First Cheque with Cheryl Mack & Maxine Minter

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/

  1. Why Australia’s AI Opportunity Is Bigger Than We Think

    7 SEPT

    Why Australia’s AI Opportunity Is Bigger Than We Think

    Episode 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 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...

    59 min
  2. How VCs Really Assess AI Startups | Cheryl Mack, Maxine Minter and Georgie Healy

    10 AUG

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

    Episode SummaryIn this crossover episode of First Cheque and In The Blink of AI, Cheryl Mack (Aussie Angels) and Maxine Minter (Co Ventures) team up with host Georgie Healy to unpack how investors are thinking about AI, beyond the hype. From pitch decks to product demos, they reveal the frameworks and gut checks they use to spot real value in AI startups, even when they’re not technical experts themselves. You’ll also get a behind-the-scenes look at how Cheryl and Maxine are integrating AI into their own workflows, not just as investors, but as operators. From using ChatGPT to summarise founder meetings, to leveraging Prompt Cowboy and NotebookLM for due diligence and research prep, they walk through real examples of how AI is saving them time, sharpening decision-making, and helping them stay ahead in deal flow. And yes, we finally answer the question: what is an agent… and does anyone actually have one? Time Stamps02:15 – Are Cheryl and Maxine AI skeptics or advocates? 06:00 – What's actually fueling the AI hype? 10:45 – Are we in a bubble—or just early in the cycle? 16:20 – Valuations, FOMO, and how investors are pricing 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 -...

    56 min
  3. Decode the VC Dictionary Before Your Next Raise

    27 JULY

    Decode the VC Dictionary Before Your Next Raise

    Episode SummarySome investor phrases sound helpful. Others feel like a riddle. In this episode, Cheryl and Maxine crack open the language investors use when talking to founders, and translate what’s actually being said behind phrases like “not a fit,” “too early,” or “let’s have one more meeting.” They walk through the subtle (and not-so-subtle) cues that signal a pass, explain what “conviction” actually means in VC-speak, and share tactics founders can use to get clearer answers during fundraising. You’ll also hear the behind-the-scenes realities of ghosting, deal timelines, internal partner politics, and why “we’d love to stay close” usually means… they won’t. Plus: a rapid-fire rundown of the weirdest (and most cringe) investor slang, from “due dilly” to “foundies.” Whether you’re raising your first round or managing investor relationships post-close, this episode helps you spot the signals, ask better questions, and avoid wasting time. Time Stamps01:45 – “Not a fit”: Why investors love this vague 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/

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

    13 JULY

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

    Episode 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 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/

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

    1 JULY

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

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

    37 min
  6. Nnamdi Okike's Playbook for Investing in Non-Obvious Winners

    1 JUNE

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

    Episode 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 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. 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/

    1h 1m
  7. How Pocket Sun Built SoGal from Angel Checks to Institutional Fund

    4 MAY

    How Pocket Sun Built SoGal from Angel Checks to Institutional Fund

    Episode 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 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: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 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/

    1h 5m

Trailers

Ratings & Reviews

5
out of 5
11 Ratings

About

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/

More From DayOne.fm

You Might Also Like