First Cheque

Episode SummaryMonique Woodard is the Founder and Solo GP of Cake Ventures, a venture fund focused on the enormous opportunities created by demographic shifts such as aging populations, rising female spending power, and America's transition to a majority-minority population. She explains how these macro-level changes expand markets across digital health, fintech, consumer brands, and AI-enabled solutions. Monique also candidly shares her experiences as a solo GP—covering the realities of fundraising, building a unique investment thesis, navigating partnership dynamics, and scaling from Fund I ($17M) to Fund II. Her insights offer a clear blueprint for investors, operators, and founders eager to capitalise on overlooked, high-growth opportunities driven by demographic change.Time Stamps03:07 – Monique’s first investment: picking stocks at age 2006:12 – Her journey from rural entrepreneurship to 500 Startups and VC12:43 – The "Three Layers of Cake": investing in demographic shifts (aging, female economy, new majority)22:56 – Why geographic focus matters (and why Cake invests only in North America24:32 – Real talk on Solo GP life: choosing partners, hiring venture partners, and building a legacy firm30:07 – Raising Fund II: bigger checks, deeper domain expertise, and firm evolution39:12 – How founders should position their companies in the AI hype cycle45:24 – Advice for operators: Understanding the difference between investing and running a venture firmResources🍰 Cake Ventures – Monique’s demographic‑change VC firm. https://cake.vc🙋‍♀️Monique Woodard on LinkedIn – Follow her insights on venture & demographics. https://www.linkedin.com/in/moniquewoodardSponsors:First Cheque is supported by our wonderful sponsors: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/chequeAussie 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_02FC Vanta Ad March 2025_02PMB Trailer+Promo_01PMB Trailer+Promo_01Aussie Angels - the preferred fund and syndicate admin platform for emerging managers in AustraliaShow Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.comFebruary 2025 - Aussie AngelsThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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 – Intro02:16 – James’s first big bet – Starting a company in Australia’s early 2000s “hellscape” and the lessons learned07:18 – Why MOOCs weren’t the answer – The early EdTech hype, misconceptions about online courses, and how Khan Academy did things differently11:12 – Assessment as the control point – How exams and credentials shape mainstream education and what might disrupt that model15:08 – AI’s impact on education – Could personalized, AI-driven learning (and cheating) force schools to rethink how we test knowledge?18:20 – Kids, dopamine, and the next-gen learning paradox – Balancing entertainment and deep learning, and why “edutainment” rules24:00 – VC skepticism vs. reality – Why it’s so hard to invest in K–12 EdTech, and where vocational and adult learning might be more promising32:00 – Rapid AI adoption – From legal tech to healthcare, how ambient tools are skyrocketing and what it means for founders37:00 – Wedges, moats, and growth – The playbook for AI startups moving from “just a feature” to a sustainable product42:00 – James’s “big kahunas” moment – Choosing Khan Academy over Stanford and why walking away from “prestige” can change everything47:07 – Wrap-up – The future of EdTech, AI’s role, and parting wisdom for founders and investorsResources MentionedJames Tynan on LinkedIn – Partner at Square Peg and former operator at Khan Academy. - https://www.linkedin.com/in/james-tynan-ba54b93/Square Peg – The VC firm James Tynan is a Partner at. - https://www.squarepeg.vc/Khan Academy – Free world-class education for anyone, anywhere.College Board + Khan Academy Partnership – Free SAT and AP test prep.Ambience Healthcare – AI for clinical documentation and patient notes.Harvey AI – Legal AI platform disrupting law firm workflows.Sponsors:First Cheque is supported by our wonderful sponsors: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/chequeAussie 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 CyberAussie Angels - the preferred fund and syndicate admin platform for emerging managers in AustraliaShow Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.comFebruary 2025 - Aussie AngelsPMB Trailer+Promo_01PMB Trailer+Promo_01November 2024 - Galah CyberNovember 2024 - Rocking HorseFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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 matters01:49 – Defining an investment thesis: What it is & why it's essential04:49 – How to break down your thesis into clear categories05:16 – Industry focus: Verticals, horizontals, and emerging trends07:05 – Stage focus: Pre-seed, seed, growth—how to pick your sweet spot08:24 – Business model focus: B2B SaaS, marketplaces, and beyond10:01 – Geography: The pros and cons of investing locally vs globally14:29 – Key questions every investor should ask themselves17:24 – Company-specific criteria: How to create your investment checklist22:33 – Evaluating market size and growth potential25:39 – Pain vs pleasure: Investing in painful problems vs unmet desires29:54 – Unique or niche theses: Second-time founders, alumni networks, and more33:46 – Access and deal flow: How to attract great opportunities38:35 – Understanding your personal risk profile & timeline expectationsResourcesAngel Academy – Comprehensive angel investing course for Australia & NZ: www.venture.academyAussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/Sponsors:First Cheque is supported by our wonderful sponsors: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/chequeAussie 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:Angel Academy - Best online angel investing course in Australia and New ZealandDon't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy February 2025 - Angels AcademyNovember 2024 - Galah CyberNovember 2024 - Rocking HorseFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Galah CyberThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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 matter01:45 – SAFE notes, convertible notes, and priced rounds explained03:47 – How founders raise money: equity vs. debt06:21 – The documents you’ll sign in a priced round10:22 – Do startups need a constitution? Red flags to watch for14:29 – Side letters: What are they, and should you be worried?19:08 – Pro-rata rights & why they matter for investors22:23 – Most Favoured Nation (MFN) clauses explained30:27 – Pre-money vs. post-money SAFEs: Which one is better?38:03 – Why valuation caps and discounts can be a double-edged sword43:53 – Investor-friendly vs. founder-friendly terms: What’s fair?Resources- A Deep Dive into ECIS, ESVCLP, and Investment Strategies - https://open.spotify.com/episode/1Agiu4dskF53m6DBZgXitD?si=KFeAlY_wTjSwOWfRMiiQFA- Angel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academy- Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/- Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/Sponsors:First Cheque is supported by our wonderful sponsors: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/chequeAussie 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:Aussie Angels - the preferred fund and syndicate admin platform for emerging managers in AustraliaShow Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.comFebruary 2025 - Aussie AngelsNovember 2024 - Galah CyberFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Rocking HorseNovember 2024 - Galah CyberThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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 & founders01:21 – Who this episode is for: Emerging fund managers & startup founders03:23 – Understanding fund cycles: Raising, deploying, and exiting05:48 – The reality of raising a fund: Why it takes 12-24 months to close09:35 – Deployment periods: How VCs decide when and where to invest12:34 – The risk of running out of money—how fund managers avoid this mistake16:57 – Fund sizes & check sizes: Why $50M is a magic number in VC21:09 – Micro VCs vs. bigger funds: How different strategies impact returns25:14 – Opportunity funds: When fund managers double down on winners30:08 – The importance of liquidity planning and secondaries in VC37:17 – Exits: How and when fund managers start planning for returns43:59 – Final thoughts: The key takeaways from this episodeResources Mentioned- Angel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academy- Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/- Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/- ESVCLP (Early Stage Venture Capital Limited Partnership) – How tax benefits impact Australian VC funds- AFR & Startup Daily – Understanding VC funding announcements in the media- Adverb Ventures (April Underwood) – Case study on fast fund cycles- Australian Super Funds & VC – Why institutional capital is hard to secure- Venture Fund Deployment Data (US vs. Australia) – Insights on how quickly funds deploy capital- Fund Liquidity & Secondaries – How fund managers plan exits when IPOs & M&A slow downSponsors:First Cheque is supported by our wonderful sponsors: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/chequeAussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence.https://www.aussieangels.com/Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.https://dayone.fm/galah First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. Mentioned in this episode:November 2024 - Galah CyberAngel Academy - Best online angel investing course in Australia and New ZealandDon't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy February 2025 - Angels AcademyNovember 2024 - Galah CyberNovember 2024 - Rocking HorseFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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 check sizes, and the dangers of deploying too fast. Plus, they break down the realities of payback periods in startup investing, why you shouldn’t expect quick returns, and how power law dynamics shape investment outcomes.Cheryl also shares her personal approach to budgeting for angel investments, alternative funding sources (like self-managed super funds and term deposits), and how investors can avoid the all-too-common mistake of running out of capital too soon.If you want to build a sustainable angel investment strategy, ensure you're making long-term, high-return decisions, and avoid costly mistakes, this is an episode you don’t want to miss!Key Takeaways:00:00 – Introduction: Why budgeting and cash planning are critical for angel investors01:49 – The golden rule: How not to run out of money when investing02:37 – Why staying liquid matters: Power law, economic cycles, and risk mitigation05:15 – Angel investing vs. stock market investing: Why you can't just sell down a position08:04 – How Cheryl funds her investments: Breaking the myth of needing huge capital10:00 – Alternative funding sources: Super funds, ETFs, term deposits, and more13:41 – The importance of knowing your risk tolerance and financial boundaries17:48 – Varying check sizes: When to double down on winners and how to strategise23:15 – Why new angel investors should start with consistent check sizes30:47 – Australian angel success stories: Real returns and lessons from Clarity Pharmaceuticals, Autra, and Instacluster34:56 – Final takeaways: Planning, patience, and how to build a sustainable angel investing portfolioResources MentionedAngel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academyAussie Angels – Cheryl’s platform for angel investingCoventures – Maxine’s venture capital firmCentral Texas Angel Network (CTAN) – Study on angel investment returnsTechCoast Angels California – Report on long-term angel investing performanceAustralian Angel Success Stories:Clarity Pharmaceuticals – 50x return for early investorsAutra (Agil) – Acquired by Schneider Electric, 91% IRRInstacluster – 63% IRR after acquisition by NetAppSponsors:First Cheque is supported by our wonderful sponsors: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/chequeAussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence.https://www.aussieangels.com/Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.https://dayone.fm/galah First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. Mentioned in this episode:November 2024 - Galah CyberAngel Academy - Best online angel investing course in Australia and New ZealandDon't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy February 2025 - Angels AcademyNovember 2024 - Galah CyberFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Rocking HorseThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode Summary:In this episode of First Cheque, Cheryl and Maxine sit down with Laura Chambers, CEO of Mozilla, to dive into the transformative power of open source technology and its role in shaping the future of the internet and artificial intelligence. Laura shares insights on Mozilla’s unique nonprofit structure, the importance of transparency and accessibility in technology, and the critical need for an open AI ecosystem to drive innovation and equity.From the historical impact of open source software like Firefox to the current challenges of balancing ethical AI development with business needs, this conversation is packed with lessons for early-stage investors and tech enthusiasts alike. Laura also provides an inside look at Mozilla Ventures and the Builders Program, which are supporting the next wave of open-source innovators. Whether you're an investor, founder, or just curious about the future of tech, this episode is a must-listen!Time Stamps:00:00 – Introduction to the episode and Laura Chambers02:06 – The origin story of open source and Mozilla’s role in internet history07:22 – Netscape, Firefox, and the fight for an open internet11:05 – The challenges of keeping AI open in a world of closed ecosystems15:19 – Why open source innovation accelerates progress19:12 – Addressing the misconceptions of open source and its role in AI safety23:18 – The potential societal impacts of closed vs. open AI29:34 – Insights into Mozilla Ventures and the Builders Program35:01 – Why transparency and accountability are essential in AI development41:16 – How open AI can empower underrepresented communities globally47:20 – Laura’s biggest lessons as a leader in tech and her vision for Mozilla’s futureResources MentionedMozilla Ventures: Supporting startups focused on privacy, AI, and open source innovation.Mozilla Builders Program: Investing in and mentoring early-stage entrepreneurs building ethical tech solutions.Harvard University Study: Open Source Software’s $8 Trillion Economic Impact A study on the global economic value created by open source technology.Anthropic Report on Bias in AI: Research highlighting the impact of bias and the importance of transparency in AI models.Sponsors:First Cheque is supported by our wonderful sponsors: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/chequeAussie 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 CyberJune 2024 – Vanta First ChequeNovember 2024 - Galah CyberNovember 2024 - Rocking HorseFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

Episode Summary:In this episode of First Cheque, hosts Cheryl and Maxine delve into the critical topic of liquidity within the venture capital ecosystem. They explore why IPOs (Initial Public Offerings) and M&A (Mergers and Acquisitions) are essential for investors and startups alike. The conversation covers the current state of the IPO market, the challenges of companies staying private longer, and how these factors impact investment strategies and returns. They also discuss the role of secondaries as a solution to liquidity issues, the potential effects of proposed regulatory changes in Australia, and the importance of proactive engagement from the tech community to address these challenges. Cheryl and Maxine offer insights into navigating the evolving landscape, emphasising the need for transparency, standardisation, and inclusive wealth creation in the venture space.Key Takeaways:00:00 - Introduction to Cheryl and Maxine; overview of the episode01:03 - Discussion on liquidity, IPOs, and M&A in the venture ecosystem02:07 - Defining liquidity, IPOs, and M&A for the audience05:21 - Importance of IPOs in venture capital and why they matter09:30 - Impact of the health of IPO markets on investment strategies14:56 - Investment strategies during different market cycles; being contrarian16:14 - Exploring opportunities in secondaries amidst liquidity challenges21:13 - Reasons companies are staying private longer; regulatory influences26:43 - Regulatory clampdown on M&A and its effects on the tech ecosystem31:45 - Closing remarks; encouraging solutions for liquidity issuesResources Mentioned:SecondQuarter Ventures: An Australian secondary fund involved in facilitating liquidity through secondaries.Airtree Ventures and Canva: Airtree's secondary transaction involving Canva as an example of internal liquidity solutions.Instacluster: An Australian company acquired by a U.S. firm, highlighting international M&A activity.Mr Yum and me&u: Example of Australian companies merging to navigate market challenges.Australian Securities Exchange (ASX): Discussed as an option for listing, particularly for small-cap companies.Jim Chalmers: Australian Treasurer proposing reforms on M&A regulations that could affect the tech ecosystem.Tech Council of Australia (TCA): Suggested as a body to engage with and advocate on behalf of the tech community regarding regulatory changes.Sponsors:First Cheque is supported by our wonderful sponsors: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/chequeAussie 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 CyberJune 2024 – Vanta First ChequeFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Rocking HorseNovember 2024 - Galah CyberThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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 investments to a diversified portfolio across industries, leveraging the collective power of mentors and founders. Gain practical insights into crafting investment theses, fostering innovation, and redefining venture capital through collaboration and bold thinking. Whether you’re revisiting this conversation or tuning in for the first time, get ready for plenty of actionable advice and behind-the-scenes stories that shaped one of our most downloaded episodes of 2024. Enjoy the replay!Time Stamps00:00 Introduction and background on Michael Batko and Startmate.02:36 Startmate’s investment thesis and evolution into hardware and non-traditional startups.07:59 The role of community and mentors in early-stage investing.14:19 Insights into the Continuity Fund and its benefits for alumni companies.23:09 The importance of equity and carry in the Australian startup ecosystem.34:09 Startmate’s unique approach to portfolio construction and decision-making.42:07 Lessons learned from non-consensus investments like Heaps Normal.48:36 Michael Batko’s "Big Cojones" moment and reflections on bold decisions.Notable Quotes:1. "It’s not about what’s probable; it’s about what’s possible." – Michael Batko2. "Backing the hungry, not the proven, is at the heart of what we do." – Michael Batko3. "Would you want to work for this founder? That question reveals everything." – Michael Batko4. "The biggest mistake in VC isn’t losing money—it’s missing the one company that could be massive." – Michael Batko5. "Startmate is built on two core principles: giving the community a job and skin in the game." – Michael BatkoResources MentionedNo-Code Tools:• Airtable• Notion• Softr• PoryHeaps NormalEucalyptus – Guide to Employee Share Options (ESOP)Cake Equity – Equity and ESOP CalculatorSponsors: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/chequeAussie 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 - Rocking HorseFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Galah CyberJune 2024 – Vanta First ChequeNovember 2024 - Galah CyberThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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’re looking for unfiltered commentary on liquidity, the fate of AI hype, and what lies ahead for the Australian and global tech markets, this episode covers it all—plus a healthy side of debate and laughter.Timestamps00:00 Introduction & Annual Wrap-Up Setup00:21 Reflecting on Last Year's Predictions & Risk Appetite Shift01:50 Investor Sentiment & Early-Stage Deal Growth03:06 ChatGPT Adoption & AI’s Embedded Productivity Gains05:00 Liquidity’s Return: M&A, Secondaries & Early Exits07:30 Increased Angel Activity & “Learning Checks” Trend09:20 Discussing Worst Investor Terms & Founder-Friendly Boundaries10:47 The State of IPO Markets, Political Shifts & Macro Effects12:40 AI Acceleration, Productivity Tools & Future Potential14:10 Spicy 2025 Predictions: IPOs, One-Person Billion-Dollar Startups & Bubble Cycles17:00 Final Takeaways, Lessons Learned & Maintaining OptimismKey Takeaways:Gradual Investor Confidence Rebuild: Despite a tough few years, investor sentiment improved slightly in 2024, with more early-stage deals and smaller check sizes indicating a return of risk appetite.More Angels, More Checks: The Australian ecosystem saw a surge in angels writing “learning checks,” reflecting a more portfolio-minded approach among first-time investors.AI’s Permanent Footing: AI is here to stay, with everyday products increasingly integrating it for productivity gains. While some skeptics remain, the hosts firmly believe AI isn’t a passing fad.M&A and IPO Prospects: Early-stage M&A activity is up and liquidity events may increase if certain geopolitical and economic shifts occur. While 2024 saw incremental gains, 2025 may bring either a return to “bubble” conditions or a more measured growth environment.Spicy Predictions for 2025: From a potential billion-dollar one-person startup to a high-profile AI company collapse, the hosts don’t hold back on bold forecasts.Resources MentionedPrograms like the Climate Salad Global Growth Program and BuildClub (discussed as ecosystem examples)Notable Quotes“We are seeing a lot more risk appetite at the earlier stages, which tells me there are more early stage companies getting funded.” – Cheryl“I think we will see a high profile AI company collapse next year.” – Cheryl on her bold 2025 prediction“My spicy take: You cannot build a generational company in a year.” – Maxine“AI is here to stay—it's not a fad, it’s going to be integrated into everything.” – CherylSponsors: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/chequeAussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence.https://www.aussieangels.com/Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.https://dayone.fm/galah First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. Mentioned in this episode:November 2024 - Galah CyberFC Vanta Ad March 2025_02FC Vanta Ad March 2025_02November 2024 - Rocking HorseNovember 2024 - Galah CyberJune 2024 – Vanta First ChequeThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/