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  1. The Copyright War That Will Shape the Future of Music and AI | With Holly Rankin (aka Jack River)

    3D AGO

    The Copyright War That Will Shape the Future of Music and AI | With Holly Rankin (aka Jack River)

    Episode SummaryEvery time you ask an AI to write a song, generate a script, or mimic a creative style, there's a good chance it learned how to do that by consuming someone's life's work, without asking, without paying, and without them ever knowing. In October 2025, the Albanese Government became the first in the world to rule out a text and data mining exception to copyright law, a landmark win for creators that is now being actively challenged by the tech industry. It's the backdrop to everything Holly and Georgie discuss here. Holly Rankin, the artist behind Jack River and founder of cultural strategy company Sentiment Agency, has testified before Australian Parliament and become one of the most articulate voices in the fight to ensure the AI economy doesn't get built on the back of stolen human culture. In this episode she and Georgie get into the staggering labour that goes into making a single song, why the "it's too complicated to license" argument from Big Tech is a convenient myth, and what the Anthropic book piracy settlement really signals about where this is all heading. But underneath the policy detail is a bigger question: if we let machines consume and replicate everything that makes us human, what exactly are we left with? Jack River - https://www.jackrivermusic.com/ Holly Rankin Linkedin - https://www.linkedin.com/in/holly-rankin-3535912b3/ In the Blink of AI is made possible by our wonderful partnersStripeFor early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe. Apply for Stripe Startups at https://www.dayone.fm/stripe ✨ Connect with Georgie HealyLinkedin: https://www.linkedin.com/in/georginahealy/ Instagram: https://www.instagram.com/georgina_healy/ Twitter: https://x.com/georgina__healy?lang=en The Day One NetworkIn The Blink of AI is part of Day One, the podcast network dedicated to founders, operators & investors. Sign up to get your weekly insights into the up-and-coming AI startups: https://dayone.fm/newsletter Mentioned in this episode: Stripe Startups For early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe. Apply for Stripe Startups at dayone.fm/stripe Stripe Ad_Nov 2025_02

    50 min
  2. Cracking AI Growth & Retention: How Instant & Relume scaled from $0 to $10m

    4D AGO

    Cracking AI Growth & Retention: How Instant & Relume scaled from $0 to $10m

    How do AI companies scale this fast without breaking? Eight figure revenue in competitive markets. Products that double revenue in a single month. Customers who tattoo your logo on their body. Not growth hacks. Not hype. Real traction, earned the hard way. Brendan Hill sits down with Daniel Slater from Relume, Liam Millward from Instant, and Sally Yu from King River Capital to unpack what actually drives breakout AI companies in 2025. The answer is not building more features. It is obsession with distribution, ruthless focus on speed to value, and teams that move faster than their competitors think is possible. Relume did not start as an AI startup. It started as an agency. Building websites manually, feeling the pain firsthand, and removing the work that should never have existed. Instant did not find product market fit once. It found it three times, killing products, rebuilding teams, and learning the hard way that revenue without stickiness is a mirage. And from Silicon Valley, Sally Yu shares what she sees across the fastest growing AI companies in the world, why community is becoming the real moat, and why founders with unwavering conviction now win disproportionately. They talk candidly about churn, mistakes, hiring A players, monthly execution cycles, and why most AI products fail not because the tech is bad, but because the company moves too slowly. This is a conversation about momentum. About earning distribution. About building products people would fight to keep. If you want to understand how modern AI companies actually scale, and what it takes to stay ahead once you do, this episode is for you. Oversubscribed is proudly supported by our sponsor Vanta 🦙 Vanta is the all-in-one solution for startups to become compliant quickly and build a security foundation with ease. Startup customers get $1000 off Vanta at vanta.com/oversubscribed The Day One Network Oversubscribed is part of Day One, the podcast network dedicated to founders, operators & investors. Guest Founders: Relume: relume.io Connect with Daniel: https://www.linkedin.com/in/daniel-james-slater-13079288/ Instant: instant.one Connect with Liam: https://www.linkedin.com/in/liammillward/ King River Capital:http://www.kingriver.co/ Connect with Sally: https://www.linkedin.com/in/sally-tech/ Stay Updated: Listen to the Oversubscribed Podcast on Spotify: https://open.spotify.com/show/6rZ9SajGVXkO8oxuvEHAsk?si=I2yR92GgRZa-Fdqbp8T4bw Listen to the Oversubscribed Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/oversubscribed/id1848789610 Please note that the content here is for informational purposes only; should NOT be taken as legal, business, or investment advice or be used to evaluate any investment or financial product. Brendan Hill is an investor in Everlab, Relevance AI and A1Base. About the Host: Brendan Hill is a Venture Partner at TEN13 and an angel investor in Australia’s fastest-growing startups, including Everlab, Heidi Health, Relevance AI and Instant. If you are interested in finding out more about angel investing, connect with Brendan on LinkedIn: https://www.linkedin.com/in/itsbrendanhill/

    1h 39m
  3. How to Make Your Fintech Pitch Unforgettable | James Horan from Phinly

    5D AGO

    How to Make Your Fintech Pitch Unforgettable | James Horan from Phinly

    Episode Summary Consumers lose billions to scams and miss out on trillions in potential savings every year. So what if everyone had their own AI-powered financial assistant working 24-7? In this episode of Pick My Brain, Alan Jones is joined by James Horan, founder of Phinly, an AI-driven personal finance platform designed to help consumers automate savings, prevent fees, and optimise their financial lives. James walks through his live pitch for Phinly, outlining the problem with doom-scrolling money advice, the rise of AI agents in personal finance, and a bold vision for owning the AI money assistant category. Phinly connects to over 20,000 institutions, identifies cost savings opportunities, and enables one-tap actions from cancelling subscriptions to switching providers. With early partnerships secured, backing from a global AI accelerator, and a savings-based revenue model, the startup is raising $800,000 on a pre-seed SAFE to scale toward $4.5M ARR in 18 months. But Alan’s feedback goes deeper than traction and TAM. He challenges James to avoid blending in with every other AI fintech startup in the room. Instead of leaning purely on logic and numbers, Alan pushes for something more memorable: behavioural insights that surprise the audience about their own financial habits. The goal is simple. Make investors go home and say, “Did you know that…?” and have that sentence start with something you taught them. If you’re building in fintech, AI, or any crowded category, this episode is a masterclass in standing out when everyone else looks the same. Time Stamps 02:08 – Meet James Horan and his founder journey 03:14 – Lessons from a failed two-sided marketplace 04:28 – The Phinly pitch begins 05:40 – Money advice, TikTok, and the cost-of-living crisis 06:50 – How Phinly works: AI-powered money automation 07:45 – Traction: 20,000 institutions connected and major partnerships 08:30 – Revenue model: percentage of savings and future subscriptions 09:10 – Alan’s first reaction: good foundation, but blends in 11:45 – The power of surprise in a crowded fintech room 12:30 – Using behavioural economics to stand out 14:00 – Stop reading your slides 15:30 – Supporting your story instead of replacing it 17:00 – Bringing emotion into a rational fintech pitch 18:00 – How to create a pitch people repeat to others Resources 💸 Phinly – https://phinly.com 🎙 Ask Alan a Question – https://speakpipe.com/pickmybrain 🎧 More from Alan Jones – https://www.startupfoundercoach.com Sponsors:Pick My Brain is supported by our wonderful sponsors:Galah Cyber offers the Foundations of Application Security course: a practical, hands-on AppSec course built for engineers who actually ship code. Two days of real-world lessons you can apply immediately. Learn more at galahcyber.com.au/learn. The Day One NetworkPick My Brain is part of Day One, the podcast network dedicated to founders, operators & investors.To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

    21 min
  4. AI Bias, Sex Robots & The Algorithms Radicalising Your Kids

    FEB 19

    AI Bias, Sex Robots & The Algorithms Radicalising Your Kids

    Episode SummaryTracey Spicer is one of Australia’s most respected journalists and the author of Man-Made: How the Bias of the Past Is Being Built into the Future. In this episode, Georgie sits down with Tracey for a sharp, funny, and occasionally jaw-dropping conversation about what happens when we treat AI like neutral math instead of what it really is: opinion written in code. They unpack why algorithmic bias is getting worse in the generative AI era, how recommendation engines can quietly radicalise people (from Andrew Tate pipelines to hyper-performative “tradwife” culture), and why “move fast” without guardrails is a dangerous blueprint. The discussion also goes into the weird and unsettling frontier of humanoid home robots, privacy risks in always-on devices, and what Tracey learned researching sex robots, including the disturbing ways consent is engineered out of the product. Plus: why Tracey’s favourite AI tool is Claude, what she thinks about Grok and the chaos machine of X, why we are not getting a four day work week anytime soon, and her case for “regulatory sandpits” to test AI safely before it hits the rest of the world. Time Stamps01:10 – Tracey’s TEDx “The lady stripped bare” moment and why it still matters 04:45 – Beauty standards, AI filters, and why expectations on young women have intensified 08:20 – Man-Made and the epiphany that sparked Tracey’s AI obsession 11:10 – The AI arms race, speed, and why we are in the “seatbelt era” of tech 14:30 – Digital natives vs critical thinking: the hallucination blind spot 16:45 – Tracey’s AI stack: why Claude is her daily driver 19:05 – Humanoid home robots: convenience vs surveillance 21:55 – Strength vs security: what actually scares Tracey about robots 24:35 – Sex robots and the consent problem manufacturers do not talk about 28:10 – Algorithms as “opinions in code” and how radicalisation happens 33:10 – Removing bias: conversations, perspective checks, and inclusive design 35:00 – Grok, MechaHitler, and what happens when platforms mirror their owners 36:45 – Deepfake porn, consent, and why regulation is finally catching up 38:10 – No, AI will not magically deliver a four day work week 41:10 – Future jobs: law, AI assistants, and why juniors still need fundamentals 44:15 – Indigenous knowledge, language revitalisation, and the full-circle AI story 46:50 – Rapid fire: brain chips, Waymo, smart glasses, and AI “snog marry avoid” 49:55 – What we should do now: regulatory sandpits and real guardrails In the Blink of AI is made possible by our wonderful partnersStripeFor early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe. Apply for Stripe Startups at https://www.dayone.fm/stripe ✨ Connect with Georgie HealyLinkedin: https://www.linkedin.com/in/georginahealy/ Instagram: https://www.instagram.com/georgina_healy/ Twitter: https://x.com/georgina__healy?lang=en The Day One NetworkIn The Blink of AI is part of Day One, the podcast network dedicated to founders, operators & investors. Sign up to get your weekly insights into the up-and-coming AI startups: https://dayone.fm/newsletter Mentioned in this episode: Stripe Startups For early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe. Apply for Stripe Startups at dayone.fm/stripe Stripe Ad_Nov 2025_02

    52 min
  5. How AI Pen Testing Actually Works (and Where It Breaks)

    FEB 18

    How AI Pen Testing Actually Works (and Where It Breaks)

    Episode SummaryAI is starting to change penetration testing, but most people are asking the wrong question. In this episode of Secured, Cole Cornford sits down with Brendan Dolan-Gavitt, AI researcher at XBOW and former NYU professor, to unpack what autonomous pen testing really is, what it can reliably do today, and what still needs humans. They explore why AI agents are great at scaling the boring parts of testing, like authenticated workflows and broad vulnerability coverage across huge attack surfaces, and why that does not automatically translate to deep, context-aware exploitation. The conversation also gets into the messy parts: AI systems overclaiming “serious” findings, business logic flaws that are hard to verify, audit expectations, and why scope control needs real guardrails, not vibes. From agent traces and validation models to cost curves and creative exfiltration tricks, this episode is a grounded look at where AI helps AppSec and where it can still cause damage if you trust it too much. Timestamps00:00 – Intro 03:10 – From academia to building autonomous security tools 05:00 – Human pen testers vs AI agents: what is actually different 06:40 – Where AI helps most: boring tasks and low hanging fruit 08:30 – Scale: a thousand targets vs hiring a thousand testers 10:20 – Accessibility, economics, and Jevons paradox 12:30 – Accountability: audit evidence, traces, and “who signs off” 14:40 – Scope control: avoiding prod and preventing out-of-scope actions 16:20 – Safety checkers, overseer agents, and persuasion resistance 18:40 – The cost question: VC money, inference pricing, and efficiency 21:20 – When AI wastes money and why prioritisation matters 23:50 – Failure mode: overclaiming business “vulnerabilities” 26:10 – Validation agents and adversarial peer review 28:40 – The scary clever stuff: exfiltrating files as images 31:00 – What AI finds well: XSS, SQLi, file traversal, hard proof bugs 33:10 – What AI struggles with: business logic and contextual judgement 35:20 – Hype vs skepticism and why nobody has a crystal ball 🐙 Secured is grateful to be sponsored and supported by Chainguard. Chainguard is the trusted source for open source. Get hardened, secure, production-ready builds so your team can ship faster, stay compliant, and reduce risk. Download your free CVE Reduction Report at https://dayone.fm/chainguard This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

    42 min
  6. Why Enterprise AI Fails and How to Fix It

    FEB 12

    Why Enterprise AI Fails and How to Fix It

    Episode SummaryEnterprise AI is past the hype phase and into the hard part: scaling what works without breaking security, blowing out costs, or shipping chaos into production. In this episode, Georgie chats with AWS technologist Rada Stanic about using AI as a “study buddy” to renew technical certifications faster, and why tools like AWS QuickSight can generate strong first drafts of strategy docs when you provide the right templates and context. They go deep on AIOps: the operational discipline enterprises need to deploy agents and GenAI reliably at scale. Rada breaks AIOps into five practical pillars: defining agent intent, identity and security boundaries, policy and governance, observability and evaluation, and managing the rapid model lifecycle as new LLMs drop constantly. The conversation also covers why security questions dominate every enterprise AI project, why data quality still makes or breaks outcomes, and why “RAG” is fading as a buzzword even though retrieval is still foundational. Finally, Rada shares a sharp concern for the next generation: what happens to junior roles when AI fills the entry level work, and why the pace of change itself may become the next generation’s greatest advantage. In the Blink of AI is made possible by our wonderful partnersStripeFor early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe. Apply for Stripe Startups at https://www.dayone.fm/stripe ✨ Connect with Georgie HealyLinkedin: https://www.linkedin.com/in/georginahealy/ Instagram: https://www.instagram.com/georgina_healy/ Twitter: https://x.com/georgina__healy?lang=en The Day One NetworkIn The Blink of AI is part of Day One, the podcast network dedicated to founders, operators & investors. Sign up to get your weekly insights into the up-and-coming AI startups: https://dayone.fm/newsletter Mentioned in this episode: Stripe Startups For early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe. Apply for Stripe Startups at dayone.fm/stripe Stripe Ad_Nov 2025_02

    52 min
  7. How to Pitch Growth to Investors and Revenue to Publishers

    FEB 10

    How to Pitch Growth to Investors and Revenue to Publishers

    Episode Summary If you have to pitch the same product to two totally different audiences, should you use one deck or two? In this episode of Pick My Brain, Alan Jones is joined by Michelle Chen, founder of Mental Jam, a startup turning real lived experiences of depression and anxiety into cozy, story-driven mobile games. Michelle is preparing to pitch in two worlds at once: to investors who care about venture-scale growth, and to game publishers who care about commercial upside and licensing rights. Alan breaks down why one pitch is rarely enough, and introduces a simple framework: three decks for each audience. A teaser deck to spark curiosity, a pitch deck to support your live story, and a leave-behind deck packed with detail for later review. They also get tactical about what makes a pitch land: fewer words on slides, stronger emotional delivery in the first 10 to 15 seconds, and building trust by keeping the audience focused on the founder, not the deck. Michelle also shares the real nerves behind pitching, including stage anxiety and how it impacts performance. Alan offers a mindset shift that helps founders separate their personal fear from the “role” they’re playing on stage, plus practical tips for pitching on video calls. They finish with concrete improvements: shorten the character section, add a clear team slide, and capture customer reactions on video to show emotional impact, not just quotes. If you’re pitching a product with multiple buyers, fundraising while still building, or struggling with confidence on stage, this episode is a masterclass in making your pitch clearer, shorter, and more human Time Stamps 02:10 – Michelle’s origin story: from PhD research to startup 04:10 – Why Catalyzer mattered for a migrant founder 05:20 – Two audiences: investors vs game publishers 06:05 – Should you build two pitches? Alan’s answer: yes, tailor 08:05 – The 6 deck framework: teaser, pitch, leave-behind for each audience 13:05 – Ideal slide counts: teaser 3 to 5, pitch 10 to 15, leave-behind as needed 14:00 – Why founders accidentally read slides and lose the room 15:00 – Video call tip: pin the person, not your slides 16:15 – Michelle’s pitch: Mental Jam and Boba Rista 23:15 – Alan’s feedback: scripting, emotion, and the first 10 seconds 26:00 – Handling stage anxiety while pitching 29:20 – Cut words per slide: aim for fewer than 10 words 31:10 – Too many characters: use one or two for investors 31:40 – Add a team slide and show real customer feedback 33:00 – Use video testimonials for emotional proof Resources Mentioned 🎮 Mental Jam – https://hellomentaljam.com 🎙 Ask Alan a Question – https://speakpipe.com/pickmybrain 🎧 More from Alan Jones – https://www.startupfoundercoach.com Sponsors:Pick My Brain is supported by our wonderful sponsors:Galah Cyber offers the Foundations of Application Security course: a practical, hands-on AppSec course built for engineers who actually ship code. Two days of real-world lessons you can apply immediately. Learn more at galahcyber.com.au/learn. The Day One NetworkPick My Brain is part of Day One, the podcast network dedicated to founders, operators & investors.To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

    36 min

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