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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 business offshore, deemed disposals, capital gains tax, family homes, land tax, Singapore’s tax system, and why timing matters when leaving or returning to Australia.

Tristan also shares practical insights from working with expats across Singapore, Hong Kong, Bali, Thailand and beyond, including the opportunities, risks and mistakes people need to avoid.

If you’re a business owner, investor, expat, or thinking about working overseas, this episode gives you a clear look at the tax and lifestyle considerations before making a major move.

⏱️ Timestamps:

00:00 Intro
01:21 Welcome back Tristan Perry
04:11 Where Australians are moving offshore
08:24 What has changed for expats and business owners
13:09 Moving a business offshore and tax residency
17:26 How deemed disposal rules work
27:19 The family home, CGT and the six-year rule
35:51 Singapore tax rates and business setup

Hit follow, leave a review, and share this episode with someone who is thinking about moving offshore or returning to Australia.

Get in touch with Tristan: https://www.linkedin.com/in/tristan-perry

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Want to find an Adviser that suits your financial needs:
https://www.linkwealth.com.au/

Get in touch with Josh:
https://www.linkwealth.com.au/josh-lee-link
Get in touch with Billy:
https://www.linkwealth.com.au/billy-norman-link

Josh's TikTok: https://www.tiktok.com/@joshleefinadv
Billy's TikTok: https://www.tiktok.com/@billynormanfp

Sign up to Link Wealth Group’s newsletter, Wealth Simplified: https://www.linkwealth.com.au/wealth-simplified

Our Financial Services + Credit Guide: https://www.linkwealth.com.au/financial-services-and-credit-guide

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General advice disclaimer: The information contained within this podcast is general in nature and does not take into account your personal circumstances. Please reach out if you wish to discuss your personal situation.

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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 record short bet against Australia’s big four banks, how commercial lending works, what banks look at behind the scenes, and the risks business owners take when using debt to grow.

Steve also shares his view on capital allocation, managing shareholders, staff and other stakeholders, and why culture, cash flow and long-term thinking matter more than most people realise.

If you run a business, want to grow one, or want to better understand how smart operators think about money, debt and decision-making, this episode is worth a listen.

⏱️ Timestamps:
00:00 Intro
01:11 Meet Steve Sloane
02:37 The $11 billion bet against Australia’s big banks
06:50 How commercial lending works
10:36 Personal guarantees and director risk
15:23 Managing shareholders, staff and stakeholders
22:32 How businesses access capital
27:14 Common capital allocation mistakes

Hit follow, leave a review, and share this episode with someone building something for the long term.

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Want to find an Adviser that suits your financial needs:
https://www.linkwealth.com.au/

Get in touch with Josh:
https://www.linkwealth.com.au/josh-lee-link
Get in touch with Billy:
https://www.linkwealth.com.au/billy-norman-link

Josh's TikTok: https://www.tiktok.com/@joshleefinadv
Billy's TikTok: https://www.tiktok.com/@billynormanfp

Sign up to Link Wealth Group’s newsletter, Wealth Simplified: https://www.linkwealth.com.au/wealth-simplified

Our Financial Services + Credit Guide: https://www.linkwealth.com.au/financial-services-and-credit-guide

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General advice disclaimer: The information contained within this podcast is general in nature and does not take into account your personal circumstances. Please reach out if you wish to discuss your personal situation.

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, vulnerable beneficiaries, business owners or larger estates.

They also unpack the risks of investing in direct shares, using WiseTech’s recent share price fall as a reminder of how quickly company-specific risk can hit investors.

Plus, they discuss the latest SpaceX update, the upcoming OpenAI and Anthropic listings, where capital is flowing in the market, and whether early retirement is actually overrated.

If you’re building wealth, thinking about estate planning, holding direct shares, or working towards financial freedom, this episode is packed with practical insights.

⏱️ Timestamps:
00:00 Intro
01:22 Testamentary trusts and the Budget update
04:05 What is a testamentary trust?
07:17 Protecting family wealth and future relationships
13:49 The risk of investing in direct shares
21:21 SpaceX, OpenAI and where capital is flowing
31:09 Is early retirement overrated?
37:52 Why too much choice can become a problem

Hit follow, leave a review, and share this episode with someone who wants to make smarter decisions around wealth, investing and long-term planning.

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Want to find an Adviser that suits your financial needs:
https://www.linkwealth.com.au/

Get in touch with Josh:
https://www.linkwealth.com.au/josh-lee-link
Get in touch with Billy:
https://www.linkwealth.com.au/billy-norman-link

Josh's TikTok: https://www.tiktok.com/@joshleefinadv
Billy's TikTok: https://www.tiktok.com/@billynormanfp

Sign up to Link Wealth Group’s newsletter, Wealth Simplified: https://www.linkwealth.com.au/wealth-simplified

Our Financial Services + Credit Guide: https://www.linkwealth.com.au/financial-services-and-credit-guide

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General advice disclaimer: The information contained within this podcast is general in nature and does not take into account your personal circumstances. Please reach out if you wish to discuss your personal situation.