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The Ryan Tan ShowAuthor: Ryan Tan
Do you want to learn how to master all areas of your life? If yes, this is the podcast for you! Through in-depth conversations, you will learn from those who are mastering a specific area of their lives, whether it be business, wealth, health, relationships, social leadership, or spirituality.Each episode features one successful leader who is an expert in a particular area of his or her life. Through their backstories, you will uncover the mistakes and lessons they made along their journey & what it really takes to master a specific area of your life.Listen in as I unpack practical, golden nuggets of wisdom from my guests which you can apply, so you can start mastering different areas of your life. Language: en-au Genres: Education Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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When the Taxman Goes Viral: Inside the ATO, Crypto Tax & Australia’s Debanking Crisis with Harry Dell
Episode 4
Sunday, 7 December, 2025
Send us a textIn this deep-dive conversation, I sit down with Harrison Dell, one of Australia’s most recognisable tax lawyers and the founder of Cadena Legal. You may know him from TikTok and LinkedIn, where he turns dense tax law into sharp, funny, brutally clear explanations - including his famous dig at the ATO’s DeFi guidance being “single-ply toilet paper.” But behind the humour is a lawyer with rare insider insight.Before founding Cadena, Harry spent years inside the Australian Taxation Office, rotating through the graduate program, complex audit teams, and eventually the Tax Avoidance Taskforce. His experience gives him a uniquely honest view of how the ATO thinks, how it selects cases, and what it gets wrong - especially as debt collection hardens and litigation outcomes slip. Across two hours, we cover:🧩 Inside the ATOHow the ATO actually works behind closed doorsData matching, AI, and the staggering amount of information the ATO holds on every taxpayerWhy technical expertise inside the ATO is declining - and how that affects audits, disputes, and outcomesThe surprising distinction between incompetence, malice, and simple misunderstanding inside audit teams⚖️ Crypto Tax & Web3The biggest crypto myths Harry still sees every monthWhy token wrapping, staking, airdrops, and smart contracts produce messy - often illogical - tax consequencesWhy Australia desperately needs safe harbour rules for digital assetsThe ATO’s limited understanding of crypto despite holding enormous amounts of dataHow Harry became the most recognisable crypto tax voice in Australia🏦 Australia’s Debanking CrisisHarry’s own story: how AirWallex abruptly shut down Cadena’s accounts mid-transaction, freezing client moneyWhat this means for crypto-aligned businessesWhy banks can quietly kill an entire industry by restricting access to payment rails💥 The ATO’s Hard Pivot on Debt & InsolvencyWhy the ATO is aggressively chasing $55 billion of outstanding tax debtHow director penalty notices (DPNs) and garnishees are being used faster and earlierWhy the ATO is rejecting Small Business Restructuring Plans (SBRs) it used to accept at 15–25¢ in the dollarThe economic consequences of forcing viable businesses into insolvencyThe quiet return of a more punitive, pre-Chris Jordan ATO culture🏛️ The Courts: Bendel, s100A, Part IVA, and Why the ATO Is Losing More OftenWhy the ATO lost Bendel at the AAT, then the Federal Court, then the Full Federal CourtWhat happened in the High Court hearing - and why the judges pushed back hardThe deeper problem: deteriorating technical capability + courts less willing to defer to the ATOWhy taxpayers should be paying attention as these test cases reshape trust distributions and family tax planning📢 Personal Branding for ProfessionalsHow Harry turned tax - the driest topic imaginable - into a social media brand people want to watchThe future of professional content on TikTok and LinkedInWhy authenticity is now a competitive advantage in lawThis episode is a true insider’s map of how tax power works in Australia - from audits to crypto rules to the evolving role of the courts. If you’re a founder, adviser, accountant, lawyer, crypto investor, or just someone who gets nervous when the ATO emails you: this conversation will change how you think.Support the show
