Day One®

Day One®

Download on the App Store

Day One® episodes

  • AI Can’t Replace Domain Expertise — Nathan Hill, Head of Telco at AWS

    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.

    ---

    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 team that helped build Blackbird Ventures' Wild Hearts. Sister shows include First Cheque, Oversubscribed and In The Blink of AI. Episodes are cross-promoted across the network.

    44 min
  • All The Ways You're Building or Breaking Your Credibility

    Welcome back to the FNDN Series, where we continue our deep dive into startup people and pay practices with industry leaders from across the startup world.

    ---

    Join Startup People Summit, a one-day virtual conference designed for startup People leaders who want practical insight, honest conversations and proven approaches to scaling their People function — get your ticket here: www.startuppeoplesummit.com 

    ---

    In our conversation with Melanie Naranjo ,Chief People Officer at Ethena, we get raw and real about the state of HR in today's employer-driven market. We explore how HR professionals can build credibility with their CEOs, navigate the pressures of AI adoption, manage the loneliness of the HR role, and find the resilience to advocate for themselves — and their function — with confidence.

    Chapters:

    00:00 Introduction to the FNDN Series
    00:44 Welcome & Setting the Stage
    01:03 The Current State of the Market
    03:07 How HR Teams Should Adapt
    03:29 Spicy Take: Mentoring Your CEO Through AI Panic
    05:35 Upskilling the Workforce for an AI-Forward World
    07:05 Making AI Accessible — Not Just Aspirational
    10:02 DEI, Change Management & Getting Company-Wide Adoption Right
    11:16 Building Credibility as a Strategic Partner to the C-Suite
    12:18 Asking the Right Questions & Holding CEOs Accountable
    14:26 Balancing Short-Term Wins with Long-Term Strategy
    15:26 Marketing the HR Function Better
    16:24 Handling "Department of Plus One" Overload
    22:39 Quarterly Leadership Feedback: Three Questions That Build Credibility
    25:46 The Power of Vulnerability in Tough Conversations
    28:54 Navigating the Fractional vs. In-House Shift
    38:53 Long-Term Career Advice for People Professionals
    43:03 Finding Joy Outside of Work
    44:54 Wrap-Up & Closing Remarks

    Connect with Melanie Naranjo

    Visit: https://www.linkedin.com/in/melanie-naranjo 

    More FNDN Episodes:

    Spotify: https://open.spotify.com/show/4GeBIeZOKrFxG1oiiPxmiM 
    Apple Podcast: https://podcasts.apple.com/us/podcast/fndn-series/id1794263484

    HRCredibility, PeopleOps, StartupHR, ChiefPeopleOfficer, HRLeadership, CEORelationship, AIAdoption, HRStrategy, StartupCompensation, ChangeManagement, FractionalHR, HRProfessionals, TalentDensity, WorkplaceWellbeing, HRCareer, PeopleStrategy, StartupCulture, HRBestPractices, EmployeeEngagement, StartupLeadership

    46 min
  • Mira Murati, the Quiet Superpower in the AI Race

    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.

    In the Blink of AI is made possible by our wonderful partnersDeel

    Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.

    Ready to expand your business?

    Build your global team with Deel at 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 Network

    In 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

    30 min
  • 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: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.

    Ready to expand your business?

    Build your global team with Deel at 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
  • Guardrails Are Just Suggestions: Securing AI Agents with Okta's Kevin Akermanis

    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 team that helped build Blackbird Ventures' Wild Hearts. Sister shows include First Cheque, Oversubscribed and In The Blink of AI. Episodes are cross-promoted across the network.

    1 hr 8 min
  • 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/

    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.

    Sponsors:First Cheque is supported by our wonderful sponsors:

    Deel: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.

    Ready to expand your business?

    Build your global team with Deel at 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

    Brought to you by 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: 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 https://dayone.fm/peartree

    Mentioned in this episode:

    Deel x PX_Script 1

    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.

    Deel x PX_Script 2



    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/
    39 min
  • The HR Leader That Brings Therapy to Work with Isidora Torres, VP of People at Beehiiv

    Description: Welcome back to the FNDN Series, where we continue our deep dive into startup people and compensation practices with industry leaders from across the startup world. In our conversation with Isidora Torres, VP of People at Beehiiv, we explore what it truly means to bring a therapist's lens into HR — from embedding wellness into high performance culture, to building radical transparency with your CEO. Isidora shares how Beehiiv has redesigned performance reviews, structured comp cycles, and created a culture where honesty and vulnerability are championed from the top down. Stay tuned to hear how she's redefining what people operations can look like in a remote-first, high-performing startup.

    Chapters:
    00:00 Introduction and Welcome
    00:44 Startup People Summit 2026 Announcement
    01:03 Guest Introduction: Isidora Torres
    01:46 Bringing a Therapist Lens into HR
    03:34 Integrating Therapeutic Skills into Leadership Development
    05:20 Building a Management Operating System
    07:16 Defining Core Values at Beehiiv
    08:13 The Role of Wellbeing in High-Performance Culture
    09:10 Rest as Part of the Performance System
    10:33 Personal Responsibility vs. Organizational Support
    12:04 Working Remotely and Maintaining Culture
    14:04 Psychological Safety and CEO Transparency
    16:55 Building an Honest Relationship with Leadership
    19:40 How Isidora Interviewed Her CEO
    23:42 Principles for a Strong CEO-HR Relationship
    26:17 Wellness Days and Their Impact
    27:29 Decoupling Performance Reviews from Comp Reviews
    30:23 How Merit-Based Pay Still Works
    33:03 Running Four Comp Cycles a Year
    35:16 Safeguarding Honesty in Reflections
    36:22 The "Sun Shining" Channel
    39:13 The Traction Framework and Rocks System
    44:47 People Analytics and Meaningful Data
    46:35 Remote Work and Talent Philosophy
    50:47 Writing a Newsletter and Growing in Public
    55:19 Final Advice: Experiment and Ask
    56:46 Closing Remarks

    Join Startup People Summit, a one-day virtual conference designed for startup People leaders who want practical insight, honest conversations and proven approaches to scaling their People function — get your ticket here: www.startuppeoplesummit.com

    Connect with Isidora

    Visit: https://www.linkedin.com/in/torresisidora/

    Resources Mentioned

    Books Mentioned: No Rules Rules by Reed Hastings and Erin Meyer — the Netflix culture book referenced for the "sun shining" concept Traction by Gino Wickman — the framework behind Beehiiv's rocks-based goal-setting system

    Companies Mentioned: Beehiiv — remote-first startup where Isidora serves as Head of People Operations Shapes — people operating system / AI tool for people data (mentioned in mid-roll) Bridgewater Associates — referenced in discussion of radical transparency culture Morning Brew — where Beehiiv's CEO Tyler learned the Traction/rocks framework Clay — mentioned as an example of companies using coaches for employee wellbeing

    Concepts Mentioned: Sun Shining — a Slack channel practice at Beehiiv where leaders publicly acknowledge mistakes and learnings Replays — Beehiiv's version of performance reviews, decoupled from compensation Rocks — goal-setting units from the Traction framework (company, team, and individual levels) Wellness Days — monthly Fridays off at Beehiiv built into company benefits

    More FNDN Episodes:

    Spotify: https://open.spotify.com/show/4GeBIeZOKrFxG1oiiPxmiM Apple Podcast: https://podcasts.apple.com/us/podcast/fndn-series/id1794263484

    TherapyAtWork, PeopleOps, HRLeadership, StartupCulture, WellbeingAtWork, PsychologicalSafety, RemoteWork, PerformanceReviews, CompensationStrategy, StartupCompensation, HighPerformance, EmployeeWellness, PeopleOperations, MentalHealthAtWork, RadicalTransparency, StartupLeadership, FlatOrganization, EmployeeEngagement, HRNewsletter, StartupBestPractices

    58 min
  • 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

    1 hr 30 min
  • 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

    59 min
  • 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.

    Chapters
    • 0:46 — Why James launched the show, and why Batko is guest #1
    • 2:00 — The first hire has flipped: go-to-market before engineers
    • 3:49 — 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 staff
    • 14:50 — 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 game
    • 20:54 — Your first 5–10 hires: attitude over skill, hungry over proven, junior over senior
    • 25:58 — Team size, layoffs, "AI-washing", and the shrinking PM-to-engineer ratio
    • 34:55 — The one skill AI can't replace: people management
    • 48:07 — Why you still want humans in the room: inspiration, fresh eyes, first-principles
    • 51:40 — Facing the fear: lean in, automate yourself out, take the skills with you
    • 58:33 — Taste, authenticity, and experience as your real moat
    • 63:54 — Batko's playbook for any company starting now

    About the Guest

    Michael 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.

    Links
    • Michael Batko — batko.ai · LinkedIn: https://www.linkedin.com/in/batkomichael
    • James 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 team that helped build Blackbird Ventures' Wild Hearts. Sister shows include First Cheque, Oversubscribed and In The Blink of AI. Episodes are cross-promoted across the network.

    1 hr 7 min

About Day One®

From the publisher's feed

We're for founders & operators.