Day One®

Shane Chanel bet his entire life savings, $20,000, on a four-wheel drive racing app when he was 14. It wasn't his last high-conviction bet. He went on to leave a stockbroking career to build Yondr Money, a digital bank that never became a bank, survived a hostile takeover attempt from his own investor, and is now building Kobble, the infrastructure that lets almost any business launch a financial product in weeks instead of years.

He's honest about where the drive comes from: a chip on his shoulder he can't fully explain, a family that worked hard for everything, and a day in 2012 he's never spoken about publicly before this episode, the day his uncle's family was found dead and he became next of kin for his baby niece. It's the reference point, he says, for everything since. Nothing has ever felt as hard.

Shane walks through the pain points that pushed him from asset management into building a bank from scratch, why he pulled out of the banking licence process, how a chance conversation with former ANZ CEO Mike Smith became one of his best investors, and how a wall covered in Post-it notes from fellow fintech Founders became Kobble.

Stick around for the hardest lesson of all: the hostile takeover attempt from an investor who'd only just come on board, and why Shane now tells every Founder to have the uncomfortable conversations early, before you need them.

Find Shane

Shane on LinkedIn: https://www.linkedin.com/in/shanechanel/

Kobble AI: https://ai.kobble.net/

Kobble: https://kobble.net/

Yondr: https://www.yondr.money/

Join the Aussie Founders Club

The Slack community, the newsletter and everything else live here: https://www.aussiefoundersclub.com

Want to partner with Life After Launch?

Explore sponsorship and partnership opportunities at https://lifeafterlaunchpod.com/partner-with-us

Time Stamps

00:00 Cold open + welcome to Life After Launch, introducing Shane Chanel

02:54 From wanting to be an aeronautical engineer to financial planning and stockbroking

08:35 Identity, the chip on the shoulder, and working twice as hard

16:51 Betting his life savings on a racing app at 14, and the idea for a bank

25:53 Building Yondr, pulling out of the banking licence, and landing Mike Smith as an investor

38:48 The 2012 story: his uncle's family found dead, and the reminder that nothing will ever be this hard

45:27 Acquiring Shouta and building Kobble from a wall of Post-it notes

53:50 Kobble AI: prototyping a financial product in 15 minutes

1:02:09 Life lesson: the hostile takeover attempt, and why you should always do the prenup

1:05:12 Closing thoughts + outro

Charles Hudson of Precursor Ventures has built one of the most ambitious solo GP models in venture capital: around 450 investments over the last decade, with a 14-person team supporting a single investment decision-maker.

In this episode of First Cheque, Charles joins Maxine and Cheryl to unpack what it really takes to build and scale a solo GP fund, why he believes partnership dynamics can be one of the biggest risks in venture, and how he thinks about delivering value to hundreds of founders without trying to be everything to everyone.

They dive deep into Charles’ philosophy on trust versus likability, why the best investors sometimes need to tell founders things they really don't want to hear, and how brutal honesty can become one of the most valuable forms of founder support. Charles also shares his approach to identifying “underappreciated” founders, why he looks for people who opt into chaos, and what he learned from backing founders who weren't necessarily great employees.

Charles reflects on leaving a safe, highly compensated investing job to start Precursor, investing internationally before it was fashionable, why themes can kill returns, and the importance of being early to categories rather than piling into them once everyone else has arrived.

00:00 – Intro

03:05 – Charles’ first investment: buying ExxonMobil in high school

06:15 – What exactly is a solo GP?

07:37 – The surprising benefits of having one decision-maker

10:28 – The problem with orphaned portfolio companies

13:04 – Why solo GPs need to be intentional about founder relationships

15:44 – How the “product” of Precursor evolved

18:00 – Building trust, setting expectations, and knowing when to step back

20:32 – Why honest feedback matters more than being liked

23:40 – “It’s you”: giving founders brutally honest feedback

25:52 – Trust is a bank account

27:47 – Likability vs. trustability in venture capital

30:58 – Why Charles backs founders who opt into chaos

33:36 – What makes a great first-time CEO?

36:39 – How Precursor started investing globally

40:08 – Investing internationally and convincing LPs afterwards

41:15 – Why themes can kill returns

44:12 – Finding venture-scale opportunities outside traditional software

45:16 – The challenge of managing 450 investments

47:52 – Being a “surgeon” investor: showing up when it matters most

52:04 – Charles’ biggest leap: leaving Uncork to start Precursor

53:40 – “You pay money to go to work?”

55:00 – Why Charles chose to make going back impossible

56:31 – Outro

Precursor Ventures - https://precursorvc.com/

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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

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Mentioned in this episode:

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.

Deel x PX_Script 1

Deel x PX_Script 2

Australia hasn't built a new steel mill in more than 30 years. Greensteel Australia is about to — a $500 million all-electric plant on the old BHP site at Mayfield, producing 600,000 tonnes of rebar a year from the first quarter of 2028. Patrick Buchan, Greensteel's Head of Government Relations, joins James MacDonald on the Danieli technology being built in Italy right now, the policy shift that made onshore steel viable again, why Newcastle beat the rest of the country for the site, and what 200 jobs means for the Hunter.

In this episode:

• The $500 million investment and what it buys — an all-electric mill on Industrial Drive at Mayfield North, the site BHP ran until 1999.
• Why the technology is the story: an electric arc furnace running at around 1,000 degrees, supplied by Danieli of Italy. "No gas, no flame, no chimneys."
• 600,000 tonnes of rebar a year — the critical input to Australian construction and housing — with a growth path into other steel products.
• The policy shift: faster approvals, Future Made in Australia incentives, and why both the federal and NSW governments moved.
• Sovereignty as the argument — oil, steel and microprocessors as the three inputs a country of 28 million can't afford to import.
• How Greensteel started: owners Meena and Romana Ibrahim couldn't get rebar for their own construction businesses through COVID, so they built a steel company.
• Why Mayfield — buildings long enough for a 400-metre rolling line, rail, power and roads, and an intergenerational steel skill base.
• The jobs: 200 direct roles, recruitment opening early 2027, Danieli training included, and no formal-qualification barrier.
• What's next — a stage two in advanced discussions for another New South Wales site, and a ground-breaking with "a very notable political figure."

Patrick Buchan is Head of Government Relations at Greensteel Australia, the company building a $500 million all-electric steel mill at Mayfield in Newcastle — Australia's first new steel plant in more than three decades. Before Greensteel he spent four years on the policy staff of the US Office of the Secretary of Defense at the Pentagon, across the Obama and first Trump administrations.

Greensteel opens recruitment for the Newcastle mill in early 2027. Patrick Buchan on LinkedIn: linkedin.com/in/patrick-buchan-56830b124

Chapters

0:00 Cold open

1:03 Welcome to Engineering in the Hunter

1:56 Patrick's path from Canberra to Greensteel

3:24 Four years inside the Pentagon

6:01 How Australian policy made this possible

9:21 The 600,000-tonne rebar plan

10:27 Inside the new steelmaking technology

14:01 The politics behind the comeback

18:43 How Greensteel Australia got started

20:29 Greensteel signs the deal

21:05 Why Mayfield, Newcastle won the site

21:56 Balancing tradition and renewables

23:34 The road to 2028

24:06 200 jobs and an open call for workers

26:38 The $500 million investment, by the numbers

27:19 How Newcastle is already talking about it

28:22 Sovereign manufacturing and sustainability

29:48 Australia's first steel plant in 30 years

31:39 The trend back to trades

32:40 What's next: stage two

35:35 On founders and entrepreneurship

36:57 On risk, reward, and having a crack

38:16 A story about his dad and the cricket

39:45 Wrapping up

Engineering in the Hunter is hosted by Melinda Sietsma with NTP Talent founder James MacDonald. James hosts this episode. Learn more at ntptalent.com.au.

Engineering in the Hunter 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.

For a decade, Elon Musk was the face of the modern entrepreneur: a self-made billionaire who bet his fortune on impossible ideas and somehow made them work.

SpaceX made reusable rockets a reality. Tesla helped turn electric cars into a global phenomenon. He became one of the most admired and influential figures in technology.

So what happened?

In this episode of In the Blink of AI, Georgie Healy traces Musk’s journey from bullied South African kid and PayPal millionaire to the man behind Tesla, SpaceX, Starlink, X, xAI and more. Along the way, we explore the moments that transformed his public image: the Tesla “funding secured” controversy, his increasingly combative behavior online, his influence over Starlink during the war in Ukraine, his takeover of Twitter, his political rise alongside Donald Trump, and the controversies surrounding Grok.

But this isn’t simply a takedown.

Using the 4Gs framework, Georgie asks the harder question: Was Elon Musk actually a genius, or was he simply in the right place at the right time?

The answer is more complicated than either side might want to admit.

Because Musk may genuinely have helped solve some of the hardest engineering problems of our time. But does extraordinary capability excuse harmful behaviour?

You be the judge.

CHAPTERS

00:00 Elon Musk: From the World’s Most Admired Entrepreneur to the Most Controversial

02:08 Growing Up in South Africa: Bullying, Obsession, and Early Signs of Genius

02:57 Leaving South Africa and Building His First Tech Ventures

04:26 Zip2: Musk’s First Major Exit and the $307 Million Sale

04:38 X.com, PayPal, and the Power Struggle That Ousted Musk

05:26 The PayPal Mafia and the Fortune That Funded Musk’s Next Bets

07:40 SpaceX and Tesla: Betting His Fortune on Impossible Ideas

08:09 Falcon 1’s Historic Launch and SpaceX’s Near-Death Experience

08:50 Tesla’s Rise and the Revolution of Electric Cars

10:28 Peak Elon: SpaceX, Tesla, Neuralink, and the Golden Years

11:06 How Much Did Elon Musk Actually Build? The Founder Debate

12:27 The Iron Man Myth and the People Behind Musk’s Companies

13:26 2018: The Year Elon Musk’s Public Image Changed

13:50 The “Funding Secured” Tweet and Tesla’s SEC Battle

15:10 The Thailand Cave Rescue and the “Pedo Guy” Controversy

15:45 Joe Rogan, Marijuana, and Musk’s Growing Pattern of Controversy

18:18 Starlink in Ukraine: When a Private Company Controls Wartime Infrastructure

19:17 Musk, Crimea, and the Limits of Private Power

20:47 Why Starlink May Be Musk’s Biggest Governance Problem

21:07 Buying Twitter for $44 Billion and Taking Over the Platform

22:00 Mass Layoffs, Free Speech Absolutism, and the Birth of X

23:43 Hate Speech, the Great Replacement Theory, and the Advertiser Exodus

25:13 The Case Against Musk’s Version of Free Speech

27:11 Musk Enters Politics and Becomes Trump’s Biggest Donor

28:02 DOGE, the Controversial Gesture, and Musk’s Growing Political Influence

28:44 Tesla Protests, DOGE’s Promised Savings, and the Fallout

30:58 Musk vs. Trump: From Political Alliance to Public Feud

31:16 xAI and Grok: Musk’s Vision for an “Anti-Woke” AI

32:08 Grok’s Hitler Controversy and the Rise of “Spicy Mode”

33:46 AI Safety, Non-Consensual Images, and the Cost of Unrestricted AI

35:00 The Expanding Musk Empire: SpaceX, Starlink, X, xAI, Tesla, and More

36:28 The 4 Gs: Is Elon Musk a Grown-Up, Genius, or Something Else?

36:49 Why Musk Fails the “Grown-Up” and “Gravitas” Tests

39:00 Genius vs. Accountability: What Musk Actually Changed

40:00 The Final Verdict: Genius Without a Hall Pass

One in three people will experience a mental health disorder in their lifetime, PTSD went more than 20 years without a new approved treatment, and spending keeps rising while outcomes keep getting worse. Against that backdrop, Australia has become the first country in the world where psychiatrists can prescribe MDMA and psilocybin.

In this episode, host Emily Casey sits down with Dr Michael Winlo, Chief Scientific Officer at Emyria, the company behind the Empax network of psychedelic-assisted therapy clinics. Michael trained as a doctor, spent four years in Palantir's healthcare team in Silicon Valley, then returned to Perth to run a clinical trial site — an experience that convinced him care delivery and evidence generation belong together, and led to Emyria.

Michael explains how the two legal treatments actually work. MDMA floods the brain with serotonin and oxytocin, quietens an overactive amygdala and lets patients with post-traumatic stress disorder work through trauma in therapy without being overwhelmed by fear or shame. Psilocybin quietens the default mode network behind rumination and negative self-talk — Michael's metaphor is shaking up a snow globe and letting the snow settle into new patterns — and both drugs open a roughly seven-day window of heightened neuroplasticity that therapy can use.

The pair trace the strange history that got us here: MDMA first synthesised by Merck in 1912, psychedelics on the cover of psychiatry journals in the 1960s, roughly 500,000 people given MDMA in therapeutic settings before the war on drugs shut the research down. Charitable funding through MAPS kept the science alive, and the resulting phase 2 and 3 trials left the TGA unable to maintain that these drugs had no therapeutic value — leading to the world-first rescheduling in 2023.

Michael then walks through what treatment at an Empax clinic involves: careful screening, a two-therapist dyad that stays with the patient for the whole journey, six-to-eight-hour dosing days in a low-stimulus room, and integration sessions that turn insights into durable habits. Emyria has now treated more than 100 patients, with rapid improvement that appears durable for most — results that have brought funders like Medibank and the Department of Veterans' Affairs on board.

The conversation closes on what it will take to make this mainstream: health-economic evidence for a treatment that costs around $10,000 a dosing cycle, the watershed of a first FDA approval, more sensible regulation of who can deliver therapy, and the infrastructure and training to meet demand. Michael argues psychedelics are still under-hyped — used today as a last resort when they may do the most good earlier in a patient's journey — and leaves clinicians with one message: learn with your patients.

Dr Michael Winlo is Chief Scientific Officer at Emyria, the ASX-listed company behind the Empax network of psychedelic-assisted therapy clinics, treating post-traumatic stress disorder and treatment-resistant depression under the TGA's Authorised Prescriber Scheme. Trained as a medical doctor, he spent four years in Palantir's healthcare team in Silicon Valley and led Perth's Linear Clinical Research before joining Emyria to build a model of care that treats patients and generates evidence at the same time.

00:00 Psychedelics return to healthcare

00:57 What Emyria and the Empax clinics do

02:08 From medicine to Palantir and back to Perth

08:32 Why mental health care is falling behind

12:37 What psychedelics actually are

13:55 How MDMA-assisted therapy works

17:44 Psilocybin and the default mode network

21:05 A century of history: from Merck to the war on drugs

24:18 The revival: MAPS, new trials and Australia's rescheduling

27:17 Why psychiatry innovates slowly

29:47 Inside treatment: screening, dosing days and integration

33:33 The data so far: 100+ patients, Medibank and the DVA

35:18 Ketamine and the coming wave of new treatments

36:47 FDA approval and the funding shift

43:30 Emyria's ten-year vision

45:47 Bottlenecks: training, regulation and infrastructure

47:31 Psychedelic therapy in 2035

49:09 Rapid fire: hype, books and one message for clinicians

Emyria: https://emyria.com/

Empax Centre: https://empaxcentre.com/

TGA — re-scheduling of psilocybin and MDMA, questions and answers: https://www.tga.gov.au/resources/publication/scheduling-decisions-final/notice-final-decision-amend-or-not-amend-current-poisons-standard-june-2022-acms-38-psilocybine-and-mdma/re-scheduling-psilocybin-and-mdma-poisons-standard-questions-and-answers

MAPS (Multidisciplinary Association for Psychedelic Studies): https://maps.org/

COMPASS Pathways: https://compasspathway.com/

The Beginning of Infinity by David Deutsch: https://en.wikipedia.org/wiki/The_Beginning_of_Infinity

Moonshots with Peter Diamandis: https://www.diamandis.com/podcast

Emily Casey is the founder of What the Health and host of the show, making major developments in health technology and innovation easier to understand.

What the Health is brought to you in partnership with Tenmile Ventures.

What the Health is part of Day One Network, the podcast and media network from W2D1 Media: https://dayone.fm/

When his co-founder announced she was going on maternity leave, Airguides co-founder Paul Rowsthorn realised he was about to lose the operational knowledge holding his tourism business together. So he set out to replace it — not with a hire, but with an AI agent.

Paul Rowsthorn, co-founder of Airguides and co-founder of AI installation company HubMind, joins Zachary King to show how that agent, Amelia, ended up running far more than he expected: performance marketing, external agency management, staff training, and Airguides' entire product-launch process.

Rowsthorn describes deciding early on to build one "super-agent" rather than a network of specialised bots, after reading advice warning that multiple agents lose context talking to each other. Amelia — who Rowsthorn treats and pitches as a co-founder in her own right — spawns sub-agents as needed but keeps one continuous memory of the business.

On screen, Rowsthorn walks through Amelia researching Meta's Ad Library for top-performing ads from similarly priced tourism operators, pulling in Airguides' brand voice, and assembling a ready-to-run ad set in Airtable, then messaging the external agency directly without Rowsthorn writing a report or reviewing a deck first. A similar pipeline rebuilt Airguides' product-launch process: work that used to take two to four weeks and a $500-a-month SaaS subscription now moves from brief to a live, branded Shopify listing in about a day.

Rowsthorn is careful to describe this as management by exception rather than removing humans from the loop — he and his staff still review Amelia's output, more so early on than now. He shares an early misstep where Amelia sent a client an email he hadn't approved, and the guardrail he built afterward: full autonomy inside his own company, far more caution with client work at HubMind.

That gap between confident enough to hand off more and not confident enough to remove review is the same thing Rowsthorn now sells. He and co-founders Chad and Rich started HubMind to compress the roughly seven months it took him to get Amelia working into a matter of weeks for other CEOs — installing what he calls a "company brain," one operational problem at a time.

Paul Rowsthorn is co-founder of Airguides, a tourism company that partners with wildlife and adventure photographers on trips around the world, and co-founder of HubMind, which installs AI systems for CEOs of small and mid-sized businesses.

Chapters:

00:00 Cold open: the moment Amelia earned her seat

00:34 Welcome to Operator AI

01:25 Airguides, and the problem Amelia was built to solve

03:44 Meet Amelia: one super-agent, not a swarm

07:15 Training Amelia into repeatable skills

08:39 Handing external agencies straight to Amelia

09:58 Cracking tourism's lead-attribution problem

12:38 The first OpenClaw win: automated agency reporting

14:53 The founder unlock: training staff instead of gatekeeping

18:58 Ad creative at scale: from ad-library research to a ready ad set

23:39 From three-week product launches to one day

27:02 Under the hood: hardware, model switches, and near-quitting

34:16 Founding HubMind to install this for other CEOs

41:22 Rapid fire, alpha sources, and advice for getting started

Links and resources:

Paul Rowsthorn: https://au.linkedin.com/in/paul-rowsthorn

Airguides: https://airguides.com

OpenClaw: https://openclaw.ai

About the host: Zachary King is the founder of Works, where he installs AI into how Australian companies operate. He has worked at the commercial pointy end of AI for almost twenty years and runs his own company largely from the command line.

About the show: Operator AI is the show where real operators open their screens and show exactly how they run the real parts of their business with AI. The real stack, not the hype.

If you want AI installed into how your business actually operates, learn more at https://workshq.com.au/ or book a time with Zachary King at https://savvycal.com/Zachary-King/zac-at-works-30

Operator AI is part of Day One Network, the podcast and media network from W2D1 Media: https://dayone.fm/

Eight guests into Building Tech Teams, one theme has shown up in every single episode: money. A principal software engineer who now manages a team of agents asks what he should be paid, and nobody in the room has a clean answer. AI has changed what one person can produce, and salaries have come off the rails behind it.

In this best-of episode, James MacDonald pulls together the sharpest thinking on compensation from five of his first eight guests. Nathan Hill, Head of Telco at AWS, on the question nobody can answer yet. Adam Witanowski with the real numbers from a live job hunt: nine companies, seven offers, US startups paying US$450–500k base against comparable local roles at $220k. Claudia Barriga-Larriviere on whether AI is making teams more productive or just faster. Matt McFarlane, founder of FNDN, on token costs eating into the people budget. And Cloe Stanbridge, Talent Lead at Airtree, on the moment a big cheque is actually worth it.

It adds up to a state of play for the Australian market on AI-era pay: why the gap with the US is structural (no hyperscalers, startup funding a tenth the size, enterprises that still think engineers are too expensive), why almost nobody is measuring the productivity gains they are paying for, what happens when ten people run five thousand agents, and why the cheapest move in the whole budget discussion is the raise nobody asked for.

CHAPTERS

0:00 - Cold open: what should a 10x engineer be paid?

0:19 - Nathan Hill: quantifying what AI is actually worth

1:05 - Million-dollar salaries as a bet on future ROI

1:28 - Adam Witanowski: nine companies, seven offers, real numbers

2:35 - US$500k in the US vs $220k here: which one would you choose?

3:50 - Why the gap is structural: funding, hyperscalers, enterprise mindset

5:37 - Claudia Barriga-Larriviere: more productive, or just faster?

6:15 - "What you don't measure, you can't change"

7:26 - Matt McFarlane: the jump is too big, because you've been underpaying

8:32 - Tokens are eating the people budget

9:55 - Ten people plus 5,000 agents: whose budget line?

11:00 - Where token costs land, and the on-cost of humans

13:01 - Leaderboards reward consumption, not value

13:31 - Cloe Stanbridge: when the big cheque is worth it, and when it isn't

15:06 - Salary bands have to enable the business

16:26 - Replacement value: getting ahead of the market

16:58 - The raise nobody asked for

ABOUT THE GUESTS

Nathan Hill is Head of Telco at AWS (episode 3). Adam Witanowski is an AI Architect, previously at NIB (episode 7). Claudia Barriga-Larriviere is a People & Culture leader at Startup Flamingo (episode 4). Cloe Stanbridge is Talent Lead at Airtree (episode 6). Matt McFarlane is the Founder and Director of FNDN, a compensation consultancy helping startups and scaling tech companies build pay practices that are clear, fair and competitive (episode 8). The full conversations with all five are in the feed.

LINKS

Nathan Hill, AWS

LinkedIn: https://www.linkedin.com/in/nathanrhill

Claudia Barriga-Larriviere, Startup Flamingo

LinkedIn: https://www.linkedin.com/in/claudiabl

Site: https://startupflamingo.com

Cloe Stanbridge, Airtree

LinkedIn: https://www.linkedin.com/in/cloestanbridge/

Adam Witanowski

linkedIn: https://www.linkedin.com/in/witanowski/

Matt McFarlane, FNDN

LinkedIn: https://www.linkedin.com/in/matthewmcfarlane/

Site: https://www.fndn.com.au/

James MacDonald, NTP Talent

LinkedIn: https://www.linkedin.com/in/jamesmacdonaldau/

Site: https://ntptalent.com.au

James's newsletter, Headcount and Code, lands every Wednesday on Substack.

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 who 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

Pick My Brain is supported by our wonderful sponsors:

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Episode Summary

Travellers can spend 15 hours over two months planning a holiday, then arrive with a messy spreadsheet, a graveyard of email confirmations and a screen full of Google Maps pins. Billy Chan and his co-founder built Alfred Travel to turn that fragmented process into a personalised, mobile itinerary travellers can edit, validate and book.

Alfred Travel had passed 1,300 users when Billy joined Pick My Brain. The company had closed a $250,000 pre-seed round and was preparing to raise $500,000 at a $5 million cap after reaching 15,000 users. Alan Jones puts on his investor hat to stress-test the story — and immediately finds the buzzword getting in its way.

They explore why “AI-powered” no longer earns points in a pitch, how Billy can teach investors something they do not already know about travel, and why a low-margin travel business has to think globally from day one. They also tackle geopolitical uncertainty, capital planning, affiliate economics and why Alfred's proposed loyalty token belongs in horizon two, after the company has built meaningful scale.

Time Stamps

00:00 – The buzzwords investors are tired of hearing

00:59 – Welcome to Pick My Brain

01:51 – Meet Billy Chan and Alfred Travel

02:18 – From curious kid to technology founder

03:49 – The 15-hour holiday-planning problem

05:13 – How Alfred Travel makes money

05:40 – The founding team and a ten-year-old idea

07:01 – Why Alfred is a native mobile app

08:08 – Early traction and the ideal customer

09:24 – Personalisation without hallucinations

12:51 – Closing the booking loop

14:12 – The affiliate revenue problem

15:20 – The $500,000 seed-round plan

16:37 – Why “AI-powered” weakens the pitch

23:06 – Addressing global travel uncertainty

27:18 – Building a global company from day one

28:58 – Teach investors something they do not know

32:32 – Why this business cannot be cautious about growth

34:13 – Escaping the Australian launchpad mindset

36:57 – Loyalty tokens and the horizon-two trap

40:12 – Wrap-up

Resources

- Alfred Travel – https://www.alfredtravel.io/

- Billy Chan on LinkedIn – https://au.linkedin.com/in/billy-chan-4527818b

- Ask Alan a Question – https://speakpipe.com/pickmybrain

- More from Alan Jones – https://www.startupfoundercoach.com

About Pick My Brain

Pick My Brain is a Day One show hosted by startup founder coach and investor Alan Jones.

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2

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

In our conversation with Hallie Condon, VP of People at Chili Piper, we unpack what it actually looks like to build AI deep into a people function. We dive into how her small team decides what to automate and what to keep human, the "company brain" she built so institutional knowledge doesn't walk out the door when someone leaves, and the surprising shift in context she's losing now that employees go to AI before they come to the people team. We also get into her sharpest take of all: why the traditional promotion path expects people to do the job for free before anyone will pay them for it. Keep watching to hear how AI is reshaping people operations, performance reviews, and the employer-employee relationship.

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 



Chapters:
00:46 Guest Introduction: Hallie Condon, VP of People at Chili Piper
01:58 Managing a Fully Remote Team Across 36 Countries
04:07 How AI Shows Up in the People Function Day-to-Day
05:19 Automating Separation Letters and Admin Work
06:56 Using AI to Cross-Check Budgets Fairly
08:31 No Clean Strategy: Automating as Problems Come Up
10:29 The Tiered System: What Should and Shouldn't Be Automated
13:53 Introducing "Company Brain": Chili Piper's AI Knowledge Repo
16:03 Skills Library and Role-Based Onboarding
17:56 How Decision Memos Get Documented and Indexed
19:37 Company Brain and Reducing Attrition Risk
21:47 Fewer Conversations: Are People Going to AI Instead of HR?
23:20 Balancing Context-Gathering with Employee Trust
26:14 What the Memory System Deliberately Doesn't Retain
28:14 More Time for Deep Work, Fewer Casual Check-Ins
29:43 What Companies Got Wrong with AI-Driven Layoffs
32:36 The Breaking of the Employee-Employer Bargain
36:07 Gen Z, Boundaries, and the "Do the Job for Free First" Problem
39:01 Rethinking How Companies Assess Impact and Potential
40:04 Chili Piper's Approach: Promoting Early, Pay Range Transparency
42:06 Why People Managers Don't Get Paid More at Chili Piper
45:43 Introducing the "Impact Intelligence" Tool
50:30 Building Performance Principles with AI's Help
51:33 Final Advice: Get Curious About AI and Rethink Reciprocity

Connect with Hallie

Visit: chilipiper.com
https://www.linkedin.com/in/hallie-condon-0b181325/ 

Resources Mentioned

Company Mentioned:

Chili Piper - B2B SaaS company where Hallie is VP of People, with ~150 employees across 36 countries
Oyster - Global employment/compliance platform Hallie credits for managing their distributed workforce
Claude - AI assistant used to power Chili Piper's "Company Brain" and impact intelligence tools
Granola - Meeting notes tool Hallie uses to capture context from conversations

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

Paloma Newton is the founder of Elita, a longevity platform for dogs that combines biological testing, clinical history, and the changes owners notice day to day into one picture of how a dog is ageing. She built it backwards by most startup standards, a stem cell bank before a product, years of science before a single marketing push, all under one rule: don't promise more than the platform can back up.

On this episode, Paloma brings that same rigor to two of the week's biggest AI headlines. She explains why South Australia's $3 million Royal Commission into AI is aimed at the wrong problem, and makes the sharper case that most of our anxiety about AI isn't really about the technology at all, it's about trust in who controls it. She also gets into the Jevons Paradox and why AI was never going to hand us more free time, her own weekly system for separating real output from busywork, and why she thinks women stepping back from AI over ethical concerns is a bigger loss than it looks.

Plus, the origin story behind Elita, starting with her dog Edgar's breed health scan, and a closing surprise guest who may or may not understand what a podcast is.

Whether you're building, funding, or just trying to make sense of the AI news cycle, this one's worth the full listen.

CHAPTERS

00:00 Cold open

01:10 Welcome & episode preview

02:14 Sponsor: Deel

02:40 AI hack of the week: the self-updating Slack to-do list

04:01 What is Elita

04:51 Headline: South Australia's $3M AI Royal Commission

11:31 Headline: Does AI actually give us more free time

14:58 Sponsor: Deel

18:29 The Elita origin story: Edgar, stem cells, and building backwards

25:35 Pet longevity vs. human longevity

32:18 Holding AI's promise and its doom and gloom at once

40:52 The AI-designed cancer vaccine that started with one dog

45:06 Why women opting out of AI should worry everyone

50:01 Rapid fire

53:23 What Australia does best in AI and deep tech

55:46 A very special guest