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...
Aug 10, 2025•56 min•Season 1Ep. 46
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 fundrai...
Jul 27, 2025•49 min•Season 1Ep. 45
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 Cha...
Jul 13, 2025•58 min•Season 1Ep. 44
Grab your copy of the Dealroom and SideStage Ventures report we talked about on the show with Cheryl Mack and Maxine Minter here - https://www.sidestage.vc/outliers-report-2025 Episode Summary Ben Grabiner is the Co-founder and General Partner at Side Stage Ventures, and the author of a landmark new report in collaboration with Dealroom and AWS. In this episode, Cheryl and Maxine sit down with Ben to unpack the data behind Australia’s rapid rise as one of the most efficient and exciting venture ...
Jul 01, 2025•37 min•Season 1Ep. 43
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 laun...
Jun 01, 2025•1 hr 1 min•Season 1Ep. 42
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 ...
May 04, 2025•1 hr 5 min•Season 1Ep. 41
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 ch...
May 03, 2025•1 min
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 fundra...
Apr 21, 2025•54 min•Season 1Ep. 40
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 happe...
Apr 06, 2025•49 min•Season 1Ep. 39
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 st...
Mar 23, 2025•45 min•Season 1Ep. 38
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...
Mar 09, 2025•57 min•Season 1Ep. 37
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 ...
Feb 23, 2025•46 min•Season 1Ep. 36
Episode Summary: In this episode of First Cheque, Cheryl and Maxine dive deep into financial planning for angel investors—how to avoid running out of money, manage liquidity, and strategically deploy capital across investment cycles. If you're an aspiring angel investor wondering how much money you need to start or an experienced investor looking to refine your cash planning strategies, this episode is packed with essential insights. They discuss the importance of staying liquid, diversifying ch...
Feb 09, 2025•38 min•Season 1Ep. 35
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 s...
Jan 26, 2025•53 min•Season 1Ep. 34
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 se...
Jan 12, 2025•34 min•Season 1Ep. 33
Episode Summary: In this special replay of our most popular episode of the year, Cheryl and Maxine sit down with Michael Batko, CEO of Startmate, to explore the transformative power of early-stage investing and community-driven entrepreneurship. From hardware startups to non-alcoholic beer companies, Batko shares how Startmate pushes boundaries, backs ambitious founders, and builds a thriving startup ecosystem in Australia and New Zealand. Discover how Startmate evolved from software-focused inv...
Dec 29, 2024•51 min•Season 1Ep. 32
Episode Summary: In this year-end wrap-up, Cheryl and Maxine reflect on 2024’s venture landscape, from shifting investor sentiment to the lingering effects of the zero-interest era. They dig into the rise in early-stage investments, the resurgence of AI enthusiasm, and the cautious optimism permeating the ecosystem. With equal doses of hindsight and foresight, they offer spicy predictions for 2025: from a potential surge in IPOs to the possibility of a one-person billion-dollar startup. If you’r...
Dec 15, 2024•46 min•Season 1Ep. 31
Episode Summary: In this episode of First Cheque, hosts Cheryl and Maxine engage in a compelling conversation with John Sharp, co-founder of Hatcher+, an innovative AI-driven venture capital platform based in Singapore. John recounts his fascinating transition from conducting orchestras to pioneering data-driven venture investing, highlighting how his early experiences with technological disruption in the music industry inspired him to embrace AI and big data. He delves into how Hatcher+ analyse...
Dec 01, 2024•48 min•Season 1Ep. 30
Episode Summary: Join Emily Rich and hosts Maxine and Cheryl in this episode where they explore the dynamic world of early-stage and deep tech investing. Emily shares her unconventional journey from being a high school dropout to making a decisive investment in her own education, a move that transformed her path and led her to become a significant player in the venture capital scene. The conversation delves into the thrills of pre-seed and seed investing, the art of identifying and navigating hy...
Nov 17, 2024•46 min•Season 1Ep. 29
Episode Summary: Join Cheryl Mack and Maxine Minter on First Cheque as they chat with Tim from Turo, one of Australia's pioneering operator angels. Tim shares his journey from working at Uber to his current role at Turo, detailing the insights and risks involved in being an early-stage investor. The conversation covers Tim's first investment, his transition from medicine to business, and the challenges of balancing operator and investor roles. They discuss the Australian tech ecosystem, liquidit...
Nov 04, 2024•49 min•Season 1Ep. 28
Episode Summary In the Blink of AI: Conversations with AI Innovators Join Georgie Healy on 'In the Blink of AI', your weekly guide to the dynamic world of artificial intelligence. Each episode features interviews with the founders of top AI startups, creative product builders, and industry leaders. With 20 years in engineering and technology, Georgie aims to distill complex AI concepts into engaging stories. The show covers business building, cutting-edge AI technology, and guests' approaches to...
Oct 27, 2024•2 min
Episode Summary Join Cheryl and Maxine on an insightful journey into early-stage investing in this episode of First Cheque. The discussion covers the transition from basic checklists to more sophisticated decision diaries, emphasizing structured evaluation and the importance of capturing and analysing decision-making processes over time. Key topics include understanding founder commitment, market size evaluation, and the balance between intuition and quantitative analysis. The episode offers pra...
Oct 17, 2024•40 min•Season 1Ep. 27
Episode Summary: Join Cheryl Mack and Maxine Minter for an engaging session as they delve into the world of early-stage investing with Matthew Browne from Black Nova Venture Capital. This episode offers an intimate look into Browne's journey from a founder's seat to a leading venture capitalist's role, with a focus on thematic investing in what he calls "boring B2B SaaS." Browne unravels the nuances of mission-critical software that businesses cannot operate without, discussing why such investme...
Oct 06, 2024•53 min•Season 1Ep. 26
Episode Summary: In this engaging episode, the hosts Cheryl Mack and Maxine Minter are joined by Georgie Turner, a partner at Tidal, to delve into the nuances of early-stage investing, cross-border strategies, and the evolving landscape of venture capital. The episode opens with a lively introduction to Georgie's background and her journey from Bailador to founding Tidal, a fund focused on B2B SaaS and AI. The hosts discuss the challenges and rewards of building a fund, the intricacies of capita...
Sep 15, 2024•46 min•Season 1Ep. 25
Episode Summary: In this episode of First Cheque , hosts Cheryl Mack and Maxine Minter sit down with biotech investment expert Paul Kelly. The conversation demystifies the complex world of biotech investing, making it accessible for even those who are new to the field. Paul shares his journey from a practising physician to a pioneering investor in the biotech space, offering valuable insights into the industry's rapid evolution and high stakes. Paul explains the fundamentals of biotech investing...
Aug 25, 2024•1 hr•Season 1Ep. 24
Episode Summary: In this episode, Cheryl Mack and Maxine Minter dive into the intricate details of tax incentives and structures for angel investors in Australia. Tackling the seemingly dry topic of tax with enthusiasm, they explore how these regulations can substantially benefit early-stage investors. Cheryl brings her wealth of experience to the table, elucidating the complexities of acronyms like ESV CLP and ASIC, while Maxine peppers the conversation with insightful queries and contextual ex...
Aug 18, 2024•37 min•Season 1Ep. 23
Episode Summary: In this episode of the First Cheque podcast, Cheryl Mack and Maxine Minter delve into the intricacies of early-stage investing, focusing on the importance of secondaries, the value of strong founder-investor relationships, and how to navigate high valuations. This episode is a milestone as it's entirely driven by audience questions, providing targeted insights and practical advice for investors and founders alike. Cheryl and Maxine kick off by discussing the significance of seco...
Aug 04, 2024•52 min•Season 1Ep. 22
Episode Summary: In this episode, host Maxine Minter and co-host Cheryl Mack dive into the world of growth stage investing with guest Christina Fa from NewView Capital. They explore the reasons why ex-investment bankers transition to VC, discuss the nuances of growth-stage investing, and shed light on the importance of secondaries in the current market landscape. Christina shares insights on company scaling in different ecosystems, the impact of GenAI innovation, and the changing dynamics of ven...
Jul 21, 2024•50 min•Season 1Ep. 21
Episode Summary: In this episode, Cheryl Mack and Maxine Minter engage in an enlightening conversation with Bronwen Clune, discussing her journey from journalism to startups and back to media. Bronwen shares insights on the Australian startup ecosystem, the future of journalism, and the intersecting landscapes of politics, markets, and entrepreneurship. Delving into the impact of risk appetite, the tension between traditional markets and startups, and the evolving dynamics of super funds, the di...
Jul 07, 2024•53 min•Season 1Ep. 20
Episode Summary: In this episode, Maxine Minter and Cheryl Mack delve deep into the essential considerations of portfolio allocation, focusing on diversification versus concentration in early-stage investing. They explore the concept of portfolio construction, risk management, power law dynamics, and the importance of strategy in maximizing returns while mitigating risks. Key themes discussed include the spectrum of diversification, the impact of concentrated investments, the role of information...
Jun 23, 2024•37 min•Season 1Ep. 19
