being reminded why diversification still matters.In th...
Is property still a good investment after the budget?
Property investing after the BudgetProperty 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 fr...
How we would fix Australia’s tax system
Trust changes, tax reform and what Australia should fixAustralia’s tax system is changing, and family trusts are now firmly in the spotlight.In this episode of The Winner’s Playbook, Josh and B...
Investing for Your Kids: What Parents Need to Know
Investing for your kids without getting the structure wrongInvesting 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....
Is it much harder to build wealth today?
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
Should you move your business offshore?
Moving offshore, tax residency and the expat opportunityWith major tax changes being proposed in Australia, more business owners, investors and professionals are asking the same question: should I consider moving offshore?I...
How to scale without losing control of your business
Business growth, bank debt and making better capital decisionsRunning 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...
Is early retirement actually overrated?
Testamentary trusts, direct shares and the retirement questionTestamentary 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 e...
Do employee shares create wealth or tax stress
SpaceX, employee shares and the Melbourne property questionSpaceX 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...
What’s really happening in Australia’s property market right now?
Negative gearing, rising rates and lazy bank depositsThe 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...
This could be the biggest IPO the world has ever seen
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 o...
Most Property Investors Are Buying Blind (and What to Do Instead)
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 Ga...
The retirement trap nobody talks about
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 bi...
The 2026 federal budget: What it really means for your money
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...
Rates, Inflation & Tax Changes: What Could Hit Your Plan
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 Australia...
What it really means to be financially ready for retirement
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 q...
