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June 22, 2025 17 mins

In this episode of Money Made Simple, Liv sits down with Josh Taylor — or JT — co-founder of Tax Traders and Taxi, two innovative businesses making waves in the world of tax. While tax might not sound like a glamorous industry, Josh’s entrepreneurial journey is packed with insight, hard-won lessons, and inspiring moments of resilience.

From getting made redundant to selling the family home to start a business, JT shares what it really takes to build a company from the ground up, and why the best opportunities often come disguised as problems.

This episode covers:

  • Why JT never thought he’d work in tax - and how it ended up changing his life
  • The early days of Tax Traders and how cashflow challenges inspired their first product
  • What tax pooling is (and why it matters for businesses of all sizes)
  • How failure, uncertainty and grit shaped their approach to growth
  • The origins of Taxi and how Simplicity’s Private Equity Fund got involved
  • Top tips for entrepreneurs - including when to trust your gut and when just to let go
  • The power of listening to customers and solving real problems
  • What’s next for JT and his team, including their new product, ProvCheck

Whether you’re dreaming of starting a business or just love a good story about determination and hard work, this episode is for you.

Websites or resources mentioned in this episode:

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Disclaimer: This podcast contains personal opinions and is intended to provide educational information only. It doesn't relate to your particular financial situation or goals and is not financial advice or recommendations. Simplicity New Zealand Limited is the issuer of the Simplicity KiwiSaver scheme and investment funds. For product disclosure statements please visit Simplicity's website simplicity. kiwi.

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