Send us a text

When the Taxman Goes Viral: Inside the ATO, Crypto Tax & Australia’s Debanking Crisis

In 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 ATO

• How the ATO actually works behind closed doors
• Data matching, AI, and the staggering amount of information the ATO holds on every taxpayer
• Why technical expertise inside the ATO is declining - and how that affects audits, disputes, and outcomes
• The surprising distinction between incompetence, malice, and simple misunderstanding inside audit teams

⚖️ Crypto Tax & Web3

• The biggest crypto myths Harry still sees every month
• Why token wrapping, staking, airdrops, and smart contracts produce messy - often illogical - tax consequences
• Why Australia desperately needs safe harbour rules for digital assets
• The ATO’s limited understanding of crypto despite holding enormous amounts of data
• How Harry became the most recognisable crypto tax voice in Australia

🏦 Australia’s Debanking Crisis

• Harry’s own story: how AirWallex abruptly shut down Cadena’s accounts mid-transaction, freezing client money
• What this means for crypto-aligned businesses
• Why banks can quietly kill an entire industry by restricting access to payment rails

💥 The ATO’s Hard Pivot on Debt & Insolvency

• Why the ATO is aggressively chasing $55 billion of outstanding tax debt
• How director penalty notices (DPNs) and garnishees are being used faster and earlier
• Why the ATO is rejecting Small Business Restructuring Plans (SBRs) it used to accept at 15–25¢ in the dollar
• The economic consequences of forcing viable businesses into insolvency
• The quiet return of a more punitive, pre-Chris Jordan ATO culture

🏛️ The Courts: Bendel, s100A, Part IVA, and Why the ATO Is Losing More Often

• Why the ATO lost Bendel at the AAT, then the Federal Court, then the Full Federal Court
• What happened in the High Court hearing - and why the judges pushed back hard
• The deeper problem: deteriorating technical capability + courts less willing to defer to the ATO
• Why taxpayers should be paying attention as these test cases reshape trust distributions and family tax planning

📢 Personal Branding for Professionals

• How Harry turned tax - the driest topic imaginable - into a social media brand people want to watch
• The future of professional content on TikTok and LinkedIn
• Why authenticity is now a competitive advantage in law

This 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

Support the show