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First Cheque with Cheryl Mack & Maxine Minter

Business & Economics Podcasts

First Cheque is dedicated to open-sourcing conversations with experienced investors globally. Our aim? To enhance the craft of early-stage investors, from those writing their first cheques to the veterans in the game. First Cheque is supported by our...

Location:

Australia

Description:

First Cheque is dedicated to open-sourcing conversations with experienced investors globally. Our aim? To enhance the craft of early-stage investors, from those writing their first cheques to the veterans in the game. First Cheque is supported by our wonderful sponsors: 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 Hosted by Cheryl Mack & Maxine Minter, First Cheque is a Day One show. Day One is the podcast network dedicated to founders, investors, and operators. Tune in for an enriching experience as we uncover the secrets to becoming a skilled early-stage investor. First Cheque on Day One https://dayone.fm/shows/first-cheque Sign up to get your weekly insights into the inner workings of early-stage investing. https://dayone.fm/newsletter/ This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Twitter:

@dayonefm

Language:

English


Episodes
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Why Every Founder & Investor Needs to Understand Open Source AI (Replay Episode)

3/8/2026
Episode Summary In this episode of First Cheque, Cheryl and Maxine sit down with Laura Chambers, CEO of @Mozilla to dive into the transformative power of open source technology and its role in shaping the future of the internet and artificial intelligence. Laura shares insights on Mozilla’s unique nonprofit structure, the importance of transparency and accessibility in technology, and the critical need for an open AI ecosystem to drive innovation and equity. From the historical impact of open source software like Firefox to the current challenges of balancing ethical AI development with business needs, this conversation is packed with lessons for early-stage investors and tech enthusiasts alike. Laura also provides an inside look at Mozilla Ventures and the Builders Program, which are supporting the next wave of open-source innovators. Whether you're an investor, founder, or just curious about the future of tech, this episode is a must-listen! Time Stamps 00:00 – Introduction to the episode and Laura Chambers 02:06 – The origin story of open source and Mozilla’s role in internet history 07:22 – Netscape, Firefox, and the fight for an open internet 11:05 – The challenges of keeping AI open in a world of closed ecosystems 15:19 – Why open source innovation accelerates progress 19:12 – Addressing the misconceptions of open source and its role in AI safety 23:18 – The potential societal impacts of closed vs. open AI 29:34 – Insights into Mozilla Ventures and the Builders Program 35:01 – Why transparency and accountability are essential in AI development 41:16 – How open AI can empower underrepresented communities globally 47:20 – Laura’s biggest lessons as a leader in tech and her vision for Mozilla’s future Resources 1) Mozilla Ventures: Supporting startups focused on privacy, AI, and open source innovation. (https://mozilla.vc/) 2) Mozilla Builders Program: Investing in and mentoring early-stage entrepreneurs building ethical tech solutions. (https://builders.mozilla.org/) 3) Harvard University Study: Open Source Software’s $8 Trillion Economic Impact A study on the global economic value created by open source technology. (https://www.hbs.edu/ris/Publication%20Files/24-038_51f8444f-502c-4139-8bf2-56eb4b65c58a.pdf) 4) Anthropic Report on Bias in AI: Research highlighting the impact of bias and the importance of transparency in AI models. (https://www.anthropic.com/research/mapping-mind-language-model) 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:51:08

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How to Pick Your First Market for International Expansion

2/8/2026
Episode Summary Frontline’s Brennan O’Donnell has spent two decades helping companies expand across borders, first as an operator at Google and later as a growth investor backing Series B to D businesses. In this episode, Cheryl and Maxine unpack what’s shifted at growth stage in the last 12 months, why the market is still a barbell of “hot or not” deals, and how AI is finally producing application layer companies mature enough for growth rounds. They go deep on Frontline’s transatlantic model: seed investing across Europe to help founders raise a Series A and enter the US earlier, and growth investing in the US to help companies expand into Europe with a hands on, concentrated portfolio approach. Brennan breaks down the four pillars Frontline uses to drive international expansion timing, go to market, talent and org design, and location plus the biggest traps founders fall into, like trying to launch in too many markets at once or optimizing for revenue targets instead of learning. You’ll also hear why the UK and Ireland are the default first step for 97 percent of US companies entering Europe, when Europe becomes a CEO level priority, how relationship driven sales cycles vary across countries, and why developer led community building can beat traditional sales led expansion for certain AI products. Brennan closes with his Big Cojones moment: moving to the Bay Area for a temporary Google job with everything in storage, then doing it again to help build Google’s European HQ in Dublin. Time Stamps 03:14 Brennan’s first investment: Mode Analytics and a lawn mowing business in Texas 06:49 What’s changed at growth stage and why “growth” is a different world 08:30 Why AI enablement came first and app layer is finally ready for Series B plus 10:10 The new risk: fast revenue that’s concentrated and not yet durable 14:22 Frontline’s model: Europe seed plus US growth and why it’s unique 15:58 What Frontline looks for: category leaders and a line of sight to a 5x outcome 16:20 The rough revenue range where growth starts paying attention 23:22 The four pillars of expansion: timing, go to market, talent, location 26:00 Timing: the 10 percent pull, exec maturity, and why waiting too long is risky 29:36 Why Europe expansion has to be a CEO level company priority 38:04 Build or buy: why most companies compete into new markets rather than acquire 39:10 Developer community expansion as a new go to market wedge 41:44 Market selection: why nearly everyone starts with London or Dublin 43:56 “Success amnesia” and why you must optimize for learning not quotas 48:28 Relationship driven sales cycles and how Europe varies market to market 52:43 Big Cojones moment: taking a temp Google job and betting on himself 54:26 Doing it again: moving to Dublin in three weeks to help build Google Europe 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:57:03

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The Australian Venture Playbook for 2026

1/11/2026
Episode Summary As 2026 kicks off, Cheryl and Maxine open the year with their annual First Cheque wrap, a grounded, opinionated take on what actually shifted in Australian tech and venture, and what that means for the year ahead. They break down why 2025 marked a genuine inflection point for the ecosystem, from Canva’s secondary and a surge in M&A to fresh signals that long-awaited liquidity is finally starting to flow. Despite minimal government support, Australia quietly proved itself as one of the most capital-efficient venture markets globally, producing unicorns at roughly twice the rate of the US per dollar invested. The conversation also tackles the harder truths investors and founders need to reckon with in 2026: early-stage funding compressing while late stage heats up, corporate venture capital retreating, and the gender funding gap sliding backwards. Looking forward, Cheryl and Maxine share their predictions for the year ahead, where funding volumes may land, why seed remains the toughest stage, how AI valuations could trigger a market correction, and why energy and infrastructure may emerge as the next premium asset class. Time Stamps 00:00 – Intro: End of year energy: why 2025 felt different to 2024 03:55 – Election fallout and the government’s “nothingburger” for startups 05:24 – Canva’s secondary and the first real signs of liquidity returning 09:49 – Aussie tech M&A heats up: Canva, Linktree, Jolt, and more 12:09 – The stat that changed the narrative: Australia’s unicorn efficiency 16:14 – The weirdest trend of the year: early stage down, late stage up 18:27 – Tech jobs, data centers, and the infrastructure bet Australia is making 22:52 – Why deep tech and climate are pulling venture dollars again 28:21 – The gender funding gap got worse (and why) 33:09 – Corporate VC is pulling out: what happened to strategic capital 37:02 – 2026 predictions: funding totals, seed pain, and where capital flows next 44:00 – AI bubble risk: tourism, ROI pressure, and the domino effect 47:42 – Hot take: electricity is the next valuation premium 49:00 – Will diversity bounce back in 2026? (vibes, but also logic) 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:50:17

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What are VC Fund Secondaries?

11/16/2025
Episode Summary Max Kausman is the founder and solo GP of Advance VC, Australia's first dedicated fund-of-funds with a focus on secondaries. Advance VC buys existing positions in Australian and New Zealand VC funds—acquiring stakes from investors seeking liquidity and giving new LPs diversified access to mature, validated portfolios across multiple vintages dating back to 2012. In this conversation, they discuss why secondaries won't "save" all of venture (only the top performers), how discounts actually work (spoiler: the average is 30-35% but it's wildly bespoke) and why vintage diversification matters as much as portfolio diversification. Time Stamps 02:47 – Max's first investment: lessons as a 14-year-old basketball coach 07:08 – Defining secondaries and Advance VC's unique LP fund focus 09:44 – Why vintage diversification matters as much as company diversification 13:57 – How secondary transactions actually work: the three-way deal between buyer, seller, and fund 19:24 – What Max learned looking under the hood of Australian VCs firms across different funds and vintages 24:09 – Why Max decided on a secondary Fund of Funds (FoF) model 34:16 - Pricing secondaries 42:20 – What discounts actually look like in practice 47:40 – Will secondaries save venture? The truth about liquidity and why it's concentrated in top performers 50:16 – Building Advance VC and the founder journey of becoming a fund manager Resources Max Kausman - https://www.linkedin.com/in/maxkausman Advance VC - https://www.advancevc.com/ This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:53:01

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Why “Boring” Businesses Make the Best Startups (Replay Ep with Matthew Browne)

10/19/2025
Episode Summary Matt Browne is the Co-founder and Managing Partner of Black Nova Venture Partners, one of Australia’s most active early-stage funds. Before becoming an investor, Matt founded multiple companies, including enterprise software firm Dunsafe, which sold to global corporates like Suncorp and Brickworks, and learned firsthand what it takes to turn “boring” B2B SaaS into beautiful business. In this episode, Cheryl and Maxine sit down with Matt to unpack what “boring but mission-critical” really means, why operators often make the best early-stage investors, and what it’s actually like to co-found a venture fund. Matt shares his frameworks for identifying resilient software businesses, the economics behind long-LTV enterprise customers, and how his founder experience shapes the way Black Nova supports startups today. They also dig into the differences between SMB and enterprise sales, why going from enterprise → small business is nearly impossible, and what it takes to build a fund that’s more startup than finance firm. And, in true Matt style, he caps it off with his Big Cojones moment, jumping off Auckland’s Sky Tower to win a customer. Sponsors: 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:50:59

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Inside Super Returns: How the Biggest Investors Pick Venture Funds

10/5/2025
Episode Summary What happens when hundreds of the world’s biggest capital allocators get together behind closed doors to talk about venture, private equity, and where the next $30B is going? Maxine found out firsthand at Super Returns Asia, where she chaired the LP–GP relations stage. In this episode, Cheryl turns the tables and grills Maxine on everything she learned, from why India and Japan are suddenly hot, to why Southeast Asia is struggling, and why Australia didn’t even make the winners or losers list. They break down how institutional investors really think about funds, what “look-through ownership” means for angels and VCs alike, and why co-investing has LPs hot under the collar. Maxine also shares how family offices are thriving in the current market, what mega-funds like a16z’s $30B raise mean for everyone else, and why building long-term LP relationships is the only real way to get “super returns.” Time Stamps 01:00 – What Super Returns is, and why it matters for VCs and angels 06:43 – The LP landscape explained: super funds, sovereign wealth funds, and family offices 10:40 – Winners and losers in APAC: India, China, Japan… but not Australia 18:00 – Why Australia needs a better “brand story” to attract capital 19:54 – Hot topic: co-investing and why LPs love it 23:39 – Look-through ownership: why everyone’s just trying to own the outliers 26:43 – Why emerging managers are struggling in today’s fundraising market 33:49 – Family offices having “the time of their lives” in this cycle 34:23 – Mega-funds, evergreen funds, and the $30B a16z raise 39:30 – Will Sequoia and a16z ever lose their dominance? 42:19 – Why APAC liquidity markets matter more than ever 45:30 – The question nobody asked at Super Returns 49:22 – How to actually build LP relationships that work 53:55 – Maxine’s big takeaway: putting Australia on the winners list Sponsors: 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:54:49

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How Prosus Ventures Became an “Honorary Australian” Fund | Sachin Bhanot

9/21/2025
Episode Summary Sachin Bhanot leads Southeast Asia & ANZ investments at Prosus Ventures, a global fund with $100B+ in assets. Though based in Singapore, Sachin has become an “honorary Australian fund manager”, with nearly half of Prosus’s regional portfolio now in Australia and New Zealand. In this episode, Cheryl and Maxine dive into why Prosus ramped up in Australia during a downturn, what paradoxical traits they see in winning founders, and how Singapore and Southeast Asia really compare as markets for expansion. They unpack the playbook for Australian startups going regional, what Singaporean family offices are actually looking for, and why relationship-building is the real cheat code in Southeast Asia. Sachin also shares his biggest Big Chon moment, and how building coffee chains in the Philippines and Malaysia reshaped his view of what it takes to be an investor. Time Stamps 02:53 – Sachin’s first and most important investment (hint: not a startup) 07:31 – The paradoxical traits of winning founders 10:26 – Singapore vs Southeast Asia: the tale of two ecosystems 18:12 – Why Prosus doubled down on Australia in 2022 28:40 – Tips and traps for Aussie founders expanding regionally 34:44 – When is the “right” time to enter Southeast Asia? 42:11 – The rise of the Australia–India–Singapore innovation corridor 48:34 – Singapore family offices and the art of relationship-driven capital 51:59 – Sachin’s Big Chon moment: learning empathy by building businesses himself Resources Resources Mentioned 🙋🏻‍♂️ Sachin Bhanot - https://www.linkedin.com/in/sachin-bhanot-15551913a/ 💰 Prosus Ventures - https://www.prosus.com/prosus-ventures Sponsors: First Cheque is supported by our wonderful sponsors: 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:57:46

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Why Australia’s AI Opportunity Is Bigger Than We Think

9/7/2025
Episode Summary Tom Humphrey, Partner at Blackbird and former operator, joins Cheryl and Maxine to reframe the conversation around Australia’s AI ecosystem. While headlines paint a picture of Australia falling behind, Tom argues we’re quietly sitting on world-class talent, global-first AI companies, and a capital-efficient edge that’s being overlooked. They unpack Tom’s recent AFR opinion piece on the AI talent landscape, why Australia’s university-to-startup pipeline is broken (and slowly improving), and how “boomerang” PhDs are returning from Anthropic, Meta, and DeepMind to build ambitious companies onshore. Plus, Tom breaks down how product-led growth is evolving in the AI era, why enterprise motions are happening sooner, and what the new GTM playbook looks like when AI agents are selling to AI agents. Time Stamps 02:21 – Tom’s first investment: BHP shares via his parents, now passing on the habit to his son 05:19 – Robinhood, meme stocks, and the shift to founder-led brands 07:06 – Why Tom wrote the AFR piece: Australia’s culture of doubt vs the US lens of opportunity 08:08 – Australia’s untapped AI talent advantage: 8% of APAC experts, top-tier unis, and PhD immigration 12:18 – Six model releases, global leaderboard wins… that no one in Australia talks about 14:03 – The dangerous cost of silence: how lack of domestic celebration dampens ambition and capital 17:33 – Why Australia is absurdly capital-efficient (and how we squeeze every dollar) 19:23 – Commercialisation bottlenecks at Aussie unis, and what’s slowly changing 25:39 – How this affects investors: AI engineering vs AI research, the boomerang effect, and talent arbitrage 30:56 – Time zones, USD revenue, and Australia’s secret weapon: the 43% R&D tax credit 33:17 – Role gaps and brand new roles: the rise of AI architects and forward deployed engineers 34:27 – What PLG really means, and why it’s not just a freemium sign-up form 39:31 – Spammy AI agents, SEO collapse, and why brand and community are back 45:15 – Why enterprise motions are showing up earlier (and how that changes GTM) 48:32 – Single-player AI value unlocks a different sales motion: fast, bottom-up adoption 51:15 – AI fits into your workflow, not the other way around 54:14 – Picking your motion: don’t force PLG if it’s not a natural fit 55:05 – Capital-starved ecosystems and why enterprise is still harder to fund in Aus 56:15 – Tom’s Big Cojones moment: three boys under six and a startup-founder partner Resources 👤 Tom Humphrey LinkedIn – https://www.linkedin.com/in/tomhumphrey1/ 🚀 Blackbird Ventures – https://blackbird.vc/ Sponsors: 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 Cyber Aussie Angels - the preferred fund and syndicate admin platform for emerging managers...

Duration:00:58:44

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How VCs Really Assess AI Startups | Cheryl Mack, Maxine Minter and Georgie Healy

8/10/2025
Episode Summary In this crossover episode of First Cheque and In The Blink of AI, Cheryl Mack (Aussie Angels) and Maxine Minter (Co Ventures) team up with host Georgie Healy to unpack how investors are thinking about AI, beyond the hype. From pitch decks to product demos, they reveal the frameworks and gut checks they use to spot real value in AI startups, even when they’re not technical experts themselves. You’ll also get a behind-the-scenes look at how Cheryl and Maxine are integrating AI into their own workflows, not just as investors, but as operators. From using ChatGPT to summarise founder meetings, to leveraging Prompt Cowboy and NotebookLM for due diligence and research prep, they walk through real examples of how AI is saving them time, sharpening decision-making, and helping them stay ahead in deal flow. And yes, we finally answer the question: what is an agent… and does anyone actually have one? Time Stamps 02:15 – Are Cheryl and Maxine AI skeptics or advocates? 06:00 – What's actually fueling the AI hype? 10:45 – Are we in a bubble—or just early in the cycle? 16:20 – Valuations, FOMO, and how investors are pricing AI 21:00 – What angel investors should look for in AI startups 27:30 – AI’s biggest red flag: When it all just sounds like magic 31:00 – Are agents real or is everyone faking it? 36:40 – AI in venture workflows: What Maxine actually automates 41:30 – The real power of personal brand in VC 44:50 – How Cheryl preps for founder calls with Google NotebookLM 49:00 – Weekly AI hacks: From flat lays to voice-mode strategy sessions 52:10 – Founder FOMO: Prompt Cowboy, Juno, and other hot startups 54:00 – The case for non-technical founders in AI 58:00 – Are one-person billion-dollar startups real? Resources 😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy 🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/ 💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/ Sponsors: 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 Cyber Angel Academy - Best online angel investing course in Australia and New Zealand Don't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy February 2025 - Angels Academy This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics -...

Duration:00:55:35

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Decode the VC Dictionary Before Your Next Raise

7/27/2025
Episode Summary Some investor phrases sound helpful. Others feel like a riddle. In this episode, Cheryl and Maxine crack open the language investors use when talking to founders, and translate what’s actually being said behind phrases like “not a fit,” “too early,” or “let’s have one more meeting.” They walk through the subtle (and not-so-subtle) cues that signal a pass, explain what “conviction” actually means in VC-speak, and share tactics founders can use to get clearer answers during fundraising. You’ll also hear the behind-the-scenes realities of ghosting, deal timelines, internal partner politics, and why “we’d love to stay close” usually means… they won’t. Plus: a rapid-fire rundown of the weirdest (and most cringe) investor slang, from “due dilly” to “foundies.” Whether you’re raising your first round or managing investor relationships post-close, this episode helps you spot the signals, ask better questions, and avoid wasting time. Time Stamps 01:45 – “Not a fit”: Why investors love this vague phrase 03:40 – What they mean when they say “you’re too early” 08:30 – “You’re too late”, how stage mismatches work both ways 15:30 – “We’ll circle back” and other signs of a slow no 17:10 – How long does VC diligence really take? 19:15 – Why June 30 is a terrible time to raise 24:10 – Optionality: The excuse behind “we love what you’re doing” 28:00 – “Let the lawyers sort it out”: A red flag or not? 30:15 – The weirdest investor slang (please don’t say “due dilly”) 33:30 – Term sheet vs. side letters: what’s actually worth negotiating 36:00 – Understanding info rights vs. investor updates 38:50 – How to share bad news without burning relationships 45:20 – The shifting goalposts of traction and growth metrics 47:00 – Spotting investor doubts through team questions 48:10 – Final thoughts for both founders and investors Resources 😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy 🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/ 💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/ Sponsors: First Cheque is supported by our wonderful sponsors: 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:49:26

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Scaling Solo: How Charles Hudson Built a High-Volume VC Model at Precursor Ventures

7/13/2025
Episode Summary Charles Hudson is the Founder and Managing Partner at Precursor Ventures, a solo GP fund that has backed over 450 startups across five funds, including dozens of category-defining companies led by underrepresented founders. In this episode, Maxine and Cheryl sit down with Charles to explore how he built one of the most successful high-volume venture strategies in the world, all while staying a solo decision-maker. They dive deep into what being a “solo GP” actually means, how Charles balances scale with intimacy across a massive portfolio, and why trust, not likability, is his north star when supporting founders. You’ll also hear his first-ever investment, the courage it took to leave a top-tier firm to start Precursor, and how he still handpicks every company Precursor backs, often long before they’re obvious. Time Stamps 03:20 – Charles’s first investment: ExxonMobil shares… mailed by cheque 06:50 – What is a solo GP fund, and how Precursor operates with one partner and 14 staff 10:28 – The pros and cons of solo decision-making in venture 12:50 – How Precursor supports 450+ companies (and avoids “orphaned” portfolios) 15:44 – Why Charles shifted from unlimited founder support to intentional check-ins 19:18 – Trust vs likability, and why real feedback matters more than being liked 24:25 – How Charles handles saying “no” to follow-ons, and still earns trust 29:31 – The case for “challenger” VCs over cap-table cheerleaders 32:11 – What Precursor looks for in a founder: not great employees, but great CEOs 36:39 – High volume investing: Why meeting 2000+ startups matters 39:00 – Global allocation: why Charles bet early on African and LatAm FinTech 42:30 – The return of themes (like AI & Women’s Health), and why they can kill judgment 47:52 – When Precursor steps in (and when they don’t): being the “surgeon, not the bandaid” 54:04 – Charles’s biggest Big Cojones moment: leaving Uncork to build Precursor from scratch 56:15 – Why most fund managers are “post-employment” and proud of it Resources 👤 Charles Hudson LinkedIn - https://www.linkedin.com/in/chudson/ 🌎 Precursor Ventures – https://precursorvc.com/ 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 Australia Show Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.com February 2025 - Aussie Angels This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:57:49

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Why Australia Builds More Unicorns per Dollar Than Anyone | with Ben Grabiner from Side Stage Ventures

7/1/2025
Grab your copy of the Dealroom and SideStage Ventures report we talked about on the show with Cheryl Mack and Maxine Minter here - https://dayone.fm/australia-venture-startup-report-2025 Episode Summary Ben Grabiner is the Co-founder and General Partner at Side Stage Ventures, and the author of a landmark new report in collaboration with Dealroom and AWS. In this episode, Cheryl and Maxine sit down with Ben to unpack the data behind Australia’s rapid rise as one of the most efficient and exciting venture ecosystems in the world. They explore how Australia produces more unicorns per dollar invested than any other country, what makes the ecosystem so resilient and capital-efficient, and why the next decade might belong to Aussie tech. From funding gaps to founder grit, from global capital flows to angel investor opportunities, this is essential listening for allocators, founders, and emerging fund managers alike. You’ll also hear Ben’s story, from buying Tottenham Hotspur shares as a teenager, to moving across the world mid-COVID, to becoming a key builder in Australia’s startup ecosystem. Time Stamps 04:49 – Ben’s first investment: £250 in Tottenham Hotspur 06:34 – What makes Australian unicorns so capital-efficient? 09:14 – Unicorn efficiency vs gross unicorn creation: what matters more 13:15 – How Australia quietly matches Israel and India on decacorn creation 14:35 – Why foreign investors see the opportunity more clearly than locals 18:41 – The power of local exits like Afterpay, and how they inspire allocation 21:19 – Can Aussie startups scale globally from home? Or must they go abroad? 23:40 – Why this next wave of operators will be our ecosystem’s secret weapon 25:54 – What global LPs need to understand about Australian venture 30:17 – Why pre-seed funds and angel investors matter more than ever Resources 🙋🏻‍♂️ Ben’s LinkedIn - https://www.linkedin.com/in/bengrabiner/ 💳 Side Stage Ventures - https://www.sidestage.vc/ 🦘 Aussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence. https://www.aussieangels.com/ 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:37:05

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Nnamdi Okike's Playbook for Investing in Non-Obvious Winners

6/1/2025
Episode Summary Nnamdi Okike is the Co-founder and Managing Partner at 645 Ventures, known for his early, contrarian bets on overlooked verticals and non-obvious industries. In this episode, Nnamdi shares how he leveraged a data-driven sourcing model to identify breakout companies like Squire and Goldbelly, and why seemingly small or niche markets often produce the biggest wins. Maxine and Cheryl dive deep into Nnamdi’s journey from Insight Partners analyst sourcing deals via cold calls, to launching his own fund and achieving a remarkable hit rate, landing him on the Midas Brink List. They explore how he evaluates founder insights, measures market inflection points, and strategically navigates the power law dynamics in venture capital. Packed with strategic insights and candid reflections, this episode is essential listening for emerging investors, fund managers, and founders curious about building defensible businesses in non-obvious spaces. Time Stamps 04:34 – Nnamdi’s first investment during the dotcom boom 06:52 – Defining “non-obvious industries” and spotting hidden TAM 10:40 – Squire: From barbershop bookings to vertical SaaS OS 13:20 – Goldbelly, marketplaces, and the power of founder insight 17:58 – Algorithmic sourcing meets founder conviction 21:30 – What 645 Ventures learned from missing Facebook 26:46 – Building a fund around risk profiles, not just stages 30:34 – Why the power law should shape every VC decision 35:16 – Does 2024 echo 2002? A macro take on the downturn 42:41 – The rise of zombie funds and quiet closures 45:20 – Bootstrapped AI startups and the future of defensibility 52:54 – When vertical AI gets sticky—and when it doesn’t 57:20 – Nnamdi’s Big Cojones moment: from Insight to starting fresh Resources 🙋‍♂️ Nnamdi Okike on LinkedIn – Follow Nnamdi’s updates and insights. https://www.linkedin.com/in/nnamdiokike 💰645 Ventures – A VC firm investing in early-stage, non-obvious software winners. https://645ventures.com/ 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: Angel Academy - Best online angel investing course in Australia and New Zealand Don't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy February 2025 - Angels Academy Aussie Angels - the preferred fund and syndicate admin platform for emerging managers in Australia Show Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.com February 2025 - Aussie Angels This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:01:01:08

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Pocket Sun’s Guide to Standing Out as an Emerging Investor

5/4/2025
Episode Summary Pocket Sun is the Founding Partner at SoGal Ventures, the first female-led, millennial VC firm investing in the future of living, working, and staying healthy. In this episode, she shares how she made her first angel investment at just 24, and how her early bets like Everly Health and Lovevery reflected a conviction in underrepresented founders well before it was a trend. Cheryl and Maxine explore how Pocket launched SoGal’s debut fund, built a deal pipeline through global pitch comps and community, and mastered the art of getting onto oversubscribed cap tables. They also unpack her consumer investing thesis, how she’s navigating fund two with more geographic focus, and what it means to lead recaps and board restructures when the power law turns brutal. For anyone curious about building a fund from scratch, going global with limited resources, or backing change-makers the market misses, this episode is packed with both tactics and courage. Time Stamps 00:00 – Pocket’s first angel check: $1K into an AI startup 05:30 – Angel investing isn’t just for the ultra-wealthy 09:45 – From building a global pitch comp to proving LP credibility 14:20 – Early wins: Everly Health, Lovevery, and chasing allocation 23:35 – “Land and expand”: getting on cap tables and earning super pro-rata 27:10 – Leading recaps and fighting for underestimated founders 35:00 – SoGal’s thesis: The future of living, working, and staying healthy 40:30 – Entering new verticals without prior expertise 46:00 – Pocket’s take on the Vancouver vs. Toronto startup ecosystems 53:00 – Betting on design-led, intentional consumer businesses 59:10 – Why consumer startups often graduate into enterprise giants 01:03:00 – Pocket’s Big Cojones moment: moving solo to the U.S. at 18 Resources 🙋‍♀️Pocket Sun on LinkedIn – Connect with Pocket and follow her updates. https://www.linkedin.com/in/pocket 💰SoGal Ventures – A VC firm backing diverse founders in the future of living, working, and staying healthy. https://www.sogalventures.com/ Sponsors: First Cheque is supported by our wonderful sponsors: Vanta automates up to 90% compliance, getting you audit-ready quickly and saving you up to 85% of associated costs. Join 10,000 global companies like Cipherstash, Handle and Indebted that use Vanta to build trust and prove security in real-time. Get 10% off http://dayone.fm/vanta/cheque 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 Cyber Angel Academy - Best online angel investing course in Australia and New Zealand Don't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy

Duration:01:08:51

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TRAILER: Perspective X with Pauline Fetaui - Perspective X with Pauline Fetaui

5/3/2025
What drives bold decisions, intentional leadership, and the courage to create something entirely new? In Perspective X, host Pauline Fetaui dives deep into conversations with extraordinary entrepreneurs and leading innovators to explore not just their successes—but the overlooked decisions, mindset shifts, and personal turning points that sparked their greatest breakthroughs. This show is about the ripple effect of choice: how deep accountability enables us to respond intentionally to life's challenges, rather than simply reacting. If you're curious about the inner journey behind meaningful achievements and how leaders evolve through adversity, this podcast is for you. Join us on Perspective X, where we move beyond the highlight reel and into the pivotal moments that changed everything. Launching on the 12th of May, wherever you get your podcasts. Mentioned in this episode: Day One sting

Duration:00:01:19

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Monique Woodard’s Cake Ventures Strategy: Big Bets on Aging, Women & Culture

4/21/2025
Episode Summary Monique Woodard is the Founder and Solo GP of Cake Ventures, a venture fund focused on the enormous opportunities created by demographic shifts such as aging populations, rising female spending power, and America's transition to a majority-minority population. She explains how these macro-level changes expand markets across digital health, fintech, consumer brands, and AI-enabled solutions. Monique also candidly shares her experiences as a solo GP—covering the realities of fundraising, building a unique investment thesis, navigating partnership dynamics, and scaling from Fund I ($17M) to Fund II. Her insights offer a clear blueprint for investors, operators, and founders eager to capitalise on overlooked, high-growth opportunities driven by demographic change. Time Stamps 03:07 – Monique’s first investment: picking stocks at age 20 06:12 – Her journey from rural entrepreneurship to 500 Startups and VC 12:43 – The "Three Layers of Cake": investing in demographic shifts (aging, female economy, new majority) 22:56 – Why geographic focus matters (and why Cake invests only in North America 24:32 – Real talk on Solo GP life: choosing partners, hiring venture partners, and building a legacy firm 30:07 – Raising Fund II: bigger checks, deeper domain expertise, and firm evolution 39:12 – How founders should position their companies in the AI hype cycle 45:24 – Advice for operators: Understanding the difference between investing and running a venture firm Resources 🍰 Cake Ventures – Monique’s demographic‑change VC firm. https://cake.vc🙋‍♀️Monique Woodard on LinkedIn – Follow her insights on venture & demographics. https://www.linkedin.com/in/moniquewoodard Sponsors: First Cheque is supported by our wonderful sponsors: Vanta automates up to 90% compliance, getting you audit-ready quickly and saving you up to 85% of associated costs. Join 10,000 global companies like Cipherstash, Handle and Indebted that use Vanta to build trust and prove security in real-time. Get 10% off http://dayone.fm/vanta/cheque 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: FC Vanta Ad March 2025_02 FC Vanta Ad March 2025_02 PMB Trailer+Promo_01 PMB Trailer+Promo_01 Aussie Angels - the preferred fund and syndicate admin platform for emerging managers in Australia Show Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.com February 2025 - Aussie Angels FC Vanta Ad March 2025_02 FC Vanta Ad March 2025_02

Duration:00:55:27

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How James Tynan from Square Peg Invests in EdTech

4/6/2025
Episode Summary: In this episode of First Cheque, Cheryl and Maxine sit down with James Tynan of Square Peg to explore why EdTech might be one of the most misunderstood (and underinvested) sectors in venture capital. James recounts his early days bootstrapping a startup in Australia’s tough 2001 tech climate, and the lessons he took with him to Khan Academy—where he witnessed firsthand how technology, when done right, can revolutionise education. Together, they dive into the massive shifts happening in learning today: how kids are skilling up at breakneck speed thanks to platforms like Scratch, YouTube, and AI tutors; why the “Prussian model” of schooling persists; and where personalisation, assessment, and vocational learning could unlock new investment opportunities. James also offers candid advice for early-stage investors trying to spot the next breakout idea in an era of AI-fueled growth—and shares why stepping away from the “prestige path” (like skipping Stanford) was one of his biggest and bravest decisions. Whether you’re an EdTech founder, an investor, or just intrigued by how fast education is evolving, this episode is a must-listen. Key Takeaways: 00:00 – Intro 02:16 – James’s first big bet – Starting a company in Australia’s early 2000s “hellscape” and the lessons learned 07:18 – Why MOOCs weren’t the answer – The early EdTech hype, misconceptions about online courses, and how Khan Academy did things differently 11:12 – Assessment as the control point – How exams and credentials shape mainstream education and what might disrupt that model 15:08 – AI’s impact on education – Could personalized, AI-driven learning (and cheating) force schools to rethink how we test knowledge? 18:20 – Kids, dopamine, and the next-gen learning paradox – Balancing entertainment and deep learning, and why “edutainment” rules 24:00 – VC skepticism vs. reality – Why it’s so hard to invest in K–12 EdTech, and where vocational and adult learning might be more promising 32:00 – Rapid AI adoption – From legal tech to healthcare, how ambient tools are skyrocketing and what it means for founders 37:00 – Wedges, moats, and growth – The playbook for AI startups moving from “just a feature” to a sustainable product 42:00 – James’s “big kahunas” moment – Choosing Khan Academy over Stanford and why walking away from “prestige” can change everything 47:07 – Wrap-up – The future of EdTech, AI’s role, and parting wisdom for founders and investors Resources Mentioned James Tynan on LinkedIn – Partner at Square Peg and former operator at Khan Academy. - https://www.linkedin.com/in/james-tynan-ba54b93/ Square Peg – The VC firm James Tynan is a Partner at. - https://www.squarepeg.vc/ Khan Academy – Free world-class education for anyone, anywhere. College Board + Khan Academy Partnership – Free SAT and AP test prep. Ambience Healthcare – AI for clinical documentation and patient notes. Harvey AI – Legal AI platform disrupting law firm workflows. Sponsors: First Cheque is supported by our wonderful sponsors: Vanta automates up to 90% compliance, getting you audit-ready quickly and saving you up to 85% of associated costs. Join 10,000 global companies like Cipherstash, Handle and Indebted that use Vanta to build trust and prove security in real-time. Get 10% off http://dayone.fm/vanta/cheque 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

Duration:00:47:24

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Crafting Your Investment Thesis: How to Decide What to Invest In

3/23/2025
Episode Summary: Having a clear investment thesis helps you make better decisions, improve your deal flow, and maximise your returns. Cheryl and Maxine break down exactly what an investment thesis is, why it matters, and how to structure one that fits your risk appetite, interests, and long-term goals. They explore the core elements of an investment thesis, including industry focus, stage, business model, and geography. Plus, they highlight key company criteria investors should consider, from strong founding teams and large market opportunities to traction and defensibility. Beyond just what to invest in, this episode also covers how to stand out as an investor, build a strong value proposition, and get access to the best deals. They wrap up with an essential discussion on portfolio construction, time horizons, and risk management, so you don’t run out of money before your portfolio has a chance to deliver returns. If you're looking to sharpen your investing strategy and back better startups with confidence, this episode is a must-listen. Key Takeaways: 00:00 – Introduction: Why your investment thesis matters 01:49 – Defining an investment thesis: What it is & why it's essential 04:49 – How to break down your thesis into clear categories 05:16 – Industry focus: Verticals, horizontals, and emerging trends 07:05 – Stage focus: Pre-seed, seed, growth—how to pick your sweet spot 08:24 – Business model focus: B2B SaaS, marketplaces, and beyond 10:01 – Geography: The pros and cons of investing locally vs globally 14:29 – Key questions every investor should ask themselves 17:24 – Company-specific criteria: How to create your investment checklist 22:33 – Evaluating market size and growth potential 25:39 – Pain vs pleasure: Investing in painful problems vs unmet desires 29:54 – Unique or niche theses: Second-time founders, alumni networks, and more 33:46 – Access and deal flow: How to attract great opportunities 38:35 – Understanding your personal risk profile & timeline expectations Resources Angel Academy – Comprehensive angel investing course for Australia & NZ: www.venture.academy Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/ Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/ Sponsors: First Cheque is supported by our wonderful sponsors: Vanta automates up to 90% compliance, getting you audit-ready quickly and saving you up to 85% of associated costs. Join 10,000 global companies like Cipherstash, Handle and Indebted that use Vanta to build trust and prove security in real-time. Get 10% off http://dayone.fm/vanta/cheque 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: Perspective X...

Duration:00:45:47

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Decoding Startup Investment: SAFE Notes, Convertible Notes & Priced Rounds

3/9/2025
Episode Summary: Understanding how to invest in startups requires more than just writing a cheque. Cheryl and Maxine break down the legal structures behind startup investing, covering SAFE notes, convertible notes, and priced rounds. Whether you're a seasoned investor or just starting out, this episode unpacks the key terms, investor-friendly vs. founder-friendly clauses, and the risks involved. They discuss the evolution of SAFEs, why they've become the dominant structure in early-stage funding, and the critical differences between pre-money and post-money SAFEs. Plus, they explore the role of pro-rata rights, most favoured nation (MFN) clauses, and side letters—so you don’t get caught off guard in your next deal. If you’ve ever wondered how to protect your equity position, when to push back on certain terms, or what legal documents you’ll actually be signing, this episode is your investor cheat sheet. Key Takeaways: 00:00 – Why startup investment structures matter 01:45 – SAFE notes, convertible notes, and priced rounds explained 03:47 – How founders raise money: equity vs. debt 06:21 – The documents you’ll sign in a priced round 10:22 – Do startups need a constitution? Red flags to watch for 14:29 – Side letters: What are they, and should you be worried? 19:08 – Pro-rata rights & why they matter for investors 22:23 – Most Favoured Nation (MFN) clauses explained 30:27 – Pre-money vs. post-money SAFEs: Which one is better? 38:03 – Why valuation caps and discounts can be a double-edged sword 43:53 – Investor-friendly vs. founder-friendly terms: What’s fair? Resources - A Deep Dive into ECIS, ESVCLP, and Investment Strategies - https://open.spotify.com/episode/1Agiu4dskF53m6DBZgXitD?si=KFeAlY_wTjSwOWfRMiiQFA - Angel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academy - Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/ - Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/ Sponsors: First Cheque is supported by our wonderful sponsors: Vanta automates up to 90% compliance, getting you audit-ready quickly and saving you up to 85% of associated costs. Join 10,000 global companies like Cipherstash, Handle and Indebted that use Vanta to build trust and prove security in real-time. Get 10% off http://dayone.fm/vanta/cheque 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-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Duration:00:55:09

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Mastering Fund Cycles: How VCs Raise, Invest & Exit

2/23/2025
Episode Summary: In this episode of First Cheque, hosts Cheryl and Maxine dive deep into the complexities of fund cycles, providing invaluable insights for emerging fund managers and entrepreneurs alike. They discuss the key aspects of raising and deploying funds, including the significance of understanding the timing and structure of fund cycles. Cheryl emphasises the importance of recognising that announcements of fundraising often indicate the beginning of the fundraising process rather than immediate capital deployment. Maxine elaborates on the differences in fund management strategies, particularly in Australia, where choices about fund structures, like ESVCLP (Early Stage Venture Capital Limited Partnership), can influence tax benefits and administrative requirements. The hosts also touch on the challenges faced by fund managers, such as the necessity to maintain liquidity and the common practice of deploying smaller checks to riskier companies at the start of a fund’s lifecycle, while gradually shifting to larger, safer investments as the fund matures. Throughout the conversation, they highlight the importance of planning for exits, the dynamics of raising subsequent funds, and the need for flexibility, especially within micro funds. They conclude by encouraging fund managers to be diligent in their planning to ensure success and sustainability in their investment journeys. This episode serves as a comprehensive guide for anyone looking to navigate the intricate world of venture capital and fund management. Time Stamps: 00:00 – Introduction: Why fund cycles matter for investors & founders 01:21 – Who this episode is for: Emerging fund managers & startup founders 03:23 – Understanding fund cycles: Raising, deploying, and exiting 05:48 – The reality of raising a fund: Why it takes 12-24 months to close 09:35 – Deployment periods: How VCs decide when and where to invest 12:34 – The risk of running out of money—how fund managers avoid this mistake 16:57 – Fund sizes & check sizes: Why $50M is a magic number in VC 21:09 – Micro VCs vs. bigger funds: How different strategies impact returns 25:14 – Opportunity funds: When fund managers double down on winners 30:08 – The importance of liquidity planning and secondaries in VC 37:17 – Exits: How and when fund managers start planning for returns 43:59 – Final thoughts: The key takeaways from this episode Resources Mentioned - Angel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academy - Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/ - Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/ - ESVCLP (Early Stage Venture Capital Limited Partnership) – How tax benefits impact Australian VC funds - AFR & Startup Daily – Understanding VC funding announcements in the media - Adverb Ventures (April Underwood) – Case study on fast fund cycles - Australian Super Funds & VC – Why institutional capital is hard to secure - Venture Fund Deployment Data (US vs. Australia) – Insights on how quickly funds deploy capital - Fund Liquidity & Secondaries – How fund managers plan exits when IPOs & M&A slow down Sponsors: First Cheque is supported by our wonderful sponsors: Vanta automates up to 90% compliance, getting you audit-ready quickly and saving you up to 85% of associated costs. Join 10,000 global companies like Cipherstash, Handle and Indebted that use Vanta to build trust and prove security in real-time. Get 10% off http://dayone.fm/vanta/cheque Aussie...

Duration:00:47:19