Episodes

  • 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.

    Timestamps

    00:00 Introduction & Annual Wrap-Up Setup

    00:21 Reflecting on Last Year's Predictions & Risk Appetite Shift

    01:50 Investor Sentiment & Early-Stage Deal Growth

    03:06 ChatGPT Adoption & AI’s Embedded Productivity Gains

    05:00 Liquidity’s Return: M&A, Secondaries & Early Exits

    07:30 Increased Angel Activity & “Learning Checks” Trend

    09:20 Discussing Worst Investor Terms & Founder-Friendly Boundaries

    10:47 The State of IPO Markets, Political Shifts & Macro Effects

    12:40 AI Acceleration, Productivity Tools & Future Potential

    14:10 Spicy 2025 Predictions: IPOs, One-Person Billion-Dollar Startups & Bubble Cycles

    17:00 Final Takeaways, Lessons Learned & Maintaining Optimism

    Key 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 Mentioned

    Programs 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.” – Cheryl

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  • 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+ analyses over 600,000 startup deals to predict investment success, emphasising the importance of the power law and large, diversified portfolios in maximising venture returns. John also shares his insights on the future of algorithmic investing in venture capital, drawing parallels to the transformation of public equities in the 1990s. Throughout the discussion, he underscores the necessity of adapting to technological advancements and offers valuable lessons for founders, operators, and investors aiming to leverage AI for smarter investment strategies.

    Key Takeaways:

    01:39 Welcome & First Investment Question

    02:10 John's First Investment: Education and Orchestration

    05:00 Technological Disruption in the Music Industry

    06:14 Management Lessons from Conducting Orchestras

    10:47 Lessons from Past Industry Disruption

    15:03 Introduction to Hatcher+ and AI Venture Model

    17:51 Hatcher+'s Methodology & Portfolio Strategy

    24:01 The Power Law in Venture Capital

    33:33 Building Hatcher+'s AI-Driven Platform

    37:12 Insights from Analysing 600,000 Companies

    42:40 Importance of Pivots and Board Support

    44:31 John's Biggest Courage Moment

    Resources

    Books:

    • Orchestration by Walter Piston

    • The Professional Arranger Composer by Russell Garcia

    • Orchestration books by Nelson Riddle

    • Jazz Orchestration by Dick Grove

    Notable Quotes

    "If you don't understand AI, figure it out as quickly as you can. Because if you embrace the AI options that are available, you'll become expert at them." – John Sharp

    "To succeed in venture, you've got to truly play the odds in a very intelligent way." – John Sharp

    "You have to worship at the altar of the power law. It dictates everything that you do." – Maxine

    "Sometimes you just got to put yourself out there and follow your gut that you know how to do this." – John Sharp

    Sponsors:First Cheque is supported by our wonderful sponsors:

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    https://dayone.fm/rockinghorse

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  • 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 hype cycles in technology—including discussions on the metaverse and blockchain—and the profound impact of backing founders in their earliest stages. Emily also reflects on her transition from founder to angel investor, highlighting the importance of supporting ambitious ideas and the courage it takes to step into the unknown. Packed with personal anecdotes, industry insights, and plenty of laughs, this episode offers both inspiration and practical advice for anyone interested in the highs and lows of venture capital.

    Key Takeaways:

    00:00 Introduction and Emily's first investment in her own education

    04:29 Discussing being bad at being told what to do; founders as bad employees

    06:12 Emily on why she invests in pre-seed and seed stages

    13:14 Navigating hype cycles; the Metaverse example

    18:14 Thoughts on blockchain and crypto as hype cycles

    22:26 Understanding and identifying hype cycles in investing

    29:28 Changes in AI over the past decade; Emily's background in AI

    32:31 Public perception of AI and fear of job loss

    37:39 Tips for non-technical investors to understand AI

    40:40 Emily's Big Kahuna moment—leaving a safe job to start angel investing

    44:44 Closing remarks and thank you

    Notable Quotes

    "You know it's gone mainstream when my mum is using it for knitting tips." - Cheryl

    "The Metaverse is my favourite hype cycle because it was so overhyped and no one is spending time in the Metaverse." -Emily Rich

    "There is some suggestion and quite a lot of research that founders are really bad employees—great founders are really bad employees." - Maxine

    "If you're hyping someone from the sidelines, it's like cheering on an athlete—they're probably going to run faster." -Cheryl

    "I started investing in myself, in my education—not from a university perspective, but from schooling in general." - Emily Rich

    Resources

    Thought Leaders to Follow:

    Fei-Fei Li – Renowned for her work in AI and computer vision.Timnit Gebru – Noted for her contributions to AI ethics.

    Reports and Articles:

    Sequoia Capital's Articles on AI: Maxine mentions that Sequoia published insightful pieces examining whether AI infrastructure can generate significant revenue, specifically questioning the potential for $600 billion in revenue.Bain & Company's Report on the Jagged Edge of Technology: Referenced by Maxine, this report discusses the adoption of AI, its impact on productivity, and how businesses are integrating AI into operations.

    Books and Quotes:

    Charlie Munger's Investment Advice: Maxine recalls his quote, "If your shoeshiner starts giving you stock tips, sell," as a metaphor for identifying when a market might be overheated.

    Sponsors:First Cheque is supported by our wonderful sponsors:

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    Rocking Horse: Rocking Horse helps startups access their R&D tax rebate early. Get up to $3M in non-dilutive finance, solve cash flow challenges, and accelerate growth. Easy application, fast approval. Smart investment for innovative startups.

    https://dayone.fm/rockinghorse

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  • 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, liquidity issues, and policy needs, along with the significance of strong talent and multicultural acceptance. Tim also shares a personal story about leading a national campaign against antisemitism in Australia. This episode is rich with practical advice for budding angel investors and insights into the growth of Australia's tech landscape.

    Key Takeaways:Importance of Top-Tier Talent: Emphasising that success is driven by individuals who are in the top 1% of their field, Tim focuses on investing in founders and teams that demonstrate exceptional capabilities.Building and Utilising Networks: The "ex-Uber mafia" and connections from his professional journey have been instrumental in providing deal flow and collaborative opportunities in both his operating and investing roles.Interplay Between Operating and Investing: While Tim views operating and investing as distinct activities, he acknowledges cross-pollination in networking and strategic opportunities, such as recruiting talent through connections made in the investment community.Successful Launch Strategies: Sharing the story of Turo's launch in Australia, Tim highlights the effectiveness of building hype and the importance of a well-executed go-to-market strategy, even when facing competition from established players like Uber CarShare.Leadership Beyond Business: In response to rising antisemitism, Tim organised an open letter from Australian business leaders condemning hate and promoting multiculturalism, demonstrating his commitment to societal impact.Advice for Aspiring Angels: Tim advocates for a balanced approach to angel investing—being available and supportive without overwhelming founders, and recognising when to offer help based on founders' requests.

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    Mentioned in this episode:

  • 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 developing AI products, finishing with rapid-fire questions for quick insights. Connect with Georgie on LinkedIn, Instagram, or via email to share your thoughts and suggestions for future guests.

    Timestamps

    00:00 Introduction to In the Blink of AI

    00:10 Meet Your Host: Georgie Healy

    00:56 Podcast Format and Content

    01:11 Engage with Us

    The Day One NetworkIn The Blink of A.I. is part of Day One, the podcast network dedicated to founders, operators & investors.

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    Mentioned in this episode:

    Rocking Horse - November 2024

  • 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 practical advice on refining investment strategies through critical thinking, timely decision-making, and mitigating biases. Additionally, it explores the qualitative nature of early-stage investments and the value of leveraging instincts effectively. Tune in to transform your investment decisions with proven frameworks and mental models.

    Key Takeaways

    00:00 Welcome to First Cheque: Your Guide to Early-Stage Investing

    00:22 Diving into Decision-Making and Mental Models

    02:05 From Checklists to Decision Diaries

    07:20 Evaluating Founders and Market Size

    16:28 The Importance of Timing in Investment Decisions

    20:13 Understanding Mid to Late-Stage Investing

    20:56 The Role of Intuition and Quantitative Measures

    22:38 Challenges of Data-Driven Investment Matching

    23:17 Personal Experience with Investment Matching

    25:49 The Potential and Limitations of AI in Investing

    28:35 Decision Diaries: A Tool for Better Investment Choices

    35:03 Key Questions for Investment Decisions

    37:14 Reflections on Decision-Making and Instincts

    37:38 Conclusion and Call for Feedback

    Resources

    Maxine's Decision Diary Template

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    https://dayone.fm/rockinghorse

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    To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

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    Mentioned in this episode:

    June 2024 – Vanta First Cheque

    November 2024 - Rocking Horse

    November 2024 - Galah Cyber



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  • 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 investment strategies are both conservative and highly lucrative.

    The episode highlights Browne's investment philosophy—characterized by rigorous thematic focus, underscoring software's unturnoffable nature in various enterprise settings. He shares insights from his venture fund experiences, discussing the competitive dynamics of boring businesses and the journey of transitioning from an entrepreneur to a fund manager. Throughout the conversation, Browne also provides valuable advice to those considering venturing into fund management, emphasizing the importance of sticking to areas of known expertise and understanding the role's demands.

    Key Takeaways:Thematic Investment Strategy: Matthew Browne emphasizes investing in enterprise SaaS that is mission-critical to operations, underscoring the intrinsic value and longevity of such investments.Importance of Execution: His first investment’s failure taught the importance of knowing how to effectively acquire customers and sticking to one's domain expertise.Transition from Entrepreneur to Investor: Browne shares his journey into VC, stating the unique challenges of fund management compared to traditional business operations.B2B SaaS Success Factors: Long-lived customer relationships and LTV are key, with an enterprise focus often yielding higher customer loyalty and lower competitive pressures.

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    Rocking Horse: Rocking Horse helps startups access their R&D tax rebate early. Get up to $3M in non-dilutive finance, solve cash flow challenges, and accelerate growth. Easy application, fast approval. Smart investment for innovative startups.

    https://dayone.fm/rockinghorse

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    https://dayone.fm/galah

    The Day One NetworkFirst Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

    To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

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    Mentioned in this episode:

    November 2024 - Rocking Horse

    June 2024 – Vanta First Cheque

    November 2024 - Galah Cyber



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  • 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 capital management, and the importance of alignment between founders and investors.

    Throughout the conversation, the trio explores the differences between the Australian and US venture capital ecosystems, touching on themes such as market size, customer sophistication, and the importance of domain expertise in founding teams. Georgie also shares insights on navigating the AI revolution and its impact on the tech stack and business models. The episode concludes with a reflective discussion on bravery in the venture capital space, emphasizing the optimistic and sometimes illogical nature of the industry.

    Key Takeaways:Cross-Border Investment: Georgie Turner discusses the importance of having a cross-border investment strategy, particularly focusing on the differences between the Australian and US venture capital ecosystems.Capital Management: Insightful exploration into how proactive capital management and accurate valuation alignment can significantly impact the success of early-stage investments.AI Investment: Detailed discussion on how AI is transforming the tech landscape and what investors should look for in AI-driven companies.Scaling Challenges: The episode highlights the challenges of scaling companies in different markets and the importance of market timing, product quality, and operational expertise.Bravery in Venture Capital: Reflections on the inherent bravery required in the venture capital profession, given its optimistic and sometimes illogical nature.
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    The Day One NetworkFirst Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

    To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

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    Mentioned in this episode:

    June 2024 – Vanta First Cheque

    November 2024 - Rocking Horse

    November 2024 - Galah Cyber



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  • 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, including the typical risks and rewards, the lengthy timeframes involved, and the importance of understanding the science and market potential behind each investment. He also touches on the significant advances in genomics and synthetic biology, emphasising how technology and data analysis are accelerating innovation in the field. The discussion delves into the importance of syndication for early-stage investments, the critical milestones that de-risk investments, and the role of pharmaceutical partnerships in increasing the likelihood of success.

    Key Takeaways:Understand the Risks and Rewards: Biotech investing involves a high level of risk and typically long hold periods, but the potential rewards can be substantial.Syndicate Investments: Due to the complexity and capital intensity of biotech, syndicating with experienced investors and funds is crucial for mitigating risk.Stages of Investment: Key milestones in biotech investing include achieving safety and efficacy in clinical trials, with significant value inflections at each stage.Technological Impact: Advances in genomics, AI, and data analysis are revolutionizing the speed and accuracy of biotech innovations.Healthcare Economics: Understanding the economic impact and potential reimbursement scenarios is essential for assessing biotech investments.

    Sponsors:

    Thanks to our sponsors for helping to make this episode of First Cheque possible.

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    Turo: Turo is the world's largest carsharing marketplace and it's the perfect app for travel.

    Download the Turo app and book cars from $38/day. https://dayone.fm/turo

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    Mentioned in this episode:

    June 2024 – Vanta First Cheque

    November 2024 - Galah Cyber

    November 2024 - Rocking Horse



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  • 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 examples.

    Cheryl explains the criteria and benefits associated with Early Stage Innovation Companies (ESIC) and Early Stage Venture Capital Limited Partnerships (ESV CLP). She details how these structures facilitate sophisticated tax offsets and capital gains exemptions for investors. Throughout the discussion, they highlight the importance of understanding these incentives to optimize investment returns. The episode culminates with practical advice on investing via trusts and navigating the nuances of capital call schedules, reflecting the duo's deep dive into the subject matter.

    Key Takeaways:Understanding ESIC: Learn about the Early Stage Innovation Company (ESIC) designation in Australia, its eligibility criteria, and the significant tax benefits it offers. ESV CLP Benefits: Discover how Early Stage Venture Capital Limited Partnerships (ESV CLP) and Venture Capital Limited Partnerships (VCLP) offer substantial tax incentives, including offsets and capital gains exemptions. Investment Structures: Get insights into the complexities of investing through safes (Simple Agreement for Future Equity) and how ESIC status impacts tax benefits. Leveraging Trusts: Explore the functional benefits and considerations when investing through discretionary (family) trusts, particularly in relation to income distribution and tax efficiency. Managing Capital Calls: Understand the importance and mechanics of capital call schedules within the context of fund investments and their fiscal implications.

    Sponsors:

    Thanks to our sponsors for helping to make this episode of First Cheque possible.

    Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time. Get 10% off https://dayone.fm/vanta

    Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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    Download the Turo app and book cars from $38/day. https://dayone.fm/turo

    The Day One NetworkFirst Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

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    Mentioned in this episode:

    June 2024 – Vanta First Cheque

    November 2024 - Rocking Horse

    November 2024 - Galah Cyber



    This...
  • 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 secondaries in the investment ecosystem. They explore how secondaries can provide liquidity options for founders, early employees, and initial investors, comparing the maturity of secondary markets in the US versus Australia. They touch on the role of secondary funds, the impact of early liquidity on the ecosystem, and how this federal flow of funds can encourage re-investment into new startups.

    Next, the duo dives into their anti-portfolios, sharing insights from companies they passed on and reflecting on biases and lessons learned. They also address gender diversity in the investment landscape, critiquing the current state of gender equity in the Australian startup ecosystem. Furthermore, Cheryl and Maxine share their strategies for balancing valuations, particularly in the context of owning small equity stakes as angel investors.

    Key Takeaways:Secondary Transactions: Understanding the role and impact of secondary transactions can provide essential liquidity to founders and early investors, fostering a healthier investment ecosystem.Anti-Portfolio Learnings: Reflecting on missed investment opportunities reveals biases and allows investors to refine their criteria and improve decision-making.Gender Diversity: There is a significant need to address the gender gap at all levels of the investment ecosystem, from founders to fund managers and LPs.Valuation Strategy: Evaluating whether a company can significantly grow its valuation by the next funding round is crucial in assessing high valuations.Founder-Investor Relationships: Strong relationships between founders and investors are imperative for successful fundraising and long-term collaboration.
    Resources:Scale Investors: led by Samar, focusing on women-led companies.EQUITY DIRECTORY: A data-focused initiative to improve reporting on gender metrics in the investment community.AirTree Pioneers Program: Supporting diverse early-stage founders.First Cheque Podcast Voicemail: Submit a question
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    Turo: Turo is the world's largest carsharing marketplace and it's the perfect app for travel.

    Download the Turo app and book cars from $38/day. https://dayone.fm/turo

    Mentioned in this episode:

    November 2024 -...

  • 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 venture capital.

    Key topics covered include the unique factors influencing growth stage investments, the difference between primary and secondary investing, and the significance of liquidity for investors and founders. The conversation delves into the evolving venture capital landscape and the role of secondary transactions in unlocking value and increasing market liquidity.

    Key Takeaways:Growth stage investing focuses on scaling proven products and ideas to dominate the market.Secondaries play a crucial role in providing liquidity to early investors, employees, and founders.The US offers a mature ecosystem with a deep talent pool for scaling companies, while Australia nurtures a hungry and talented workforce.Investors can access growth stage opportunities through platforms like Angellist and secondary transaction platforms.Exploring new frontiers in AI and emerging technologies drives investor interest and excitement in growth-stage companies.
    Notable Quotes:"Investing in the AI space is both exciting and challenging due to the rapid platform shift and exploration phase." - Christina Fa"Unlocking liquidity through secondaries is beneficial for both investors and the ecosystem as a whole." - Christina Fa"The US ecosystem offers a deep talent pool, while Australia fosters a culture of first principles thinking and innovation." - Christina Fa
    Resources:NewView CapitalNewView Capital LinkedinChristina Fa LinkedIn
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    November...

  • 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 discussion provides a comprehensive view of the current landscape.

    Key themes include the shifting risk perceptions in Australia, the resilience and adaptability of Australian startups, and the impact of broader economic and political factors on the ecosystem. With a focus on building stronger companies and navigating challenges, Bronwen offers valuable perspectives on driving innovation and growth in an ever-changing environment.

    Key Takeaways:

    • Risk appetite plays a fundamental role in distinguishing between traditional markets and startups.

    • Australia's startup ecosystem demonstrates resilience and efficiency in the face of challenges.

    • The housing crisis and changing economic landscapes are fuelling interest in startups and alternative investments.

    • Tension between super funds and risk-taking behaviours may influence the entrepreneurial landscape.

    • Australian founders are embracing independence and innovation, shaping the future of the industry.

    Notable Quotes:

    • "I think Australia punches above its weight in terms of producing founders that international investors are looking at favourably." - Bronwen Clune

    • "The housing crisis has spurred interest in alternative investments as young people seek to grow capital." - Bronwen Clune

    • "Risk appetite, or lack thereof, is a defining factor between traditional market players and startup enthusiasts." - Bronwen Clune

    Resources:

    • Capital Brief Website

    • Bronwen Clune's LinkedIn Profile

    Sponsors:

    Thanks to our sponsors for helping to make this episode of First Cheque possible.

    Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time. Get 10% off https://dayone.fm/vanta

    Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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    Download the Turo app and book cars from $38/day. https://dayone.fm/turo

    The Day One NetworkFirst Cheque is part of Day One, the podcast network dedicated to founders, operators & investors.

    To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

    If you want to learn about upcoming guests and when a new First Cheque episode is available, join the First Cheque newsletter.

    Mentioned in this episode:

    June 2024 – Vanta First Cheque

    November 2024 - Rocking Horse

    November 2024 - Galah Cyber



    This...
  • 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 informational asymmetry in decision-making, the power of outliers in generating alpha, and the influence of expertise and thesis investing on portfolio performance.

    Key Takeaways:Portfolio construction is crucial in early-stage investing to manage risks and optimize returns.Diversification versus concentration impacts the average quality and performance of a portfolio.Specialized first and second funds tend to outperform, emphasizing the importance of focused investment strategies.The power law concept highlights the significance of outliers in driving fund performance.Investors must strike a balance between diversification and concentration based on risk tolerance and investment goals.
    Notable Quotes:"Thinking about building your investment strategy and what is the right level of risk tolerance is essential for successful portfolio construction." - Maxine Minter"The power law is king in the investment landscape, emphasizing the impact of outliers on fund performance." - Cheryl Mack
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    Thanks to our sponsors for helping to make this episode of First Cheque possible.

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    Download the Turo app and book cars from $38/day. https://dayone.fm/turo

    Mentioned in this episode:

    June 2024 – Vanta First Cheque

    November 2024 - Galah Cyber

    November 2024 - Rocking Horse



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  • Episode Summary:

    In this episode of First Cheque hosts Cheryl Mack and Maxine Minter sit down with the distinguished investor Ash Fontana to explore the intricacies of early-stage investing and the evolving landscape of artificial intelligence (AI). The conversation delves into Fontana's diverse experiences, ranging from his formative years building web-based marketplaces to his critical role in establishing the AI investment frontier.

    Fontana shares a captivating narrative of his investment philosophy, advocating for the significance of first-check investments in shaping the trajectories of startups. With an emphasis on determining the long-term competitive advantages of AI ventures, the discussion uncovers the importance of specialization and the strategic deployment of venture funds amidst a rapidly transforming technology sector. Key themes revolve around adapting venture capital models, the intersection of network building, and the fortune of investment careers, providing listeners with a wealth of actionable insights.

    Key Takeaways:First Cheque investments are critical in establishing a startup's potential and culture.AI investments should focus on companies that exhibit a sustainable competitive advantage, potentially characterized by data network effects.Venture Capital (VC) requires specialisation, especially in fast-evolving fields like AI, to keep pace with rapid advancements and make informed investment decisions.The traditional VC model faces criticism for its performance and lack of innovation; exploring models with lower fees and higher carry could better align incentives.Building and maintaining a robust network is essential for success and longevity in the venture capital industry.
    Notable Quotes:"The existence proof of adding value is that you allowed the entity through which all subsequent value is created to exist.""As soon as you're competing, you're losing. You should just aim to be in non-competitive situations.""I invest in technology cycles, not market cycles.""I find it really hard to work for other people and in big companies, but I would have worked for a big growth stage or growth stage fund, like Insight, Summit, Bain, one of them.""The bigger the network you can build, the better, the more useful you will be, and therefore, the more lucky you will get."
    Resources:Ash Fontana's book: "The AI-First Company"Ash Fontana's LinkedIn profile
    Thanks to our sponsors for helping to make this episode of First Cheque possible:

    Vanta: Join 7,000 global companies like Atlassian and Dovetail that use Vanta to build trust and prove security in real-time. Get 10% off

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    Mentioned in this episode:

    November 2024 - Galah Cyber

  • Episode Summary:

    In this episode of the First Cheque podcast, our co-hosts Cheryl Mack and Maxine Minter welcome venture capital trailblazer Marvin Liao to discuss the multifaceted experience of early-stage investing, the evolution of global startup ecosystems, and the profound lessons learned from economic cycles in the tech industry. The conversation kicks off with stories from Marvin's background in Silicon Valley, including his first steps into the startup world, a decade at Yahoo, angel investing experiences, and defining years with 500 Startups.

    Marvin delves into the intricate dynamics of venture capital, sharing his hands-on approach to international investing and offering a candid perspective on navigating competitive markets during downturns. With an emphasis on founder qualities, market-fit, and the significance of geographies like the US for ambitious startups, Marvin provides a remarkable guide for those looking to excel in the unpredictable venture capital terrain.

    As the dialogue unfolds, Marvin's strategic astute observations reveal practical strategies for both investors and entrepreneurs looking to leverage opportunities within the constantly shifting sands of the tech landscape.

    Key Takeaways:Successful early-stage investing requires engaging with 'unconventional' ventures before they gain popularity, often necessitating courage to oppose the crowd.The true test of an investor is how one navigates downturns, emphasising resilience and adhering to personal investment theses rather than market sentiment.The US remains a central hub for ambitious startup founders due to its unmatched network effects and competitive ecosystem that fosters excellence.Marvin advocates a founder-first investment philosophy, prioritizing the drive, capacity to learn, and responsiveness of founders over all else.Cultural capital, such as an appreciation for science fiction, is considered crucial for anyone investing in technology's future, as it helps shape one's vision for innovation.
    Notable Quotes:"Chips on shoulders, leads to chips in pockets." - Marvin quotes Josh Wolf to describe the motivation needed for successful entrepreneurship."How you do anything is how you do everything." - A philosophy Marvin adheres to when assessing founder diligence and reliability."Steel sharpens steel." - On the importance of founders being present in high-impact ecosystems to push themselves to their limits and grow.
    Resources:Marvin Liao's personal ventures and insights can be followed through his LinkedIn profile.Reference to Lux Capital and Josh Wolf's investment philosophy might be of interest to listeners who wish to explore further.
    Thanks to our sponsors for helping to make this episode of First Cheque possible:

    Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

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    Mentioned in this episode:

    November 2024 - Galah Cyber

    November 2024 - Rocking Horse

    June 2024 – Vanta First Cheque



    This podcast uses the following...
  • Episode Summary:

    In this thought-provoking episode of First Cheque experienced investors Cheryl Mack and Maxine Minter delve into the meticulous world of follow-on investment strategies. The episode serves as a beacon for those who wish to refine their approaches in early-stage investing, especially as they grapple with the decision of whether to follow on or not in subsequent investment rounds. The conversation explores the intricate balance between optimizing returns and supporting growing companies at various funding stages.

    Cheryl represents the school of thought advocating for doubling down on winners, focusing on reserving funds for follow-on investments based on the company's performance. Maxine, on the other hand, takes a contrarian view, emphasizing the importance of an initial strong pre-seed commitment without reserving for follow-on. Together, they unpack the underpinnings of each method, providing listeners with an insightful analysis centred on investment strategy, fund management, and the implications of the power-law in startup investing.

    Key Takeaways:A follow-on investment strategy involves investing additional funds in a company during later financing rounds, usually at a different share price.Traditional wisdom encourages investors to reserve funds to double down on winning companies, but Maxine challenges this idea, promoting initial, larger investments at the pre-seed stage.Discussion on the importance of pro rata rights and the potential signaling risks associated with not following on in subsequent rounds.Cheryl shares her angel investment approach, which emphasizes growth metrics evaluation, fund allocation decisions against other opportunities, and backing companies that have shown significant progress.The conversation highlights the need for personalized investment strategies that reflect individual goals and resources, as well as the potential influence of received wisdom on investment decisions.
    Notable Quotes:"The conventional wisdom... you want to reserve follow on money in order to double down on your winners." - Cheryl Mack"If you want to maximize IRR, then it's deploying all of your capital in that first check." - Maxine Minter"The power law operates in our industry... it's not necessarily a one for one trade off... you need to make resource allocation trade offs." - Maxine Minter"I really have to believe that I'm still going to get outsized value from this valuation further on." - Cheryl Mack"The only thing that stops you from getting squeezed out over time is adding enormous value and having a great relationship with the founders." - Maxine Minter
    Thanks to our sponsors for helping to make this episode of First Cheque possible:

    Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

    Turo: Turo is the world's largest carsharing marketplace and it's the perfect app for travel. Download the Turo app and book cars from $38/day Download the Turo app and book cars from $38/day. https://dayone.fm/turo

    Mentioned in this episode:

    November 2024 - Galah Cyber

    November 2024 - Rocking Horse

    June 2024 – Vanta First Cheque



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  • Episode Summary:

    In the latest instalment of our podcast series, Cheryl Mack and Maxine Minter delve into the intricate world of early-stage investing, shedding light on the varied approaches to gaining investment conviction. This episode serves as a guide for both novice and experienced investors who aim to refine their decision-making strategies when backing new ventures.

    As Cheryl and Maxine unravel the decision-making fabric of early-stage investing, listeners are taken on a journey through the critical thought processes that investors employ. From angel investing intuition to fund management rigour, the diverse strategies and considerations are laid bare. Key topics such as founder assessment, market sizing, and investment criteria are explored in detail, offering a valuable distilled wisdom that promises to enhance the listener's own perspective on startup investment.

    Key Takeaways:Every investor has a unique process for achieving conviction in startup investments, which can evolve over time through experience and iterative learning.The consideration of factors like founder qualities, market potential, and existing competition varies between individual investors and forms the basis of their investment decisions.Portfolio construction and risk assessment play significant roles in an investor's decision to back a company, mainly when operating within a fund structure.Intuition and instinct also influence investment choices, sometimes siding with conviction even when faced with incomplete or ambiguous information.The balance between personal investment ethos and the structured approach required by funds highlights the complexity and art form of early-stage investing.
    Notable Quotes:"It's a process...an invitation to iterate your way to a successful process and continue to measure yourself." - Maxine Minter"The nature of especially early stage investing is that it's risky." - Maxine Minter"For me, it's founder... I need to feel like this is the right founder for the...market problem space." - Cheryl Mack"It's really rare, if ever, that you get to a...definitely yes...always no questions." - Maxine Minter"The spectrum of yes to hell yes...there are so many different ways of doing it and so many different timescales to be considering on." - Maxine Minter
    Thanks to our sponsors for helping to make this episode of First Cheque possible:

    Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

    Turo: Turo is the world's largest carsharing marketplace and it's the perfect app for travel. Download the Turo app and book cars from $38/day Download the Turo app and book cars from $38/day. https://dayone.fm/turo

    Mentioned in this episode:

    June 2024 – Vanta First Cheque

    November 2024 - Galah Cyber

    November 2024 - Rocking Horse



    This podcast uses the following third-party services for analysis:

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  • Episode Summary:

    In this insight-packed episode, Cheryl Mack and Maxine Minter sit down with Michael Batko, the driving force behind Startmate, to explore the intricacies of early stage investing and the power of community in the startup realm. Batko shares his journey, starting from his first investment to steering one of the most active seed stage investing funds in the industry. This episode offers a behind-the-scenes look at how Batko and his world-class team utilize a community-driven approach to identify, select, and uplift transformative business ideas across Australia and New Zealand.

    Diving into the Startmate selection process, Batko reveals the operational complexities of coordinating a vast network of mentors and how their personal investment in the fund aligns interests and boosts engagement. The conversation also uncovers the evolution of Startmate's investment thesis, its expansion into diverse industries, and Batko's approach to encouraging non-consensus thinking to unlock extraordinary potential. The episode delves into the significance of carry in VC funds, the strategic role of a continuity fund, and the decision-making framework for follow-on investments, all while reflecting on Batko's philosophy of betting on the hungry rather than the proven.

    Michael Batko began his career in corporate finance and consulting before contributing to the growth of two major Australian marketplaces, MadPaws and also played a pivotal role in Expert360's $14 million Series B funding round. After joining as Head of Operations, Batko quickly became CEO of Startmate which is now ANZ’s largest community driven seed fund raising ~$3 million from 100+ investors every 6 months.

    Key Takeaways:Startmate's success is rooted in a mentor-driven model, where community engagement and personal investment are key to its decision-making process.Batko emphasizes the importance of looking beyond what's probable and considering what's possible when evaluating investment opportunities.The alignment of mentor incentives with fund performance, through carry, is highlighted as a significant motivational factor.A robust debate around investment thesis expansion led to backing diverse ventures, including non-software startups like non-alcoholic beer brand Heaps Normal.The establishment of a continuity fund at Startmate allows for continuous support of alumni companies, signaling strong belief in their ongoing success.
    Notable Quotes:"I remember this entire thread coming up and everybody discussing whether or not we should invest in that non-alcoholic beer company. And it was at that time when I jumped in as start mate CEO and actually had to be like, 'Hey, we can't just rest on our laurels and do things the way we've always done them.'""We've expanded the investment thesis a lot around, essentially always doubling down on people and what they care about.""One of my favorite questions is, and I always keep coming back to it whenever I critically assess a company for myself, is rather than what is probable... what is possible?""One thing I love about being a microfund is that we only invest $120,000 into companies, but at that stage, it actually makes such a massive difference."
    Resources:Startmate website for more insights into their accelerator programs. StartmateMichael Batko's professional background and contributions, visit LinkedInDiscussion of eucalyptus's ESOP primer and equity importance. Eucalyptus

    Encouraging all curious investors and founders to tune

  • Episode Summary:

    In this insightful conversation, co-hosts Cheryl Mack and Maxine Minter unpack the often misunderstood world of 'fund of funds'—investment vehicles that pool capital to invest in a variety of venture funds rather than in startups directly. Tailored for early-stage investors and industry observers, this talk reveals the nuances of fund structures and investment strategies designed to mitigate risk and maximize returns.

    Diving into a no-nonsense explanation, Maxine elucidates the two foundational structures of venture funds—management companies and the standalone investing funds—and how funds of funds play into this ecosystem by investing in multiple funds. This episode shines a spotlight on the intricacies of fund growth, managerial sophistication, and the dynamic relationship between funds, funds of funds, and their limited partners (LPs). Cheryl probes into the motivations behind why LPs choose to invest in fund of funds, including access to top-tier funds and diversification that extends across emerging ventures.

    Key Takeaways:A 'fund of funds' is an investment strategy where the fund invests in other venture capital funds rather than directly in companies.Most venture funds fail to return capital; however, emerging managers often are part of the top-performing funds, despite potential difficulty in scaling from one fund to the next.Institutions like pension and super funds, which frequently invest in funds of funds, face unique challenges such as VP clauses and monthly asset pricing pressures.Funds of funds can offer investors a lower-risk profile and a more diversified exposure to the venture capital market.There is a potential growth opportunity for fund-of-funds in Australia, which is currently a nascent market in this space.
    Notable Quotes:"If you invest alongside, say, CoVentures, and CoVentures has a fund of fund that's invested in them, what does that mean for the potential success of the company later on down the road?" - Cheryl Mack"Venture funds being an indexation of the underlying assets... Our success is driven by, you know, an outlier in our portfolio." - Maxine Minter"Emerging managers consistently are in the top ten performing funds of every single vintage." - Maxine Minter"The venture funds themselves, their returns perform on a power law curve. So there's only a handful of funds, venture funds, that will deliver outlier returns to their investors." - Maxine Minter
    Sponsors:

    Thanks to our sponsors for helping to make this episode of First Cheque possible.

    Scendar: Scendar is the OG startup accounting firm in Australia. Free 1-hour consultation about your Business' growth plans and finance needs. https://dayone.fm/scendar

    Turo: Turo is the world's largest carsharing marketplace and it's the perfect app for travel.

    Download the Turo app and book cars from $38/day. https://dayone.fm/turo

    Mentioned in this episode:

    June 2024 – Vanta First Cheque

    November 2024 - Galah Cyber

    November 2024 - Rocking Horse



    This podcast uses the following third-party services for analysis:

    Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/