First Cheque with Cheryl Mack & Maxine Minter

Episode SummaryIn 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 Stamps00:00 Intro & Guest Highlights00:21 Why We're Excited About Laura Chambers03:14 Interview Begins: Laura's First Investment at Age 1005:20 Open Source 101: What It Is & Why It Matters07:08 Firefox vs Internet Explorer: The Open Source Origin Story09:58 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 Seatbelts19:37 The Case For & Against Closed Source AI21:35 Why Researchers, Academics & Governments Need Open Access22:17 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 Gap29:16 Open vs Closed: Who's Winning Right Now?33:49 Meta's Llama & the Strategic Logic of Going Open35:21 Advice for Founders & Investors Building on Open vs Closed Models39:21 Inside Mozilla Ventures: What They're Investing In41:31 Prompt Engineering Tips From a CEO (Say Please!)46:13 The Biggest Brave Moment: Moving Her Family & a 17-Year-Old Dog to Australia49:20 The Weight of Being CEO & What That Feels LikeResources1) 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)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.This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode SummaryFrontline’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 Stamps03:14 Brennan’s first investment: Mode Analytics and a lawn mowing business in Texas06:49 What’s changed at growth stage and why “growth” is a different world08:30 Why AI enablement came first and app layer is finally ready for Series B plus10:10 The new risk: fast revenue that’s concentrated and not yet durable14:22 Frontline’s model: Europe seed plus US growth and why it’s unique15:58 What Frontline looks for: category leaders and a line of sight to a 5x outcome16:20 The rough revenue range where growth starts paying attention23:22 The four pillars of expansion: timing, go to market, talent, location26:00 Timing: the 10 percent pull, exec maturity, and why waiting too long is risky29:36 Why Europe expansion has to be a CEO level company priority38:04 Build or buy: why most companies compete into new markets rather than acquire39:10 Developer community expansion as a new go to market wedge41:44 Market selection: why nearly everyone starts with London or Dublin43:56 “Success amnesia” and why you must optimize for learning not quotas48:28 Relationship driven sales cycles and how Europe varies market to market52:43 Big Cojones moment: taking a temp Google job and betting on himself54:26 Doing it again: moving to Dublin in three weeks to help build Google EuropeFirst 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.This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode SummaryAs 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 Stamps00:00 – Intro: End of year energy: why 2025 felt different to 202403:55 – Election fallout and the government’s “nothingburger” for startups05:24 – Canva’s secondary and the first real signs of liquidity returning09:49 – Aussie tech M&A heats up: Canva, Linktree, Jolt, and more12:09 – The stat that changed the narrative: Australia’s unicorn efficiency16:14 – The weirdest trend of the year: early stage down, late stage up18:27 – Tech jobs, data centers, and the infrastructure bet Australia is making22:52 – Why deep tech and climate are pulling venture dollars again28:21 – The gender funding gap got worse (and why)33:09 – Corporate VC is pulling out: what happened to strategic capital37:02 – 2026 predictions: funding totals, seed pain, and where capital flows next44:00 – AI bubble risk: tourism, ROI pressure, and the domino effect47:42 – Hot take: electricity is the next valuation premium49:00 – Will diversity bounce back in 2026? (vibes, but also logic)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.This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode SummaryMax 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 Stamps02:47 – Max's first investment: lessons as a 14-year-old basketball coach07:08 – Defining secondaries and Advance VC's unique LP fund focus09:44 – Why vintage diversification matters as much as company diversification13:57 – How secondary transactions actually work: the three-way deal between buyer, seller, and fund19:24 – What Max learned looking under the hood of Australian VCs firms across different funds and vintages24:09 – Why Max decided on a secondary Fund of Funds (FoF) model34:16 - Pricing secondaries42:20 – What discounts actually look like in practice47:40 – Will secondaries save venture? The truth about liquidity and why it's concentrated in top performers50:16 – Building Advance VC and the founder journey of becoming a fund managerResourcesMax Kausman - https://www.linkedin.com/in/maxkausmanAdvance VC - https://www.advancevc.com/This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode SummaryMatt 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:First Cheque is supported by our wonderful sponsors: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/Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.https://dayone.fm/galah 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. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode SummaryWhat 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 Stamps01:00 – What Super Returns is, and why it matters for VCs and angels06:43 – The LP landscape explained: super funds, sovereign wealth funds, and family offices10:40 – Winners and losers in APAC: India, China, Japan… but not Australia18:00 – Why Australia needs a better “brand story” to attract capital19:54 – Hot topic: co-investing and why LPs love it23:39 – Look-through ownership: why everyone’s just trying to own the outliers26:43 – Why emerging managers are struggling in today’s fundraising market33:49 – Family offices having “the time of their lives” in this cycle34:23 – Mega-funds, evergreen funds, and the $30B a16z raise39:30 – Will Sequoia and a16z ever lose their dominance?42:19 – Why APAC liquidity markets matter more than ever45:30 – The question nobody asked at Super Returns49:22 – How to actually build LP relationships that work53:55 – Maxine’s big takeaway: putting Australia on the winners listSponsors:First Cheque is supported by our wonderful sponsors: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/Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.https://dayone.fm/galah 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. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode SummarySachin 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 Stamps02:53 – Sachin’s first and most important investment (hint: not a startup)07:31 – The paradoxical traits of winning founders10:26 – Singapore vs Southeast Asia: the tale of two ecosystems18:12 – Why Prosus doubled down on Australia in 202228:40 – Tips and traps for Aussie founders expanding regionally34:44 – When is the “right” time to enter Southeast Asia?42:11 – The rise of the Australia–India–Singapore innovation corridor48:34 – Singapore family offices and the art of relationship-driven capital51:59 – Sachin’s Big Chon moment: learning empathy by building businesses himselfResourcesResources Mentioned🙋🏻‍♂️ Sachin Bhanot - https://www.linkedin.com/in/sachin-bhanot-15551913a/💰 Prosus Ventures - https://www.prosus.com/prosus-venturesSponsors:First Cheque is supported by our wonderful sponsors: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/Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.https://dayone.fm/galah 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. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Tom Humphrey, Partner at Blackbird and a former operator, reshapes perceptions of Australia's AI landscape. He highlights the overlooked world-class talent and potential in AI, arguing against the narrative of Australia lagging behind. Discussions include the challenges of the university-to-startup pipeline, the return of skilled PhDs from top tech firms, and the effectiveness of Australia's capital-efficient model. Tom also explores how AI is redefining go-to-market strategies and emphasizes the need for local recognition to boost ambition and investment.

Episode SummaryIn 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 Stamps02:15 – 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 AI21:00 – What angel investors should look for in AI startups27:30 – AI’s biggest red flag: When it all just sounds like magic31:00 – Are agents real or is everyone faking it?36:40 – AI in venture workflows: What Maxine actually automates41:30 – The real power of personal brand in VC44:50 – How Cheryl preps for founder calls with Google NotebookLM49:00 – Weekly AI hacks: From flat lays to voice-mode strategy sessions52:10 – Founder FOMO: Prompt Cowboy, Juno, and other hot startups54:00 – The case for non-technical founders in AI58:00 – 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:First Cheque is supported by our wonderful sponsors: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/Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.https://dayone.fm/galah 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:November 2024 - Galah CyberAngel Academy - Best online angel investing course in Australia and New ZealandDon'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 AcademyThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode SummarySome 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 Stamps01:45 – “Not a fit”: Why investors love this vague phrase03:40 – What they mean when they say “you’re too early”08:30 – “You’re too late”, how stage mismatches work both ways15:30 – “We’ll circle back” and other signs of a slow no17:10 – How long does VC diligence really take?19:15 – Why June 30 is a terrible time to raise24:10 – 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 negotiating36:00 – Understanding info rights vs. investor updates38:50 – How to share bad news without burning relationships45:20 – The shifting goalposts of traction and growth metrics47:00 – Spotting investor doubts through team questions48:10 – Final thoughts for both founders and investorsResources😇 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: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/Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.https://dayone.fm/galah 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. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/