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The Ryan Tan Show

The Ryan Tan Show

著者: Ryan Tan
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今ならプレミアムプランが3カ月 月額99円

2026年5月12日まで。4か月目以降は月額1,500円で自動更新します。

概要

The Ryan Tan Show is a long-form interview podcast for professionals, founders, and anyone who wants to understand how business, law, finance, and technology actually work in Australia.


Each episode features a deep conversation with practitioners, operators, and experts who have built something, fought something, or know something most people don't. No fluff, no motivational filler - just substantive, honest conversations that go well beyond the surface.


Guests have included insolvency partners, tax lawyers, credit reporting advocates, legal tech founders, and corporate insiders. Conversations regularly run 90 minutes to two hours because the best insights don't come in soundbites.


If you're a founder, director, accountant, lawyer, or just someone who wants to understand the systems that shape Australian business and finance - this is the show for you.

© 2026 The Ryan Tan Show
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  • He Won Young Accountant of the Year. Then He Broke Every Rule the Profession Runs On with Davie Mach
    2026/05/02

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    Most accountants charge by the hour, guard their knowledge, and wait for referrals.

    Davie Mach does none of that.

    He started in accounting at 17, went through KPMG, and at 26 launched Box Advisory from his brother's pink bedroom. Today the firm works with over 500 small businesses, generates 140 inbound leads a month, and Davie has built 51,000 YouTube subscribers by giving away what most accountants charge for.

    But the story behind it isn't clean. Vietnamese immigrant family. Mother's chronic illness. A father who broke down in his son's bedroom at 15 and said he couldn't pay for tutoring anymore. A $700k mortgage that felt like a life sentence. Depression, gambling, credit card debt at 21.

    This conversation is about all of it.

    👨‍👩‍👧 The Origin Story

    • The day his father broke down and said the family couldn't afford tutoring anymore - and why that moment changed everything
    • Being 15 and realising a $700k-$1M mortgage was sitting on his shoulders
    • The depression, gambling and credit card debt phase nobody talks about - and the brother who pulled him out of it
    • How watching his parents get financially destroyed by bad advice became the entire foundation of Box Advisory

    🏗️ Building Box Advisory

    • Launching at 26 with $25,000, no clients, and a terrible golf networking strategy
    • Muting himself on client calls every time the garage door opened - what the first 12 months actually looked like
    • Why he killed timesheets from day one - and the one-third formula that made the whole model work
    • Hiring a salesperson with zero accounting experience and pairing them with a junior accountant - why everyone said it wouldn't work and why it did

    📊 The Business Model That Broke the Rules

    • Why hourly billing is a cash flow trap - and why most accounting firms are running on overdrafts because of it
    • The deep dive content strategy that generates 140 inbound leads a month - and why the videos with 500 views made more money than the ones with 100,000

    🤖 AI and the Accounting Profession

    • Why Davie isn't afraid of AI for himself - but is genuinely worried about what it does to his team
    • The back-office accountants and bookkeepers whose jobs are most exposed - and why it's happening faster than anyone expected
    • Why 58% of Australian tax agents are retiring in the next decade - and why that creates more demand, not less
    • What younger accountants should be doing right now

    📋 AML/CTF Tranche 2 - What Every Accountant Needs to Know

    • From July 2026, accountants come under AUSTRAC's AML/CTF regime for the first time - what that actually means in practice
    • Why Davie thinks it's a good thing - and what the NDIS fraud crisis reveals about what happens without proper gatekeeping
    • The compliance costs, the VOI requirements, the onboarding overhaul - and who bears it

    🧠 The Real Cost of Building

    • Working until 11:30pm with a six-month-old at home - and being honest about what that actually feels like
    • Why there's no such thing as permanent balance - only cycles
    • Why working with your life partner is like playing a video game together - and why beating each boss round together creates memories nothing else can match

    Davie Mach built his business from the same wound his parents couldn't recover from. This is what that looks like when it works.

    If you're a founder, accountant, small business owner, or just someone trying to understand money better - this episode will stay with you.

    🌐 www.boxas.com.au 📺 YouTube: Davie Mach 💼 LinkedIn: Davie Mach

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    1 時間 27 分
  • He Left Cambridge, Walked Away from Law & Built an AI Lawyers Actually Use with Will McCartney
    2026/04/23

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    What happens when a Cambridge-educated humanities student walks away from a Sydney Law degree to build AI for one of the most risk-averse industries in the world?

    Will McCartney did exactly that. At 23, with no law degree and no track record in legal practice, he started building Habeas - an Australian legal AI platform that finds real case law, cites it to paragraph level, and doesn't make things up.

    Three years later it's winning Australian AI Awards, integrating with major legal platforms, and being used daily by some of Australia's most experienced litigators. This conversation is the honest version of what building that actually took.

    🎓 The Origin Story

    • He left Cambridge, transferred to Sydney Law, then walked away from the degree entirely - and the single administrative decision that made it inevitable
    • He built a better product in crypto and still lost to vaporware - and nearly made the same mistake again with Habeas

    🔧 Building Habeas

    • The first version wasn't good enough - and he pitched it to a Big Six firm anyway. Here's what happened
    • Why the lawyers who pressure-test Habeas hardest are the ones with 15 to 20 years experience - not juniors
    • The moment compliance stopped being optional - and what forced that reckoning earlier than planned

    🧠 The Hallucination Problem

    • A lawyer used Claude to research a case and Copilot to check Claude's work. It still hallucinated. That submission went to Federal Court
    • The hallucination problem nobody talks about - it's not fake cases, it's real cases that get twisted. And it's harder to fix
    • Why Habeas searches first and thinks second - and why every legal AI that does it the other way round is gambling with someone's client
    • Anyone promising zero hallucination in legal AI is either lying or doesn't understand how law works

    ⚖️ AI and the Legal Profession

    • Big Law has innovation teams, enterprise budgets and dedicated IT. They're still losing to 20-person boutique firms on AI adoption. Why
    • The billable hour is dying and most partners are pretending it isn't - what's actually replacing it
    • 80% of Australian legal matters never get properly resolved. AI could change that. Or it could just make expensive lawyers faster. Which one is happening
    • What he actually tells law grads who ask if they have a future in the profession

    🏗️ The Moat & Distribution

    • The technical advantage in legal AI is disappearing faster than anyone wants to admit - here's where the real defensibility actually lives
    • What stops a well-resourced competitor building the same thing tomorrow - and whether that answer should make you nervous

    💰 Bootstrapping vs Raising

    • Money was available. He chose not to take it. What that cost him and what it gave back
    • Why he's building a syndicate of lawyers who use the product instead of going to VC - and what that says about where Habeas is headed

    🚀 The Future

    • Why the next twelve months is about going deeper not wider - and what that looks like in practice
    • Australia first. But the next markets are closer to ready than you'd think

    If you're a lawyer, a founder, or just someone trying to understand where AI is taking one of the world's oldest professions - this is the episode.

    🌐 habeas.ai 📧 will@habeas.ai 💼 linkedin.com/in/willmccartney

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    1 時間 59 分
  • Behind the Appointment: The Human Side of Insolvency with Glenn Livingstone
    2026/04/11

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    What actually happens when an Australian business fails?

    Not the sanitised version. The real one - the day-one phone calls, the employees demanding wages to put food on the table that night, the childcare centres where a commercial decision becomes a moral one, and the directors who waited six months too long to pick up the phone.

    In this episode I sit down with Glenn Livingstone, founding partner of WLP Restructuring - one of Australia's fastest-growing independent insolvency firms. Glenn has nearly two decades in the profession, over 1,000 formal appointments, and $64.8 million returned across every class of creditor since co-founding WLP out of COVID in 2021.

    But before any of that - Glenn first read a creditors report at age 13. His father had just lost his entitlements in a corporate collapse. The liquidator recovered $400,000. Their fees were $400,000. That moment chose his career for him.

    This conversation goes well beyond the mechanics of insolvency. It's honest, commercially sharp, and at times genuinely moving.

    🏗️ Building WLP from Nothing

    • Walking away from KPMG during COVID to start an independent firm with three people and no guaranteed work
    • How WLP landed 4 voluntary administration appointments in its first week

    ⚠️ Early Warning Signs of Business Distress

    • The financial red flags directors consistently ignore until it's too late
    • Why the ATO has functioned as a de facto bank for struggling SMEs - and why that era is ending fast
    • Why directors wait too long - and what it costs them when they do

    🚨 Payday Super: The Coming Reckoning

    • Why the introduction of payday super is "a little bit frightening" from an insolvency perspective
    • What the closure of clearing houses means for businesses already under pressure
    • Why this change won't increase the number of insolvencies - but will dramatically accelerate their timing

    🔄 The Small Business Restructuring Regime

    • Why SBR was a genuine game changer for viable businesses in distress
    • Why the ATO is now rejecting proposals it used to wave through and what that means for directors
    • The one-shot nature of SBR - and why botching it is catastrophic
    • The uncomfortable question nobody in the profession is asking yet about the 2023-24 SBR cohort

    ⚖️ Insolvent Trading & Section 588G

    • Whether Australia's insolvent trading regime is actually working as intended
    • Why 588G plays completely differently for SME directors versus ASX-listed companies
    • How liquidators decide when to pursue insolvent trading claims - and when it's simply uneconomic

    😔 The Human Side of Appointments

    • What day one actually looks like inside a failing business - the staff, the suppliers, the distress
    • Why childcare appointments are among the hardest in the profession
    • How to stay calm when employees are demanding money

    📰 Media, Scrutiny & High Profile Collapses

    • The role media plays in major administrations - when it helps versus hurts
    • How administrators navigate the press when a high-profile business goes under
    • The story of Daryl Lee chocolates - and how a media announcement accidentally saved the business

    Glenn Livingstone is one of the most commercially pragmatic and genuinely human practitioners in Australian insolvency. This is the conversation most directors never have - until it's too late.

    If you're a director, founder, accountant, lawyer, or creditor - this episode will change how you think about business distress.

    Connect with Glenn: wlpr.com.au

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    51 分
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