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  1. What's Your Moat When AI Can Copy Your Product in 48 Hours? | Dilip Jacob from Pitchberry

    1d ago

    What's Your Moat When AI Can Copy Your Product in 48 Hours? | Dilip Jacob from Pitchberry

    Dilip Jacob is the solo founder and CEO of Pitchberry, an AI platform that helps people in high-stakes professions practice the conversations their careers depend on. The idea came from a very personal place: diagnosed with high anxiety, Dilip froze during an investment pitch and went looking for a way to get better. What began as a tool for founders found an unexpected first market in dentistry, where internationally trained dentists must pass a communication-heavy exam to work in Australia. Pitchberry now has 300+ users. This episode is a masterclass in the decisions every early-stage founder faces. Dilip and Alan work through how to find a co-founder without rushing into the wrong partnership, why the language you use changes how convincing you sound, and whether to raise capital or bootstrap when you already have paying customers in sight. Alan also breaks down the four things every founder needs before they're investible, including the one most solo founders never fix. Stick around for the last section, where Alan tackles the question keeping most AI founders up at night: what counts as a defensible moat when anyone can rebuild your product in 48 hours? His answer, user context and brand relationship, might change how you think about your entire product strategy. Timestamps 02:30 – How Pitchberry was born from Dilip's own struggle with pitch anxiety 04:00 – The professions that rely on credibility: doctors, dentists, lawyers, police and founders 05:30 – Why dentistry became Pitchberry's unexpected first market 06:15 – The go-to-market model: free practices, paid subscriptions and token costs 07:30 – Pivoting from individual users to selling into institutions and academies 09:00 – The challenges of being a solo founder and reaching out for a co-founder 10:00 – How small language changes make you sound more convincing to any audience 11:30 – Why a co-founder relationship is harder than a marriage, and how to date first 13:30 – Where to find co-founders: YC's co-founder matching and networking events 15:00 – Should you raise funding or bootstrap? The case for staying in control 18:00 – Why bootstrapped Aussie success stories like Atlassian and Campaign Monitor matter 20:00 – The four things every founder needs to be investible 22:00 – What counts as a defensible moat now that AI can replicate any product 25:00 – Why user context and brand relationship are the real moats in the age of AI Sponsors:Pick My Brain is supported by our wonderful sponsors:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone ___ Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess 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. Mentioned in this episode: 5 I’s of Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at galahcyber.com.au/assess. Deel x PX_Script 2 Deel x PX_Script 1

    29 min
  2. 2d ago

    Guardrails Are Just Suggestions: Securing AI Agents with Okta's Kevin Akermanis

    The business wants AI, and it wants it now. Meanwhile security budgets are flatlining, breaches are becoming a line item, and agents can wander places no one scoped them for. Kevin Akermanis, Solutions Architect at Okta and a 15-year Salesforce veteran, joins James to talk about what actually breaks when you bolt AI onto an enterprise, and why experience is quietly becoming the scarcest asset in tech. In this episode: - Why "the business says we need to AI now" collides head-on with the teams who have to make it safe, and why pumping the brakes gets you branded the blocker. - The uncomfortable finding from a customer security council: security funding is flat or shrinking while every dollar with "AI" in front of it gets funded. - How breaches have quietly become "the cost of doing business", and the apathy that creates. - Why the old three-tier architecture has collapsed into the model layer, forcing security all the way down to the data level where it never lived before. - The new attack surfaces agents open up, including the hiring bot that leaked applicant data through prompt engineering. - Why agents are non-human identities that behave nothing like the service accounts we're used to, and why guardrails are "just suggestions" for something non-deterministic. - The fix: valet keys not master keys, scoped and time-limited access, token vaulting and traceability, on behalf of a known person for a known context. - The junior squeeze: if entry-level roles get automated away, who backfills the seniors when they retire, and why knowing "what good looks like" still can't be vibe-coded. - Where an SMB should actually start: internal first, read-only, inside the Microsoft or Google walled garden, and why Australian buyers care more about MCP than agents. Kevin Akermanis is a Solutions Architect at Okta, the digital identity and security company behind Auth0, where he works across the Asia Pacific region on identity, security and agentic AI. Before Okta he spent roughly 15 years at Salesforce across pre-sales and an internal CTO role, giving him a rare view from both the selling and buying sides of enterprise tech. Building the team that has to make AI safe? This one's for you. --- Episode Summary The business wants AI now. The people who have to secure it are being told to move faster while their budgets shrink. Kevin Akermanis, Solutions Architect at Okta and a 15-year Salesforce veteran, sits down with James MacDonald to unpack what really happens when enterprises rush AI into production: security funding flatlining, breaches becoming the cost of doing business, and a collapsed architecture that pushes security down to the data layer. They dig into why AI agents are a new class of non-human identity that can roam anywhere, why guardrails are only suggestions for something non-deterministic, and the scoped, time-limited, valet-key approach that actually contains the risk. They also tackle the harder people problem: if juniors get automated out, who backfills the seniors, and why knowing what good looks like still beats anything you can vibe-code. Practical, sceptical, no hype. Time Stamps 0:00 The business says "we need to AI now" 2:53 The real tension: speed vs protecting company IP 7:22 Security budgets shrink while AI gets the money 11:28 When breaches become the cost of doing business 13:42 New attack surfaces and the hiring-bot breach 18:14 Experience still matters: who backfills the seniors? 46:39 Agents as non-human identities: scope and guardrails 55:03 Where to start with AI safely 57:37 Why the Australian market cares about MCP About the host James MacDonald is the founder and Managing Director of NTP Talent (Newy Tech People), an Australian tech and engineering recruitment firm headquartered in Newcastle with teams in Sydney and Melbourne. He hosts Building Tech Teams, helping companies up the East Coast of Australia find and recruit the best technology talent. Connect with James on LinkedIn (/JamesMacDonaldAU) or at ntp-talent.com.au. About Day One Network Day One is a podcast production company and trusted partner in the technology space, producing shows for founders, investors and operators across Australia and beyond. Building Tech Teams is part of the Day One Network, which cross-promotes episodes across a slate of technology and venture shows. Building Tech Teams is produced by Day One®, trusted partners in the technology space and the production partner behind Blackbird Ventures' Wild Hearts. Sister shows include First Cheque, Oversubscribed and In The Blink of AI. Episodes are cross-promoted across the network.

    1h 7m
  3. Why Australia Builds More Unicorns per Dollar Than Anyone (Replay) | Ben Grabiner, Side Stage Ventures

    4d ago

    Why Australia Builds More Unicorns per Dollar Than Anyone (Replay) | Ben Grabiner, Side Stage Ventures

    Side Stage Ventures and Dealroom have just released the 2026 edition of their landmark report on Australian venture. Grab your copy of the Australia Venture & Startup Report 2026 here: https://www.sidestage.vc/outliers-report-2026 Australia has created more unicorns per dollar of VC invested than anywhere else in the world — and Ben Grabiner has the data to prove it. In this replay, Cheryl and Maxine sit down with the Side Stage Ventures co-founder to unpack why the ecosystem punches so far above its weight, and why the next decade could belong to Aussie tech. Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It's why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone Episode Summary Ben Grabiner is the co-founder and General Partner of Side Stage Ventures and the author of a landmark report, produced with Dealroom and AWS, on Australia's venture ecosystem. Cheryl and Maxine sit down with Ben to unpack the data behind Australia's rise as one of the most efficient and exciting venture ecosystems in the world. They dig into why Australia produces more unicorns per dollar of VC invested than anywhere on earth, how the country quietly matches Israel and India on decacorn creation, and why roughly 40% of local seed capital now comes from overseas, a sign global funds see the opportunity more clearly than we do. Ben explains why capital constraints have bred a culture of doing more with less, why fewer than 30 Australian seed funds made more than five investments last year, and what has to change to close the early-stage funding gap. You'll also hear why the next wave of second- and third-time founders could be the ecosystem's secret weapon, what global LPs still need to understand about Australian venture, and Ben's own Big Cojones moment: throwing it all in mid-COVID to move from London to Australia. Time Stamps 00:00 - Cold open: more unicorns per dollar than anywhere 00:52 - Intro 04:48 - Ben's first investment: 250 pounds in Tottenham Hotspur 07:01 - The headline stat and what drives Australia's capital efficiency 09:24 - Why constraints breed efficiency, and why it's good for VCs 12:31 - Decacorn creation: Australia on par with Israel and India 14:35 - 40% of seed capital comes from overseas 16:24 - What needs to happen to close the capital gap 20:41 - Can startups scale globally from Australia? 26:14 - What global LPs need to understand about Australian venture 28:28 - The rise of second- and third-time founders 30:37 - Why pre-seed funds and angel investors matter more than ever 34:41 - Ben's Big Cojones moment: moving to Australia mid-COVID Resources Ben Grabiner on LinkedIn - https://www.linkedin.com/in/bengrabiner/ Side Stage Ventures - https://www.sidestage.vc/ Australia Venture & Startup Report 2026 - https://www.sidestage.vc/outliers-report-2026 Aussie Angels - https://www.aussieangels.com/ 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/

    37 min
  4. How AI Models Are Really Judged, with Peter Gostev (Arena / LMArena)

    6d ago

    How AI Models Are Really Judged, with Peter Gostev (Arena / LMArena)

    Peter Gostev is head of AI capabilities at Arena (LMArena), the community-based platform where millions of real people vote in blind tests to rank AI models, born out of research at UC Berkeley. Before Arena, Peter was Head of AI at Moonpig and built a large following sharing hands-on explorations of what the latest models can actually do. He joins Georgie Healy from London for a genuinely nerdy, insider look at how models are judged and where the frontier is heading. In this episode, Peter explains the difference between static benchmarks and human judgment, and why a model can pass every test you write and still produce something that looks completely awful. He breaks down the current state of the leaderboards, why Anthropic's models are dominating and how that tracks with real world adoption, and gives a sharp comparison of the top Western models, including why Anthropic's non-reasoning models are exceptional while OpenAI's strength lies in deep reasoning. Georgie and Peter get into why people aren't using Chinese models more despite their quality, the economics behind AI pricing and how enterprise usage is priced very differently from consumer subscriptions, why release cadence matters as much as capability, and what the wave of data centre investment means for the models arriving next. Along the way there's a fond detour on Opus 3 as the model you could talk to for hours, and why better models can sometimes feel worse. Tune in for a clear-eyed, hype-free guide to how AI models are really evaluated, straight from someone who watches the charts move in real time. Mentioned in this episode: Deel x PX_Post Intro

    58 min
  5. Taryn Williams: Building and Exiting 6 Companies and the Cost No One Talks About, where humans sit in the creator economy and AI Slop

    6d ago

    Taryn Williams: Building and Exiting 6 Companies and the Cost No One Talks About, where humans sit in the creator economy and AI Slop

    Taryn Williams started her first company, Wink Models, at 21 with $30,000 and no roadmap. She didn't stop there. Over the next two decades she built and ran a string of ventures, the talent marketplace The Right Fit (backed by Airtree, scaled to 17,000 talent and 11,000 clients across APAC), The Influencers Agency, the contra-gifting platform #Gifted, the B2B talent business Notable, and Online Model Academy, exiting two of them to international acquirers in 2023. Today she sits across boards, invests as an angel, and advises organisations on AI transformation with Think & Grow. In this episode Pauline sits down with Taryn for an honest conversation about what it actually costs to build like this: why and how she runs multiple companies at once, why she loves the 0-to-2-year stage and does not want to be the CEO, and the quieter things founders rarely say out loud, the toll on her relationships and health, freezing her eggs at 35 and what she wishes she'd known about fertility, and the mentor question she still works through every day: when is enough, enough? Plus sharp takes on AI, the creator economy, "AI slop", and whether AI will replace human models. Time Stamps 00:00 - Cold open: "I was 21 when I started Wink" 01:20 - Welcome — meeting Taryn at South Start, and the snapshot of a serial founder 04:08 - Scouted at 15: modelling as an accidental business education 06:21 - Starting Wink Models at 21 — fixing a broken, fragmented industry 09:04 - Building the first tech product (and the trap of gold-plating instead of an MVP) 12:21 - Launching The Right Fit and raising capital from Airtree 17:56 - How big Wink and The Right Fit actually grew 19:34 - Running multiple companies at once — and stepping fully out of Wink 22:13 - #Gifted, Notable and Online Model Academy: "every year, birth a new child" 28:27 - Why it isn't "the Taryn Williams show" 31:37 - The 2023 exits: running a formal process and the transition 38:56 - The real cost: relationships, health and never being fully switched off 43:27 - Fertility, freezing eggs at 35, and what no one tells you early enough 50:15 - From operator to board chair — breaking the habit of being all-in 54:17 - Why every founder should understand governance (the AICD course) 56:28 - In the investor seat: what Taryn backs and the founders she looks for 59:33 - Advising on AI transformation with Think & Grow 64:56 - AI, creators and the "AI slop" problem 69:07 - Will AI models replace human talent in advertising? 73:32 - Dating, connection and AI: why we've lost the resilience for friction 80:45 - Tying self-worth to success — the question she still works through 85:16 - One thing she knows to be true that the world hasn't caught up on yet 87:36 - Close Links Wink Models — https://www.winkmodels.com.au Airtree Ventures — https://www.airtree.vc Think & Grow — https://www.thinkandgrow.com Australian Institute of Company Directors (AICD) — https://www.aicd.com.au Perspective X is produced by Day One — the podcast network for founders, operators and investors — https://www.dayone.fm Mentioned in this episode: Deel x PX_Script 2 Deel x PX_Script 1 Day One sting

    1h 29m
  6. Why Your First Hire Isn't an Engineer Anymore — Michael Batko, ex-Startmate CEO

    Jun 29

    Why Your First Hire Isn't an Engineer Anymore — Michael Batko, ex-Startmate CEO

    The first hire used to be an engineer. Michael Batko thinks that's now backwards — and that's just the start of how AI is rewiring the way you build a tech team. In the first episode of Building Tech Teams, James MacDonald sits down with Michael Batko — who spent eight years as CEO of Startmate backing 240+ startups, and now runs the AI-native venture batko.ai. They get into what actually changes when the cost of building drops to near zero: why go-to-market now comes before engineering, why the 10x engineer is finally real, what "AI-native" means for a person and for a company, and how to lead a team through it without torching your culture. It's a practitioner-to-practitioner conversation with real opinions and real scar tissue — hiring for attitude over skill, the rise of the AI chief of staff, the squeeze on middle management, and why your hard-won experience is the one moat AI can't copy. Chapters0:46 — Why James launched the show, and why Batko is guest #12:00 — The first hire has flipped: go-to-market before engineers3:49 — Where real software engineers still matter (and the "vibe-coding" ceiling)9:01 — What "AI-native" actually means — building your personal, then company, "brain"12:06 — Agent hierarchies: one agent / one job, and the AI chief of staff14:50 — Getting AI into a traditional business: permission to play + an AI policy (and the IP-leak risk)17:25 — Quick wins: process-mapping by voice, and the dictation tool that changes the game20:54 — Your first 5–10 hires: attitude over skill, hungry over proven, junior over senior25:58 — Team size, layoffs, "AI-washing", and the shrinking PM-to-engineer ratio34:55 — The one skill AI can't replace: people management48:07 — Why you still want humans in the room: inspiration, fresh eyes, first-principles51:40 — Facing the fear: lean in, automate yourself out, take the skills with you58:33 — Taste, authenticity, and experience as your real moat63:54 — Batko's playbook for any company starting now About the GuestMichael Batko spent eight years as CEO of Startmate, where he backed 240+ early-stage companies, and now builds AI-native tools for founders and businesses at batko.ai. LinksMichael Batko — batko.ai · LinkedIn: https://www.linkedin.com/in/batkomichaelJames MacDonald — LinkedIn: https://www.linkedin.com/in/james-macdonald-au · NTP Talent: https://ntptalent.com.au Hosted by James MacDonald, Managing Director of NTP Talent. Building Tech Teams is produced by Day One®, trusted partners in the technology space and the production partner behind Blackbird Ventures' Wild Hearts. Sister shows include First Cheque, Oversubscribed and In The Blink of AI. Episodes are cross-promoted across the network.

    1h 7m
  7. Inside ElevenLabs: Voice AI, Cloning Ethics, and the End of the Call Centre?

    Jun 25

    Inside ElevenLabs: Voice AI, Cloning Ethics, and the End of the Call Centre?

    Damian Naughton is the General Manager of ANZ at ElevenLabs, the voice AI company now past US$500 million in ARR, just four years after its 2022 founding. Formerly a regional VP at Slack and an early team member at Sydney's Hyper Anna (acquired by Alteryx), Damian is leading ElevenLabs' new Sydney office and tripling the local team as enterprise demand for voice AI accelerates. In this episode, Damian and Georgie Healy cover why ElevenLabs is planting a flag in ANZ now and the local customers already on board, including Xero, Employment Hero, Heidi Health, Australia Post, and Andromeda Robotics' aged care companion robot Abby. Damian unpacks the company's high performance culture and the "11x yourself" philosophy, why intrinsic motivation beats top down pressure, and how he co-designs stretch goals with new hires. They get into voice cloning and the ethics behind it, how little audio you actually need to clone a voice, and how ElevenLabs handles consent, safety, and scammers, including a clever "reverse" use case that keeps fraudsters on the line to gather intel for banks. Damian also shares his view that enterprise AI needs to be led by the business rather than tech, why the BPO and consulting worlds are facing real disruption, and his take that tall poppy syndrome is a scourge holding Australian tech back. Tune in for a candid conversation on voice AI, building a high performing team, and how enterprises should prepare for a near future where your own AI assistant takes action on your behalf. Time Stamps 00:00 – Intro: Your AI Assistant Will Soon Take Action For You 02:17 – AI Hack of the Week: A Michael Caine Voice Butler On The Fridge 04:57 – ElevenLabs Launches in Australia and New Zealand 07:14 – Why Voice AI Is Ready Now (Xero, Employment Hero, Heidi, Andromeda) 10:52 – From Journalist to Voice AI: How AI Is Changing the News 13:40 – Inside Hyper Anna, the Aussie Startup Acquired by Alteryx 15:31 – ElevenLabs' High Performance Culture and the "11x Yourself" Rule 25:38 – The ElevenLabs Founding Story: Two Polish Founders and Bad Dubbing 28:42 – How Will Australia React to Voice AI? 31:24 – Voice Cloning Ethics, Consent, and Celebrity Voices 34:12 – How Little Audio You Need to Clone a Voice 37:17 – Voice AI and Scammers: How ElevenLabs Fights Fraud 42:05 – Can AI Bring Back Music From Artists Who Have Passed? 45:11 – Can Enterprise Companies Actually Adapt to AI? 53:05 – Advice for Heads of AI: Let Business Lead, Not Tech 56:39 – Rapid Fire: Tall Poppy Syndrome, Hiring, and Spicy Takes 1:02:05 – Where to Follow Damian and ElevenLabs In the Blink of AI is made possible by our wonderful partnersDeelFounders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone ✨ Connect with Georgie HealyWeekly Substack: https://georgiehealy.substack.com/ Linkedin: https://www.linkedin.com/in/georginahealy/ Instagram: https://www.instagram.com/georginahealytech/ 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: Deel x PX_Post Intro

    1h 4m

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