The Debrief

Kristian and Tristan

Welcome to The Debrief - real conversations between founders about the business of building businesses. Every week, Kristian and Tristan share unfiltered insights from their entrepreneurial journeys and the Australian startup ecosystem. We explore: • Practical strategies for starting and scaling businesses • Real founder stories - the wins, losses, and lessons learned • Marketing and growth tactics that work on Australian budgets • Tools and systems that actually improve your business • What's working (and what's not) in modern business No fluff. No corporate speak. Just two mates who run businesses sharing honest insights about entrepreneurship and technology. Perfect for founders, business owners, side hustlers, and anyone thinking about starting their own venture. New episodes every Tuesday.

Episodes

  1. William McCartney - Bridging Law and AI Innovation

    13/10/2025

    William McCartney - Bridging Law and AI Innovation

    Can a Sydney startup compete with billion-dollar legal tech giants? William McCartney proves it's possible by going deeper on specific problems rather than trying to outspend competitors. In 2023, Will founded Habeas - an AI-powered legal research platform built specifically for Australian lawyers. His approach is contrarian: search-first, inference-second, ensuring every citation is verifiable and every claim is traceable back to real case law. EPISODE HIGHLIGHTS: • How AI hallucinations led to federal court sanctions for Australian lawyers submitting fake citations • Why Will's humanities background (Cambridge, USYD Law) gives him a unique lens on legal tech innovation • The technical approach: retrieval augmented generation (RAG) that searches real case law before synthesising answers • Learning that product excellence is "only half the journey"—distribution and sales strategy matter just as much • Why you can't build B2B SaaS "just all from your keyboard at home" in 2025 • Previous crypto startup taught him the best product doesn't always win—sometimes it's just better marketing • Navigating Australia's compliance-heavy regulatory environment as a bootstrapped startup competing with billion-dollar giants KEY INSIGHTS: - Distribution strategy matters as much (or more) than product excellence for B2B SaaS founders - Rejection is a skill you have to develop—even when your solution genuinely helps, that doesn't entitle you to someone's business - Face-to-face community-building and conferences trump cold email and LinkedIn funnels in 2025 - Australia's risk-averse culture both protects users and stifles innovation—understanding this tension is critical - Staying in the game longer matters more than overnight success, but you need to realign if you're not enjoying the work Will's journey reveals what it takes to build in heavily regulated industries. From self-teaching code during COVID to running pilots with major Australian law firms, he's learned that competing with giants requires creative distribution strategies, not just technical excellence. The conversation explores the reality that 80% of legal matters in Australia don't get adequate access to justice, why legal fees of $300-$500 per hour drive self-represented litigants to risky AI tools, and how Habeas serves the underserved: small to mid-size firms, universities, and access-to-justice centres. Will also shares hard-won founder lessons: embracing rejection, allocating time to community-building, understanding that compliance complexity in Australia can be a moat rather than just a barrier, and why the longer you're in the game, the more you achieve - as long as you're still enjoying it. NOTABLE QUOTES: "You can build a great product. But that's only really half the journey. The hardest struggle now is about figuring out a way to differentiate in some creative way on distribution or your sales strategy." "Don't assume that you can build a business just all from your keyboard at home." "Get good at that, you know, enduring rejection thing." "The longer in the game you are, the more you achieve." Perfect for: Founders building in regulated industries, legal tech innovators, B2B SaaS founders navigating distribution challenges, and anyone interested in how AI is reshaping professional services. CONNECT WITH THE DEBRIEF: 🔗 LinkedIn: https://linkedin.com/company/thedebriefpodcast 🌐 Website: https://thedebriefpodcast.com 🎧 Spotify: https://open.spotify.com/show/7utxTp6CxLeDVg54EYqWw3 Hosted by Kristian (Employment Compass) and Tristan (Grand West Consulting) New episodes every Tuesday!

    1hr 1min
  2. Dave Newman - Building What's Bigger Than Yourself

    22/09/2025

    Dave Newman - Building What's Bigger Than Yourself

    In our fourth episode, we sit down with Dave Newman, CEO & Founder of PlanCare, who's improving Australian aged care by reducing management fees from 35% to just 13% using a digital first solution. Dave shares his extraordinary journey from winning UK Systems Professional of the Year at Best Buy to building Perth's most influential startup community (Morning Startup - 7,000+ members) to walking away from a $3 million opportunity to pursue his mission of transforming aged care. EPISODE HIGHLIGHTS: • How AI detected cognitive decline by connecting lost keys, a remote in the fridge, and medication confusion • The Silicon Valley breakdown that changed everything • Building three AI agents (Churchill, Smiley, Florence) making 10,000+ decisions daily • Why he calls 35% aged care management fees "criminal" • Scaling from 0 to 90+ employees while bootstrapping KEY INSIGHTS: - Data is your competitive moat in the AI age - Failed founders make the best mentors and advisors - Niche is where you start, not where you finish - Government regulations can be a competitive advantage - AI is only as good as the data you feed it Dave reveals the moment their AI identified elder abuse patterns that humans had missed, how they're using technology to keep 1 million Australians in their homes longer, and why building in highly regulated industries creates natural barriers to competition. His current mission with PlanCare is to provide accessible aged care while dramatically reducing costs for Australian families. The company now serves over 5,000 care providers and is expanding rapidly. NOTABLE QUOTES: "AI is only as good as the data you feed it" "If you don't do it, you'll always be asking yourself, what if?" "Those who have failed often come back with better stories" "Building something that's bigger than yourself" Perfect for: Healthcare innovators, startup founders, AI enthusiasts, aged care professionals, and anyone interested in how technology can solve real human problems. CONNECT WITH THE DEBRIEF: 🔗 LinkedIn: https://linkedin.com/company/thedebriefpodcast 🌐 Website: https://thedebriefpodcast.com 🎧 Spotify: https://open.spotify.com/show/7utxTp6CxLeDVg54EYqWw3 Hosted by Kristian (Employment Compass) and Tristan (Grand West Consulting) New episodes every Tuesday!

    1hr 4min
  3. Caroline Lepron - From France to Serial Entrepreneur

    08/09/2025

    Caroline Lepron - From France to Serial Entrepreneur

    In our third episode, we sit down with Caroline Lepron, a French-Australian serial entrepreneur who's reshaping Western Sydney's startup landscape. Caroline shares her remarkable 17-year journey from a temporary internship to founding three marketplace ventures, managing the Western Sydney Startup Hub, and leading the Plus 8 Pre-Accelerator program. EPISODE HIGHLIGHTS: • From France to Australia via Mexico - an international perspective • The reality of building marketplaces in Australia • Challenges facing female founders in the VC ecosystem • Creating community-driven innovation in Western Sydney • Balancing motherhood with multiple ventures KEY INSIGHTS: - Why marketplaces are the hardest businesses to build - The "fake it till you make it" approach that launched Skoutli - How Western Sydney is becoming Australia's next tech hub - The uncomfortable truth about Australian VCs - Building a 1000+ member tech community from scratch Caroline's current ventures include Skoutli (Airbnb for creative locations), and she's passionate about connecting people and creating win-win scenarios for everyone involved. Her vision for Western Sydney 2030 includes transparency, connection, and ensuring everyone gets a chance in the AI revolution. CONNECT WITH THE DEBRIEF: 🔗 LinkedIn: https://linkedin.com/company/thedebriefpodcast Hosted by Kristian (Employment Compass) and Tristan (Grand West Consulting) New episodes every Tuesday!

    1hr 4min

  4. 01/09/2025

    Speed Is Your Best Weapon

    Week two and we're already seeing momentum! After 100+ viewers on Episode 1 and multiple guest requests flooding in, we dive into what's actually working in our businesses right now. Kristian reveals his complete client automation workflow - from initial inquiry to researched email draft in minutes, not days. We discuss the coaching opportunity with ASX-listed Decidr, why a Queensland tech founder told us "speed is your best weapon," and break down Google's mysterious new AI model that's secretly topping the charts. Plus: The court case that shows why you're still responsible for AI output, how MCP agents found red flags in a potential client before the first meeting, and why a major bank just reached out for HR compliance help. TOPICS COVERED: • Automated client research using AI agents • The importance of shipping fast vs waiting for perfection • Google's "banana" model on LLM Arena • Building products with user feedback loops • Why SMBs adopt AI faster than enterprises • The AI lawyer citation failure • Using Perplexity and MCP for business intelligence ABOUT THE HOSTS: Kristian runs Employment Compass, helping Australian SMBs navigate HR compliance. Recently won the AI pitch night at Startup to Scale-up Summit. Tristan is Principal Consultant at Grand West Consulting, specialising in digital transformation and practical business implementation. CONNECT: LinkedIn: https://linkedin.com/company/thedebriefpodcast Website: https://thedebriefpodcast.com Spotify: https://open.spotify.com/show/7utxTp6CxLeDVg54EYqWw3 New episodes every Tuesday.

    56 min

  5. 25/08/2025

    Why We're Starting This Podcast

    In this inaugural episode of The Debrief, co-hosts Kristian and Tristan kick off their unfiltered conversations about building businesses in Australia. They dive into: • Why LinkedIn is a "necessary evil" for founders • The truth about job hunting becoming an AI vs AI game • Why SMBs are crushing it with AI while enterprises struggle • Model Context Protocol (MCP) - the game-changing tech no one knows about • Microsoft's surprise AI play that might change everything • Why being called a "tech bro" might just mean you're a nerd in denial ABOUT THE HOSTS: Kristian runs Employment Compass, helping Australian SMBs navigate HR compliance. Recently won the AI pitch night at Startup to Scale-up Summit. Tristan is Principal Consultant at Grand West Consulting, specialising in digital transformation and practical AI implementation. CONNECT: LinkedIn: https://linkedin.com/company/thedebriefpodcast Website: https://thedebriefpodcast.com Spotify: https://open.spotify.com/show/7utxTp6CxLeDVg54EYqWw3 New episodes every Tuesday.

    57 min
  • 5 Episodes

About

Welcome to The Debrief - real conversations between founders about the business of building businesses. Every week, Kristian and Tristan share unfiltered insights from their entrepreneurial journeys and the Australian startup ecosystem. We explore: • Practical strategies for starting and scaling businesses • Real founder stories - the wins, losses, and lessons learned • Marketing and growth tactics that work on Australian budgets • Tools and systems that actually improve your business • What's working (and what's not) in modern business No fluff. No corporate speak. Just two mates who run businesses sharing honest insights about entrepreneurship and technology. Perfect for founders, business owners, side hustlers, and anyone thinking about starting their own venture. New episodes every Tuesday.

Information

  • Creator
    Kristian and Tristan
  • Years Active
    2k
  • Episodes
    5
  • Show Website
    The Debrief