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.

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

Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.

It’s why more than 40,000 fast-growing companies trust Deel to move fast.

Visit https://www.deel.com/dayone

___

Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman.

As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs.

The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business.

As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartree

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

Noga Edelstein is the lead of the Equity Clear initiative, a not-for-profit effort to get Australian investors tracking pipeline diversity data with a common standard. She's also a former General Counsel at Yahoo, a multi-time founder, and has had her fingerprints across the Australian startup ecosystem for over a decade.

In this episode, Cheryl and Maxine unpack why pre-seed funding to women is at its lowest level ever and how Equity Clear is building the data infrastructure to finally see where diverse founders are falling out of the pipeline. Noga shares what the UK's five-year head start has revealed, including that angel groups with at least 15% women invest in 10X the number of women-led companies, and why the mere act of tracking your own pipeline drives better outcomes.

You'll also hear how a broken website form accidentally proved that women disproportionately use cold inbound to reach investors, why male founders and LPs should be asking their investors about diversity tracking, and what sport can teach us about leveling the playing field through systemic tweaks like funded childcare for founders. Noga closes with her Big Cojones moment: quitting her General Counsel role at Yahoo with a newborn to go all in on a startup.

00:00 Intro

02:27 – Noga's first investment: dollar-mite savings accounts in primary school

10:02 – What is Equity Clear and why pipeline data is the missing piece

14:40 – Why closing the gender gap matters now: productivity, economics, and AI bias

19:27 – Pre-seed funding to women is at its lowest ever despite lower barriers to building

24:44 – Why collecting diversity data feels hard but isn't

28:32 – Lessons from the UK: what five years of tracking has revealed

32:02 – Maxine's accidental experiment: when a broken form hid all the women founders

37:39 – How male founders and LPs can push for change by asking simple questions

48:16 – Why funds are missing a trick on sourcing diverse founders

51:32 – Breaking the archetype: leveling the playing field with systemic tweaks

57:15 – Big Cojones moment: quitting law with a newborn to start a company

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

Deel x PX_Script 1

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

Elizabeth Yin is the co-founder and General Partner of Hustle Fund, a pre-seed venture fund now on its fourth fund that backs companies globally. Before Hustle Fund, she was a partner at 500 Global, founded adtech company LaunchBit, and was an early employee at Google.

In this episode, Cheryl and Maxine unpack how Hustle Fund sources deals across continents, why Elizabeth avoids noisy competitive markets in favor of "small waves" that will swell over five years, and why valuation discipline matters more than founder pedigree when product-market fit risk is the same at every stage.

You'll also hear how Hustle Fund runs a 30-person team with only four on investments, why Fund 2 was the hardest fund to raise, how the AI wave is creating companies that hit $10M ARR and lose it overnight, and why international valuations still offer significant arbitrage. Elizabeth closes with her Big Cojones moment: being called a "meek Asian woman" by an angel investor while pitching LaunchBit, and how building a platform changed the power dynamic entirely.

00:00 – Intro

01:54 - Elizabeth's first investment: three shares of Coca-Cola at age 10

06:50 – What Hustle Fund is investing in now and why vertical SaaS still matters in the AI era

09:31 – How Hustle Fund sources deals globally through co-investors and content

15:09 – Elizabeth's two-part framework: founder quality vs. idea quality

18:10 – Why competitive markets are a double whammy for small-check investors

22:57 – The surfing analogy: spotting small waves that grow big in five years

25:06 – Biggest investing lessons from Fund 1 to Fund 4: valuation and follow-on discipline

27:58 – Camp Hustle, content marketing, and running VC like a lead generation business

30:09 – Does valuation really matter at pre-seed? When it does and when it doesn't

37:39 – Growing AUM: why Fund 2 was the hardest and the "event ticket sales" fundraising pattern

44:15 – Which fund graduation was hardest and the DPI reality at pre-seed

46:21 – Big Cojones moment: confronting bias as a female founder and how platform changes power dynamics

Mentioned in this episode:

Deel x PX_Script 1

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

In this episode of First Cheque, Cheryl and Maxine sit down with Laura Chambers, CEO of @Mozilla to dive into the transformative power of open source technology and its role in shaping the future of the internet and artificial intelligence. Laura shares insights on Mozilla’s unique nonprofit structure, the importance of transparency and accessibility in technology, and the critical need for an open AI ecosystem to drive innovation and equity. From the historical impact of open source software like Firefox to the current challenges of balancing ethical AI development with business needs, this conversation is packed with lessons for early-stage investors and tech enthusiasts alike. Laura also provides an inside look at Mozilla Ventures and the Builders Program, which are supporting the next wave of open-source innovators. Whether you're an investor, founder, or just curious about the future of tech, this episode is a must-listen!

00:00 Intro & Guest Highlights

00:21 Why We're Excited About Laura Chambers

03:14 Interview Begins: Laura's First Investment at Age 10

05:20 Open Source 101: What It Is & Why It Matters

07:08 Firefox vs Internet Explorer: The Open Source Origin Story

09:58 How Healthy Is the Internet Today?

13:50 Can You Actually Make Money From Open Source?

15:45 What If the Internet Had Stayed Behind Paywalls?

17:33 Gen AI Is the New Model T: We're Missing the Seatbelts

19:37 The Case For & Against Closed Source AI

21:35 Why Researchers, Academics & Governments Need Open Access

22:17 Where Are We in the Gen AI Infrastructure Cycle?

24:18 AI in Education: What Skills Do Kids Actually Need?

26:36 Older Generations & the AI Learning Gap

29:16 Open vs Closed: Who's Winning Right Now?

33:49 Meta's Llama & the Strategic Logic of Going Open

35:21 Advice for Founders & Investors Building on Open vs Closed Models

39:21 Inside Mozilla Ventures: What They're Investing In

41:31 Prompt Engineering Tips From a CEO (Say Please!)

46:13 The Biggest Brave Moment: Moving Her Family & a 17-Year-Old Dog to Australia

49:20 The Weight of Being CEO & What That Feels Like

1) Mozilla Ventures: Supporting startups focused on privacy, AI, and open source innovation. (https://mozilla.vc/)

2) Mozilla Builders Program: Investing in and mentoring early-stage entrepreneurs building ethical tech solutions. (https://builders.mozilla.org/)

3) Harvard University Study: Open Source Software’s $8 Trillion Economic Impact A study on the global economic value created by open source technology. (https://www.hbs.edu/ris/Publication%20Files/24-038_51f8444f-502c-4139-8bf2-56eb4b65c58a.pdf)

4) Anthropic Report on Bias in AI: Research highlighting the impact of bias and the importance of transparency in AI models. (https://www.anthropic.com/research/mapping-mind-language-model)

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

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

Frontline’s Brennan O’Donnell has spent two decades helping companies expand across borders, first as an operator at Google and later as a growth investor backing Series B to D businesses. In this episode, Cheryl and Maxine unpack what’s shifted at growth stage in the last 12 months, why the market is still a barbell of “hot or not” deals, and how AI is finally producing application layer companies mature enough for growth rounds.

They go deep on Frontline’s transatlantic model: seed investing across Europe to help founders raise a Series A and enter the US earlier, and growth investing in the US to help companies expand into Europe with a hands on, concentrated portfolio approach. Brennan breaks down the four pillars Frontline uses to drive international expansion timing, go to market, talent and org design, and location plus the biggest traps founders fall into, like trying to launch in too many markets at once or optimizing for revenue targets instead of learning.

You’ll also hear why the UK and Ireland are the default first step for 97 percent of US companies entering Europe, when Europe becomes a CEO level priority, how relationship driven sales cycles vary across countries, and why developer led community building can beat traditional sales led expansion for certain AI products. Brennan closes with his Big Cojones moment: moving to the Bay Area for a temporary Google job with everything in storage, then doing it again to help build Google’s European HQ in Dublin.

03:14 Brennan’s first investment: Mode Analytics and a lawn mowing business in Texas

06:49 What’s changed at growth stage and why “growth” is a different world

08:30 Why AI enablement came first and app layer is finally ready for Series B plus

10:10 The new risk: fast revenue that’s concentrated and not yet durable

14:22 Frontline’s model: Europe seed plus US growth and why it’s unique

15:58 What Frontline looks for: category leaders and a line of sight to a 5x outcome

16:20 The rough revenue range where growth starts paying attention

23:22 The four pillars of expansion: timing, go to market, talent, location

26:00 Timing: the 10 percent pull, exec maturity, and why waiting too long is risky

29:36 Why Europe expansion has to be a CEO level company priority

38:04 Build or buy: why most companies compete into new markets rather than acquire

39:10 Developer community expansion as a new go to market wedge

41:44 Market selection: why nearly everyone starts with London or Dublin

43:56 “Success amnesia” and why you must optimize for learning not quotas

48:28 Relationship driven sales cycles and how Europe varies market to market

52:43 Big Cojones moment: taking a temp Google job and betting on himself

54:26 Doing it again: moving to Dublin in three weeks to help build Google Europe

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

As 2026 kicks off, Cheryl and Maxine open the year with their annual First Cheque wrap, a grounded, opinionated take on what actually shifted in Australian tech and venture, and what that means for the year ahead.

They break down why 2025 marked a genuine inflection point for the ecosystem, from Canva’s secondary and a surge in M&A to fresh signals that long-awaited liquidity is finally starting to flow. Despite minimal government support, Australia quietly proved itself as one of the most capital-efficient venture markets globally, producing unicorns at roughly twice the rate of the US per dollar invested.

The conversation also tackles the harder truths investors and founders need to reckon with in 2026: early-stage funding compressing while late stage heats up, corporate venture capital retreating, and the gender funding gap sliding backwards. Looking forward, Cheryl and Maxine share their predictions for the year ahead, where funding volumes may land, why seed remains the toughest stage, how AI valuations could trigger a market correction, and why energy and infrastructure may emerge as the next premium asset class.

00:00 – Intro: End of year energy: why 2025 felt different to 2024

03:55 – Election fallout and the government’s “nothingburger” for startups

05:24 – Canva’s secondary and the first real signs of liquidity returning

09:49 – Aussie tech M&A heats up: Canva, Linktree, Jolt, and more

12:09 – The stat that changed the narrative: Australia’s unicorn efficiency

16:14 – The weirdest trend of the year: early stage down, late stage up

18:27 – Tech jobs, data centers, and the infrastructure bet Australia is making

22:52 – Why deep tech and climate are pulling venture dollars again

28:21 – The gender funding gap got worse (and why)

33:09 – Corporate VC is pulling out: what happened to strategic capital

37:02 – 2026 predictions: funding totals, seed pain, and where capital flows next

44:00 – AI bubble risk: tourism, ROI pressure, and the domino effect

47:42 – Hot take: electricity is the next valuation premium

49:00 – Will diversity bounce back in 2026? (vibes, but also logic)

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

Max Kausman is the founder and solo GP of Advance VC, Australia's first dedicated fund-of-funds with a focus on secondaries.

In this conversation, they discuss why secondaries won't "save" all of venture (only the top performers), how discounts actually work (spoiler: the average is 30-35% but it's wildly bespoke) and why vintage diversification matters as much as portfolio diversification.

02:47 – Max's first investment: lessons as a 14-year-old basketball coach

07:08 – Defining secondaries and Advance VC's unique LP fund focus

09:44 – Why vintage diversification matters as much as company diversification

13:57 – How secondary transactions actually work: the three-way deal between buyer, seller, and fund

19:24 – What Max learned looking under the hood of Australian VCs firms across different funds and vintages

24:09 – Why Max decided on a secondary Fund of Funds (FoF) model

34:16 - Pricing secondaries

42:20 – What discounts actually look like in practice

47:40 – Will secondaries save venture? The truth about liquidity and why it's concentrated in top performers

50:16 – Building Advance VC and the founder journey of becoming a fund manager

Max Kausman - https://www.linkedin.com/in/maxkausman

Advance VC - https://www.advancevc.com/

Mentioned in this episode:

Deel x PX_Script 1