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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

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What happens when one of Australia’s fastest-growing accounting startups signs clients faster than it can service them, scales a delivery engine that can’t keep up, and collapses under the weight of its own ambition?

In this episode of The Ryan Tan Show, I sit down with Elvis Sehovic - former Head of Tax & Accounting at Retinue - for the first in-depth, insider account of a hyper-growth accounting firm that went from meteoric rise… to operational free fall… to collapse.

Elvis was there for all of it: the explosive sales machine, the offshore scale-up, the cultural pressure cooker, the client churn, the staff burnout, the internal panic, and ultimately, the voluntary liquidation that shocked the industry.

This conversation is raw, emotional, and disarmingly honest.

At points, Elvis needed to pause, breathe, and process the memories.

If you’ve ever worked in accounting, professional services, operations, startups, leadership or culture, this is unmissable.

It’s a blueprint for everything that can go wrong when speed outruns structure - and a rare, human look inside a business unraveling in real time.

Today, Elvis leads Accounting & Tax at The Polyglot Group, applying the hard-earned lessons from Retinue to help businesses scale sustainably into Australia.

🔥 The ignition point of Retinue’s rise - how an aggressive sales engine, flat-fee pricing, and relentless marketing created unstoppable early momentum.

📈 The growth model that looked bulletproof - and why it worked brilliantly at first.

💸 The economics behind collapse - how underpricing, misaligned incentives, and unrealistic delivery assumptions quietly dug the company’s grave.

🧨 The internal cracks no one could ignore - staff breakdowns, crying in the office, walkouts, burnout, and operational chaos as the workload became unmanageable.

🏗️ Why scaling a services business is nothing like scaling tech - and how Retinue tried to force a SaaS playbook onto a labour-driven industry.

👥 The culture inside hyper-growth - panic, pressure, competing egos, denial at the leadership table, and the emotional cost on staff trying to hold everything together.

🚨 The moment staff started whispering: “This can’t last.” - from impossible client loads to compliance backlogs to frantic internal firefights.

💥 The inside story of the attempted sale - why multiple firms refused to touch the client book, and how Squeeze ended up acquiring it in a distressed state.

📉 The boardroom reality - optimism vs panic, “we’re fine” vs “we’re drowning,” and the psychological theatre behind a business in free fall.

😔 The human toll - Elvis’ experience supporting a team under extreme pressure, dealing with distressed clients, and confronting the emotional aftermath of a collapsing model.

🧭 The lessons every founder, accountant, operator, or startup leader must hear:

• Speed without structure is a death sentence
• You cannot out-scale poor unit economics
• You cannot offshore your way out of chaos
• Culture breaks before numbers do
• Leadership denial is fatal
• “Fastest-growing” often predicts “fastest-collapsing”

🚀 How to build a services business that scales without imploding - sustainable pricing, capacity planning, ethical leadership, operational backbone, and protecting your people.

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What happens when a fourth-generation lawyer walks away from big-firm life and builds one of the most recognisable legal brands in Australia - using coffee, clarity, and a deep command of corporate law?

In this episode of The Ryan Tan Show, I sit down with James d’Apice - founder and principal of Gravamen, and creator of the viral series Coffee and a Case Note - to explore how he’s modernising the legal profession while remaining anchored in serious commercial expertise.

A seasoned commercial litigator, James specialises in shareholder and co-owner disputes, oppression proceedings, and equity claims under the Corporations Act 2001 (Cth) - representing clients in complex matters that often determine control, value, and the future of their businesses. His ability to translate that technical depth into plain English has made Coffee and a Case Note a national phenomenon - a masterclass in accessible, human-centred legal storytelling.

At Gravamen, James applies the same rigour to his practice as he does to his content. The firm’s focus on high-stakes disputes and tailored strategic advice attracts founders, directors, and investors navigating breakdowns in trust and governance. Beyond the courtroom, his Values in Action initiative donates at least $1,000 each month to organisations addressing inequality, wealth disparity, and environmental sustainability - embedding social responsibility into the DNA of the firm.

From litigation strategy and corporate governance to communication and ethics, James shares how discipline, authenticity, and courage can redefine what modern legal leadership looks like.

💡 What You’ll Learn

☕ How Coffee and a Case Note evolved from a one-minute experiment into a national legal micro-brand

📱 Why short-form storytelling and platforms like TikTok are transforming professional credibility and client trust

💸 The economics of charging your rate - and why underpricing erodes both respect and results

⚖️ Lessons from shareholder and oppression disputes - how to recognise, prevent, and resolve co-owner conflicts before they escalate

💼 How Gravamen’s Values in Action program turns principle into policy - proving profit and purpose can coexist

🚀 The blueprint for building a high-value boutique practice grounded in focus, integrity, and client alignment

🌍 Why the next generation of lawyers will need as much fluency in communication and ethics as they do in law

🔗 Connect with James d’Apice

🌐 Website: gravamen.com.au

☕ Watch: Coffee and a Case Note on YouTube

📱 TikTok: @coffeeandacasenote

💼 LinkedIn: James d’Apice

📸 Instagram: @coffeeandacasenote

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