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
117 episodes
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...
Money mistakes that can set you back in your 40s
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 me...
Stop chasing trends, start controlling your strategy!
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 ...
Is now a good time to buy property in 2026?
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 i...
Trusts explained: how the wealthy legally pay less tax
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 ac...
The biggest mistake people make after a pay rise
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 ...
The retirement move most people don’t know about
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 sta...
How your business cash could be losing value
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 ...
The silent killer of family business success
Thinking of selling your business? Start hereWhat 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 reas...
Getting insurance right: protection that actually pays
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 diff...
Planning your kids’ school costs the smart way
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 ...
How Aussies can claim the UK state pension
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 i...
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