First Cheque with Cheryl Mack & Maxine Minter

M&A Is a Muscle: Alex Feldman on Buying & Selling in Chaos

Alex Feldman's first-ever investment was a bet on the BHP–Rio Tinto merger.

How to Think About Equity as a Startup Employee

Alexei Mitko is a partner at Co-Ventures, the architect behind Eucalyptus' ESOP plan, and widely known in the Australian ecosystem as "ESOP Guy." He was around employee number twenty at Canva and one of the early employees at Koala, giving him a front-row seat to three of Australia's biggest consumer tech outcomes. In this episode, Cheryl and Maxine unpack how Alexei designed the ESOP plan that led to roughly $300 million distributed back to Eucalyptus employees, the largest ESOP payout in Australian history. He walks through the three questions every founder faces but rarely verbalizes: who gets equity, how much, and why you have an ESOP plan in the first place. You'll also hear how he modeled allocation across multiple rounds and hundreds of hires to avoid giving too much away early, why he personally walked the first two hundred employees through their equity, and why Australia's lack of a secondary market keeps ESOP feeling like monopoly money. Alexei closes with his Big Cojones moment: proposing to his wife, the most nervous he's ever been despite having climbed Europe's highest mountain.

How to Pick Pre-Seed Winners Before There's Any Data

In this 101 episode, Cheryl and Maxine go deep on the fundamentals of pre-seed investing, from how the stage came to exist to why the perceived risk gap between pre-seed and seed is much smaller than most investors think. They break down the history of how venture stages evolved from single rounds to alphabetized series, how seed investors eventually got pushed up the stack, and why pre-seed emerged around 2017 to 2019 as a distinct category. They unpack why PitchBook's definition of pre-seed as "whatever the investor calls it" muddies the water, how seed preempts from larger funds are inflating average valuations, and why thinking in risk stages rather than round labels is a better framework for evaluating early companies. You'll also hear why graduation rates from pre-seed to seed don't support the idea that pre-seed is two to three times riskier, why the Australian ecosystem is sitting on a talent surplus with a capital gap at pre-seed, and why this stage is particularly well suited for angels building diversified portfolios of 20 to 40 companies. Cheryl shares her framework for evaluating pre-seed opportunities through the lens of problem pain, frequency, and market size, and Maxine walks through how to think about return profiles, dilution, and valuation at a stage where there are no outputs to measure.

Closing the Gender Investment Gap with Data with Noga Edelstein

Noga Edelstein is the lead of the Equity Clear initiative, a not-for-profit effort to get Australian investors tracking pipeline diversity data with a common standard. She's also a former General Counsel at Yahoo, a multi-time founder, and has had her fingerprints across the Australian startup ecosystem for over a decade. In this episode, Cheryl and Maxine unpack why pre-seed funding to women is at its lowest level ever and how Equity Clear is building the data infrastructure to finally see where diverse founders are falling out of the pipeline. Noga shares what the UK's five-year head start has revealed, including that angel groups with at least 15% women invest in 10X the number of women-led companies, and why the mere act of tracking your own pipeline drives better outcomes. You'll also hear how a broken website form accidentally proved that women disproportionately use cold inbound to reach investors, why male founders and LPs should be asking their investors about diversity tracking, and what sport can teach us about leveling the playing field through systemic tweaks like funded childcare for founders. Noga closes with her Big Cojones moment: quitting her General Counsel role at Yahoo with a newborn to go all in on a startup.

How to Build a Global Pre-Seed Fund from Scratch

Elizabeth Yin is the co-founder and General Partner of Hustle Fund, a pre-seed venture fund now on its fourth fund that backs companies globally. Before Hustle Fund, she was a partner at 500 Global, founded adtech company LaunchBit, and was an early employee at Google. In this episode, Cheryl and Maxine unpack how Hustle Fund sources deals across continents, why Elizabeth avoids noisy competitive markets in favor of "small waves" that will swell over five years, and why valuation discipline matters more than founder pedigree when product-market fit risk is the same at every stage. You'll also hear how Hustle Fund runs a 30-person team with only four on investments, why Fund 2 was the hardest fund to raise, how the AI wave is creating companies that hit $10M ARR and lose it overnight, and why international valuations still offer significant arbitrage. Elizabeth closes with her Big Cojones moment: being called a "meek Asian woman" by an angel investor while pitching LaunchBit, and how building a platform changed the power dynamic entirely.

How to Pick Your First Market for International Expansion

Frontline’s Brennan O’Donnell has spent two decades helping companies expand across borders, first as an operator at Google and later as a growth investor backing Series B to D businesses. In this episode, Cheryl and Maxine unpack what’s shifted at growth stage in the last 12 months, why the market is still a barbell of “hot or not” deals, and how AI is finally producing application layer companies mature enough for growth rounds. They go deep on Frontline’s transatlantic model: seed investing across Europe to help founders raise a Series A and enter the US earlier, and growth investing in the US to help companies expand into Europe with a hands on, concentrated portfolio approach. Brennan breaks down the four pillars Frontline uses to drive international expansion timing, go to market, talent and org design, and location plus the biggest traps founders fall into, like trying to launch in too many markets at once or optimizing for revenue targets instead of learning. You’ll also hear why the UK and Ireland are the default first step for 97 percent of US companies entering Europe, when Europe becomes a CEO level priority, how relationship driven sales cycles vary across countries, and why developer led community building can beat traditional sales led expansion for certain AI products. Brennan closes with his Big Cojones moment: moving to the Bay Area for a temporary Google job with everything in storage, then doing it again to help build Google’s European HQ in Dublin.

The Australian Venture Playbook for 2026

As 2026 kicks off, Cheryl and Maxine open the year with their annual First Cheque wrap, a grounded, opinionated take on what actually shifted in Australian tech and venture, and what that means for the year ahead. They break down why 2025 marked a genuine inflection point for the ecosystem, from Canva’s secondary and a surge in M&A to fresh signals that long-awaited liquidity is finally starting to flow. Despite minimal government support, Australia quietly proved itself as one of the most capital-efficient venture markets globally, producing unicorns at roughly twice the rate of the US per dollar invested. The conversation also tackles the harder truths investors and founders need to reckon with in 2026: early-stage funding compressing while late stage heats up, corporate venture capital retreating, and the gender funding gap sliding backwards. Looking forward, Cheryl and Maxine share their predictions for the year ahead, where funding volumes may land, why seed remains the toughest stage, how AI valuations could trigger a market correction, and why energy and infrastructure may emerge as the next premium asset class.

What are VC Fund Secondaries?

Max Kausman is the founder and solo GP of Advance VC, Australia's first dedicated fund-of-funds with a focus on secondaries.

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

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

Inside Super Returns: How the Biggest Investors Pick Venture Funds

What happens when hundreds of the world’s biggest capital allocators get together behind closed doors to talk about venture, private equity, and where the next $30B is going? Maxine found out firsthand at Super Returns Asia, where she chaired the LP–GP relations stage. In this episode, Cheryl turns the tables and grills Maxine on everything she learned — from why India and Japan are suddenly hot, to why Southeast Asia is struggling, and why Australia didn’t even make the winners or losers list. They break down how institutional investors really think about funds, what “look-through ownership” means for angels and VCs alike, and why co-investing has LPs hot under the collar. Maxine also shares how family offices are thriving in the current market, what mega-funds like a16z’s $30B raise mean for everyone else, and why building long-term LP relationships is the only real way to get “super returns.”

How Prosus Ventures Became an “Honorary Australian” Fund

Sachin Bhanot leads Southeast Asia & ANZ investments at Prosus Ventures, a global fund with $100B+ in assets. Though based in Singapore, Sachin has become an “honorary Australian fund manager”, with nearly half of Prosus’s regional portfolio now in Australia and New Zealand. In this episode, Cheryl and Maxine dive into why Prosus ramped up in Australia during a downturn, what paradoxical traits they see in winning founders, and how Singapore and Southeast Asia really compare as markets for expansion. They unpack the playbook for Australian startups going regional, what Singaporean family offices are actually looking for, and why relationship-building is the real cheat code in Southeast Asia. Sachin also shares his biggest Big Chon moment, and how building coffee chains in the Philippines and Malaysia reshaped his view of what it takes to be an investor.

Why Australia’s AI Opportunity Is Bigger Than We Think

Tom Humphrey, Partner at Blackbird and former operator, joins Cheryl and Maxine to reframe the conversation around Australia’s AI ecosystem. While headlines paint a picture of Australia falling behind, Tom argues we’re quietly sitting on world-class talent, global-first AI companies, and a capital-efficient edge that’s being overlooked. They unpack Tom’s recent AFR opinion piece on the AI talent landscape, why Australia’s university-to-startup pipeline is broken (and slowly improving), and how “boomerang” PhDs are returning from Anthropic, Meta, and DeepMind to build ambitious companies onshore. Plus, Tom breaks down how product-led growth is evolving in the AI era, why enterprise motions are happening sooner, and what the new GTM playbook looks like when AI agents are selling to AI agents.

Decode the VC Dictionary Before Your Next Raise

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

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

Charles Hudson is the Founder and Managing Partner at Precursor Ventures, a solo GP fund that has backed over 450 startups across five funds, including dozens of category-defining companies led by underrepresented founders. In this episode, Maxine and Cheryl sit down with Charles to explore how he built one of the most successful high-volume venture strategies in the world, all while staying a solo decision-maker. They dive deep into what being a “solo GP” actually means, how Charles balances scale with intimacy across a massive portfolio, and why trust, not likability, is his north star when supporting founders. You’ll also hear his first-ever investment, the courage it took to leave a top-tier firm to start Precursor, and how he still handpicks every company Precursor backs, often long before they’re obvious.

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

Ben Grabiner is the Co-founder and General Partner at Side Stage Ventures, and the author of a landmark new report in collaboration with Dealroom and AWS. In this episode, Cheryl and Maxine sit down with Ben to unpack the data behind Australia’s rapid rise as one of the most efficient and exciting venture ecosystems in the world. They explore how Australia produces more unicorns per dollar invested than any other country, what makes the ecosystem so resilient and capital-efficient, and why the next decade might belong to Aussie tech. From funding gaps to founder grit, from global capital flows to angel investor opportunities, this is essential listening for allocators, founders, and emerging fund managers alike. You’ll also hear Ben’s story, from buying Tottenham Hotspur shares as a teenager, to moving across the world mid-COVID, to becoming a key builder in Australia’s startup ecosystem.

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

Nnamdi Okike is the Co-founder and Managing Partner at 645 Ventures, known for his early, contrarian bets on overlooked verticals and non-obvious industries. In this episode, Nnamdi shares how he leveraged a data-driven sourcing model to identify breakout companies like Squire and Goldbelly, and why seemingly small or niche markets often produce the biggest wins. Maxine and Cheryl dive deep into Nnamdi’s journey from Insight Partners analyst sourcing deals via cold calls, to launching his own fund and achieving a remarkable hit rate, landing him on the Midas Brink List. They explore how he evaluates founder insights, measures market inflection points, and strategically navigates the power law dynamics in venture capital. Packed with strategic insights and candid reflections, this episode is essential listening for emerging investors, fund managers, and founders curious about building defensible businesses in non-obvious spaces.

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

Pocket Sun is the Founding Partner at SoGal Ventures, the first female-led, millennial VC firm investing in the future of living, working, and staying healthy. In this episode, she shares how she made her first angel investment at just 24, and how her early bets like Everly Health and Lovevery reflected a conviction in underrepresented founders well before it was a trend. Cheryl and Maxine explore how Pocket launched SoGal’s debut fund, built a deal pipeline through global pitch comps and community, and mastered the art of getting onto oversubscribed cap tables.

Inside Monique Woodard’s Solo GP Playbook

Monique Woodard is the Founder and Solo GP of Cake Ventures, a venture fund focused on the enormous opportunities created by demographic shifts such as aging populations, rising female spending power, and America's transition to a majority-minority population. She explains how these macro-level changes expand markets across digital health, fintech, consumer brands, and AI-enabled solutions. Monique also candidly shares her experiences as a solo GP—covering the realities of fundraising, building a unique investment thesis, navigating partnership dynamics, and scaling from Fund I ($17M) to Fund II. Her insights offer a clear blueprint for investors, operators, and founders eager to capitalise on overlooked, high-growth opportunities driven by demographic change.

How James Tynan from Square Peg Invests in EdTech

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.

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

Deciding what startups to invest in can feel overwhelming, but it doesn't have to be. Cheryl and Maxine unpack one of the most critical (and enjoyable!) parts of angel investing: crafting your investment thesis. Whether you're brand new to investing or an experienced angel refining your approach, this episode helps you structure your thinking and clarify exactly what to look for in potential investments.

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

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.

Mastering Early-Stage Investing: From Checklists to Decision Diaries

The Venture Fund Playbook: Raising, Deploying & Exiting Smarter

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.

Angel Investing 101: How To Not Run Out Of Money

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!

From Firefox to AI: Mozilla’s Fight for Open Technology

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!

The 2024 Wrap-Up and Spicy Predictions with Cheryl & Maxine

Leveraging AI to Predict Venture Success: John Sharp's Journey with Hatcher+

Navigating the Hype Cycles and Early-Stage Deep Tech Investing with Emily

Navigating Early-Stage Investing and Scaling with Tim from Turo

From Zero to One: Why Founders Make Exceptional Early Stage Investors with Matthew Browne

Navigating Venture Capital: Aligning Incentives and Realistic Outcomes with Georgie Turner

From Scalpel to Syndicate: Paul Kelly's Guide to Navigating Biotech Investing

Unlocking Tax Benefits for Angel Investors: A Deep Dive into ESIC, ESVCLP, and Investment Strategies with Cheryl Mack and Maxine Minter

Q&A: Practical Advice on Secondaries, Valuations, and Building Strong Investor Relations

Exploring Growth Stage Investing with Ex-Investment Banker Turned VC

Bronwen Clune on Risk Appetite and the Future of Australian Startups

Portfolio Allocation: Diversification vs. Concentration Strategies Unpacked

The Value of Being the First Investor: Insights from Ash Fontana

Marvin Liao Shares Insights on Investing and Developing an Edge in Startup Ecosystems

The Debate Over Follow-On Investments in Early-Stage Investing

The Art of Getting to Conviction: Strategies for Successful Investing

Startmate CEO Michael Batko discusses community-building and portfolio construction in early-stage investing.

Understanding Fund of Funds: A Primer on Investing in Venture Capital

Elicia McDonald discusses resilience and founder empathy in venture investing

Trang Nguyen on Investing in Ambitious Founders and Building Lasting Venture Franchises

Craig Blair Shares Insights on Investing and Building a VC Fund

Sam Wong discusses building an ecosystem, leverage, and investing in New Zealand.

Angel Investing: On-Ramps, Communities, and Maximizing Learning

Angel investing is a team sport - building your network funnel with Anabel Lippincott Paksoy

Tis the season to be reflective - 2023 in review on First Cheque

Elaine Stead discusses bravery, diversity, and changing the investing ecosystem

The Art of Building a Network: How Rayn Ong Became the All-Seeing Eye of the Australian Startup Ecosystem

Building a Network-Powered Family Office for Impactful Investing with Judy Anderson-Firth Group CEO of Euphemia

Dan Gavel on Building a Diversified Investment Strategy in Venture Capital

Investor Jessy Wu discusses the importance of bravery and building a personal brand in the VC industry

Your Warm Intro to First Cheque with Cheryl Mack & Maxine Minter