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:

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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.

Time Stamps

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

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Mentioned in this episode:

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Episode Summary

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.

Time Stamps

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

Episode Summary

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!

Time Stamps

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

Resources

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)

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Episode Summary

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.

Time Stamps

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

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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.

Time Stamps

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)

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

Advance VC buys existing positions in Australian and New Zealand VC funds—acquiring stakes from investors seeking liquidity and giving new LPs diversified access to mature, validated portfolios across multiple vintages dating back to 2012.

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.

Time Stamps

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

Resources

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

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

Mentioned in this episode:

Deel x PX_Script 1

Episode Summary

Matt Browne is the Co-founder and Managing Partner of Black Nova Venture Partners, one of Australia’s most active early-stage funds. Before becoming an investor, Matt founded multiple companies, including enterprise software firm Dunsafe, which sold to global corporates like Suncorp and Brickworks, and learned firsthand what it takes to turn “boring” B2B SaaS into beautiful business.

In this episode, Cheryl and Maxine sit down with Matt to unpack what “boring but mission-critical” really means, why operators often make the best early-stage investors, and what it’s actually like to co-found a venture fund. Matt shares his frameworks for identifying resilient software businesses, the economics behind long-LTV enterprise customers, and how his founder experience shapes the way Black Nova supports startups today.

They also dig into the differences between SMB and enterprise sales, why going from enterprise → small business is nearly impossible, and what it takes to build a fund that’s more startup than finance firm. And, in true Matt style, he caps it off with his Big Cojones moment, jumping off Auckland’s Sky Tower to win a customer.

Sponsors:

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

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

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Episode Summary

What happens when hundreds of the world’s biggest capital allocators get together behind closed doors to talk about venture, private equity, and where the next $30B is going? Maxine found out firsthand at Super Returns Asia, where she chaired the LP–GP relations stage.

In this episode, Cheryl turns the tables and grills Maxine on everything she learned, from why India and Japan are suddenly hot, to why Southeast Asia is struggling, and why Australia didn’t even make the winners or losers list.

They break down how institutional investors really think about funds, what “look-through ownership” means for angels and VCs alike, and why co-investing has LPs hot under the collar. Maxine also shares how family offices are thriving in the current market, what mega-funds like a16z’s $30B raise mean for everyone else, and why building long-term LP relationships is the only real way to get “super returns.”

Time Stamps

01:00 – What Super Returns is, and why it matters for VCs and angels

06:43 – The LP landscape explained: super funds, sovereign wealth funds, and family offices

10:40 – Winners and losers in APAC: India, China, Japan… but not Australia

18:00 – Why Australia needs a better “brand story” to attract capital

19:54 – Hot topic: co-investing and why LPs love it

23:39 – Look-through ownership: why everyone’s just trying to own the outliers

26:43 – Why emerging managers are struggling in today’s fundraising market

33:49 – Family offices having “the time of their lives” in this cycle

34:23 – Mega-funds, evergreen funds, and the $30B a16z raise

39:30 – Will Sequoia and a16z ever lose their dominance?

42:19 – Why APAC liquidity markets matter more than ever

45:30 – The question nobody asked at Super Returns

49:22 – How to actually build LP relationships that work

53:55 – Maxine’s big takeaway: putting Australia on the winners list

Sponsors:

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Episode Summary

Sachin Bhanot leads Southeast Asia & ANZ investments at Prosus Ventures, a global fund with $100B+ in assets. Though based in Singapore, Sachin has become an “honorary Australian fund manager”, with nearly half of Prosus’s regional portfolio now in Australia and New Zealand.

In this episode, Cheryl and Maxine dive into why Prosus ramped up in Australia during a downturn, what paradoxical traits they see in winning founders, and how Singapore and Southeast Asia really compare as markets for expansion.

They unpack the playbook for Australian startups going regional, what Singaporean family offices are actually looking for, and why relationship-building is the real cheat code in Southeast Asia. Sachin also shares his biggest Big Chon moment, and how building coffee chains in the Philippines and Malaysia reshaped his view of what it takes to be an investor.

Time Stamps

02:53 – Sachin’s first and most important investment (hint: not a startup)

07:31 – The paradoxical traits of winning founders

10:26 – Singapore vs Southeast Asia: the tale of two ecosystems

18:12 – Why Prosus doubled down on Australia in 2022

28:40 – Tips and traps for Aussie founders expanding regionally

34:44 – When is the “right” time to enter Southeast Asia?

42:11 – The rise of the Australia–India–Singapore innovation corridor

48:34 – Singapore family offices and the art of relationship-driven capital

51:59 – Sachin’s Big Chon moment: learning empathy by building businesses himself

Resources

Resources Mentioned

🙋🏻‍♂️ Sachin Bhanot - https://www.linkedin.com/in/sachin-bhanot-15551913a/

💰 Prosus Ventures - https://www.prosus.com/prosus-ventures

Sponsors:

First Cheque is supported by our wonderful sponsors:

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

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

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Episode Summary

Tom Humphrey, Partner at Blackbird and former operator, joins Cheryl and Maxine to reframe the conversation around Australia’s AI ecosystem. While headlines paint a picture of Australia falling behind, Tom argues we’re quietly sitting on world-class talent, global-first AI companies, and a capital-efficient edge that’s being overlooked.

They unpack Tom’s recent AFR opinion piece on the AI talent landscape, why Australia’s university-to-startup pipeline is broken (and slowly improving), and how “boomerang” PhDs are returning from Anthropic, Meta, and DeepMind to build ambitious companies onshore. Plus, Tom breaks down how product-led growth is evolving in the AI era, why enterprise motions are happening sooner, and what the new GTM playbook looks like when AI agents are selling to AI agents.

Time Stamps

02:21 – Tom’s first investment: BHP shares via his parents, now passing on the habit to his son

05:19 – Robinhood, meme stocks, and the shift to founder-led brands

07:06 – Why Tom wrote the AFR piece: Australia’s culture of doubt vs the US lens of opportunity

08:08 – Australia’s untapped AI talent advantage: 8% of APAC experts, top-tier unis, and PhD immigration

12:18 – Six model releases, global leaderboard wins… that no one in Australia talks about

14:03 – The dangerous cost of silence: how lack of domestic celebration dampens ambition and capital

17:33 – Why Australia is absurdly capital-efficient (and how we squeeze every dollar)

19:23 – Commercialisation bottlenecks at Aussie unis, and what’s slowly changing

25:39 – How this affects investors: AI engineering vs AI research, the boomerang effect, and talent arbitrage

30:56 – Time zones, USD revenue, and Australia’s secret weapon: the 43% R&D tax credit

33:17 – Role gaps and brand new roles: the rise of AI architects and forward deployed engineers

34:27 – What PLG really means, and why it’s not just a freemium sign-up form

39:31 – Spammy AI agents, SEO collapse, and why brand and community are back

45:15 – Why enterprise motions are showing up earlier (and how that changes GTM)

48:32 – Single-player AI value unlocks a different sales motion: fast, bottom-up adoption

51:15 – AI fits into your workflow, not the other way around

54:14 – Picking your motion: don’t force PLG if it’s not a natural fit

55:05 – Capital-starved ecosystems and why enterprise is still harder to fund in Aus

56:15 – Tom’s Big Cojones moment: three boys under six and a startup-founder partner

Resources

👤 Tom Humphrey LinkedIn – https://www.linkedin.com/in/tomhumphrey1/

🚀 Blackbird Ventures – https://blackbird.vc/

Sponsors:

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

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Aussie Angels - the preferred fund and syndicate admin platform for emerging managers in Australia

Show Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.com

February 2025 - Aussie Angels

Episode Summary

In this crossover episode of First Cheque and In The Blink of AI, Cheryl Mack (Aussie Angels) and Maxine Minter (Co Ventures) team up with host Georgie Healy to unpack how investors are thinking about AI, beyond the hype. From pitch decks to product demos, they reveal the frameworks and gut checks they use to spot real value in AI startups, even when they’re not technical experts themselves.

You’ll also get a behind-the-scenes look at how Cheryl and Maxine are integrating AI into their own workflows, not just as investors, but as operators. From using ChatGPT to summarise founder meetings, to leveraging Prompt Cowboy and NotebookLM for due diligence and research prep, they walk through real examples of how AI is saving them time, sharpening decision-making, and helping them stay ahead in deal flow. And yes, we finally answer the question: what is an agent… and does anyone actually have one?

Time Stamps

02:15 – Are Cheryl and Maxine AI skeptics or advocates?

06:00 – What's actually fueling the AI hype?

10:45 – Are we in a bubble—or just early in the cycle?

16:20 – Valuations, FOMO, and how investors are pricing AI

21:00 – What angel investors should look for in AI startups

27:30 – AI’s biggest red flag: When it all just sounds like magic

31:00 – Are agents real or is everyone faking it?

36:40 – AI in venture workflows: What Maxine actually automates

41:30 – The real power of personal brand in VC

44:50 – How Cheryl preps for founder calls with Google NotebookLM

49:00 – Weekly AI hacks: From flat lays to voice-mode strategy sessions

52:10 – Founder FOMO: Prompt Cowboy, Juno, and other hot startups

54:00 – The case for non-technical founders in AI

58:00 – Are one-person billion-dollar startups real?

Resources

😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy

🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/

💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/

Sponsors:

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

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

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Mentioned in this episode:

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Angel Academy - Best online angel investing course in Australia and New Zealand

Don't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy

February 2025 - Angels Academy

Episode Summary

Some investor phrases sound helpful. Others feel like a riddle. In this episode, Cheryl and Maxine crack open the language investors use when talking to founders, and translate what’s actually being said behind phrases like “not a fit,” “too early,” or “let’s have one more meeting.”

They walk through the subtle (and not-so-subtle) cues that signal a pass, explain what “conviction” actually means in VC-speak, and share tactics founders can use to get clearer answers during fundraising. You’ll also hear the behind-the-scenes realities of ghosting, deal timelines, internal partner politics, and why “we’d love to stay close” usually means… they won’t.

Plus: a rapid-fire rundown of the weirdest (and most cringe) investor slang, from “due dilly” to “foundies.”

Whether you’re raising your first round or managing investor relationships post-close, this episode helps you spot the signals, ask better questions, and avoid wasting time.

Time Stamps

01:45 – “Not a fit”: Why investors love this vague phrase

03:40 – What they mean when they say “you’re too early”

08:30 – “You’re too late”, how stage mismatches work both ways

15:30 – “We’ll circle back” and other signs of a slow no

17:10 – How long does VC diligence really take?

19:15 – Why June 30 is a terrible time to raise

24:10 – Optionality: The excuse behind “we love what you’re doing”

28:00 – “Let the lawyers sort it out”: A red flag or not?

30:15 – The weirdest investor slang (please don’t say “due dilly”)

33:30 – Term sheet vs. side letters: what’s actually worth negotiating

36:00 – Understanding info rights vs. investor updates

38:50 – How to share bad news without burning relationships

45:20 – The shifting goalposts of traction and growth metrics

47:00 – Spotting investor doubts through team questions

48:10 – Final thoughts for both founders and investors

Resources

😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy

🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/

💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/

Sponsors:

First Cheque is supported by our wonderful sponsors:

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

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Episode Summary

Charles Hudson is the Founder and Managing Partner at Precursor Ventures, a solo GP fund that has backed over 450 startups across five funds, including dozens of category-defining companies led by underrepresented founders. In this episode, Maxine and Cheryl sit down with Charles to explore how he built one of the most successful high-volume venture strategies in the world, all while staying a solo decision-maker.

They dive deep into what being a “solo GP” actually means, how Charles balances scale with intimacy across a massive portfolio, and why trust, not likability, is his north star when supporting founders. You’ll also hear his first-ever investment, the courage it took to leave a top-tier firm to start Precursor, and how he still handpicks every company Precursor backs, often long before they’re obvious.

Time Stamps

03:20 – Charles’s first investment: ExxonMobil shares… mailed by cheque

06:50 – What is a solo GP fund, and how Precursor operates with one partner and 14 staff

10:28 – The pros and cons of solo decision-making in venture

12:50 – How Precursor supports 450+ companies (and avoids “orphaned” portfolios)

15:44 – Why Charles shifted from unlimited founder support to intentional check-ins

19:18 – Trust vs likability, and why real feedback matters more than being liked

24:25 – How Charles handles saying “no” to follow-ons, and still earns trust

29:31 – The case for “challenger” VCs over cap-table cheerleaders

32:11 – What Precursor looks for in a founder: not great employees, but great CEOs

36:39 – High volume investing: Why meeting 2000+ startups matters

39:00 – Global allocation: why Charles bet early on African and LatAm FinTech

42:30 – The return of themes (like AI & Women’s Health), and why they can kill judgment

47:52 – When Precursor steps in (and when they don’t): being the “surgeon, not the bandaid”

54:04 – Charles’s biggest Big Cojones moment: leaving Uncork to build Precursor from scratch

56:15 – Why most fund managers are “post-employment” and proud of it

Resources

👤 Charles Hudson LinkedIn - https://www.linkedin.com/in/chudson/

🌎 Precursor Ventures – https://precursorvc.com/

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

Grab your copy of the Dealroom and SideStage Ventures report we talked about on the show with Cheryl Mack and Maxine Minter here - https://www.sidestage.vc/outliers-report-2025

Episode Summary

Ben Grabiner is the Co-founder and General Partner at Side Stage Ventures, and the author of a landmark new report in collaboration with Dealroom and AWS. In this episode, Cheryl and Maxine sit down with Ben to unpack the data behind Australia’s rapid rise as one of the most efficient and exciting venture ecosystems in the world.

They explore how Australia produces more unicorns per dollar invested than any other country, what makes the ecosystem so resilient and capital-efficient, and why the next decade might belong to Aussie tech. From funding gaps to founder grit, from global capital flows to angel investor opportunities, this is essential listening for allocators, founders, and emerging fund managers alike.

You’ll also hear Ben’s story, from buying Tottenham Hotspur shares as a teenager, to moving across the world mid-COVID, to becoming a key builder in Australia’s startup ecosystem.

Time Stamps

04:49 – Ben’s first investment: £250 in Tottenham Hotspur

06:34 – What makes Australian unicorns so capital-efficient?

09:14 – Unicorn efficiency vs gross unicorn creation: what matters more

13:15 – How Australia quietly matches Israel and India on decacorn creation

14:35 – Why foreign investors see the opportunity more clearly than locals

18:41 – The power of local exits like Afterpay, and how they inspire allocation

21:19 – Can Aussie startups scale globally from home? Or must they go abroad?

23:40 – Why this next wave of operators will be our ecosystem’s secret weapon

25:54 – What global LPs need to understand about Australian venture

30:17 – Why pre-seed funds and angel investors matter more than ever

Resources

🙋🏻‍♂️ Ben’s LinkedIn - https://www.linkedin.com/in/bengrabiner/

💳 Side Stage Ventures - https://www.sidestage.vc/

🦘 Aussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence.

https://www.aussieangels.com/

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Episode Summary

Nnamdi Okike is the Co-founder and Managing Partner at 645 Ventures, known for his early, contrarian bets on overlooked verticals and non-obvious industries. In this episode, Nnamdi shares how he leveraged a data-driven sourcing model to identify breakout companies like Squire and Goldbelly, and why seemingly small or niche markets often produce the biggest wins. Maxine and Cheryl dive deep into Nnamdi’s journey from Insight Partners analyst sourcing deals via cold calls, to launching his own fund and achieving a remarkable hit rate, landing him on the Midas Brink List. They explore how he evaluates founder insights, measures market inflection points, and strategically navigates the power law dynamics in venture capital. Packed with strategic insights and candid reflections, this episode is essential listening for emerging investors, fund managers, and founders curious about building defensible businesses in non-obvious spaces.

Time Stamps

04:34 – Nnamdi’s first investment during the dotcom boom

06:52 – Defining “non-obvious industries” and spotting hidden TAM

10:40 – Squire: From barbershop bookings to vertical SaaS OS

13:20 – Goldbelly, marketplaces, and the power of founder insight

17:58 – Algorithmic sourcing meets founder conviction

21:30 – What 645 Ventures learned from missing Facebook

26:46 – Building a fund around risk profiles, not just stages

30:34 – Why the power law should shape every VC decision

35:16 – Does 2024 echo 2002? A macro take on the downturn

42:41 – The rise of zombie funds and quiet closures

45:20 – Bootstrapped AI startups and the future of defensibility

52:54 – When vertical AI gets sticky—and when it doesn’t

57:20 – Nnamdi’s Big Cojones moment: from Insight to starting fresh

Resources

🙋‍♂️ Nnamdi Okike on LinkedIn – Follow Nnamdi’s updates and insights. https://www.linkedin.com/in/nnamdiokike

💰645 Ventures – A VC firm investing in early-stage, non-obvious software winners. https://645ventures.com/

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Episode Summary

Pocket Sun is the Founding Partner at SoGal Ventures, the first female-led, millennial VC firm investing in the future of living, working, and staying healthy. In this episode, she shares how she made her first angel investment at just 24, and how her early bets like Everly Health and Lovevery reflected a conviction in underrepresented founders well before it was a trend. Cheryl and Maxine explore how Pocket launched SoGal’s debut fund, built a deal pipeline through global pitch comps and community, and mastered the art of getting onto oversubscribed cap tables. They also unpack her consumer investing thesis, how she’s navigating fund two with more geographic focus, and what it means to lead recaps and board restructures when the power law turns brutal. For anyone curious about building a fund from scratch, going global with limited resources, or backing change-makers the market misses, this episode is packed with both tactics and courage.

Time Stamps

00:00 – Pocket’s first angel check: $1K into an AI startup

05:30 – Angel investing isn’t just for the ultra-wealthy

09:45 – From building a global pitch comp to proving LP credibility

14:20 – Early wins: Everly Health, Lovevery, and chasing allocation

23:35 – “Land and expand”: getting on cap tables and earning super pro-rata

27:10 – Leading recaps and fighting for underestimated founders

35:00 – SoGal’s thesis: The future of living, working, and staying healthy

40:30 – Entering new verticals without prior expertise

46:00 – Pocket’s take on the Vancouver vs. Toronto startup ecosystems

53:00 – Betting on design-led, intentional consumer businesses

59:10 – Why consumer startups often graduate into enterprise giants

01:03:00 – Pocket’s Big Cojones moment: moving solo to the U.S. at 18

Resources

🙋‍♀️Pocket Sun on LinkedIn – Connect with Pocket and follow her updates. https://www.linkedin.com/in/pocket

💰SoGal Ventures – A VC firm backing diverse founders in the future of living, working, and staying healthy. https://www.sogalventures.com/

Sponsors:

First Cheque is supported by our wonderful sponsors:

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.

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What drives bold decisions, intentional leadership, and the courage to create something entirely new?

In Perspective X, host Pauline Fetaui dives deep into conversations with extraordinary entrepreneurs and leading innovators to explore not just their successes—but the overlooked decisions, mindset shifts, and personal turning points that sparked their greatest breakthroughs.

This show is about the ripple effect of choice: how deep accountability enables us to respond intentionally to life's challenges, rather than simply reacting. If you're curious about the inner journey behind meaningful achievements and how leaders evolve through adversity, this podcast is for you.

Join us on Perspective X, where we move beyond the highlight reel and into the pivotal moments that changed everything.

Launching on the 12th of May, wherever you get your podcasts.

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Episode Summary

Monique Woodard is the Founder and Solo GP of Cake Ventures, a venture fund focused on the enormous opportunities created by demographic shifts such as aging populations, rising female spending power, and America's transition to a majority-minority population. She explains how these macro-level changes expand markets across digital health, fintech, consumer brands, and AI-enabled solutions. Monique also candidly shares her experiences as a solo GP—covering the realities of fundraising, building a unique investment thesis, navigating partnership dynamics, and scaling from Fund I ($17M) to Fund II. Her insights offer a clear blueprint for investors, operators, and founders eager to capitalise on overlooked, high-growth opportunities driven by demographic change.

Time Stamps

03:07 – Monique’s first investment: picking stocks at age 20

06:12 – Her journey from rural entrepreneurship to 500 Startups and VC

12:43 – The "Three Layers of Cake": investing in demographic shifts (aging, female economy, new majority)

22:56 – Why geographic focus matters (and why Cake invests only in North America

24:32 – Real talk on Solo GP life: choosing partners, hiring venture partners, and building a legacy firm

30:07 – Raising Fund II: bigger checks, deeper domain expertise, and firm evolution

39:12 – How founders should position their companies in the AI hype cycle

45:24 – Advice for operators: Understanding the difference between investing and running a venture firm

Resources

🍰 Cake Ventures – Monique’s demographic‑change VC firm. https://cake.vc🙋‍♀️Monique Woodard on LinkedIn – Follow her insights on venture & demographics. https://www.linkedin.com/in/moniquewoodard

Sponsors:

First Cheque is supported by our wonderful sponsors:

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

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Episode Summary:

In this episode of First Cheque, Cheryl and Maxine sit down with James Tynan of Square Peg to explore why EdTech might be one of the most misunderstood (and underinvested) sectors in venture capital. James recounts his early days bootstrapping a startup in Australia’s tough 2001 tech climate, and the lessons he took with him to Khan Academy—where he witnessed firsthand how technology, when done right, can revolutionise education.

Together, they dive into the massive shifts happening in learning today: how kids are skilling up at breakneck speed thanks to platforms like Scratch, YouTube, and AI tutors; why the “Prussian model” of schooling persists; and where personalisation, assessment, and vocational learning could unlock new investment opportunities. James also offers candid advice for early-stage investors trying to spot the next breakout idea in an era of AI-fueled growth—and shares why stepping away from the “prestige path” (like skipping Stanford) was one of his biggest and bravest decisions. Whether you’re an EdTech founder, an investor, or just intrigued by how fast education is evolving, this episode is a must-listen.

Key Takeaways:

00:00 – Intro

02:16 – James’s first big bet – Starting a company in Australia’s early 2000s “hellscape” and the lessons learned

07:18 – Why MOOCs weren’t the answer – The early EdTech hype, misconceptions about online courses, and how Khan Academy did things differently

11:12 – Assessment as the control point – How exams and credentials shape mainstream education and what might disrupt that model

15:08 – AI’s impact on education – Could personalized, AI-driven learning (and cheating) force schools to rethink how we test knowledge?

18:20 – Kids, dopamine, and the next-gen learning paradox – Balancing entertainment and deep learning, and why “edutainment” rules

24:00 – VC skepticism vs. reality – Why it’s so hard to invest in K–12 EdTech, and where vocational and adult learning might be more promising

32:00 – Rapid AI adoption – From legal tech to healthcare, how ambient tools are skyrocketing and what it means for founders

37:00 – Wedges, moats, and growth – The playbook for AI startups moving from “just a feature” to a sustainable product

42:00 – James’s “big kahunas” moment – Choosing Khan Academy over Stanford and why walking away from “prestige” can change everything

47:07 – Wrap-up – The future of EdTech, AI’s role, and parting wisdom for founders and investors

Resources Mentioned

James Tynan on LinkedIn – Partner at Square Peg and former operator at Khan Academy. - https://www.linkedin.com/in/james-tynan-ba54b93/

Square Peg – The VC firm James Tynan is a Partner at. - https://www.squarepeg.vc/

Khan Academy – Free world-class education for anyone, anywhere.

College Board + Khan Academy Partnership – Free SAT and AP test prep.

Ambience Healthcare – AI for clinical documentation and patient notes.

Harvey AI – Legal AI platform disrupting law firm workflows.

Sponsors:

First Cheque is supported by our wonderful sponsors:

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

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Episode Summary:

Having a clear investment thesis helps you make better decisions, improve your deal flow, and maximise your returns. Cheryl and Maxine break down exactly what an investment thesis is, why it matters, and how to structure one that fits your risk appetite, interests, and long-term goals.

They explore the core elements of an investment thesis, including industry focus, stage, business model, and geography. Plus, they highlight key company criteria investors should consider, from strong founding teams and large market opportunities to traction and defensibility.

Beyond just what to invest in, this episode also covers how to stand out as an investor, build a strong value proposition, and get access to the best deals. They wrap up with an essential discussion on portfolio construction, time horizons, and risk management, so you don’t run out of money before your portfolio has a chance to deliver returns.

If you're looking to sharpen your investing strategy and back better startups with confidence, this episode is a must-listen.

Key Takeaways:

00:00 – Introduction: Why your investment thesis matters

01:49 – Defining an investment thesis: What it is & why it's essential

04:49 – How to break down your thesis into clear categories

05:16 – Industry focus: Verticals, horizontals, and emerging trends

07:05 – Stage focus: Pre-seed, seed, growth—how to pick your sweet spot

08:24 – Business model focus: B2B SaaS, marketplaces, and beyond

10:01 – Geography: The pros and cons of investing locally vs globally

14:29 – Key questions every investor should ask themselves

17:24 – Company-specific criteria: How to create your investment checklist

22:33 – Evaluating market size and growth potential

25:39 – Pain vs pleasure: Investing in painful problems vs unmet desires

29:54 – Unique or niche theses: Second-time founders, alumni networks, and more

33:46 – Access and deal flow: How to attract great opportunities

38:35 – Understanding your personal risk profile & timeline expectations

Resources

Angel Academy – Comprehensive angel investing course for Australia & NZ: www.venture.academy

Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/

Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/

Sponsors:

First Cheque is supported by our wonderful sponsors:

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

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Episode Summary:

Understanding how to invest in startups requires more than just writing a cheque. Cheryl and Maxine break down the legal structures behind startup investing, covering SAFE notes, convertible notes, and priced rounds. Whether you're a seasoned investor or just starting out, this episode unpacks the key terms, investor-friendly vs. founder-friendly clauses, and the risks involved.

They discuss the evolution of SAFEs, why they've become the dominant structure in early-stage funding, and the critical differences between pre-money and post-money SAFEs. Plus, they explore the role of pro-rata rights, most favoured nation (MFN) clauses, and side letters—so you don’t get caught off guard in your next deal.

If you’ve ever wondered how to protect your equity position, when to push back on certain terms, or what legal documents you’ll actually be signing, this episode is your investor cheat sheet.

Key Takeaways:

00:00 – Why startup investment structures matter

01:45 – SAFE notes, convertible notes, and priced rounds explained

03:47 – How founders raise money: equity vs. debt

06:21 – The documents you’ll sign in a priced round

10:22 – Do startups need a constitution? Red flags to watch for

14:29 – Side letters: What are they, and should you be worried?

19:08 – Pro-rata rights & why they matter for investors

22:23 – Most Favoured Nation (MFN) clauses explained

30:27 – Pre-money vs. post-money SAFEs: Which one is better?

38:03 – Why valuation caps and discounts can be a double-edged sword

43:53 – Investor-friendly vs. founder-friendly terms: What’s fair?

Resources

- A Deep Dive into ECIS, ESVCLP, and Investment Strategies - https://open.spotify.com/episode/1Agiu4dskF53m6DBZgXitD?si=KFeAlY_wTjSwOWfRMiiQFA

- Angel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academy

- Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/

- Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/

Sponsors:

First Cheque is supported by our wonderful sponsors:

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

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.

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Episode Summary:

In this episode of First Cheque, hosts Cheryl and Maxine dive deep into the complexities of fund cycles, providing invaluable insights for emerging fund managers and entrepreneurs alike. They discuss the key aspects of raising and deploying funds, including the significance of understanding the timing and structure of fund cycles. Cheryl emphasises the importance of recognising that announcements of fundraising often indicate the beginning of the fundraising process rather than immediate capital deployment.

Maxine elaborates on the differences in fund management strategies, particularly in Australia, where choices about fund structures, like ESVCLP (Early Stage Venture Capital Limited Partnership), can influence tax benefits and administrative requirements. The hosts also touch on the challenges faced by fund managers, such as the necessity to maintain liquidity and the common practice of deploying smaller checks to riskier companies at the start of a fund’s lifecycle, while gradually shifting to larger, safer investments as the fund matures.

Throughout the conversation, they highlight the importance of planning for exits, the dynamics of raising subsequent funds, and the need for flexibility, especially within micro funds. They conclude by encouraging fund managers to be diligent in their planning to ensure success and sustainability in their investment journeys. This episode serves as a comprehensive guide for anyone looking to navigate the intricate world of venture capital and fund management.

Time Stamps:

00:00 – Introduction: Why fund cycles matter for investors & founders

01:21 – Who this episode is for: Emerging fund managers & startup founders

03:23 – Understanding fund cycles: Raising, deploying, and exiting

05:48 – The reality of raising a fund: Why it takes 12-24 months to close

09:35 – Deployment periods: How VCs decide when and where to invest

12:34 – The risk of running out of money—how fund managers avoid this mistake

16:57 – Fund sizes & check sizes: Why $50M is a magic number in VC

21:09 – Micro VCs vs. bigger funds: How different strategies impact returns

25:14 – Opportunity funds: When fund managers double down on winners

30:08 – The importance of liquidity planning and secondaries in VC

37:17 – Exits: How and when fund managers start planning for returns

43:59 – Final thoughts: The key takeaways from this episode

Resources Mentioned

- Angel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academy

- Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/

- Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/

- ESVCLP (Early Stage Venture Capital Limited Partnership) – How tax benefits impact Australian VC funds

- AFR & Startup Daily – Understanding VC funding announcements in the media

- Adverb Ventures (April Underwood) – Case study on fast fund cycles

- Australian Super Funds & VC – Why institutional capital is hard to secure

- Venture Fund Deployment Data (US vs. Australia) – Insights on how quickly funds deploy capital

- Fund Liquidity & Secondaries – How fund managers plan exits when IPOs & M&A slow down

Sponsors:

First Cheque is supported by our wonderful sponsors:

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

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:

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Episode Summary:

In this episode of First Cheque, Cheryl and Maxine dive deep into financial planning for angel investors—how to avoid running out of money, manage liquidity, and strategically deploy capital across investment cycles. If you're an aspiring angel investor wondering how much money you need to start or an experienced investor looking to refine your cash planning strategies, this episode is packed with essential insights.

They discuss the importance of staying liquid, diversifying check sizes, and the dangers of deploying too fast. Plus, they break down the realities of payback periods in startup investing, why you shouldn’t expect quick returns, and how power law dynamics shape investment outcomes.

Cheryl also shares her personal approach to budgeting for angel investments, alternative funding sources (like self-managed super funds and term deposits), and how investors can avoid the all-too-common mistake of running out of capital too soon.

If you want to build a sustainable angel investment strategy, ensure you're making long-term, high-return decisions, and avoid costly mistakes, this is an episode you don’t want to miss!

Key Takeaways:

00:00 – Introduction: Why budgeting and cash planning are critical for angel investors

01:49 – The golden rule: How not to run out of money when investing

02:37 – Why staying liquid matters: Power law, economic cycles, and risk mitigation

05:15 – Angel investing vs. stock market investing: Why you can't just sell down a position

08:04 – How Cheryl funds her investments: Breaking the myth of needing huge capital

10:00 – Alternative funding sources: Super funds, ETFs, term deposits, and more

13:41 – The importance of knowing your risk tolerance and financial boundaries

17:48 – Varying check sizes: When to double down on winners and how to strategise

23:15 – Why new angel investors should start with consistent check sizes

30:47 – Australian angel success stories: Real returns and lessons from Clarity Pharmaceuticals, Autra, and Instacluster

34:56 – Final takeaways: Planning, patience, and how to build a sustainable angel investing portfolio

Resources Mentioned

1. Angel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academy
2. Aussie Angels – Cheryl’s platform for angel investing
3. Coventures – Maxine’s venture capital firm
4. Central Texas Angel Network (CTAN) – Study on angel investment returns
5. TechCoast Angels California – Report on long-term angel investing performance
6. Australian Angel Success Stories:

• Clarity Pharmaceuticals – 50x return for early investors
• Autra (Agil) – Acquired by Schneider Electric, 91% IRR
• Instacluster – 63% IRR after acquisition by NetApp

Sponsors:

First Cheque is supported by our wonderful sponsors:

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

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:

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Episode Summary:

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!

Time Stamps:

00:00 – Introduction to the episode and Laura Chambers

02:06 – The origin story of open source and Mozilla’s role in internet history

07:22 – Netscape, Firefox, and the fight for an open internet

11:05 – The challenges of keeping AI open in a world of closed ecosystems

15:19 – Why open source innovation accelerates progress

19:12 – Addressing the misconceptions of open source and its role in AI safety

23:18 – The potential societal impacts of closed vs. open AI

29:34 – Insights into Mozilla Ventures and the Builders Program

35:01 – Why transparency and accountability are essential in AI development

41:16 – How open AI can empower underrepresented communities globally

47:20 – Laura’s biggest lessons as a leader in tech and her vision for Mozilla’s future

Resources Mentioned

Mozilla Ventures: Supporting startups focused on privacy, AI, and open source innovation.

Mozilla Builders Program: Investing in and mentoring early-stage entrepreneurs building ethical tech solutions.

Harvard University Study: Open Source Software’s $8 Trillion Economic Impact A study on the global economic value created by open source technology.

Anthropic Report on Bias in AI: Research highlighting the impact of bias and the importance of transparency in AI models.

Sponsors:

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In this episode of First Cheque, hosts Cheryl and Maxine delve into the critical topic of liquidity within the venture capital ecosystem. They explore why IPOs (Initial Public Offerings) and M&A (Mergers and Acquisitions) are essential for investors and startups alike. The conversation covers the current state of the IPO market, the challenges of companies staying private longer, and how these factors impact investment strategies and returns. They also discuss the role of secondaries as a solution to liquidity issues, the potential effects of proposed regulatory changes in Australia, and the importance of proactive engagement from the tech community to address these challenges. Cheryl and Maxine offer insights into navigating the evolving landscape, emphasising the need for transparency, standardisation, and inclusive wealth creation in the venture space.

Key Takeaways:

00:00 - Introduction to Cheryl and Maxine; overview of the episode

01:03 - Discussion on liquidity, IPOs, and M&A in the venture ecosystem

02:07 - Defining liquidity, IPOs, and M&A for the audience

05:21 - Importance of IPOs in venture capital and why they matter

09:30 - Impact of the health of IPO markets on investment strategies

14:56 - Investment strategies during different market cycles; being contrarian

16:14 - Exploring opportunities in secondaries amidst liquidity challenges

21:13 - Reasons companies are staying private longer; regulatory influences

26:43 - Regulatory clampdown on M&A and its effects on the tech ecosystem

31:45 - Closing remarks; encouraging solutions for liquidity issues

Resources Mentioned:

SecondQuarter Ventures: An Australian secondary fund involved in facilitating liquidity through secondaries.

Airtree Ventures and Canva: Airtree's secondary transaction involving Canva as an example of internal liquidity solutions.

Instacluster: An Australian company acquired by a U.S. firm, highlighting international M&A activity.

Mr Yum and me&u: Example of Australian companies merging to navigate market challenges.

Australian Securities Exchange (ASX): Discussed as an option for listing, particularly for small-cap companies.

Jim Chalmers: Australian Treasurer proposing reforms on M&A regulations that could affect the tech ecosystem.

Tech Council of Australia (TCA): Suggested as a body to engage with and advocate on behalf of the tech community regarding regulatory changes.

Sponsors:

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In this special replay of our most popular episode of the year, Cheryl and Maxine sit down with Michael Batko, CEO of Startmate, to explore the transformative power of early-stage investing and community-driven entrepreneurship. From hardware startups to non-alcoholic beer companies, Batko shares how Startmate pushes boundaries, backs ambitious founders, and builds a thriving startup ecosystem in Australia and New Zealand. Discover how Startmate evolved from software-focused investments to a diversified portfolio across industries, leveraging the collective power of mentors and founders. Gain practical insights into crafting investment theses, fostering innovation, and redefining venture capital through collaboration and bold thinking. Whether you’re revisiting this conversation or tuning in for the first time, get ready for plenty of actionable advice and behind-the-scenes stories that shaped one of our most downloaded episodes of 2024. Enjoy the replay!

Time Stamps

00:00 Introduction and background on Michael Batko and Startmate.

02:36 Startmate’s investment thesis and evolution into hardware and non-traditional startups.

07:59 The role of community and mentors in early-stage investing.

14:19 Insights into the Continuity Fund and its benefits for alumni companies.

23:09 The importance of equity and carry in the Australian startup ecosystem.

34:09 Startmate’s unique approach to portfolio construction and decision-making.

42:07 Lessons learned from non-consensus investments like Heaps Normal.

48:36 Michael Batko’s "Big Cojones" moment and reflections on bold decisions.

Notable Quotes:

1. "It’s not about what’s probable; it’s about what’s possible." – Michael Batko

2. "Backing the hungry, not the proven, is at the heart of what we do." – Michael Batko

3. "Would you want to work for this founder? That question reveals everything." – Michael Batko

4. "The biggest mistake in VC isn’t losing money—it’s missing the one company that could be massive." – Michael Batko

5. "Startmate is built on two core principles: giving the community a job and skin in the game." – Michael Batko

Resources Mentioned

No-Code Tools:

• Airtable

• Notion

• Softr

• Pory

Heaps Normal

Eucalyptus – Guide to Employee Share Options (ESOP)

Cake Equity – Equity and ESOP Calculator

Sponsors:

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In this year-end wrap-up, Cheryl and Maxine reflect on 2024’s venture landscape, from shifting investor sentiment to the lingering effects of the zero-interest era. They dig into the rise in early-stage investments, the resurgence of AI enthusiasm, and the cautious optimism permeating the ecosystem. With equal doses of hindsight and foresight, they offer spicy predictions for 2025: from a potential surge in IPOs to the possibility of a one-person billion-dollar startup. If you’re looking for unfiltered commentary on liquidity, the fate of AI hype, and what lies ahead for the Australian and global tech markets, this episode covers it all—plus a healthy side of debate and laughter.

Timestamps

00:00 Introduction & Annual Wrap-Up Setup

00:21 Reflecting on Last Year's Predictions & Risk Appetite Shift

01:50 Investor Sentiment & Early-Stage Deal Growth

03:06 ChatGPT Adoption & AI’s Embedded Productivity Gains

05:00 Liquidity’s Return: M&A, Secondaries & Early Exits

07:30 Increased Angel Activity & “Learning Checks” Trend

09:20 Discussing Worst Investor Terms & Founder-Friendly Boundaries

10:47 The State of IPO Markets, Political Shifts & Macro Effects

12:40 AI Acceleration, Productivity Tools & Future Potential

14:10 Spicy 2025 Predictions: IPOs, One-Person Billion-Dollar Startups & Bubble Cycles

17:00 Final Takeaways, Lessons Learned & Maintaining Optimism

Key Takeaways:

• Gradual Investor Confidence Rebuild: Despite a tough few years, investor sentiment improved slightly in 2024, with more early-stage deals and smaller check sizes indicating a return of risk appetite.
• More Angels, More Checks: The Australian ecosystem saw a surge in angels writing “learning checks,” reflecting a more portfolio-minded approach among first-time investors.
• AI’s Permanent Footing: AI is here to stay, with everyday products increasingly integrating it for productivity gains. While some skeptics remain, the hosts firmly believe AI isn’t a passing fad.
• M&A and IPO Prospects: Early-stage M&A activity is up and liquidity events may increase if certain geopolitical and economic shifts occur. While 2024 saw incremental gains, 2025 may bring either a return to “bubble” conditions or a more measured growth environment.
• Spicy Predictions for 2025: From a potential billion-dollar one-person startup to a high-profile AI company collapse, the hosts don’t hold back on bold forecasts.

Resources Mentioned

Programs like the Climate Salad Global Growth Program and BuildClub (discussed as ecosystem examples)

Notable Quotes

“We are seeing a lot more risk appetite at the earlier stages, which tells me there are more early stage companies getting funded.” – Cheryl

“I think we will see a high profile AI company collapse next year.” – Cheryl on her bold 2025 prediction

“My spicy take: You cannot build a generational company in a year.” – Maxine

“AI is here to stay—it's not a fad, it’s going to be integrated into everything.” – Cheryl

Sponsors:

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In this episode of First Cheque, hosts Cheryl and Maxine engage in a compelling conversation with John Sharp, co-founder of Hatcher+, an innovative AI-driven venture capital platform based in Singapore. John recounts his fascinating transition from conducting orchestras to pioneering data-driven venture investing, highlighting how his early experiences with technological disruption in the music industry inspired him to embrace AI and big data. He delves into how Hatcher+ analyses over 600,000 startup deals to predict investment success, emphasising the importance of the power law and large, diversified portfolios in maximising venture returns. John also shares his insights on the future of algorithmic investing in venture capital, drawing parallels to the transformation of public equities in the 1990s. Throughout the discussion, he underscores the necessity of adapting to technological advancements and offers valuable lessons for founders, operators, and investors aiming to leverage AI for smarter investment strategies.

Key Takeaways:

01:39 Welcome & First Investment Question

02:10 John's First Investment: Education and Orchestration

05:00 Technological Disruption in the Music Industry

06:14 Management Lessons from Conducting Orchestras

10:47 Lessons from Past Industry Disruption

15:03 Introduction to Hatcher+ and AI Venture Model

17:51 Hatcher+'s Methodology & Portfolio Strategy

24:01 The Power Law in Venture Capital

33:33 Building Hatcher+'s AI-Driven Platform

37:12 Insights from Analysing 600,000 Companies

42:40 Importance of Pivots and Board Support

44:31 John's Biggest Courage Moment

Resources

Books:

• Orchestration by Walter Piston

• The Professional Arranger Composer by Russell Garcia

• Orchestration books by Nelson Riddle

• Jazz Orchestration by Dick Grove

Notable Quotes

"If you don't understand AI, figure it out as quickly as you can. Because if you embrace the AI options that are available, you'll become expert at them." – John Sharp

"To succeed in venture, you've got to truly play the odds in a very intelligent way." – John Sharp

"You have to worship at the altar of the power law. It dictates everything that you do." – Maxine

"Sometimes you just got to put yourself out there and follow your gut that you know how to do this." – John Sharp

Sponsors:

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Join Emily Rich and hosts Maxine and Cheryl in this episode where they explore the dynamic world of early-stage and deep tech investing. Emily shares her unconventional journey from being a high school dropout to making a decisive investment in her own education, a move that transformed her path and led her to become a significant player in the venture capital scene. The conversation delves into the thrills of pre-seed and seed investing, the art of identifying and navigating hype cycles in technology—including discussions on the metaverse and blockchain—and the profound impact of backing founders in their earliest stages. Emily also reflects on her transition from founder to angel investor, highlighting the importance of supporting ambitious ideas and the courage it takes to step into the unknown. Packed with personal anecdotes, industry insights, and plenty of laughs, this episode offers both inspiration and practical advice for anyone interested in the highs and lows of venture capital.

Key Takeaways:

00:00 Introduction and Emily's first investment in her own education

04:29 Discussing being bad at being told what to do; founders as bad employees

06:12 Emily on why she invests in pre-seed and seed stages

13:14 Navigating hype cycles; the Metaverse example

18:14 Thoughts on blockchain and crypto as hype cycles

22:26 Understanding and identifying hype cycles in investing

29:28 Changes in AI over the past decade; Emily's background in AI

32:31 Public perception of AI and fear of job loss

37:39 Tips for non-technical investors to understand AI

40:40 Emily's Big Kahuna moment—leaving a safe job to start angel investing

44:44 Closing remarks and thank you

Notable Quotes

"You know it's gone mainstream when my mum is using it for knitting tips." - Cheryl

"The Metaverse is my favourite hype cycle because it was so overhyped and no one is spending time in the Metaverse." -Emily Rich

"There is some suggestion and quite a lot of research that founders are really bad employees—great founders are really bad employees." - Maxine

"If you're hyping someone from the sidelines, it's like cheering on an athlete—they're probably going to run faster." -Cheryl

"I started investing in myself, in my education—not from a university perspective, but from schooling in general." - Emily Rich

Resources

Thought Leaders to Follow:

• Fei-Fei Li – Renowned for her work in AI and computer vision.
• Timnit Gebru – Noted for her contributions to AI ethics.

Reports and Articles:

• Sequoia Capital's Articles on AI: Maxine mentions that Sequoia published insightful pieces examining whether AI infrastructure can generate significant revenue, specifically questioning the potential for $600 billion in revenue.
• Bain & Company's Report on the Jagged Edge of Technology: Referenced by Maxine, this report discusses the adoption of AI, its impact on productivity, and how businesses are integrating AI into operations.

Books and Quotes:

• Charlie Munger's Investment Advice: Maxine recalls his quote, "If your shoeshiner starts giving you stock tips, sell," as a metaphor for identifying when a market might be overheated.

Sponsors:

First Cheque is supported by our wonderful sponsors:

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Join Cheryl Mack and Maxine Minter on First Cheque as they chat with Tim from Turo, one of Australia's pioneering operator angels. Tim shares his journey from working at Uber to his current role at Turo, detailing the insights and risks involved in being an early-stage investor. The conversation covers Tim's first investment, his transition from medicine to business, and the challenges of balancing operator and investor roles. They discuss the Australian tech ecosystem, liquidity issues, and policy needs, along with the significance of strong talent and multicultural acceptance. Tim also shares a personal story about leading a national campaign against antisemitism in Australia. This episode is rich with practical advice for budding angel investors and insights into the growth of Australia's tech landscape.

Key Takeaways:

• Importance of Top-Tier Talent: Emphasising that success is driven by individuals who are in the top 1% of their field, Tim focuses on investing in founders and teams that demonstrate exceptional capabilities.
• Building and Utilising Networks: The "ex-Uber mafia" and connections from his professional journey have been instrumental in providing deal flow and collaborative opportunities in both his operating and investing roles.
• Interplay Between Operating and Investing: While Tim views operating and investing as distinct activities, he acknowledges cross-pollination in networking and strategic opportunities, such as recruiting talent through connections made in the investment community.
• Successful Launch Strategies: Sharing the story of Turo's launch in Australia, Tim highlights the effectiveness of building hype and the importance of a well-executed go-to-market strategy, even when facing competition from established players like Uber CarShare.
• Leadership Beyond Business: In response to rising antisemitism, Tim organised an open letter from Australian business leaders condemning hate and promoting multiculturalism, demonstrating his commitment to societal impact.
• Advice for Aspiring Angels: Tim advocates for a balanced approach to angel investing—being available and supportive without overwhelming founders, and recognising when to offer help based on founders' requests.

Sponsors:

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

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In the Blink of AI: Conversations with AI Innovators Join Georgie Healy on 'In the Blink of AI', your weekly guide to the dynamic world of artificial intelligence. Each episode features interviews with the founders of top AI startups, creative product builders, and industry leaders. With 20 years in engineering and technology, Georgie aims to distill complex AI concepts into engaging stories.

The show covers business building, cutting-edge AI technology, and guests' approaches to developing AI products, finishing with rapid-fire questions for quick insights. Connect with Georgie on LinkedIn, Instagram, or via email to share your thoughts and suggestions for future guests.

Timestamps

00:00 Introduction to In the Blink of AI

00:10 Meet Your Host: Georgie Healy

00:56 Podcast Format and Content

01:11 Engage with Us

✨ Connect with Georgie Healy

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

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

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

The Day One Network

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Sign up to get your weekly insights into the up-and-coming AI startups: https://dayone.fm/newsletter

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Join Cheryl and Maxine on an insightful journey into early-stage investing in this episode of First Cheque. The discussion covers the transition from basic checklists to more sophisticated decision diaries, emphasizing structured evaluation and the importance of capturing and analysing decision-making processes over time. Key topics include understanding founder commitment, market size evaluation, and the balance between intuition and quantitative analysis. The episode offers practical advice on refining investment strategies through critical thinking, timely decision-making, and mitigating biases. Additionally, it explores the qualitative nature of early-stage investments and the value of leveraging instincts effectively. Tune in to transform your investment decisions with proven frameworks and mental models.

Key Takeaways

00:00 Welcome to First Cheque: Your Guide to Early-Stage Investing

00:22 Diving into Decision-Making and Mental Models

02:05 From Checklists to Decision Diaries

07:20 Evaluating Founders and Market Size

16:28 The Importance of Timing in Investment Decisions

20:13 Understanding Mid to Late-Stage Investing

20:56 The Role of Intuition and Quantitative Measures

22:38 Challenges of Data-Driven Investment Matching

23:17 Personal Experience with Investment Matching

25:49 The Potential and Limitations of AI in Investing

28:35 Decision Diaries: A Tool for Better Investment Choices

35:03 Key Questions for Investment Decisions

37:14 Reflections on Decision-Making and Instincts

37:38 Conclusion and Call for Feedback

Resources

Maxine's Decision Diary Template

Sponsors:

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Join Cheryl Mack and Maxine Minter for an engaging session as they delve into the world of early-stage investing with Matthew Browne from Black Nova Venture Capital. This episode offers an intimate look into Browne's journey from a founder's seat to a leading venture capitalist's role, with a focus on thematic investing in what he calls "boring B2B SaaS." Browne unravels the nuances of mission-critical software that businesses cannot operate without, discussing why such investment strategies are both conservative and highly lucrative.

The episode highlights Browne's investment philosophy—characterized by rigorous thematic focus, underscoring software's unturnoffable nature in various enterprise settings. He shares insights from his venture fund experiences, discussing the competitive dynamics of boring businesses and the journey of transitioning from an entrepreneur to a fund manager. Throughout the conversation, Browne also provides valuable advice to those considering venturing into fund management, emphasizing the importance of sticking to areas of known expertise and understanding the role's demands.

Key Takeaways:

• Thematic Investment Strategy: Matthew Browne emphasizes investing in enterprise SaaS that is mission-critical to operations, underscoring the intrinsic value and longevity of such investments.
• Importance of Execution: His first investment’s failure taught the importance of knowing how to effectively acquire customers and sticking to one's domain expertise.
• Transition from Entrepreneur to Investor: Browne shares his journey into VC, stating the unique challenges of fund management compared to traditional business operations.
• B2B SaaS Success Factors: Long-lived customer relationships and LTV are key, with an enterprise focus often yielding higher customer loyalty and lower competitive pressures.

Sponsors:

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In this engaging episode, the hosts Cheryl Mack and Maxine Minter are joined by Georgie Turner, a partner at Tidal, to delve into the nuances of early-stage investing, cross-border strategies, and the evolving landscape of venture capital. The episode opens with a lively introduction to Georgie's background and her journey from Bailador to founding Tidal, a fund focused on B2B SaaS and AI. The hosts discuss the challenges and rewards of building a fund, the intricacies of capital management, and the importance of alignment between founders and investors.

Throughout the conversation, the trio explores the differences between the Australian and US venture capital ecosystems, touching on themes such as market size, customer sophistication, and the importance of domain expertise in founding teams. Georgie also shares insights on navigating the AI revolution and its impact on the tech stack and business models. The episode concludes with a reflective discussion on bravery in the venture capital space, emphasizing the optimistic and sometimes illogical nature of the industry.

Key Takeaways:

• Cross-Border Investment: Georgie Turner discusses the importance of having a cross-border investment strategy, particularly focusing on the differences between the Australian and US venture capital ecosystems.
• Capital Management: Insightful exploration into how proactive capital management and accurate valuation alignment can significantly impact the success of early-stage investments.
• AI Investment: Detailed discussion on how AI is transforming the tech landscape and what investors should look for in AI-driven companies.
• Scaling Challenges: The episode highlights the challenges of scaling companies in different markets and the importance of market timing, product quality, and operational expertise.
• Bravery in Venture Capital: Reflections on the inherent bravery required in the venture capital profession, given its optimistic and sometimes illogical nature.

Sponsors:

Thanks to our sponsors for helping to make this episode of First Cheque possible.

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In this episode of First Cheque, hosts Cheryl Mack and Maxine Minter sit down with biotech investment expert Paul Kelly. The conversation demystifies the complex world of biotech investing, making it accessible for even those who are new to the field. Paul shares his journey from a practising physician to a pioneering investor in the biotech space, offering valuable insights into the industry's rapid evolution and high stakes.

Paul explains the fundamentals of biotech investing, including the typical risks and rewards, the lengthy timeframes involved, and the importance of understanding the science and market potential behind each investment. He also touches on the significant advances in genomics and synthetic biology, emphasising how technology and data analysis are accelerating innovation in the field. The discussion delves into the importance of syndication for early-stage investments, the critical milestones that de-risk investments, and the role of pharmaceutical partnerships in increasing the likelihood of success.

Key Takeaways:

• Understand the Risks and Rewards: Biotech investing involves a high level of risk and typically long hold periods, but the potential rewards can be substantial.
• Syndicate Investments: Due to the complexity and capital intensity of biotech, syndicating with experienced investors and funds is crucial for mitigating risk.
• Stages of Investment: Key milestones in biotech investing include achieving safety and efficacy in clinical trials, with significant value inflections at each stage.
• Technological Impact: Advances in genomics, AI, and data analysis are revolutionizing the speed and accuracy of biotech innovations.
• Healthcare Economics: Understanding the economic impact and potential reimbursement scenarios is essential for assessing biotech investments.

Sponsors:

Thanks to our sponsors for helping to make this episode of First Cheque possible.

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Download the Turo app and book cars from $38/day. https://dayone.fm/turo

The Day One Network

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

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In this episode, Cheryl Mack and Maxine Minter dive into the intricate details of tax incentives and structures for angel investors in Australia. Tackling the seemingly dry topic of tax with enthusiasm, they explore how these regulations can substantially benefit early-stage investors. Cheryl brings her wealth of experience to the table, elucidating the complexities of acronyms like ESV CLP and ASIC, while Maxine peppers the conversation with insightful queries and contextual examples.

Cheryl explains the criteria and benefits associated with Early Stage Innovation Companies (ESIC) and Early Stage Venture Capital Limited Partnerships (ESV CLP). She details how these structures facilitate sophisticated tax offsets and capital gains exemptions for investors. Throughout the discussion, they highlight the importance of understanding these incentives to optimize investment returns. The episode culminates with practical advice on investing via trusts and navigating the nuances of capital call schedules, reflecting the duo's deep dive into the subject matter.

Key Takeaways:

• Understanding ESIC: Learn about the Early Stage Innovation Company (ESIC) designation in Australia, its eligibility criteria, and the significant tax benefits it offers.
• ESV CLP Benefits: Discover how Early Stage Venture Capital Limited Partnerships (ESV CLP) and Venture Capital Limited Partnerships (VCLP) offer substantial tax incentives, including offsets and capital gains exemptions.
• Investment Structures: Get insights into the complexities of investing through safes (Simple Agreement for Future Equity) and how ESIC status impacts tax benefits.
• Leveraging Trusts: Explore the functional benefits and considerations when investing through discretionary (family) trusts, particularly in relation to income distribution and tax efficiency.
• Managing Capital Calls: Understand the importance and mechanics of capital call schedules within the context of fund investments and their fiscal implications.

Sponsors:

Thanks to our sponsors for helping to make this episode of First Cheque possible.

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Download the Turo app and book cars from $38/day. https://dayone.fm/turo

The Day One Network

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

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Episode Summary:

In this episode of the First Cheque podcast, Cheryl Mack and Maxine Minter delve into the intricacies of early-stage investing, focusing on the importance of secondaries, the value of strong founder-investor relationships, and how to navigate high valuations. This episode is a milestone as it's entirely driven by audience questions, providing targeted insights and practical advice for investors and founders alike.

Cheryl and Maxine kick off by discussing the significance of secondaries in the investment ecosystem. They explore how secondaries can provide liquidity options for founders, early employees, and initial investors, comparing the maturity of secondary markets in the US versus Australia. They touch on the role of secondary funds, the impact of early liquidity on the ecosystem, and how this federal flow of funds can encourage re-investment into new startups.

Next, the duo dives into their anti-portfolios, sharing insights from companies they passed on and reflecting on biases and lessons learned. They also address gender diversity in the investment landscape, critiquing the current state of gender equity in the Australian startup ecosystem. Furthermore, Cheryl and Maxine share their strategies for balancing valuations, particularly in the context of owning small equity stakes as angel investors.

Key Takeaways:

• Secondary Transactions: Understanding the role and impact of secondary transactions can provide essential liquidity to founders and early investors, fostering a healthier investment ecosystem.
• Anti-Portfolio Learnings: Reflecting on missed investment opportunities reveals biases and allows investors to refine their criteria and improve decision-making.
• Gender Diversity: There is a significant need to address the gender gap at all levels of the investment ecosystem, from founders to fund managers and LPs.
• Valuation Strategy: Evaluating whether a company can significantly grow its valuation by the next funding round is crucial in assessing high valuations.
• Founder-Investor Relationships: Strong relationships between founders and investors are imperative for successful fundraising and long-term collaboration.

Resources:

• Scale Investors: led by Samar, focusing on women-led companies.
• EQUITY DIRECTORY: A data-focused initiative to improve reporting on gender metrics in the investment community.
• AirTree Pioneers Program: Supporting diverse early-stage founders.
• First Cheque Podcast Voicemail: Submit a question

Sponsors:

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In this episode, host Maxine Minter and co-host Cheryl Mack dive into the world of growth stage investing with guest Christina Fa from NewView Capital. They explore the reasons why ex-investment bankers transition to VC, discuss the nuances of growth-stage investing, and shed light on the importance of secondaries in the current market landscape. Christina shares insights on company scaling in different ecosystems, the impact of GenAI innovation, and the changing dynamics of venture capital.

Key topics covered include the unique factors influencing growth stage investments, the difference between primary and secondary investing, and the significance of liquidity for investors and founders. The conversation delves into the evolving venture capital landscape and the role of secondary transactions in unlocking value and increasing market liquidity.

Key Takeaways:

• Growth stage investing focuses on scaling proven products and ideas to dominate the market.
• Secondaries play a crucial role in providing liquidity to early investors, employees, and founders.
• The US offers a mature ecosystem with a deep talent pool for scaling companies, while Australia nurtures a hungry and talented workforce.
• Investors can access growth stage opportunities through platforms like Angellist and secondary transaction platforms.
• Exploring new frontiers in AI and emerging technologies drives investor interest and excitement in growth-stage companies.

Notable Quotes:

• "Investing in the AI space is both exciting and challenging due to the rapid platform shift and exploration phase." - Christina Fa
• "Unlocking liquidity through secondaries is beneficial for both investors and the ecosystem as a whole." - Christina Fa
• "The US ecosystem offers a deep talent pool, while Australia fosters a culture of first principles thinking and innovation." - Christina Fa

Resources:

• NewView Capital
• NewView Capital Linkedin
• Christina Fa LinkedIn

Sponsors:

Thanks to our sponsors for helping to make this episode of First Cheque possible.

Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time. Get 10% off https://dayone.fm/vanta

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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Download the Turo app and book cars from $38/day. https://dayone.fm/turo

The Day One Network

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

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Episode Summary:

In this episode, Cheryl Mack and Maxine Minter engage in an enlightening conversation with Bronwen Clune, discussing her journey from journalism to startups and back to media. Bronwen shares insights on the Australian startup ecosystem, the future of journalism, and the intersecting landscapes of politics, markets, and entrepreneurship. Delving into the impact of risk appetite, the tension between traditional markets and startups, and the evolving dynamics of super funds, the discussion provides a comprehensive view of the current landscape.

Key themes include the shifting risk perceptions in Australia, the resilience and adaptability of Australian startups, and the impact of broader economic and political factors on the ecosystem. With a focus on building stronger companies and navigating challenges, Bronwen offers valuable perspectives on driving innovation and growth in an ever-changing environment.

Key Takeaways:

• Risk appetite plays a fundamental role in distinguishing between traditional markets and startups.

• Australia's startup ecosystem demonstrates resilience and efficiency in the face of challenges.

• The housing crisis and changing economic landscapes are fuelling interest in startups and alternative investments.

• Tension between super funds and risk-taking behaviours may influence the entrepreneurial landscape.

• Australian founders are embracing independence and innovation, shaping the future of the industry.

Notable Quotes:

• "I think Australia punches above its weight in terms of producing founders that international investors are looking at favourably." - Bronwen Clune

• "The housing crisis has spurred interest in alternative investments as young people seek to grow capital." - Bronwen Clune

• "Risk appetite, or lack thereof, is a defining factor between traditional market players and startup enthusiasts." - Bronwen Clune

Resources:

• Capital Brief Website

• Bronwen Clune's LinkedIn Profile

Sponsors:

Thanks to our sponsors for helping to make this episode of First Cheque possible.

Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time. Get 10% off https://dayone.fm/vanta

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

Turo: Turo is the world's largest carsharing marketplace and it's the perfect app for travel.

Download the Turo app and book cars from $38/day. https://dayone.fm/turo

The Day One Network

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

If you want to learn about upcoming guests and when a new First Cheque episode is available, join the First Cheque newsletter.

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Episode Summary:

In this episode, Maxine Minter and Cheryl Mack delve deep into the essential considerations of portfolio allocation, focusing on diversification versus concentration in early-stage investing. They explore the concept of portfolio construction, risk management, power law dynamics, and the importance of strategy in maximizing returns while mitigating risks.

Key themes discussed include the spectrum of diversification, the impact of concentrated investments, the role of informational asymmetry in decision-making, the power of outliers in generating alpha, and the influence of expertise and thesis investing on portfolio performance.

Key Takeaways:

• Portfolio construction is crucial in early-stage investing to manage risks and optimize returns.
• Diversification versus concentration impacts the average quality and performance of a portfolio.
• Specialized first and second funds tend to outperform, emphasizing the importance of focused investment strategies.
• The power law concept highlights the significance of outliers in driving fund performance.
• Investors must strike a balance between diversification and concentration based on risk tolerance and investment goals.

Notable Quotes:

• "Thinking about building your investment strategy and what is the right level of risk tolerance is essential for successful portfolio construction." - Maxine Minter
• "The power law is king in the investment landscape, emphasizing the impact of outliers on fund performance." - Cheryl Mack

Sponsors:

Thanks to our sponsors for helping to make this episode of First Cheque possible.

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Get 10% off

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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Episode Summary:

In this episode of the First Cheque podcast, our co-hosts Cheryl Mack and Maxine Minter welcome venture capital trailblazer Marvin Liao to discuss the multifaceted experience of early-stage investing, the evolution of global startup ecosystems, and the profound lessons learned from economic cycles in the tech industry. The conversation kicks off with stories from Marvin's background in Silicon Valley, including his first steps into the startup world, a decade at Yahoo, angel investing experiences, and defining years with 500 Startups.

Marvin delves into the intricate dynamics of venture capital, sharing his hands-on approach to international investing and offering a candid perspective on navigating competitive markets during downturns. With an emphasis on founder qualities, market-fit, and the significance of geographies like the US for ambitious startups, Marvin provides a remarkable guide for those looking to excel in the unpredictable venture capital terrain.

As the dialogue unfolds, Marvin's strategic astute observations reveal practical strategies for both investors and entrepreneurs looking to leverage opportunities within the constantly shifting sands of the tech landscape.

Key Takeaways:

• Successful early-stage investing requires engaging with 'unconventional' ventures before they gain popularity, often necessitating courage to oppose the crowd.
• The true test of an investor is how one navigates downturns, emphasising resilience and adhering to personal investment theses rather than market sentiment.
• The US remains a central hub for ambitious startup founders due to its unmatched network effects and competitive ecosystem that fosters excellence.
• Marvin advocates a founder-first investment philosophy, prioritizing the drive, capacity to learn, and responsiveness of founders over all else.
• Cultural capital, such as an appreciation for science fiction, is considered crucial for anyone investing in technology's future, as it helps shape one's vision for innovation.

Notable Quotes:

• "Chips on shoulders, leads to chips in pockets." - Marvin quotes Josh Wolf to describe the motivation needed for successful entrepreneurship.
• "How you do anything is how you do everything." - A philosophy Marvin adheres to when assessing founder diligence and reliability.
• "Steel sharpens steel." - On the importance of founders being present in high-impact ecosystems to push themselves to their limits and grow.

Resources:

• Marvin Liao's personal ventures and insights can be followed through his LinkedIn profile.
• Reference to Lux Capital and Josh Wolf's investment philosophy might be of interest to listeners who wish to explore further.

Thanks to our sponsors for helping to make this episode of First Cheque possible:

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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In this thought-provoking episode of First Cheque experienced investors Cheryl Mack and Maxine Minter delve into the meticulous world of follow-on investment strategies. The episode serves as a beacon for those who wish to refine their approaches in early-stage investing, especially as they grapple with the decision of whether to follow on or not in subsequent investment rounds. The conversation explores the intricate balance between optimizing returns and supporting growing companies at various funding stages.

Cheryl represents the school of thought advocating for doubling down on winners, focusing on reserving funds for follow-on investments based on the company's performance. Maxine, on the other hand, takes a contrarian view, emphasizing the importance of an initial strong pre-seed commitment without reserving for follow-on. Together, they unpack the underpinnings of each method, providing listeners with an insightful analysis centred on investment strategy, fund management, and the implications of the power-law in startup investing.

Key Takeaways:

• A follow-on investment strategy involves investing additional funds in a company during later financing rounds, usually at a different share price.
• Traditional wisdom encourages investors to reserve funds to double down on winning companies, but Maxine challenges this idea, promoting initial, larger investments at the pre-seed stage.
• Discussion on the importance of pro rata rights and the potential signaling risks associated with not following on in subsequent rounds.
• Cheryl shares her angel investment approach, which emphasizes growth metrics evaluation, fund allocation decisions against other opportunities, and backing companies that have shown significant progress.
• The conversation highlights the need for personalized investment strategies that reflect individual goals and resources, as well as the potential influence of received wisdom on investment decisions.

Notable Quotes:

• "The conventional wisdom... you want to reserve follow on money in order to double down on your winners." - Cheryl Mack
• "If you want to maximize IRR, then it's deploying all of your capital in that first check." - Maxine Minter
• "The power law operates in our industry... it's not necessarily a one for one trade off... you need to make resource allocation trade offs." - Maxine Minter
• "I really have to believe that I'm still going to get outsized value from this valuation further on." - Cheryl Mack
• "The only thing that stops you from getting squeezed out over time is adding enormous value and having a great relationship with the founders." - Maxine Minter

Thanks to our sponsors for helping to make this episode of First Cheque possible:

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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Episode Summary:

In the latest instalment of our podcast series, Cheryl Mack and Maxine Minter delve into the intricate world of early-stage investing, shedding light on the varied approaches to gaining investment conviction. This episode serves as a guide for both novice and experienced investors who aim to refine their decision-making strategies when backing new ventures.

As Cheryl and Maxine unravel the decision-making fabric of early-stage investing, listeners are taken on a journey through the critical thought processes that investors employ. From angel investing intuition to fund management rigour, the diverse strategies and considerations are laid bare. Key topics such as founder assessment, market sizing, and investment criteria are explored in detail, offering a valuable distilled wisdom that promises to enhance the listener's own perspective on startup investment.

Key Takeaways:

• Every investor has a unique process for achieving conviction in startup investments, which can evolve over time through experience and iterative learning.
• The consideration of factors like founder qualities, market potential, and existing competition varies between individual investors and forms the basis of their investment decisions.
• Portfolio construction and risk assessment play significant roles in an investor's decision to back a company, mainly when operating within a fund structure.
• Intuition and instinct also influence investment choices, sometimes siding with conviction even when faced with incomplete or ambiguous information.
• The balance between personal investment ethos and the structured approach required by funds highlights the complexity and art form of early-stage investing.

Notable Quotes:

• "It's a process...an invitation to iterate your way to a successful process and continue to measure yourself." - Maxine Minter
• "The nature of especially early stage investing is that it's risky." - Maxine Minter
• "For me, it's founder... I need to feel like this is the right founder for the...market problem space." - Cheryl Mack
• "It's really rare, if ever, that you get to a...definitely yes...always no questions." - Maxine Minter
• "The spectrum of yes to hell yes...there are so many different ways of doing it and so many different timescales to be considering on." - Maxine Minter

Thanks to our sponsors for helping to make this episode of First Cheque possible:

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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Episode Summary:

In this insight-packed episode, Cheryl Mack and Maxine Minter sit down with Michael Batko, the driving force behind Startmate, to explore the intricacies of early stage investing and the power of community in the startup realm. Batko shares his journey, starting from his first investment to steering one of the most active seed stage investing funds in the industry. This episode offers a behind-the-scenes look at how Batko and his world-class team utilize a community-driven approach to identify, select, and uplift transformative business ideas across Australia and New Zealand.

Diving into the Startmate selection process, Batko reveals the operational complexities of coordinating a vast network of mentors and how their personal investment in the fund aligns interests and boosts engagement. The conversation also uncovers the evolution of Startmate's investment thesis, its expansion into diverse industries, and Batko's approach to encouraging non-consensus thinking to unlock extraordinary potential. The episode delves into the significance of carry in VC funds, the strategic role of a continuity fund, and the decision-making framework for follow-on investments, all while reflecting on Batko's philosophy of betting on the hungry rather than the proven.

Michael Batko began his career in corporate finance and consulting before contributing to the growth of two major Australian marketplaces, MadPaws and also played a pivotal role in Expert360's $14 million Series B funding round. After joining as Head of Operations, Batko quickly became CEO of Startmate which is now ANZ’s largest community driven seed fund raising ~$3 million from 100+ investors every 6 months.

Key Takeaways:

• Startmate's success is rooted in a mentor-driven model, where community engagement and personal investment are key to its decision-making process.
• Batko emphasizes the importance of looking beyond what's probable and considering what's possible when evaluating investment opportunities.
• The alignment of mentor incentives with fund performance, through carry, is highlighted as a significant motivational factor.
• A robust debate around investment thesis expansion led to backing diverse ventures, including non-software startups like non-alcoholic beer brand Heaps Normal.
• The establishment of a continuity fund at Startmate allows for continuous support of alumni companies, signaling strong belief in their ongoing success.

Notable Quotes:

• "I remember this entire thread coming up and everybody discussing whether or not we should invest in that non-alcoholic beer company. And it was at that time when I jumped in as start mate CEO and actually had to be like, 'Hey, we can't just rest on our laurels and do things the way we've always done them.'"
• "We've expanded the investment thesis a lot around, essentially always doubling down on people and what they care about."
• "One of my favorite questions is, and I always keep coming back to it whenever I critically assess a company for myself, is rather than what is probable... what is possible?"
• "One thing I love about being a microfund is that we only invest $120,000 into companies, but at that stage, it actually makes such a massive difference."

Resources:

• Startmate website for more insights into their accelerator programs. Startmate
• Michael Batko's professional background and contributions, visit LinkedIn
• Discussion of eucalyptus's ESOP primer and equity importance. Eucalyptus

Encouraging all curious investors and founders to tune in and glean actionable insights from Michael Batko's valuable experiences in this episode, as well as to keep an ear out for more enriching discussions in the upcoming sessions.

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In this insightful conversation, co-hosts Cheryl Mack and Maxine Minter unpack the often misunderstood world of 'fund of funds'—investment vehicles that pool capital to invest in a variety of venture funds rather than in startups directly. Tailored for early-stage investors and industry observers, this talk reveals the nuances of fund structures and investment strategies designed to mitigate risk and maximize returns.

Diving into a no-nonsense explanation, Maxine elucidates the two foundational structures of venture funds—management companies and the standalone investing funds—and how funds of funds play into this ecosystem by investing in multiple funds. This episode shines a spotlight on the intricacies of fund growth, managerial sophistication, and the dynamic relationship between funds, funds of funds, and their limited partners (LPs). Cheryl probes into the motivations behind why LPs choose to invest in fund of funds, including access to top-tier funds and diversification that extends across emerging ventures.

Key Takeaways:

• A 'fund of funds' is an investment strategy where the fund invests in other venture capital funds rather than directly in companies.
• Most venture funds fail to return capital; however, emerging managers often are part of the top-performing funds, despite potential difficulty in scaling from one fund to the next.
• Institutions like pension and super funds, which frequently invest in funds of funds, face unique challenges such as VP clauses and monthly asset pricing pressures.
• Funds of funds can offer investors a lower-risk profile and a more diversified exposure to the venture capital market.
• There is a potential growth opportunity for fund-of-funds in Australia, which is currently a nascent market in this space.

Notable Quotes:

• "If you invest alongside, say, CoVentures, and CoVentures has a fund of fund that's invested in them, what does that mean for the potential success of the company later on down the road?" - Cheryl Mack
• "Venture funds being an indexation of the underlying assets... Our success is driven by, you know, an outlier in our portfolio." - Maxine Minter
• "Emerging managers consistently are in the top ten performing funds of every single vintage." - Maxine Minter
• "The venture funds themselves, their returns perform on a power law curve. So there's only a handful of funds, venture funds, that will deliver outlier returns to their investors." - Maxine Minter

Sponsors:

Thanks to our sponsors for helping to make this episode of First Cheque possible.

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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Download the Turo app and book cars from $38/day. https://dayone.fm/turo

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Episode Summary:

In this insightful episode of First Cheque, hosts Cheryl Mack and Maxine Minter have a raw conversation with Elicia McDonald, a venture capital expert renowned for her remarkable work at Airtree Ventures. Elicia's holistic approach to early-stage investing and her deep commitment to nurturing founder relationships are at the forefront of this discussion.

Opening with an introduction that paints Elicia as a superhuman in her work-life balance, the episode delves into the intricacies of venture capital investing. With Elicia's insightful anecdotes and experiences, this podcast provides an intimate look at the dynamics of the VC world, particularly in uncovering what makes an early-stage investor successful. The conversation spans various subjects, including the principles of investment, fostering resilience, and the importance of embracing constant industry change.

About the Guest(s):

Elicia McDonald is a prominent figure in the venture capital industry, mainly known for her work at Airtree Ventures, where she has made a significant impact through her skills in early-stage investing. Elicia is known for her keen ability to identify and invest in promising startups, contributing to various successful ventures. Regrow (formerly known as Fluorosat) is among her notable investments, reflecting her knack for spotting early potential in innovative companies. Besides her professional achievements, Elicia is recognised for her leadership in balancing family life with a demanding career, setting an empowering example for professionals, especially women in the tech industry.

Key Takeaways:

• Resilience and founder empathy are vital traits Elicia values in herself and the founders she invests in.
• Thorough decision-making and maintaining high-quality standards are pivotal points in Elicia's approach to investing and entrepreneurship.
• Building trusted relationships within the startup ecosystem significantly contributes to successful sourcing and working with founders.
• Parenthood and career balance is a personal challenge that Elicia navigated with bravery, setting a progressive example for others in the industry.
• The venture capital industry is marked by constant change, and embracing this dynamism is crucial for long-term success.

Notable Quotes:

• "Life is 10% what happens to your 90% how you respond to it." - Reflexive insight on the importance of perspective.
• "Everything is a multi-shot game." - Maxine Minter on the long-term nature of venture investing.

Resources:

• Elicia McDonald's LinkedIn profile
• Airtree Ventures website for more information on Elicia's investment firm.

Listen in to this enlightening episode to hear Elicia McDonald's full insights on venture capital, founder relationships, and building resilience amid industry fluctuations. Stay tuned to First Cheque for more captivating discussions with leading figures shaping the tech and investment world.

Sponsors:

Thanks to our sponsors for helping to make this episode of First Cheque possible.

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

Turo: Turo is the world's largest carsharing marketplace and it's the perfect app for travel.

Download the Turo app and book cars from $38/day. https://dayone.fm/turo

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Episode Summary:

In the latest compelling episode, we delve into the investment philosophy and keen insights of Trang Nguyen, a trailblazing figure in venture capital. Nguyen shares her journey from placing an early bet on Tesla to her current efforts in redefining the startup ecosystem. She outlines her criteria for backing emerging fund managers and underscores the importance of founders who aim to build venture firms that transcend personal branding and leave a lasting impression.

Nguyen advocates for a platform approach where venture firms offer scalable services to startups, akin to corporate giants like Apple or Amazon. She argues this is crucial for a venture firm's sustainability and ability to scale, detailing why simply being a good investor isn't always enough. Moreover, Nguyen provides a peek into the future of startups, highlighting the potential for AI to revolutionize the way companies are founded and grown.

Hosted by Cheryl Mack & Maxine Minter, First Cheque is a Day One show. Day One is the podcast network dedicated to founders, investors, and operators.

About the Guest(s):

Trang Nguyen is a pioneering investor with a bold approach to venture capital. She has made notable investments in transformative companies, including an early investment in Tesla. Trang is known for her long-term vision and commitment to supporting ambitious entrepreneurs in creating impactful venture firms and startups. Her work revolves around the principles of venture as a future-facing and influential asset class, embracing the role of technology in shaping investment paradigms.

Key Takeaways:

• Trang Nguyen made a pivotal early investment in Tesla, signifying her long-term investment mindset and dedication to visionary founders.
• Nguyen emphasizes the necessity for venture capital firms to build platforms that deliver scalable services to startups, not just make investments.
• The future startup landscape, according to Nguyen, will be heavily influenced by AI, possibly becoming co-founders alongside human entrepreneurs.
• Nguyen believes venture capital is deeply intertwined with technology and will continue to be a critical asset class for the foreseeable future.
• Despite current market sentiments, Nguyen is bullish on venture capital and its role in driving innovation across all sectors.

Notable Quotes:

• "Venture is in every single asset class."
• "In order to identify the future of venture capital, ... you just need to go and look really stupid in front of a lot of people for a long period of time."
• "Everything you do is venture. It's just whether you recognize it."

Thanks to our sponsors for helping to make this episode of First Cheque possible:

Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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Episode Summary:

In this enlightening episode of the podcast, co-hosts Cheryl Mack and Maxine Minter engage with venture capital veteran Craig Blair to unpack the intricacies of successful early-stage investing. From sage wisdom to navigating the ever-evolving VC landscape, this conversation is a trove of insights for aspiring and seasoned investors alike.

Craig discusses his journey starting from an entrepreneurial venture in the Czech Republic to establishing AirTree Ventures, which has shaped the Australian investment scene. With a particular emphasis on strategic risk-taking and intuition in investment, the episode dissects the balance between data-driven decision-making and the human element in evaluating startups. Craig also shares his pivotal ‘big cajones’ moment—a personal story of bravery and recovery.

About the Guest(s):

Craig Blair is a seasoned venture capitalist with an entrepreneurial background and a track record of successful investments in the tech industry. With a career spanning over two decades, Craig has become a distinguished figure in the VC market since 2002. He co-founded AirTree Ventures, a leading Australian venture capital fund dedicated to investing in visionary technology entrepreneurs. With his expertise, Craig has developed a reputation for making strategic and often contrarian investment decisions that have significantly impacted the Australian ecosystem. His risk-taking prowess isn't limited to investments though; he's also known for engaging in adventurous activities such as ocean sailing.

Key Takeaways:

• A founding partner of AirTree Ventures, Craig Blair emphasizes the importance of being contrarian in investment decisions.
• The discussion reveals the significance of developing investment theses and being prepared with better information about verticals or opportunities.
• Avoiding the herd mentality and challenging personal biases are vital for successful VC investments, underscoring the need for continuous learning.
• Craig shares a personal anecdote of tenacity, underlining the importance of dedication and resilience in the face of adversity.
• Discipline surrounding fund size and alignment with LPs helps maintain investment theses, ensuring the sustainability of both venture funds and startups.

Notable Quotes:

• "If everyone in VC, for example, is going into something right now, I don't want to be there. I want to be somewhere outside that."
• "It's a humbling experience to see a company and be like, oh, it's not going to work for these reasons, or it hasn't worked in the past, and therefore it's not going to work again in the future, and then it really works in the future."
• "It's very dangerous if you start morphing your investment plan to suit your LPs."
• "You might not work before, but why would it work now?"
• "I've done a lot of adventurous things. I do a lot in my previous...well, probably still do a lot of crazy stuff. I love risk."

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Summa ry:

In this insightful episode of the podcast, listeners are introduced to the world of venture capital through the lens of Sam Wong, a seasoned Partner at Blackbird Ventures. Delving into her journey from the early investments to scaling venture funds across markets, this conversation provides an intimate look at what it means to both contribute to and grow within a startup ecosystem. Sam shares her experiences in identifying alpha opportunities, scaling venture fund operations, and the unique challenges and triumphs found in burgeoning markets like New Zealand.

As the podcast unfolds, Sam recalls her first investment and the lessons learned from its considerable return, offering a gateway to discussions on angel investing, ecosystem building, and the dedication needed to manage venture funds successfully. She provides a clearer understanding of the nuanced journey from fund one to the subsequent funds, highlighting the responsibilities of fund managers to their LPs and the critical considerations leading up to successful fund raises. This episode is not just about past decisions but also the leveraging of opportunities, strategizing for long-term outcomes, and the bold moves that define a venture capital career.

Key Takeaways:

• The transition from angel investing to venture capital management involves long-term commitment and strategic relationship building with founders and LPs.
• The phenomenon of market asymmetry can provide disproportionate access to quality deals, creating opportunities for generating alpha in venture capital investments.
• Scaling a venture fund from one iteration to the next requires more than historical performance; it necessitates team growth, market positioning, and an alignment with LP expectations.
• Early-stage ecosystems, like New Zealand's, possess unique characteristics such as strong vertical SaaS and deep tech capabilities, influenced by successful local companies and founder backgrounds.
• Personal conviction and the ability to take calculated risks, as demonstrated by Sam's decision to relocate and spearhead Blackbird's New Zealand fund, are essential traits for success in venture capital.

Notable Quotes:

• "I think that [small checks] are actually more about the relationship. And can a founder be bothered giving you a line on their cap table when the money doesn't even cover a week of Runway?" - Sam Wong
• "You can't just profit from the ecosystem, you have to take responsibility for building it too, and building it in a certain way." - Sam Wong
• "That asymmetry of capital supply to founder talent is what creates alpha opportunities, right? And you just don't get many of those in a venture lifetime." - Sam Wong
• "It didn't really take very long before I only grew in conviction that there was a sort of Australia 2013 esque opportunity where you had...a real scarcity of quality options for capital" - Sam Wong
• "I think starting New Zealand has probably been the biggest, big cojones thing because I felt it at the time too. It did feel very risky at the time." - Sam Wong

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Summary

In this episode, Maxine Minter and Cheryl Mack discuss their journeys into angel investing and share valuable insights for aspiring investors. They highlight the importance of community and learning in the early stages of angel investing and provide guidance on different investment strategies. Maxine and Cheryl also emphasize the need for diversity in the investor landscape and discuss the changing dynamics of the startup ecosystem. They address common misconceptions about angel investing and offer practical advice for those looking to get started in the field.

Key topics discussed in this episode include the different paths to angel investing, the role of education and community in learning about investing, the significance of diversity in the investor landscape, and the challenges and rewards of angel investing.

Key Takeaways

• Angel investing can be approached through various paths, including direct investments, syndicates, and investing in funds. Each approach offers unique benefits and learning opportunities.
• Building a strong community of fellow investors is crucial for learning and making informed investment decisions. Angel groups and syndicates provide valuable platforms for collaboration and knowledge sharing.
• Diversity in the investor landscape is essential for supporting underrepresented founders and driving innovation. Investors should actively seek out opportunities to invest in diverse founders and contribute to a more inclusive startup ecosystem.
• Angel investing requires a willingness to take risks and a long-term perspective. It is important to be prepared for potential losses and understand that returns may take time to materialize.
• Continuous learning and staying informed about the latest trends and developments in the startup ecosystem are key to becoming a successful angel investor.

Quotes

• "There is nothing more powerful than being the 'dumbest' person in the room. Give yourself permission to ask all the 'stupid' questions and learn as much as possible." - Maxine Minter
• "Investing in startups is a riskier asset class, and it's important to have a stomach for potential losses. But it also offers the potential for outsized returns and the opportunity to support innovative companies." - Cheryl Mack

Resources

• The Council: An organisation mentioned by Maxine Minter, formed by a group of friends from a coworking space who started an angel investing group. It has scaled into a larger organisation now.
• Zeta: The first company Maxine Minter invested in. It’s led by a founder named Aditi.
• Aussie Angels: Mentioned as a platform for angel investing in various identity groups.
• University Programs on Angel Investing:
• UQ (University of Queensland) has an angel investing program.
• UNSW (University of New South Wales) offers an angel investor course.
• Wade Institute runs the VC Catalyst course.
• Southern Angels in SA (South Australia) is reportedly working with the University of South Australia on a similar program.
• First Believers and Explorers Program: Both Cheryl Mack and Maxine Minter mention participating in this program.

Mentioned in this episode:

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Summary

Anabel Lippincott Paksoy, partner at 43, discusses the importance of building communities and their role in early-stage investing.

She shares her experience creating the council, a female-first investing group, and emphasises the need for a deep understanding of founders and their motivations.

Anabel also highlights the value of professionalising angel investing and finding founders with a strong sense of purpose and followership.

She concludes by discussing her investment preferences, focusing on niche communities and founders with a deep understanding of unsexy problems.

About The Guest

Anabel Lippincott Paksoy is a partner at 43, a pre-seed fund based in the Bay Area. She is also a partner at The Council, a female-first investing group. Anabel has a background in people operations and has a passion for building communities and supporting early-stage founders.

Key Takeaways

• Building a community is about creating a space for like-minded individuals to connect and share deal flow.
• Investing in early-stage startups is a high-risk asset class and should not be undertaken unless one is aware of the risks and willing to lose the money.
• Angel investing can be treated as a learning budget, focusing on maximising learning and gaining experience rather than making immediate financial gains.
• When evaluating founders, looking for a deep, authentic “why” behind their venture and a strong sense of purpose is essential.
• The ability to pivot and adapt is crucial for founders, as it demonstrates a willingness to learn and iterate based on feedback and market conditions.
• Successful founders' ability to attract top talent and inspire followership is a crucial trait.

Quotes

• “I think the thing that I needed, and again, it’s interesting how trends have shifted, too. Even in 2018, five years ago, it was a little new for operators. These female operators were not already super independently wealthy, to think about deploying capital as independent investors into startups.” - Anabel Lippincott Paksoy.
• “I think the thing that I know that I look for in people is some kind of deep, deep, deep, deep why that they’re doing what they’re doing.” - Anabel Lippincott Paksoy.
• “I want to feel that conviction, and there’s no way to vet that. That’s where it gets super personal. I want to ask, could I fall in love with this founder, and I don’t mean romantically? I mean, would I go work for them?” - Anabel Lippincott Paksoy

Resources

• Anabel Lippincott Paksoy
• 43
• The Council
• The Assembly

Timestamps

0:00:00 - Introduction to the podcast and guest.

0:01:57 - Discussion about Anabel’s first investment.

0:05:04 - Conversation about nostalgia and fashion trends.

0:06:12 - Exploring the concept of building communities.

0:09:48 - Challenges and principles of community design.

0:10:30 - Constructing a community for sharing investment deals.

0:11:55 - Creating a learning platform through a consortium of investors.

0:13:14 - Frustration with lack of conversation about deals in the peer group.

0:15:15 - Directing new angel investors to be aware of high risk.

0:17:31 - Treating angel investing as a learning budget.

0:18:48 - Normalising lower entry prices for angel investing in Australia.

0:19:24 - Contributing to the founder’s

Mentioned in this episode:

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Summary

Cheryl Mack and Maxine Minter reflect on the year 2023 and discuss the challenges and trends in the startup ecosystem. They talk about the tough environment for founders and investors, with many companies struggling to raise funds and facing down rounds. However, they also highlight the resilience and determination of founders who were able to survive and even thrive in the face of adversity.

The hosts discuss the increase in funding for female founders, although there is still a long way to go in achieving gender parity in the industry. They also touch on the growth of climate tech and AI as key areas of investment, with these sectors propping up the funding ecosystem.

Cheryl and Maxine express cautious optimism for the year 2024, noting the need for continued creativity and resilience in the face of challenges. They also highlight the importance of addressing issues of behaviour and inclusivity in the startup ecosystem.

Key Takeaways

• Challenges in the Startup Ecosystem (2023): The year was marked by difficulties for many companies in raising funds, with instances of down rounds reflecting a challenging environment for the startup ecosystem.
• Resilience of Founders: Success in these tough times was often attributed to the resilience and determination of founders, who demonstrated the ability to navigate through the demanding market conditions effectively.
• Funding for Female Founders: While there was a notable increase in funding for female founders, reaching a historical high, the conversation acknowledges that more efforts are necessary to achieve gender parity in funding.
• Growth of Climate Tech and AI: Both climate tech and AI emerged as standout sectors, drawing significant investments and spearheading innovation despite the broader economic challenges.
• Outlook for 2024: The year ahead is approached with cautious optimism. The emphasis is on the necessity for ongoing creativity and resilience to address and overcome upcoming challenges.

Quotes

- "I think ingenuity was a real theme. I'm excited to dive in today, obviously. Tis the season to be reflecting." - Cheryl Mack

- "The founders that survive this are the ones that we are so excited to back as investors." - Maxine Minter

- "I think optimism and holding on to a sense of optimism won this year. Pairing it with creativity, also really effective." - Maxine Minter

- "I think 2024 is looking cautiously optimistic. Cautiously optimistic." - Maxine Minter

Chapters

00:05 - Introduction to the podcast

00:25 - Reflecting on the year and the challenges faced

02:02 - Difficulty of raising funds and the resilience of founders

04:32 - Founders' determination to survive and adapt

05:08 - Employment Hero becoming a unicorn

06:31 - Tentative re-entry of international investors into the Australian ecosystem

07:38 - Gap between top founders and average deals narrowing

08:49 - Overpaying in the early stages of funding

09:05 - Australian tech facing criticism from the media

10:46 - Turning point in sentiment with SVB collapse and Milk Run

11:18 - Discussion about the impact of FTX and Sam Bankman-Fried's sentencing

12:13 - AI and climate tech propping up the funding industry in 2023

13:56 - AI adoption curve and its impact on the legal tech industry

15:01 - Tight capital environment in Q1 and Q2 of 2023

15:32 - Increase in interest and funding for climate tech

17:10 - Rise of climate tech-focused funds in Australia

18:19 - Lack of AI-focused funds in Australia

20:06 - Creativity in funding and rise of professionalized fund management

21:30 - Optimism about more fund raising in 2024

21:52 - Increase in funding for female founders, but still low overall

22:33 - Matching population demographics

22:48 - Lack of data on women-led...

Mentioned in this episode:

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Summary:

Elaine Stead joins the podcast to discuss bravery and courage in the investing world, particularly as a woman in the Australian ecosystem. She shares her journey as an investor and highlights the importance of investing in education and building networks.

Elaine also challenges the notion of being a contrarian investor and emphasizes the need for a high tolerance for risk. She discusses portfolio construction and the importance of managing risk and diversification.

The conversation also touches on the challenges faced by women in the industry and the need for change in the ecosystem.

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About The Guest:

Elaine Stead is a General Partner at M8 Ventures and an experienced investor in the Australian ecosystem. With nearly 100 investments under her belt, she is known for her bravery and courage in making investment decisions. She has a background in science and innovation and has built a strong network in the industry.

Key Takeaways:

• Investing in education is a crucial investment that can change the trajectory of one's life.
• Building networks is essential for success in the investing world, particularly for women.
• Being a contrarian investor is about having a higher tolerance for risk and being able to see opportunities early.
• The Australian ecosystem needs more diversity in capital allocation and investment decisions.
• Wealth creation and equity allocation should be more inclusive to drive change in the industry.

Quotes:

• "Being brave is about being fearful of something, but doing it anyway." - Elaine Stead
• "Diversity in teams signals the ability to manage conflict and work with people who think differently." - Elaine Stead
• "Making room for others is a show of strength and confidence." - Elaine Stead

Resources:

• M8 Ventures: Elaine Stead, the guest on the podcast, is the General Partner at M8 Ventures, a venture capital firm. (Timestamp: [00:00:49])
• Day One Network: The podcast is part of the Day One network, dedicated to founders, operators, and investors. (Timestamp: [00:00:08])
• Elaine Stead: A prominent figure in the Australian investing ecosystem, recognized for her experience and insights into investing. (Various Timestamps)
• Alex Rampell: Mentioned by Maxine Minter in the context of investing perspectives. (Timestamp: [00:10:15])
• South by Southwest Sydney: Elaine Stead mentions she will be on a panel at this event. (Timestamp: [00:25:20])
• Aussie Angels: Discussed in the context of making investment...

Mentioned in this episode:

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Summary

Rayn Ong, an angel investor and founder of Archangel, shares his insights on early-stage investing in this episode of First Cheque. Rayn discusses his first investment in Blackbird Fund One and how he built his network in the Australian startup ecosystem.

He emphasises the importance of compounding value in both networks and investments. Rayn also talks about his investment strategy, including his focus on breakout companies and his approach to evaluating opportunities.

He shares his thoughts on portfolio synergy and competition within his portfolio. Overall, Rayn's entrepreneurial approach to investing has led to his success in the industry.

About The Guest(s)

Rayn has been an active angel investor since 2014. He has invested in the early rounds of Instaclustr, Propeller Aero, HappyCo, Morse Micro, Carbar, Eucalyptus, Vow Food and StepN which are all valued at over $100 million now.

Rayn is a partner at Archangel Ventures, an angel fund that backs founders at the earliest stage possible. Rayn made his debut on the AFR Young Rich List in 2022 as an angel investor.

Key Takeaways

• Cultivating a strong network and building relationships is crucial for sourcing high-quality deals in the startup ecosystem.
• Specialising in a certain vertical or industry can provide a competitive advantage in evaluating startups and making informed investment decisions.
• The ability to identify breakout companies and double down on successful investments is key to achieving high returns in early-stage investing.
• Investing in companies that have synergy with existing portfolio companies can help derisk investments and create value for the entire portfolio.
• Setting clear expectations with founders and providing guidance throughout the investment journey can lead to successful outcomes and future funding rounds.

Quotes

• "We want to align for a good founder experience. We disclose upfront if we have exposure to potential competitors and encourage sharing to benefit the entire ecosystem." - Rayn Ong
• "We minimise risk by starting with small checks and gathering information over time before making larger investments." - Rayn Ong
• "The ability to compound value in networks is as valuable for early-stage investors as it is for the assets we invest in." - Rayn Ong

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

Learn more by joining Day One's newsletter. We create content to help founders. https://dayone.fm

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Judy Anderson-Firth, the Group CEO of Euphemia, shares insights into their investment strategy, including their focus on supporting diverse founders and making a positive impact on the Australian startup ecosystem. She emphasizes the importance of transparency and accessibility in the family office world and discusses the value of building a strong network and connecting founders within their portfolio. Judy also explores the concept of gracefully exiting failed startups and the potential for an "anti-accelerator" that rewards founders for pivoting and trying new ideas. She concludes by introducing the Euphemia Syndicate, a platform that provides access to unique deal flow and lowers the minimum check size for angel investors.

About The Guest(s)

Judy Anderson-Firth is the Group CEO of Euphemia, a family office that invests in fintech, climate tech, and women-led startups. She has extensive experience in the startup ecosystem, having previously served as the CEO of Startup Victoria, Australia's largest startup community for entrepreneurs.

Key Takeaways

• Euphemia invests in fintech, climate tech, and women-led startups, prioritizing founders from disadvantaged backgrounds.
• Transparency and accessibility are crucial in the family office world.
• Building a strong network and connecting founders within their portfolio is highly valuable.
• Celebrating and facilitating the graceful exit of failed startups can accelerate the growth of the ecosystem.
• The Euphemia Syndicate offers access to unique deal flow and lowers the minimum check size for angel investors.

Quotes

• "A failed founder is an experienced founder." - Judy Anderson-Firth
• "Australia is not doing a good job at the moment of celebrating and facilitating founders to gracefully exit." - Maxine Minter
• "If we make failing easier, more respectful, and celebrate the benefits, we'll move much faster as an ecosystem." - Maxine Minter
• "We've now built the Euphemia Syndicate... to share some of those deals and lower the minimum check size and share the love." - Judy Anderson-Firth
• "Cheryl, you're building an incredible platform, a piece of financial infrastructure for the startup ecosystem to unlock capital." - Judy Anderson-Firth

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First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

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Mentioned in this episode:

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Summary

Dan Gavel, founder of Black Sheep Capital Fund and the Flock Syndicate, shares his unique approach to investing and discusses the importance of understanding risk. He emphasizes the need for investors to have the capacity to accept risk and adapt their investment strategies to the changing market. Dan also talks about the benefits of running a fund, a syndicate, and making personal angel investments simultaneously. He explains how he decides which investments go to each channel and the importance of building relationships with founders. Dan believes that being a lead investor is more about post-investment support and guidance rather than pre-investment due diligence. He also shares a personal story of a risky investment that didn't go as planned.

About The Guest(s)

Dan Gavel is the founder of Black Sheep Capital Fund and the Flock Syndicate. He has a background in financial planning and has made numerous successful angel investments. Dan is known for his down-to-earth and innovative approach to investing.

Key Takeaways

• Understanding risk is more important than trying to fully comprehend it.
• The investment landscape is constantly changing, and investors need to adapt their strategies accordingly.
• Running a fund, a syndicate, and making personal angel investments simultaneously allows for a more diversified portfolio and greater exposure to the ecosystem.
• Being a lead investor is about building relationships with founders and providing post-investment support and guidance.
• It's important to have conviction in an investment and be willing to take risks.

Quotes

• "For us, the pre-seed stage is all or nothing. We're aware that it's a risky business, and we accept that." - Dan Gavel
• "The lead investor is the person who wants to build a relationship with the founder and do what it takes to get the deal across the line." - Dan Gavel

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

Learn more by joining Day One's newsletter. We create content to help founders. https://dayone.fm

Learn about upcoming guests and new First Cheque episodes are available, join the First Cheque newsletter https://dayone.fm/podcast-network/first-cheque/newsletter

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Mentioned in this episode:

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Summary

Jessy Wu discusses the importance of having the confidence to speak up and share your opinions. She shares that her confidence comes from being deeply loved and supported by her parents, which instilled in her a strong sense of self-worth. She also discusses the role of building a personal brand as a small fund and how being a lightning rod for certain conversations can align with a fund’s strategy.

About The Guest(s)

Jessy Wu is an investor at Afterwork Ventures. She is known for her bold and thought-provoking insights on social media and is passionate about supporting early-stage companies.

Key Takeaways

• Confidence comes from a strong sense of self-worth and being supported by loved ones.
• Building a personal brand as a small fund can help differentiate and create a unique value proposition.
• Being a lightning rod for certain conversations can attract attention and align with a fund’s strategy.

Quotes

• “I’ve never felt like an imposter or like I didn’t deserve to have a seat at the table.” – Jessy Wu
• “There is a way to be known for something as a small fund and have an active reason for someone to want you on their cap table.” – Jessy Wu

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

Learn more by joining Day One's newsletter. We create content to help founders. https://dayone.fm

Learn about upcoming guests and new First Cheque episodes are available, join the First Cheque newsletter https://dayone.fm/podcast-network/first-cheque/newsletter

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Maxine and Cheryl kick off the First Cheque podcast, a show dedicated to helping early-stage investors become better at their craft. They aim to open source conversations and insights from experienced investors to provide valuable information and education for emerging investors. The podcast focuses on the Australian ecosystem but also explores international perspectives on investing. They discuss the importance of understanding risk, the distinction between betting and investing, and the need for better decision-making processes. They also touch on the current state of the market, noting some green shoots and increased deal flow, but also expressing concerns about the sluggishness in the series C to E stages.

Key Takeaways

- Open-sourcing conversations and insights from experienced investors can help emerging investors become better at their craft.

- Understanding risk and making intelligent risk-taking decisions is crucial for successful investing.

- The distinction between betting and investing lies in the ability to control risk factors and make informed decisions.

- The current market shows some green shoots and increased deal flow, but there are concerns about sluggishness in the series C to E stages.

- This is a great time to be investing, especially in early-stage companies that demonstrate resilience and have the potential to thrive in the future.

Quotes

- "If you want to be a better early-stage investor, this is the show for you." - Maxine Minter

- "Being compensated for risk is the variable of return profiles in different asset classes." - Maxine Minter

- "Investing in startups is risky, but there are factors you can control and levers you can pull." - Cheryl Mack

- "Great investing is good decision process plus great information." - Maxine Minter

- "This is a great time to be greedy and invest in early-stage companies." - Maxine Minter

First Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

To learn more, head to https://dayone.fm and join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

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Mentioned in this episode:

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