Day One®

Watch this space.

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

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.

Weekly Substack: https://georgiehealy.substack.com/

Linkedin: https://www.linkedin.com/in/georginahealy/

Instagram: https://www.instagram.com/georginahealytech/

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

Mentioned in this episode:

Deel x PX_Post Intro

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

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

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:

Deel x PX_Script 2

Deel x PX_Script 1

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.

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.

00:00 - 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

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

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

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

Brought to you by Deel. Founders scale faster on Deel — set up payroll in any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Learn more at https://deel.com/dayone

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2

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.

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.

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.

Weekly Substack: https://georgiehealy.substack.com/

Linkedin: https://www.linkedin.com/in/georginahealy/

Instagram: https://www.instagram.com/georginahealytech/

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

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.

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Mentioned in this episode:

Deel x PX_Script 1

Day One sting

Deel x PX_Script 2

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/

Description: Welcome back to the FNDN Series, where we continue our deep dive into startup compensation with industry leaders from across the startup world. In our conversation with Shani Brisilovsky, AI Product Lead at Shapes and behavioral economics researcher, we explore how AI is fundamentally reshaping the HR function — from automating admin-heavy processes to positioning people teams as the drivers of organization-wide AI transformation. We dig into the shortcomings of legacy HRIS platforms, the rise of agentic AI in people operations, and why the future of HR is less about rigid calendars and more about real-time, human-centered decision-making. Stick around to hear Shani's advice on how people leaders can get ahead of the curve before it's too late.

Chapters:

00:00 Welcome to the FNDN Series
00:44 Guest Introduction: Shani Brisilovsky
01:37 Keeping Up with AI's Rapid Pace of Change
03:34 How a Behavioral Economics Master's Informs AI Thinking
05:21 The Evolving Role of HR in the Age of AI
06:39 HR as the Driver of AI Transformation: The Atlassian Example
08:22 Challenges of Leading Transformative Organizational Change
09:30 Moving from Rigid HR Cadences to Real-Time Processes
13:35 Preserving the Human Element Amid Automation
14:17 Lessons from Healthcare: Freeing Up Time for What Matters
18:09 The Emergency Room Story: Human Connection Throughout the Process
20:10 Where Current HRIS Systems Are Falling Short
24:50 Agentic AI and How Shapes Is Building for the Future
30:32 Addressing AI Concerns: Privacy, Security, and Hallucinations
32:33 Vibe Feature Demo: Generating Salary Bands with a Single Prompt
33:44 Advice for People Leaders: Start Now, Don't Wait
35:14 Closing Remarks

Connect with Shani

Visit: https://shapes.co/

https://www.linkedin.com/in/shanibrusi/

Resources Mentioned

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 

Companies & Organisations Mentioned: Shapes — AI-native HRIS platform where Shani serves as AI Product Lead

MIT AHA (Advanced Humans with AI) Research Center — Research hub studying how people interact with AI tools; conferences available online

Atlassian — Notable example of a company placing AI transformation under its HR/People team

Zapier — Another example where the Chief People Officer took ownership of AI transformation

Anthropic — Recommended by Shani as a direct, high-quality source for learning how AI is being built and used

A16z — Published the article Workday's Last Workday, referenced in the discussion on legacy HRIS limitations  

More FNDN Episodes:

Spotify: https://open.spotify.com/show/4GeBIeZOKrFxG1oiiPxmiM

Apple Podcast: https://podcasts.apple.com/us/podcast/fndn-series/id1794263484

AIinHR, FutureOfWork, HRTechnology, PeopleOperations, BehavioralEconomics, AgenticAI, HRISPlatforms, StartupCompensation, HRLeadership, AITransformation, PeopleTeams, WorkplaceInnovation, HRAutomation, StartupCulture, CompensationStrategy, RealTimeHR, HumanCenteredAI, EmployeeExperience, TalentManagement, StartupBestPractices

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

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

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

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.

00:00 – 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

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

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.