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Recent episodes
Closing the Gender Investment Gap with Data with Noga Edelstein
May 4, 2026
Unknown duration
How to Build a Global Pre-Seed Fund from Scratch
Apr 19, 2026
Unknown duration
Why Every Founder & Investor Needs to Understand Open Source AI (Replay Episode)
Mar 8, 2026
Unknown duration
How to Pick Your First Market for International Expansion
Feb 8, 2026
Unknown duration
The Australian Venture Playbook for 2026
Jan 11, 2026
Unknown duration
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 5/4/26 |  Closing the Gender Investment Gap with Data with Noga Edelstein | Episode SummaryNoga 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 Stamps00:00 Intro02:27 – Noga's first investment: dollar-mite savings accounts in primary school10:02 – What is Equity Clear and why pipeline data is the missing piece14:40 – Why closing the gender gap matters now: productivity, economics, and AI bias19:27 – Pre-seed funding to women is at its lowest ever despite lower barriers to building24:44 – Why collecting diversity data feels hard but isn't28:32 – Lessons from the UK: what five years of tracking has revealed32:02 – Maxine's accidental experiment: when a broken form hid all the women founders37:39 – How male founders and LPs can push for change by asking simple questions48:16 – Why funds are missing a trick on sourcing diverse founders51:32 – Breaking the archetype: leveling the playing field with systemic tweaks57:15 – Big Cojones moment: quitting law with a newborn to start a companyFirst 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/ | — | ||||||
| 4/19/26 |  How to Build a Global Pre-Seed Fund from Scratch | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode SummaryElizabeth 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 Stamps00:00 – Intro01:54 - Elizabeth's first investment: three shares of Coca-Cola at age 1006:50 – What Hustle Fund is investing in now and why vertical SaaS still matters in the AI era09:31 – How Hustle Fund sources deals globally through co-investors and content15:09 – Elizabeth's two-part framework: founder quality vs. idea quality18:10 – Why competitive markets are a double whammy for small-check investors22:57 – The surfing analogy: spotting small waves that grow big in five years25:06 – Biggest investing lessons from Fund 1 to Fund 4: valuation and follow-on discipline27:58 – Camp Hustle, content marketing, and running VC like a lead generation business30:09 – Does valuation really matter at pre-seed? When it does and when it doesn't37:39 – Growing AUM: why Fund 2 was the hardest and the "event ticket sales" fundraising pattern44:15 – Which fund graduation was hardest and the DPI reality at pre-seed46:21 – Big Cojones moment: confronting bias as a female founder and how platform changes power dynamicsThis 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/ | — | ||||||
| 3/8/26 |  Why Every Founder & Investor Needs to Understand Open Source AI (Replay Episode) | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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/ | — | ||||||
| 2/8/26 |  How to Pick Your First Market for International Expansion | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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/ | — | ||||||
| 1/11/26 |  The Australian Venture Playbook for 2026 | 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/ | — | ||||||
| 11/16/25 |  What are VC Fund Secondaries? | 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/ | — | ||||||
| 10/19/25 |  Why “Boring” Businesses Make the Best Startups (Replay Ep with Matthew Browne) | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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/galahFirst 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/ | — | ||||||
| 10/5/25 |  Inside Super Returns: How the Biggest Investors Pick Venture Funds | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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/galahFirst 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/ | — | ||||||
| 9/21/25 |  How Prosus Ventures Became an “Honorary Australian” Fund | Sachin Bhanot | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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/galahFirst 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/ | — | ||||||
| 9/7/25 |  Why Australia’s AI Opportunity Is Bigger Than We Think | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode SummaryTom 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 Stamps02:21 – Tom’s first investment: BHP shares via his parents, now passing on the habit to his son05:19 – Robinhood, meme stocks, and the shift to founder-led brands07:06 – Why Tom wrote the AFR piece: Australia’s culture of doubt vs the US lens of opportunity08:08 – Australia’s untapped AI talent advantage: 8% of APAC experts, top-tier unis, and PhD immigration12:18 – Six model releases, global leaderboard wins… that no one in Australia talks about14:03 – The dangerous cost of silence: how lack of domestic celebration dampens ambition and capital17:33 – Why Australia is absurdly capital-efficient (and how we squeeze every dollar)19:23 – Commercialisation bottlenecks at Aussie unis, and what’s slowly changing25:39 – How this affects investors: AI engineering vs AI research, the boomerang effect, and talent arbitrage30:56 – Time zones, USD revenue, and Australia’s secret weapon: the 43% R&D tax credit33:17 – Role gaps and brand new roles: the rise of AI architects and forward deployed engineers34:27 – What PLG really means, and why it’s not just a freemium sign-up form39:31 – Spammy AI agents, SEO collapse, and why brand and community are back45:15 – 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 adoption51:15 – AI fits into your workflow, not the other way around54:14 – Picking your motion: don’t force PLG if it’s not a natural fit55:05 – Capital-starved ecosystems and why enterprise is still harder to fund in Aus56:15 – Tom’s Big Cojones moment: three boys under six and a startup-founder partnerResources👤 Tom Humphrey LinkedIn – https://www.linkedin.com/in/tomhumphrey1/🚀 Blackbird Ventures – https://blackbird.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/galahFirst 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 CyberAussie Angels - the preferred fund and syndicate admin platform for emerging managers in AustraliaShow 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.comFebruary 2025 - Aussie AngelsThis 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/ | — | ||||||
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| 8/10/25 |  How VCs Really Assess AI Startups | Cheryl Mack, Maxine Minter and Georgie Healy | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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/galahFirst 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/ | — | ||||||
| 7/27/25 |  Decode the VC Dictionary Before Your Next Raise | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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/galahFirst 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/ | — | ||||||
| 7/13/25 |  Scaling Solo: How Charles Hudson Built a High-Volume VC Model at Precursor Ventures | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode SummaryCharles 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 Stamps03:20 – Charles’s first investment: ExxonMobil shares… mailed by cheque06:50 – What is a solo GP fund, and how Precursor operates with one partner and 14 staff10:28 – The pros and cons of solo decision-making in venture12:50 – How Precursor supports 450+ companies (and avoids “orphaned” portfolios)15:44 – Why Charles shifted from unlimited founder support to intentional check-ins19:18 – Trust vs likability, and why real feedback matters more than being liked24:25 – How Charles handles saying “no” to follow-ons, and still earns trust29:31 – The case for “challenger” VCs over cap-table cheerleaders32:11 – What Precursor looks for in a founder: not great employees, but great CEOs36:39 – High volume investing: Why meeting 2000+ startups matters39:00 – Global allocation: why Charles bet early on African and LatAm FinTech42:30 – The return of themes (like AI & Women’s Health), and why they can kill judgment47:52 – 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 scratch56:15 – Why most fund managers are “post-employment” and proud of itResources👤 Charles Hudson LinkedIn - https://www.linkedin.com/in/chudson/🌎 Precursor Ventures – https://precursorvc.com/First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.Mentioned in this episode:Aussie Angels - the preferred fund and syndicate admin platform for emerging managers in AustraliaShow 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.comFebruary 2025 - Aussie AngelsThis 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/ | — | ||||||
| 7/1/25 |  Why Australia Builds More Unicorns per Dollar Than Anyone | with Ben Grabiner from Side Stage Ventures | 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-2025Episode SummaryBen 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 Stamps04:49 – Ben’s first investment: £250 in Tottenham Hotspur06:34 – What makes Australian unicorns so capital-efficient?09:14 – Unicorn efficiency vs gross unicorn creation: what matters more13:15 – How Australia quietly matches Israel and India on decacorn creation14:35 – Why foreign investors see the opportunity more clearly than locals18:41 – The power of local exits like Afterpay, and how they inspire allocation21:19 – 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 weapon25:54 – What global LPs need to understand about Australian venture30:17 – Why pre-seed funds and angel investors matter more than everResources🙋🏻♂️ 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/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/ | — | ||||||
| 6/1/25 |  Nnamdi Okike's Playbook for Investing in Non-Obvious Winners | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode SummaryNnamdi 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 Stamps04:34 – Nnamdi’s first investment during the dotcom boom06:52 – Defining “non-obvious industries” and spotting hidden TAM10:40 – Squire: From barbershop bookings to vertical SaaS OS13:20 – Goldbelly, marketplaces, and the power of founder insight17:58 – Algorithmic sourcing meets founder conviction21:30 – What 645 Ventures learned from missing Facebook26:46 – Building a fund around risk profiles, not just stages30:34 – Why the power law should shape every VC decision35:16 – Does 2024 echo 2002? A macro take on the downturn42:41 – The rise of zombie funds and quiet closures45:20 – Bootstrapped AI startups and the future of defensibility52:54 – When vertical AI gets sticky—and when it doesn’t57:20 – Nnamdi’s Big Cojones moment: from Insight to starting freshResources🙋♂️ 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/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/ | — | ||||||
| 5/4/25 |  Pocket Sun’s Guide to Standing Out as an Emerging Investor | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode SummaryPocket 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 Stamps00:00 – Pocket’s first angel check: $1K into an AI startup05:30 – Angel investing isn’t just for the ultra-wealthy09:45 – From building a global pitch comp to proving LP credibility14:20 – Early wins: Everly Health, Lovevery, and chasing allocation23:35 – “Land and expand”: getting on cap tables and earning super pro-rata27:10 – Leading recaps and fighting for underestimated founders35:00 – SoGal’s thesis: The future of living, working, and staying healthy40:30 – Entering new verticals without prior expertise46:00 – Pocket’s take on the Vancouver vs. Toronto startup ecosystems53:00 – Betting on design-led, intentional consumer businesses59:10 – Why consumer startups often graduate into enterprise giants01:03:00 – Pocket’s Big Cojones moment: moving solo to the U.S. at 18Resources🙋♀️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: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/galahFirst 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:FC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This 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/ | — | ||||||
| 5/3/25 |  Introducing Perspective X | Hosted by Pauline Fetaui - Perspective X with Pauline Fetaui | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyWhat 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.Mentioned in this episode:Day One sting | — | ||||||
| 4/21/25 |  Monique Woodard’s Cake Ventures Strategy: Big Bets on Aging, Women & Culture | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode SummaryMonique 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 Stamps03:07 – Monique’s first investment: picking stocks at age 2006:12 – Her journey from rural entrepreneurship to 500 Startups and VC12:43 – 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 America24:32 – Real talk on Solo GP life: choosing partners, hiring venture partners, and building a legacy firm30:07 – Raising Fund II: bigger checks, deeper domain expertise, and firm evolution39:12 – How founders should position their companies in the AI hype cycle45:24 – Advice for operators: Understanding the difference between investing and running a venture firmResources🍰 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/moniquewoodardSponsors: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/galahFirst 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 CyberFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This 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/ | — | ||||||
| 4/6/25 |  How James Tynan from Square Peg Invests in EdTech | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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 – Intro02:16 – James’s first big bet – Starting a company in Australia’s early 2000s “hellscape” and the lessons learned07:18 – Why MOOCs weren’t the answer – The early EdTech hype, misconceptions about online courses, and how Khan Academy did things differently11:12 – Assessment as the control point – How exams and credentials shape mainstream education and what might disrupt that model15:08 – 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” rules24:00 – VC skepticism vs. reality – Why it’s so hard to invest in K–12 EdTech, and where vocational and adult learning might be more promising32:00 – Rapid AI adoption – From legal tech to healthcare, how ambient tools are skyrocketing and what it means for founders37:00 – Wedges, moats, and growth – The playbook for AI startups moving from “just a feature” to a sustainable product42:00 – James’s “big kahunas” moment – Choosing Khan Academy over Stanford and why walking away from “prestige” can change everything47:07 – Wrap-up – The future of EdTech, AI’s role, and parting wisdom for founders and investorsResources MentionedJames 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: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/galahFirst 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:FC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Galah CyberThis 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/ | — | ||||||
| 3/23/25 |  Crafting Your Investment Thesis: How to Decide What to Invest In | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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 matters01:49 – Defining an investment thesis: What it is & why it's essential04:49 – How to break down your thesis into clear categories05:16 – Industry focus: Verticals, horizontals, and emerging trends07:05 – Stage focus: Pre-seed, seed, growth—how to pick your sweet spot08:24 – Business model focus: B2B SaaS, marketplaces, and beyond10:01 – Geography: The pros and cons of investing locally vs globally14:29 – Key questions every investor should ask themselves17:24 – Company-specific criteria: How to create your investment checklist22:33 – Evaluating market size and growth potential25:39 – Pain vs pleasure: Investing in painful problems vs unmet desires29:54 – Unique or niche theses: Second-time founders, alumni networks, and more33:46 – Access and deal flow: How to attract great opportunities38:35 – Understanding your personal risk profile & timeline expectationsResourcesAngel Academy – Comprehensive angel investing course for Australia & NZ: www.venture.academyAussie 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/galahFirst 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 CyberFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This 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/ | — | ||||||
| 3/9/25 |  Decoding Startup Investment: SAFE Notes, Convertible Notes & Priced Rounds | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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 matter01:45 – SAFE notes, convertible notes, and priced rounds explained03:47 – How founders raise money: equity vs. debt06:21 – The documents you’ll sign in a priced round10:22 – Do startups need a constitution? Red flags to watch for14:29 – Side letters: What are they, and should you be worried?19:08 – Pro-rata rights & why they matter for investors22:23 – Most Favoured Nation (MFN) clauses explained30:27 – Pre-money vs. post-money SAFEs: Which one is better?38:03 – Why valuation caps and discounts can be a double-edged sword43:53 – 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: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/galahFirst 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 CyberFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This 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/ | — | ||||||
| 2/23/25 |  Mastering Fund Cycles: How VCs Raise, Invest & Exit | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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 & founders01:21 – Who this episode is for: Emerging fund managers & startup founders03:23 – Understanding fund cycles: Raising, deploying, and exiting05:48 – The reality of raising a fund: Why it takes 12-24 months to close09:35 – Deployment periods: How VCs decide when and where to invest12:34 – The risk of running out of money—how fund managers avoid this mistake16:57 – Fund sizes & check sizes: Why $50M is a magic number in VC21:09 – Micro VCs vs. bigger funds: How different strategies impact returns25:14 – Opportunity funds: When fund managers double down on winners30:08 – The importance of liquidity planning and secondaries in VC37:17 – Exits: How and when fund managers start planning for returns43:59 – Final thoughts: The key takeaways from this episodeResources 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 downSponsors: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/galahFirst 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 CyberFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This 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/ | — | ||||||
| 2/9/25 |  Angel Investing 101: How To Not Run Out Of Money | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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 investors01:49 – The golden rule: How not to run out of money when investing02:37 – Why staying liquid matters: Power law, economic cycles, and risk mitigation05:15 – Angel investing vs. stock market investing: Why you can't just sell down a position08:04 – How Cheryl funds her investments: Breaking the myth of needing huge capital10:00 – Alternative funding sources: Super funds, ETFs, term deposits, and more13:41 – The importance of knowing your risk tolerance and financial boundaries17:48 – Varying check sizes: When to double down on winners and how to strategise23:15 – Why new angel investors should start with consistent check sizes30:47 – Australian angel success stories: Real returns and lessons from Clarity Pharmaceuticals, Autra, and Instacluster34:56 – Final takeaways: Planning, patience, and how to build a sustainable angel investing portfolioResources MentionedAngel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academyAussie Angels – Cheryl’s platform for angel investingCoventures – Maxine’s venture capital firmCentral Texas Angel Network (CTAN) – Study on angel investment returnsTechCoast Angels California – Report on long-term angel investing performanceAustralian Angel Success Stories:Clarity Pharmaceuticals – 50x return for early investorsAutra (Agil) – Acquired by Schneider Electric, 91% IRRInstacluster – 63% IRR after acquisition by NetAppSponsors: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/galahFirst 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:FC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Galah CyberThis 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/ | — | ||||||
| 1/26/25 |  From Firefox to AI: Mozilla’s Fight for Open Technology | Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/surveyEpisode 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 Chambers02:06 – The origin story of open source and Mozilla’s role in internet history07:22 – Netscape, Firefox, and the fight for an open internet11:05 – The challenges of keeping AI open in a world of closed ecosystems15:19 – Why open source innovation accelerates progress19:12 – Addressing the misconceptions of open source and its role in AI safety23:18 – The potential societal impacts of closed vs. open AI29:34 – Insights into Mozilla Ventures and the Builders Program35:01 – Why transparency and accountability are essential in AI development41:16 – How open AI can empower underrepresented communities globally47:20 – Laura’s biggest lessons as a leader in tech and her vision for Mozilla’s futureResources MentionedMozilla 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: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/galahFirst 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:FC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Galah CyberThis 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/ | — | ||||||
| 1/12/25 |  Liquidity Talks: The Future of IPOs and M&As | Episode Summary: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 episode01:03 - Discussion on liquidity, IPOs, and M&A in the venture ecosystem02:07 - Defining liquidity, IPOs, and M&A for the audience05:21 - Importance of IPOs in venture capital and why they matter09:30 - Impact of the health of IPO markets on investment strategies14:56 - Investment strategies during different market cycles; being contrarian16:14 - Exploring opportunities in secondaries amidst liquidity challenges21:13 - Reasons companies are staying private longer; regulatory influences26:43 - Regulatory clampdown on M&A and its effects on the tech ecosystem31:45 - Closing remarks; encouraging solutions for liquidity issuesResources 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: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 CyberFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This 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/ | — | ||||||
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