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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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What does it take to go from fighting Nintendo in court to leading one of Australia’s largest online legal teams at Lawpath, the country’s leading online legal platform for small businesses and startups, and then launching your own AI-powered boutique law firm?

In this episode of The Ryan Tan Show, I sit down with Damin Murdock - founder of Leo Lawyers and former Chief Legal Officer at Lawpath - to unpack how one lawyer went from courtroom battles to building a modern legal practice that’s changing how law gets done.

Over nearly two decades, Damin has advised on over $100 million in capital raises, represented clients in high-stakes intellectual property disputes (including against global giant Nintendo), and helped thousands of startups and SMEs access affordable legal services through Lawpath’s fixed-fee and subscription models.

Now, he’s applying that experience to Leo Lawyers, a new breed of firm that blends courtroom craftsmanship with automation, AI, and deep commercial expertise - spanning corporate law, litigation, and construction.

From early lessons in perfection and advocacy, to his time scaling Lawpath’s legal arm and experimenting with AI avatars, automation, and research tools like Habeas, Damin reveals how technology and law are converging - and what that means for founders, lawyers, and anyone building in a fast-changing world.

This conversation is part war story, part masterclass - and a must-listen for anyone curious about the intersection of law, innovation, and the human touch.

💡 What You’ll Learn From This Interview

• How Damin took on Nintendo in a landmark IP dispute - and what it taught him about innovation, risk, and resilience.
• The journey from founding Murdock Cheng Legal Practice to leading the legal operations of Lawpath, and the lessons from advising over 2,000 startups.
• The truth about AI in law - what’s actually useful, what’s hype, and how new tools are reshaping legal research and drafting.
• Insights from advising on $100M+ capital raises and helping founders avoid the most common fundraising mistakes.
• Why Damin believes lawyers should “stay in their lane” - and how deep focus and efficiency create better outcomes for clients.
• What the next decade of law looks like: automation, pricing disruption, human connection, and the death of the billable hour.

🔗 Connect with Damin:

Website: leolawyers.com.au

Instagram: https://www.instagram.com/leolawyers

Facebook: https://www.facebook.com/people/Leo-Lawyers

LinkedIn: https://www.linkedin.com/company/leo-lawyers

YouTube: https://www.youtube.com/@Leo.Lawyers

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Natasha is the head of operations and part of the executive team that plays a critical role in driving the growth and success of Lawpath - Australia's number one online legal platform that has helped over 300,000 small businesses across Australia.

As a strong female leader, Natasha gets to champion the voice of women whilst also helping people fulfil their dreams of starting their businesses, something she is very passionate about after working in a startup that assisted both migrants and refugees in starting their businesses.

When Natasha first started at Lawpath, the team was very small but growing rapidly. Armed with a commercial law degree, she was employee number 7 and saw that the challenges and opportunities ahead of her were huge. Her initial role was in sales and customer support, setting processes, and building the foundations of the product, which has now evolved to focus more on operations and strategy development, and today she is the Chief of Staff at Lawpath.

As a strong advocate for diversity and inclusion, it was due to her efforts that the company rolled out an inclusive parental leave policy that gave all parents the flexibility to adjust to their new family life. Today, with the platform's explosive growth, her leadership is constantly focused on building trust, loyalty, transparency, and results-oriented objectives in the team.

Natasha has been awarded as a finalist in the Lawyer's Weekly Women for Legal Operations Professional of The Year and is often featured in the media. She is also a speaker for Salesforce Live - The Small Business Show.

What You’ll Learn From This Interview:

1. Lawpath's early systems and processes and how they've systemised as the company as grown to serve beyond 300,000 businesses.

2. How Lawpath has built a strong company culture that has led the business to being nominated as a Top 4 finalist in the AFR's Best Places to Work in 2022. Natasha also shares how the business has managed to stay consistent as the business has scaled and grown headcount from a few employees to over 70 today.

3. How Natasha champions women in the workplace and has embraced diversity and inclusion initiatives at Lawpath.

4. How Natasha balances motherhood with leadership, and her advice to aspiring female leaders who are looking to develop their career and/or business.

If you want to keep in touch with Natasha, you can reach her on LinkedIn. If you'd like to learn more about Lawpath, you can do so on their website: https://lawpath.com.au/

Thank you for listening to this episode of The Ryan Tan Show. If you enjoyed this episode, please help me hit the ‘subscribe’ button if you’re listening on Apple Podcasts or hit the ‘follow’ button if you are listening on Spotify.

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Are you looking to build a world class network and make an impact along the way? Or perhaps you're contemplating launching a podcast and are looking for inspiration. If so, this week's guest will inspire you as he has done just that.

His name is Rohit Bhargava. Rohit is the host of the Startup Playbook Podcast, a top ranking podcast which has seen him interview hundreds of successful founders, investors and operators globally in sharing their journey and lessons to help the next generation of startup founders.

Rohit is also the Founder and Partner of Playbook Angel Network, a new syndicate investment fund that invests deal by deal into startups. More recently, Rohit has just launched One Future Football.

What You’ll Learn From This Interview:

1. How Rohit launched a podcast which #3 on iTunes within days of launching and has gone onto becoming a leading startup podcast in Australia which has interviewed guests like Malcolm Turnbull (Former Prime Minister & Investor) and Cal Henderson (Co-Founder & CTO of Slack).

2. How Rohit leveraged his podcast to build a world class network within the startup and venture capital space, and how this has led to numerous personal and professional opportunities.

3. Rohit's new angel syndicate network - the vision, team, criteria they're using to assess startups, mandate and how they're looking at opportunities in current market climate.

If you want to keep in touch with Rohit, you can reach him on LinkedIn. The Startup Playbook Podcast is available to listen on iTunes and Spotify. If you'd like to learn more about Playbook Ventures, you can do so on their website: https://www.playbookventures.com.au/

Thank you for listening to this episode of The Ryan Tan Show. If you enjoyed this episode, please help me hit the ‘subscribe’ button if you’re listening on Apple Podcasts or hit the ‘follow’ button if you are listening on Spotify.

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Are you looking to accelerate the growth of your business? Or perhaps you're looking to implement some growth hacks to turbocharge your product and/or service? If the answer is yes, you will love this week's episode.

His name is Tom Willis. Tom is the co-founder and Chief Marketing Officer of Lawpath — Australia's number one online legal platform that has helped over 250,000 small businesses across Australia.

After working at group buying business Spreets, he saw the power of combining marketing with tech to create explosive growth. This jet fuelled his interest in the tech space, and he went on to launch an online music tuition company as well as a Facebook community of over 250,000 followers.

Since then, he has won a slew of awards for his marketing genius, including being named finalist for the ADMA, Young Marketer of the Year, 2020 and Marketing Leader to watch in CMO 2020 and was the B&T 30 Under 30 marketing finalist. Tom also runs the online publication Marketing Trends, focused on what drives Australia's top marketers.

To add to his many accomplishments, Tom is also the marketing whiz at General Assembly. He has taught over 50 digital marketing courses and has provided bespoke workshops for leading national and global companies including Uber and the Commonwealth Bank.

In 2014, he met other aspiring entrepreneurs trying to solve a similar problem when together they founded Lawpath and today the business is responsible for starting 5 percent of all companies in Australia. His ultimate mission is to see small businesses succeed and break down the barriers to working for themselves and creating a livelihood.

What You’ll Learn From This Interview:

1. How you can nurture relationships with other founders as a founder yourself, as well as how Tom met the current founders of Lawpath.

2. How Tom thinks of growth and has utilised growth hacks at Lawpath over the last 8 years to serve over 300,000 Australian businesses, and how is he is continuing to think about it over the next 18 months with current market conditions.

3. How you can intimately understand the different components (levers) of your business in order to successfully utilise growth hacking, as well as understanding which levers you can pull for maximum effect.

4. Some of the marketing challenges that startups are facing and Tom's advice on how they can overcome them.

5. How you can leverage all the data within an organisation to drive marketing efforts, including which metrics to look out for.

6. What Tom sees as the biggest marketing opportunity for Lawpath right now.

If you want to keep in touch with Tom, you can reach him on LinkedIn. If you'd like to learn more about Lawpath, you can do so on their website: https://lawpath.com.au/

Thank you for listening to this episode of The Ryan Tan Show. If you enjoyed this episode, please help me hit the ‘subscribe’ button if you’re listening on Apple Podcasts or hit the ‘follow’ button if you are listening on Spotify.

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Are you looking to grow your Instagram or TikTok? Or perhaps you're already a content creator and would love to work with big brands. If so, you will love today's guest because he has done exactly that.

His name is Adrian Widjonarko. Adrian is a digital creator best known for the catchphrase Places in Sydney You Must Visit. By day, he is an Account Manager at Sanofi. By night, he is a foodie trying out the latest and greatest restaurants and foodie spots around Sydney, sharing his findings and experiences on social media.

Since starting content creation, Adrian has amassed over 107k followers on Instagram, while growing his TikTok to over 178k followers. His Tiktoks have amassed close to 12m likes collectively and he is constantly featured in News.com.au, Daily Mail and Good Food for his unique finds and food hacks. Adrian has also worked with top brands like AMEX, Pinterest and Ben & Jerry’s.

So if you're a content creator, stay tuned as Adrian shares about his journey online and how he's growing his influence.

What You’ll Learn From This Interview:

1. How Adrian started his content creation journey as a food influencer and what inspires him to continue sharing and growing.

2. Adrian's creative process from ideation to post-production, including how he has systemised and streamlined the process.

3. Adrian's experience working with big brands like AMEX, Woolworths and Ben & Jerry's, including what it's like working with them, what they're looking for and how you can work with them too.

4. How Adrian is continuously been featured in media outlets, such as News.com.au, The Daily Mail and Good Food for his unique finds and food hacks, and how these features have helped him to grow his personal brand partnerships.

5. Adrian's general advice to entrepreneurs and aspiring content creators.

If you want to keep in touch with Adrian, you can reach him on Instagram (@adrianwidjy) or on TikTok (@adrianwidjy).

Thank you for listening to this episode of The Ryan Tan Show. If you enjoyed this episode, please help me hit the ‘subscribe’ button if you’re listening on Apple Podcasts or hit the ‘follow’ button if you are listening on Spotify.

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