First Cheque with Cheryl Mack & Maxine Minter

Episode Summary

Blackbird partner Tom has spent the last decade obsessing over one thing: why Australia talks about innovation from a place of doubt, while the US talks about it from a place of opportunity.

From buying BHP as a kid through his parents, to operating at Canopy before it was acquired, to spending most of the 2010s investing out of Colorado and now back in Australia at Blackbird, Tom has seen both sides of the talent arbitrage.

In this episode of First Cheque, Tom joins Maxine and Cheryl to share why 8 percent of all AI experts in Asia-Pac are based in Australia, why we have more AI PhDs than any other country in the world and why no one is celebrating it, and what it really means that 88 percent of our PhD students are immigrated talent. They also dive deep into why commercialization is still broken, how Foundry and Baker Street are trying to fix the bridge from lab to seed, and why product-led growth is not dead — it just changed.

Tom also reflects on the boomerang effect, the R and D tax credit as Australia's secret weapon, and why the next decade of Australian companies will be built with a base in Australia and a base on the West Coast.

Time Stamps

00:00:00 - Intro: Doubt versus opportunity

00:01:12 - Hey, I'm Cheryl. I'm Maxine. This is First Cheque

00:03:45 - What was the first thing you ever invested in? BHP and the Canva vs BHP math

00:05:51 - Invest early and hold: learning compounding from his parents

00:06:52 - Invest America: what happens when every kid gets $1,000 to compound until 18

00:08:14 - Robinhood, retail, and the new CEO playbook

00:11:02 - Why aren't we more excited about Australia? The AFR talent piece

00:12:29 - 8 percent of Asia-Pac AI experts are in Australia and we have 6 of the top 100 AI universities

00:13:59 - The output story: 6 foundational models trained in Australia, Leonardo at number 5 globally

00:16:52 - Why Australia builds global-first: Heidi and Leonardo are 90 percent offshore revenue

00:18:20 - The cost of not celebrating: US pre-seed up 70 percent, Australia going backwards

00:20:33 - Capital constrained but the most capital efficient market in the world

00:21:31 - Sourcing from universities: the good and the bad

00:23:20 - Why we are last on the OECD for commercialization: Google Maps, Wi-Fi, and Bluey

00:25:10 - What is working: UNSW 10x, Melbourne NextGen, and defence tech accelerators

00:27:28 - Baker Street and the rise of alumni syndicates

00:28:40 - Foundry: building the bridge from lab to seed round

00:30:18 - What this means for your average angel investor

00:30:42 - Grading Australian talent: from C minus to B minus

00:31:16 - Two types of AI talent: engineering versus research PhDs

00:32:54 - The boomerang effect: Jesse Clark and why top researchers will come back

00:33:41 - The Australia plus US operating model and the 14-hour flight

00:35:13 - Talent arbitrage and the 43 cent R and D secret weapon

00:36:45 - Do you take a talent haircut outside the Bay Area? No.

00:39:18 - Is product-led growth out of vogue? 2019 to 2021 and why Australia got so good at it

00:41:14 - What PLG actually is: methodology, not freemium

00:44:15 - AI agents in the sales funnel and why go-to-market feels stale

00:46:15 - Back to the Stone Ages: brand, community, podcasts, and in-person events

00:49:47 - Building in public, hype cycles, and Manus AI

00:51:20 - Why enterprise is coming earlier: 2023 consumer AI, 2024 prosumer AI, 2025 enterprise AI

00:53:18 - Single-player versus multiplayer mode: why AI changes the buyer

00:57:48 - Palantir, CrowdStrike, and when enterprise motion makes sense

00:59:20 - What does a capital-starved ecosystem mean for enterprise go-to-market

01:00:38 - Biggest big cojones moment: 3 boys under 6 with a founder CEO wife

Resources

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

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

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 FC_Script 01 - Sep 2026

Deel x FC_Script 02 - Sep 2026

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/

Episode Summary

“It’s not a fit.” “You’re too early.” “Let’s have one more meeting.” “We’re still building conviction.” If you’ve ever walked out of an investor meeting wondering what the hell any of that actually meant, this episode is for you.

In this episode of First Cheque, Cheryl and Maxine decode the language of venture capital — from fundraising and negotiations to what happens once an investor is on your cap table. They unpack what investors might really mean when they say you’re too early (or somehow too far along), why “one more meeting” can be a sign they’re sitting on the fence, and when “keep us in the loop” is actually just a polite no.

They also get into the weird world of VC jargon — including “conviction”, “due dilly”, “foundies”, “bridgie” and the ever-popular “let the lawyers sort it out”.

Once the cheque has landed, they unpack what it really means when investors ask for an update, start asking about runway and burn, want to see revenue hit a certain milestone, or suddenly ask, “How’s it going with X?” They also talk about why regular communication matters, even when things aren’t going well.

The big lesson? Founders shouldn’t have to speak fluent VC — and investors could probably do a much better job of explaining themselves.

Time Stamps

00:00 – Intro: Welcome to VC Gibberish

01:20 – “It’s not a fit for us”: what does that actually mean?

03:05 – Is it the company, the stage… or the founder?

05:00 – The value of asking for honest feedback

06:03 – Investors could be clearer too

07:09 – “You’re too early”: is it really a no?

08:45 – What “too far along” actually means

11:05 – “Let’s have one more meeting”

11:59 – Why investors ghost

13:23 – Sitting on the fence and waiting for FOMO

15:00 – “We’re discussing internally” and what happens inside a VC

16:41 – When a slow process means you’re not a priority

17:08 – Why the “momentum raise” is dead

18:35 – The dangers of a June 30 deadline

20:16 – What investors mean by “conviction”

23:17 – “Keep us in the loop”: the polite no

24:59 – When investors want to stay close for the next round

25:28 – “Let us know when you have a lead”

26:16 – When investors simply don’t have the capital

27:16 – Negotiating the deal: welcome to the jargon

28:23 – “Val”, “do dilly” and other questionable VC vocabulary

30:03 – Information rights vs. investor updates

32:01 – Foundies, Cindy and Bridgie

32:47 – ESIC, ESVCLP and other acronyms

33:40 – “Let the lawyers sort it out”

35:50 – The strange two-week period when founders and investors aren’t on the same side

36:38 – Once they’re on the cap table

36:45 – “Can we get an update?”

38:09 – What investors really mean when they ask about runway

39:05 – Why you should update investors when things aren’t going well

41:26 – When investors don’t want to lead or follow your next round

42:40 – “Get to this revenue number and then we’ll talk”

43:37 – The moving goalposts of investor benchmarks

44:21 – How to benchmark against the best companies instead

45:15 – “How’s it going with X?”

46:23 – Ask why before you answer

47:03 – Please send us your VC gibberish

47:50 – Outro

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

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

Deel x FC_Script 01 - Sep 2026

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 FC_Script 02 - Sep 2026

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/

Episode Summary

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.

Time Stamps

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

Resources

Precursor Ventures - https://precursorvc.com/

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

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

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 1

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/

Episode Summary

Sidecars have gone mainstream. Once something mostly associated with larger venture funds, they’re now increasingly common in Australia, with emerging managers using them alongside their first funds and sophisticated LPs increasingly expecting access to them.

But what exactly is a sidecar, and why would you use one instead of simply investing directly?

In this episode of First Track, Cheryl and Maxine break down sidecars from the ground up: how they differ from co-investments, why LPs use them to double down on companies they’re excited about, and how lower fees and carry can make them attractive to larger investors.

They also unpack the less obvious reasons fund managers use sidecars—from getting more capital into high-conviction companies and giving venture-curious investors a way to get reps, to preserving pro rata in follow-on rounds without changing the core strategy of the fund.

The conversation gets into opportunity funds, the history of sidecars, and why a vehicle that was once niche is now a standard part of the venture fund playbook. They also dive into the surprisingly complicated world of Australian SPVs, the four main structures available, and the regulatory challenges facing super funds investing in venture.

Finally, Cheryl and Maxine look at how the venture ecosystem is evolving, why sidecars are becoming part of the progression from syndicate to fund manager, and what the growing expectations of institutional LPs could mean for the next generation of Australian funds.

Time Stamps

00:00 – From venture outsider to “everyone is building companies”

01:12 – Why sidecars have suddenly gone mainstream

02:23 – What exactly is a sidecar?

03:14 – Sidecars vs. co-investments

04:12 – The Uber for Cats problem 🐈

05:12 – Why LPs and fund managers use sidecars

05:40 – Doubling down on the companies you love

07:27 – How sidecars can lower fees and carry

08:40 – The paradox of picking winners to average down fees

09:29 – Why sidecars make more sense at growth stage

10:30 – Drafting off someone else’s diligence

11:30 – Follow-on sidecars and pro rata

13:31 – Why competitive rounds make sidecars valuable

14:50 – The admin headache of investing directly

15:05 – Why sidecars can make investing easier

16:02 – The surprising history of opportunity funds

17:25 – When should emerging managers start using sidecars?

19:10 – Why fund managers run sidecars

21:00 – Sidecars, carry and staying disciplined

22:00 – Why sophisticated LPs increasingly expect sidecars

23:10 – SPVs aren’t actually a legal structure

24:10 – The four main Australian SPV structures

25:23 – Why Australia is different from the US

26:00 – The evolution from angel to syndicate to fund

27:08 – The super fund fee problem

28:17 – Should venture be treated differently?

29:11 – The regulatory challenge for Australian venture

30:24 – What happens as Australian funds mature?

31:23 – Why building a fund is still building a company

32:01 – Sidecars 101: did we cover it all?

32:49 – Send us your sidecar questions

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

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

Deel x PX_Script 2

Pear Tree

If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost.

Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business.

As a Day One listener, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire.

Deel x PX_Script 1

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/

Episode Summary

Eric Ries is the author of The Lean Startup and The Startup Way, and the founder of IMVU and the Long-Term Stock Exchange. His new book, Incorruptible, examines why companies drift from their mission once investors and boards take over, and what founders and early investors can do to prevent it.

In this episode, Cheryl and Maxine unpack what Eric calls "financial gravity," the force that pulls companies toward extractive, value-destroying behavior even when everyone believes they're pursuing profit. Eric explains why many widely taught governance best practices are actually shareholder-value destroying, and why the earliest stage of a company is the easiest time to build in protections against this drift.

You'll also hear Eric break down the "spiritual holding company" structure, using Novo Nordisk's century-old nonprofit foundation as an example of why mission-guardian structures make companies far more likely to survive long term. The conversation covers why founders get talked out of protective provisions until it's suddenly too late, and Eric shares the real story of a startup that took a million dollars from Purdue Pharma to push opioids to doctors, and why it destroyed the company.

He closes with his Big Cojones moment: a board meeting early in his career where he expected to be fired for refusing to abandon his unconventional methods, and the lesson that "harder is easier" when you stand for something you believe in.

Time Stamps

00:00 – Intro

04:10 – Eric's first investment: putting his own money into IMVU's friends and family round

09:15 – From Lean Startup to Incorruptible: why it's always felt like one continuous project to Eric

17:40 – The tortilla company, private equity, and why "pricing power" explains so much bad behavior

21:30 – Why so-called governance best practices are often value destroying

25:50 – Naming the problem: financial gravity and why our grandparents would have called it corruption

30:20 – What founders and early investors can actually do at the earliest stage

36:45 – The Olympic athlete analogy: why protective structures only work if built in early

41:10 – The spiritual holding company explained through Novo Nordisk's origin story

48:30 – Why companies rated for "good governance" have underperformed since 2008

52:15 – The Purdue Pharma story and how a million dollars destroyed a company

58:40 – Big Cojones moment: the board meeting Eric thought would get him fired

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

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

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 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.

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/

Episode Summary

Ilana Elbaz was employee number five and the first go-to-market hire at Deel, helping scale the company from its early pivots through blockchain and payments to a business she helped grow from zero to hundreds of millions in ARR in just a few years. She's now an active angel investor and runs Deel's global pitch competition, which received tens of thousands of applications this year.

In this episode, Cheryl and Maxine unpack how operating inside one of the fastest-scaling companies in the world shapes the way Ilana evaluates founders as an investor. She breaks down her "3-star model" for backing companies (right infrastructure, right team, right timing, read from right to left), why she looks for founders with velocity and speed over founders who claim to have it all figured out, and why the biggest red flag at pre-seed is a founder who narrows their market too early.

You'll also hear why she pushes back on founders who insist on enterprise-only or single-market strategies before they even know their ICP, why treating international hiring as a growth problem rather than an HR problem is critical for founders building outside the US, and why Australian founders' instinct to think global from day one is a genuine advantage. Ilana shares what she learned scaling Deel's own go-to-market using the company's own product across dozens of countries, and why staying close to your first hundred customers matters more than shipping a polished product.

She closes with her Big Cojones moment: repeatedly landing alone in unfamiliar countries, from opening entities in Thailand to sourcing product in China at 19, with no support system and straight into meetings with lawyers she'd never met.

Time Stamps

00:00 - Intro

04:15 – Ilana's first investment: buying Amazon stock at age 10 and the lesson she learned selling too early

09:30 – Why Ilana joined Deel as employee five, drawn in by the labor law and compliance nightmare of scaling internationally

14:05 – The 3-star model: right infrastructure, right team, right timing, and why it should be read backwards

17:50 – Why founders who claim to have it all figured out should be a pass

21:40 – The danger of narrowing your market too early at pre-seed

28:10 – Why treating global hiring as a growth problem, not an HR problem, changes everything

33:00 – What makes Australian founders well suited to thinking global from day one

36:45 – How to answer "what's your expansion plan" as a green flag for investors

40:20 – Inside Deel's global pitch competition: 35,000 applications and five investments

46:10 – Big Cojones moment: landing alone in unfamiliar countries to open new markets

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

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:

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

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.

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/

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/

Episode Summary

Alex Feldman is the founder of Tiger and Bear, an M&A advisory focused on tech and services businesses. Before that, he was Chief Strategy Officer and General Counsel at Amaysim, where he ran three acquisitions simultaneously during full lockdown in 2020 and 2021 to build a dominant player that was ultimately sold.

In this episode, Cheryl and Maxine unpack how to buy and sell businesses when the world is doing crazy stuff around you. Alex breaks down why today's volatility isn't actually that different from the GFC or COVID, why timing is the single most important variable in any deal, and what the SaaSpocalypse means for tech companies thinking about selling when their natural buyers are struggling.

You'll also hear why more than half of Tiger and Bear's recent deals involved European and Asian capital rather than American, why profitable venture-backed businesses are suddenly more attractive to strategics, and what happens when the IPO market disappears as an exit path. For founders who can't raise their next round, he offers blunt advice: never waste a crisis, cut costs to buy yourself runway, and remember that raising and selling are the same activity, you're just selling different amounts of shares.

Alex closes with his Big Cojones moment: putting every spare $500 into the stock market during the GFC with no idea where the bottom was, buying Macquarie Bank shares at $30 and riding them back up.

Time Stamps

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

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

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.

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.

Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business.

As a Day One listener, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire.

This podcast uses the following third-party services for analysis:

Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode Summary

Alexey Mitko is a partner at Co-Ventures, the architect behind Eucalyptus' ESOP plan, and widely known in the Australian ecosystem as "ESOP Guy." He was around employee number twenty at Canva and one of the early employees at Koala, giving him a front-row seat to three of Australia's biggest consumer tech outcomes.

In this episode, Cheryl and Maxine unpack how Alexey designed the ESOP plan that led to roughly $300 million distributed back to Eucalyptus employees, the largest ESOP payout in Australian history. He walks through the three questions every founder faces but rarely verbalises: who gets equity, how much, and why you have an ESOP plan in the first place.

You'll also hear how he modelled allocation across multiple rounds and hundreds of hires to avoid giving too much away early, why he personally walked the first two hundred employees through their equity, and why Australia's lack of a secondary market keeps ESOP feeling like monopoly money. Alexey closes with his Big Cojones moment: proposing to his wife, the most nervous he's ever been despite having climbed Europe's highest mountain.

Time Stamps

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

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

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2

Pear Tree

If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost.

Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business.

As a Day One listener, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire.

This podcast uses the following third-party services for analysis:

Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp
Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode Summary

In this 101 episode, Cheryl and Maxine go deep on the fundamentals of pre-seed investing, from how the stage came to exist to why the perceived risk gap between pre-seed and seed is much smaller than most investors think.

They break down the history of how venture stages evolved from single rounds to alphabetized series, how seed investors eventually got pushed up the stack, and why pre-seed emerged around 2017 to 2019 as a distinct category. They unpack why PitchBook's definition of pre-seed as "whatever the investor calls it" muddies the water, how seed preempts from larger funds are inflating average valuations, and why thinking in risk stages rather than round labels is a better framework for evaluating early companies.

You'll also hear why graduation rates from pre-seed to seed don't support the idea that pre-seed is two to three times riskier, why the Australian ecosystem is sitting on a talent surplus with a capital gap at pre-seed, and why this stage is particularly well suited for angels building diversified portfolios of 20 to 40 companies. Cheryl shares her framework for evaluating pre-seed opportunities through the lens of problem pain, frequency, and market size, and Maxine walks through how to think about return profiles, dilution, and valuation at a stage where there are no outputs to measure.

Time Stamps

00:00 Intro

01:56 – A brief history of venture stages: how pre-seed became a thing

07:14 – Why round labels are broken and risk stages are a better framework

09:23 – Seed preempts: how big funds are blurring the line between pre-seed and seed

11:48 – Is pre-seed actually riskier than seed? The case that it's not

16:41 – Graduation rates: what the data says about pre-seed to seed conversion

22:59 – Valuation dynamics: what pre-seed rounds look like in Australia vs the US

28:36 – Why Australian founders are leaving for the US at pre-seed and what that means

31:29 – How to evaluate pre-seed companies: inputs over outputs

35:05 – Cheryl's pain framework: frequency, intensity, and willingness to pay

38:28 – Why pre-seed is the best stage for diversifying who gets funded

43:44 – The AI revenue problem: why getting in early matters more than ever

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

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2

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/