Episodes
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The business wants AI, and it wants it yesterday. But once the proof of concept works and the partner goes home, someone inside the company has to keep the thing running. Nathan Hill, Head of Telco at AWS and a 20-year veteran of the telco industry, joins James to talk about what actually happens when enterprises push AI into production — and why the scarcest asset in the room is still deep domain knowledge.
In this episode:
- Why "we need to do AI, the board's pushing for it" so often collides with the buy-versus-build question no one has answered internally.
- Where AI rollouts go wrong: over-engineering a basic problem, or buying an off-the-shelf tool and expecting it to be bespoke.
- The proof-of-concept trap — projects that "prove AI works" but were never built with a path to production.
- Why "AI native" doesn't translate cleanly to banks and telcos carrying 20–30 years of legacy and technical debt, and why the outcome should drive the tech strategy, not the reverse.
- The handover problem in one line: "If your chatbot starts spitting out Gordon Ramsay recipes instead of the answer, who in your organisation can fix it?"
- Centralise-then-seed: standing up an AI centre of excellence without creating an isolated team of "cool kids" cut off from the business (with a NASA analogy on risk).
- Why you can't take 20 years of experience, grab a dev and say "now you know telco" — and how the tooling finally lets domain experts build.
- Human-in-the-loop for critical infrastructure, digital twins of telco networks, and ICs becoming managers of agents.
- The question James keeps asking: if I'm managing a team of agents at 10x productivity, what should I actually be paid?
- Deep versus broad careers, how go-to-market has changed, and whether it's easier to teach a salesperson the tech or an engineer to sell.
Nathan Hill is Head of Telco at AWS, leading the company's engagement across Australian telcos. Before AWS he spent more than 20 years inside the telco industry — operations, engineering, pre-sales and sales — and ran sales and marketing for a challenger telco. He has a rare view across both the technical build and the go-to-market that sells it.
Building the team that has to make AI stick in production? This one's for you.
Connect with Nathan Hill on LinkedIn. Learn more about AWS in telco at aws.amazon.com.
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Episode Summary
The business wants AI now — but who keeps it running once it's live? Nathan Hill, Head of Telco at AWS and a 20-year telco veteran, sits down with James MacDonald to unpack what really happens when enterprises move AI from proof of concept to production. They dig into the buy-versus-build decision most organisations skip, why so many AI projects stall with no path to production, and the operating-model questions — who maintains it, who fixes it when it breaks — that companies leave until it's too late. Nathan makes the case that deep domain expertise is the asset AI can't replace: you can't grab a dev and say "now you know telco," but you can finally give 20-year network engineers the tools to build. They also get into human-in-the-loop for critical infrastructure, ICs becoming managers of agents and what that's worth, deep-versus-broad careers, and how the go-to-market function is changing now that the salesperson has to understand the tech. Practical, grounded, no hype.
Time Stamps
0:00 "I'm managing a team of agents now — what should I be paid?"
1:30 Meet Nathan Hill, Head of Telco at AWS
2:58 "The board wants AI": the buy-versus-build question
4:30 Where AI rollouts go wrong
6:35 Start with a use case — but build a path to production
8:09 Is "AI native" realistic for banks and telcos?
9:36 Speed versus security in regulated industries
11:56 The handover problem: who maintains it?
15:21 AI centres of excellence and the NASA analogy
18:26 "You can't grab a dev and say now you know telco"
21:30 Why agents won't replace engineers
23:41 Managing a team of agents — what's that worth?
25:03 Deep versus broad: staying in one vertical
27:08 How go-to-market has changed
29:59 Teach a salesperson the tech, or an engineer to sell?
32:58 Building a go-to-market function from scratch
38:03 Why the "SaaS apocalypse" is wrong
39:56 Upskilling into modern go-to-market
41:21 Career advice: back yourself
42:42 James's takeaway: domain experts who learn to build
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.
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Welcome to the first ever episode of AI Icons, a new thing I'm launching on the show. Here's the idea: the people reshaping tech have stories more entertaining than anything Hollywood is putting out, so in under 30 minutes I'm going to tell you the whole story, the good, the bad, and the ugly, but only the facts. No spin. And at the end, I'll give you my two cents on what actually made them an icon, and whether it's something you and I could ever replicate.
First up is Mira Murati, and I'll admit it, I'm a fan. I take you all the way back to her childhood in isolated post-communist Albania, where maths was the one subject the party couldn't rewrite, through a scholarship in Canada, degrees in maths and mechanical engineering, and a Goldman Sachs floor in Tokyo at 21. Then it's Tesla and those ridiculous Falcon Wing doors, a risky bet on a startup called Leap Motion, and the move that made her famous: OpenAI, where she rose to CTO and helped bring DALL-E and ChatGPT into your life.
And then there's the part that genuinely reads like a thriller. The 72 hours in November 2023 when Sam Altman was fired, Mira was named CEO, and a 52-page memo and a string of 2:30am texts sat right at the center of it. I walk you through what we know, what we still don't, and what came out under oath. I finish on her next act, Thinking Machines Lab, the record-breaking raise, the talent exodus, and why, out of my four Gs, I think one of them explains her better than the rest. Come find out which one.
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Missing episodes?
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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
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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.
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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.
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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/ -
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
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Day One sting
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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.
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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.auHosted 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.
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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
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✨ Connect with Georgie Healy
Weekly Substack: https://georgiehealy.substack.com/
Linkedin: https://www.linkedin.com/in/georginahealy/
Instagram: https://www.instagram.com/georginahealytech/
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Sign up to get your weekly insights into the up-and-coming AI startups: https://dayone.fm/newsletter
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Neel Bhattacharya is the founder of LeadTrackAI, a platform built to solve one of the most common and costly problems in sales: leads that go cold because nobody followed up fast enough. After more than a decade in product management across the energy sector, Neel built an AI voice agent that calls a new lead the moment they submit a form, speaks just like a real person, and qualifies them before handing them off to a human salesperson.
Neel started with solar and battery installers, an industry she knows intimately, and has since expanded into automotive. In this episode, Neel joins Alan to talk about the very real challenge of being a solo founder spread too thin, why documenting your own sales process is just as important as building the product, and how to decide whether to go deeper into one industry or wider into new ones.
Alan also shares a genuinely useful productivity framework and a tool recommendation that any solo founder drowning in admin will want to steal.
Timestamps:
01:27 – Neel's origin story: from wanting to be an architect to a decade in energy product management
03:01 – Why Neel left corporate to become a founder
03:44 – Who LeadTrackAI is for and the problem it solves for solar and battery resellers
05:06 – How the AI voice agent works: calling leads the moment they come in
06:32 – Why a fresh, qualified lead is worth more than ten cold ones
07:01 – Where LeadTrackAI is today: three large customers and expanding to Sydney
08:55 – Why every call is transcribed and how that builds an audit trail for regulated industries
09:57 – The founder's trap: chasing shiny objects instead of documenting what works
11:27 – Alan's four-quadrant framework for prioritising urgent vs important tasks
14:28 – Why SOPs and financial admin always end up in the "important but not urgent" pile
16:01 – Using AI to observe your own work as a founder, not just to build product
17:39 – Neel's big question: go deeper into solar and automotive, or go wider into new industries
18:17 – Alan's advice: run a cheap landing page experiment before committing to a new vertical
22:31 – Why charitable and nonprofit donation pipelines could be the next great use case for LeadTrackAI
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
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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:
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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.
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Episode Summary
Alex Feldman is the founder of Tiger and Bear, an M&A advisory focused on tech and services businesses. Before that, he was Chief Strategy Officer and General Counsel at Amaysim, where he ran three acquisitions simultaneously during full lockdown in 2020 and 2021 to build a dominant player that was ultimately sold.
In this episode, Cheryl and Maxine unpack how to buy and sell businesses when the world is doing crazy stuff around you. Alex breaks down why today's volatility isn't actually that different from the GFC or COVID, why timing is the single most important variable in any deal, and what the SaaSpocalypse means for tech companies thinking about selling when their natural buyers are struggling.
You'll also hear why more than half of Tiger and Bear's recent deals involved European and Asian capital rather than American, why profitable venture-backed businesses are suddenly more attractive to strategics, and what happens when the IPO market disappears as an exit path. For founders who can't raise their next round, he offers blunt advice: never waste a crisis, cut costs to buy yourself runway, and remember that raising and selling are the same activity, you're just selling different amounts of shares.
Alex closes with his Big Cojones moment: putting every spare $500 into the stock market during the GFC with no idea where the bottom was, buying Macquarie Bank shares at $30 and riding them back up.
Time Stamps00:00 - Intro
02:25 – Alex's first investment: going all in on the BHP Rio Tinto merger that never happened
06:19 – How to do M&A in volatile markets and why this cycle isn't that different
11:50 – Timing for buyers vs sellers: why uncertainty kills deals, not direction
13:08 – The SaaSpocalypse: what happens when your natural buyer is struggling
18:10 – Why European and Asian capital is replacing American buyers in Australia
21:08 – What M&A looks like in the Australian tech ecosystem right now
24:01 – When is a company big enough to buy and too small to be acquired
28:30 – Mergers of equals: why similar-sized companies come together in downturns
38:39 – How to become a disciplined buyer: capital, internal muscle, and integration
43:08 – Why the hardest part of any deal is admitting the other side does it better
47:54 – What to do when you can't raise: never waste a crisis
55:01 – Big Cojones moment: investing every spare dollar during the GFC
Sponsors:First Cheque 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
___
Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman.
As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs.
The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business.
As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartree
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
Deel x PX_Script 2
Pear Tree
If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost.Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business.As a Day One listener, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire.
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/ -
Akshay Kothari is the COO and co-founder of Notion, the workspace platform now used by over a hundred million people. Before Notion, he co-founded Pulse, the newsreader app built as a Stanford class project that Steve Jobs name-checked on stage at WWDC 2010 before LinkedIn acquired it. He joined Notion in 2018 when the team was fewer than ten people, and in this conversation with Georgie Healy he traces that journey and where knowledge work is heading as agents take centre stage.
Akshay shares his AI hack of the week, turning a screenshot of restaurant recommendations into a shareable Notion database, and explains how the unit of work has shifted from taking notes to simply having a chat. He unpacks the design obsession behind Notion's identity, the block architecture that lets anyone build their own tools, and the new Developer Platform that brings outside agents like Claude and Codex onto Notion's context graph. He paints a picture of a "factory of agents" working round the clock while humans move to reviewing and applying taste, makes the case for model optionality and cost control, and shares his rule for custom agents: macro delegate, then micro steer.
In the Blink of AI is made possible by our wonderful partnersDeel
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
✨ Connect with Georgie Healy
Weekly 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
-
She raised $4 million just before Christmas, moved out of her marital home inside sixty days, and came back from a two-week break to find an interim CEO appointed and the doors of her own company closed to her. In Part 2 of her Perspective X conversation with Pauline Fetaui, Yas Grigaliunas tells the part founders almost never say out loud: nine months locked out of World's Biggest Garage Sale, watching the brand she built be steered somewhere she would never have taken it.
Yas walks through the pattern that ran underneath the whole journey — high highs and low lows landing on top of each other. The Lord Mayor's award the same week her mum died. The $4 million raise the same month as her divorce. And then "prove your value, Yas" — sell to customers from home, no access to the product, no hand in the brand, while a million dollars of the raise went on things she would never have signed off.
She is unsparing but never vengeful about the board and advisers who did it. Two truths can be true at once, she says: they believed they were giving her space to manage a hard year; what it actually was, was a displacement. It took a founder friend shoving a lawyer's number at her in a bar to get her back inside the company she still majority-owned.
The numbers tell the rest. A $200,000 Ignite Ideas grant ten days before liquidation. A $20-odd million large global retailer partnership ready to sign. A $6,000 bank balance the month after half a million in revenue. Yas unpacks the over-engineered structure, the siloed executives, the curated board papers, and the moment the safe-harbour report from BDO finally backed what she had been saying all along.
What she does with the ending is the lesson. She rang every investor by phone before the liquidation notice went public. She traded through so staff got their final pay. She stayed thirty days after the liquidator was appointed to hand back a spotless warehouse — because, as her liquidator put it, the best stay and the worst disappear.
There is also the human spine of it: building a team around neurodiverse people and "the cracks you can't see", the scars she is not ashamed of, and her daughters watching her lose everything and land — without, in their eyes, any effort — back at Videopro, the company she helped build twenty years ago. "I lost my company," she says, "but I didn't lose myself."
Yas Grigaliunas is the founder of World's Biggest Garage Sale and Circonomy, a pioneer of Australia's circular economy who raised $4 million and partnered with a large domestic retailer before the company went into liquidation in 2024. She is now part of the leadership team at Videopro.
Links:
- Day One: https://dayone.fm
- Join the Day One newsletter: https://dayone.fm/newsletter
- Videopro: https://www.videopro.com.au
- Deel (sponsor): https://www.deel.com/dayone
If it doesn't feel right, it probably isn't. This is Perspective X.
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
Part 2 of Yas Grigaliunas on Perspective X is the harder chapter: the $4 million raise, the divorce, and nine months locked out of the company she founded. She walks through the liquidation of World's Biggest Garage Sale — the large global retailer deal, the grant, the $6,000 bank balance — and how she led the ending with integrity, then landed back at Videopro. She lost the company. She did not lose herself.
Time Stamps
00:00 - The part no one tells
00:51 - Building a team around neurodiversity
08:49 - Leading the narrative into liquidation
10:43 - High highs, low lows: the pattern
12:03 - Raised $4M, then locked out
14:10 - "Prove your value": nine months outside
19:43 - When founders take the fall in silence
21:19 - Two truths about the board
28:13 - The large global retailer deal and the $6,000 call
38:29 - Closing the company with integrity
47:40 - Lessons for founders raising capital
55:21 - Landing back at Videopro
66:53 - What the world hasn't caught up on
About the host
Pauline Fetaui hosts Perspective X, drawing out the founder stories that usually stay hidden — the cost, the conviction, and the decisions made under real pressure.
About Day One Network
Perspective X is part of Day One, the podcast network dedicated to founders, operators and investors. To learn more, join our newsletter (https://dayone.fm/newsletter) to be notified of new and upcoming shows. Day One helps founders and startup operators make better business decisions more often.
Follow our socials
LinkedIn: https://www.linkedin.com/showcase/dayonefm/
Instagram: https://www.instagram.com/dayone.fm/
TikTok: https://www.tiktok.com/@dayone.fm
Mentioned in this episode:
Deel x PX_Script 1
Day One sting
Deel x PX_Script 2
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HEO co-founder and CTO Dr Hiranya Jayakody (HJ) started out trying to mine asteroids. Instead, he and co-founder Will Crowe built a way to photograph satellites in space using other people's cameras, pointed one at the International Space Station during COVID lockdown, and got a call from US regulators asking what they'd done. Today HEO runs 7 cameras in orbit and sells space intelligence to governments across the US, Europe and Japan.
That story opens up the bigger question this episode keeps returning to: do you have to be "damaged" to build something big? Encour founder Jessy Wu makes the case that investors quietly prefer founders who stay triggered and hungry for vindication. Beaten Zone Venture Partners and TEN13 founder Steve Baxter isn't having it, his view is that a lot of what gets called founder intensity is just people being arseholes and dressing it up. HJ, who grew up through war and a tsunami in Sri Lanka, offers a third answer none of them saw coming.
Host Brendan Hill takes the Oversubscribed Season 1 finale through defence tech and why Steve calls it "irrationally unloved," the real difference between US and Australian hiring culture, ESG, AUKUS, and the story of how Steve actually landed his Shark Tank gig. Stay to the end for the asteroid still sitting on HEO's roadmap.
Time Stamps
00:00 Intro
03:52 How HEO Began: Two PhDs Who Wanted to Mine Asteroids
05:00 What Non-Earth Imaging Actually Is
08:15 Steve's "Uber for Secret Space Cameras" Pitch
09:55 Sponsor: Vanta
10:23 Imaging the ISS & the Call From US Regulators
15:35 What You Actually See Up There
17:30 Australia's Sovereign Space Capability & AUKUS
22:29 Space Weapons & Why Orbital War Is Madness
24:50 The Department of War & the US Defence Market
29:55 Sponsor: TEN13
30:46 The Branding Problem of Defence Tech
36:00 Why Steve Hates ESG Investing
39:57 Steelmanning the Case Against Building Weapons
43:00 Arms Balance, Not Arms Control, Keeps the Peace
45:30 Dual-Use Tech: Debris Removal to Blood Delivery
48:37 How the New US Administration Changed Defence Investing
50:47 The "Damaged Founder" Debate Begins
54:28 "Arseholes Can Make Any Excuse to Be Arseholes"
1:00:04 Australia vs the US on Hiring & Firing Culture
1:03:32 HJ on Tunnel Vision & the Self-Checkout Story
1:09:43 Childhood, Trauma & Founders
1:10:30 HJ's Sri Lanka: War, Tsunami & Going Numb
1:14:00 Jessy Wu on Reinvention & Building Encour
1:19:45 Steve's Path: Army, Telecom, Google & Angel Investing
1:26:09 How Steve Landed the Shark Tank Gig
1:35:12 Launching TEN13 & Going Harder Through COVID
1:38:35 Why Join HEO (And the Asteroid Still on the Roadmap)
1:40:13 The Cliff From Canva Timer & Sign-Offs
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.
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 and Steve Baxter are investors in HEO.
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/
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Most people think private messaging is already solved. Chris Fresle is proof it isn't.
Chris Fresle is the founder of Just Us, a private messaging app built to prevent image-based abuse. He's a year nine dropout with no tech background, a patent pending across six countries, and a product that uses facial recognition and object detection to make private messages genuinely impossible to screenshot, forward, or capture on another device.
In this episode, Chris joins Alan at the Cremorne Digital Hub in Melbourne to talk through how he built something everyone said was impossible, how he found and trusted a development team in Vietnam with no technical knowledge of his own, and how he's using survivor-led influencer marketing to build trust with a Gen Z audience that WhatsApp and Signal have never been able to reach.
Stay until the end for Chris's take on why Australian investors are harder to crack than US investors, and Alan's advice on how to pitch a product that people struggle to believe actually works.
Timestamps
00:00 Intro
03:00 The Journey to Creating Just Us
06:02 Building a Trustworthy Team
08:55 Navigating Skepticism in the Startup World
12:00 Monetization and User Engagement Strategies
15:07 User Feedback and App Development
17:58 Marketing and Influencer Partnerships
20:50 Protecting Intellectual Property
23:56 The Vision for Just Us
27:14 Passion for Change and Helping Others
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 1
Deel x PX_Script 2
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Yas Grigaliunas turned a backyard charity garage sale into Circonomy, one of Australia's most recognised circular-economy companies — years before "circular economy" was even a phrase. In Part 1 of her Perspective X conversation with Pauline Fetaui, she traces the rise: from selling homemade cupcakes at 5am triathlon training and asking herself "how do you raise money without asking people for money," to $15,000 in a single day, to quitting her job with no plan B, to a $4 million raise in four weeks with Officeworks on the cap table.
It's also a portrait of the engine underneath: a relentlessly data-obsessed, "burn bright, not burn out" founder who walked into rooms she was told she didn't belong in — including a memorable run-in with Steve Baxter at River City Labs — turned "surprise chain" into supply chain for Officeworks the weekend COVID shut the world down, and built a company on the conviction that idle assets, and overlooked people, are worth far more than anyone assumes.
Part 2 is the harder conversation — the cost, and what happened when it all changed.
Episode Summary
Yas Grigaliunas, founder of World's Biggest Garage Sale and Circonomy, joins Pauline Fetaui for Part 1 of a Perspective X conversation about building a circular-economy company in Australia before the term existed. From a charity garage sale that did $15,000 in a day to a $4 million capital raise in four weeks, Yas unpacks the data discipline, the conviction, and the well-timed moments that turned "dormant goods for good" into a national enterprise — and the energy source that, after 30 years of people predicting her burnout, still hasn't run dry.
Time Stamps
00:00 - A garage full of stuff, and one question: how do you raise money without asking for money?
02:10 - Welcome to Perspective X: Pauline's "love letter" introduction to Yas
03:13 - The cancer-charity origin and "dormant goods for good"
05:30 - The first World's Biggest Garage Sale: $15k in a day, 50 volunteers
12:58 - Scaling the events: $15k to $60k to $150k in a single day
18:06 - River City Labs, Steve Baxter, and "I'm not a tech founder, I'm a business builder"
24:55 - 168 hours in a week: time, data, and consistency
31:14 - Confidence, the seesaw, and falling in love with yourself
36:57 - Coining "Circonomy" before circular economy was a buzzword
41:29 - From events to a warehouse: building a real business
48:07 - Officeworks, "surprise chain," and the Retail Rescue the weekend COVID hit
49:54 - The $4 million raise and the "capital raise cave"
51:13 - Raising $4M in four weeks as a female founder
58:55 - Preparation, persistence, and watching who opened the pitch deck
About the host
Pauline Fetaui hosts Perspective X, the Day One Network show that goes beyond the highlight reel to explore the inner worlds, convictions and turning points of founders and leaders.
About Day One Network
Perspective X is part of Day One, the podcast network dedicated to founders, operators and investors. Join our newsletter at https://dayone.fm/newsletter to hear about new and upcoming shows.
Perspective X is powered by Deel.
Sponsors:Perspective X 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
Follow Day One: LinkedIn https://www.linkedin.com/showcase/dayonefm/ · Instagram https://www.instagram.com/dayone.fm/ · TikTok https://www.tiktok.com/@dayone.fm
Mentioned in this episode:
Deel x PX_Script 2
Deel x PX_Script 1
-
Episode Summary
Alexey Mitko is a partner at Co-Ventures, the architect behind Eucalyptus' ESOP plan, and widely known in the Australian ecosystem as "ESOP Guy." He was around employee number twenty at Canva and one of the early employees at Koala, giving him a front-row seat to three of Australia's biggest consumer tech outcomes.
In this episode, Cheryl and Maxine unpack how Alexey designed the ESOP plan that led to roughly $300 million distributed back to Eucalyptus employees, the largest ESOP payout in Australian history. He walks through the three questions every founder faces but rarely verbalises: who gets equity, how much, and why you have an ESOP plan in the first place.
You'll also hear how he modelled allocation across multiple rounds and hundreds of hires to avoid giving too much away early, why he personally walked the first two hundred employees through their equity, and why Australia's lack of a secondary market keeps ESOP feeling like monopoly money. Alexey closes with his Big Cojones moment: proposing to his wife, the most nervous he's ever been despite having climbed Europe's highest mountain.
Time Stamps00:00 – Intro
03:01 – The three ESOP questions every founder needs to answer
05:58 – How to model equity allocation across rounds and hundreds of hires
09:10 – Using ESOP as your most powerful recruitment and retention tool
12:02 – How walking 200 employees through their equity built culture and trust
15:02 – Open financials, shrinking cash balances, and what went wrong along the way
17:55 – Why Australia's ESOP ecosystem is still behind Silicon Valley
26:48 – Teaching employees to understand equity: the Google Sheet that started at zero
29:20 – High salary vs heavy equity: giving employees a real choice
32:16 – Common ESOP mistakes founders make and how to avoid them
35:03 – Why Australians treat startup equity like monopoly money
39:11 – The secondary market problem: why liquidity changes everything for ESOP
43:25 – Why your startup career is a portfolio of equity bets
46:36 – What angel investors can do to help portfolio companies build better ESOP plans
Sponsors:First Cheque 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
___
Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman.
As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs.
The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business.
As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartree
First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.
To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.
Mentioned in this episode:
Deel x PX_Script 1
Deel x PX_Script 2
Pear Tree
If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost.Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business.As a Day One listener, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire.
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/ -
This is a #paidpartnership with Commonwealth Bank
Episode SummaryBlair is the Chief Engineer of Generative AI at Commonwealth Bank, overseeing nine to ten teams building the AI platform that powers Australia’s largest bank and its millions of customers. Including me, a Dollar Mite since primary school.
His origin story is not what you would expect. He was a self-described hacker who grew up clicking through every system configuration setting he could find on his mum’s school computers after hours. That curiosity took him from building on GPT-2 before ChatGPT even existed, to the heart of one of Australia’s most important institutions.
In this episode we get into:
The litmus test he uses to spot bad AI use immediatelyWhy context matters more than promptingWhat an AI platform actually is and why your company probably needs oneWhy software engineers need to take more accountability for what they buildThe single security mistake most people are still makingWhy it is absolutely not too late to figure AI out for yourselfPractical, candid, and full of things you can action today.
Time Stamps00:00 Intro
03:05 What Does a Chief Engineer of AI at a Bank Actually Do
06:02 How CBA Collaborates Across Hundreds of Engineering Teams
08:56 How to Keep Up With AI Tools Without Getting Overwhelmed
12:04 Why Tool Consistency Matters in Enterprise AI
14:56 Why Blair Shares His AI Insights Publicly
17:51 What Being a Hacker Really Means in Tech
20:50 How Blair Hudson Went From Startup AI to Commonwealth Bank
23:59 Why CBA Starts Every Sprint With a Real Customer Call
27:06 Why Over-Engineering Is Killing Your AI Projects
29:47 Where AI Is Actually Moving the Needle in Banking Right Now
32:15 Why the Year of the Agent Was Overhyped
34:41 How to Build AI Fast Without Cutting Corners on Safety
39:28 What Is an AI Platform and Why Does Your Company Need One
41:49 How CBA Handles Shadow AI and Tool Adoption at Scale
45:09 Why Context Is More Important Than Prompting
50:29 The Number One Security Mistake You Are Still Making
52:30 The Easiest Way to Start Using AI to Save Time Today
54:05 Why You Should Never Ship AI Output Without Reviewing It
55:38 Why It Is Not Too Late to Learn AI
In the Blink of AI is made possible by our wonderful partnersDeel
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
✨ 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
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"Can does not imply should."
That one line from Dr Simon Longstaff cuts to the heart of everything wrong with how the tech industry is currently building AI. The Executive Director of The Ethics Centre and one of Australia's most respected moral philosophers joins Georgie for a conversation that is equal parts grounding and mind-expanding, and one of the most important episodes the show has produced.
Simon's path to becoming Australia's foremost ethics expert is not what you would expect. He left school at 16, cleaned toilets on a remote island in the Gulf of Carpentaria, drove ambulances, became a paramedic and fire officer, and was eventually adopted by one of the clans of the Anindilyakwa people. It was at the end of a ship loading wharf that an indigenous elder taught him something about seeing patterns in the world, a lesson he has carried through 35 years of philosophical work and only recently realised had shaped everything.
In this episode he unpacks why ethics is not an optional extra bolted onto technology but the foundation it has to be built on, why the pharmaceutical approval model could be the blueprint for governing AI, and why "necessary fictions" mean that CEOs deploying AI are responsible for outcomes they literally cannot understand. He also makes the case that the coming wave of job displacement does not have to be a catastrophe, and explains what ancient Athens and pre-colonial Indigenous life have to do with universal basic income.
In the Blink of AI is made possible by our wonderful partnersDeel
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
✨ Connect with Georgie Healy
Weekly 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
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Quinnie Chen is the founder of Profit Plainly, a web app built for solo founders and freelancers who have no finance team, no CFO, and no clear picture of whether their business is actually working for them. Quinnie built it to solve her own problem, after years of running a website and software design business post Canva, she kept reaching the end of the month and realising she had underpriced her work, taken on the wrong clients, and had no way of knowing what she actually needed to earn to replace a salary.
In this episode, recorded live at the Cremorne Digital Hub in Melbourne, Quinnie joins Alan to talk through the early stages of bringing Profit Plainly to market. Alan challenges her to think more carefully about who her first customer really is, why accountants and bookkeepers might be her smartest go-to-market channel, and why per-usage pricing could unlock growth that a traditional SaaS model would block. It's a candid, practical conversation about the decisions every solo founder faces before they have any customers, any pricing, and any real clarity on where to focus.
If you're building something early and trying to figure out where to start, this episode is for you.
Time Stamps
00:00 Trailer and Intro
03:01 How Quinnie Chen Built Profit Plainly to Solve Her Own Freelancing Finance Problem
05:47 Why Emotional Labor and Opportunity Cost Are Missing From Most Business Finance Tools
08:52 How the Business Ikigai Framework Helps Solo Founders Identify Their Best Clients
12:05 Why Accountants and Bookkeepers Are the Smartest First Customer for Profit Plainly
14:54 How to Find a Go-To-Market Channel That Generates Both Revenue and Referrals
18:02 Why Traditional SaaS Pricing May Not Work for Price-Sensitive Solo Founders
21:04 How Per-Usage Pricing Could Help Profit Plainly Convert More Early Stage Users
23:46 How to Start Experimenting With Paid Marketing Before Your Product Is Ready
27:14 How to Build a Community and Reward Engaged Users on a Zero Budget
30:03 How to Join the Profit Plainly Early Access Beta and What Comes Next
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
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Mentioned in this episode:
Deel x PX_Script 1
Deel x PX_Script 2
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.
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