First Cheque with Cheryl Mack & Maxine Minter

Day One
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First Cheque is dedicated to open-sourcing conversations with experienced investors globally. Our aim? To enhance the craft of early-stage investors, from those writing their first cheques to the veterans in the game. Hosted by Cheryl Mack & Maxine Minter, First Cheque is a Day One® show. Day One is the podcast network dedicated to founders, investors, and operators. Tune in for an enriching experience as we uncover the secrets to becoming a skilled early-stage investor. First Cheque on Day One https://dayone.fm/show/first-cheque Sign up to get your weekly insights into the inner workings of early-stage investing. https://dayone.fm/newsletter/ This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

  1. How to Pick Winners in Markets You Don't Live In

    5 DAYS AGO

    How to Pick Winners in Markets You Don't Live In

    Episode SummaryElizabeth 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. Time Stamps00:00 – Intro 01:54 - Elizabeth's first investment: three shares of Coca-Cola at age 10 06:50 – What Hustle Fund is investing in now and why vertical SaaS still matters in the AI era 09:31 – How Hustle Fund sources deals globally through co-investors and content 15:09 – Elizabeth's two-part framework: founder quality vs. idea quality 18:10 – Why competitive markets are a double whammy for small-check investors 22:57 – The surfing analogy: spotting small waves that grow big in five years 25:06 – Biggest investing lessons from Fund 1 to Fund 4: valuation and follow-on discipline 27:58 – Camp Hustle, content marketing, and running VC like a lead generation business 30:09 – Does valuation really matter at pre-seed? When it does and when it doesn't 37:39 – Growing AUM: why Fund 2 was the hardest and the "event ticket sales" fundraising pattern 44:15 – Which fund graduation was hardest and the DPI reality at pre-seed 46:21 – Big Cojones moment: confronting bias as a female founder and how platform changes power dynamics This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

    51 min
  2. Why Every Founder & Investor Needs to Understand Open Source AI (Replay Episode)

    8 MAR

    Why Every Founder & Investor Needs to Understand Open Source AI (Replay Episode)

    Episode SummaryIn 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 Stamps00:00 Intro & Guest Highlights 00:21 Why We're Excited About Laura Chambers 03:14 Interview Begins: Laura's First Investment at Age 10 05:20 Open Source 101: What It Is & Why It Matters 07:08 Firefox vs Internet Explorer: The Open Source Origin Story 09:58 How Healthy Is the Internet Today? 13:50 Can You Actually Make Money From Open Source? 15:45 What If the Internet Had Stayed Behind Paywalls? 17:33 Gen AI Is the New Model T: We're Missing the Seatbelts 19:37 The Case For & Against Closed Source AI 21:35 Why Researchers, Academics & Governments Need Open Access 22:17 Where Are We in the Gen AI Infrastructure Cycle? 24:18 AI in Education: What Skills Do Kids Actually Need? 26:36 Older Generations & the AI Learning Gap 29:16 Open vs Closed: Who's Winning Right Now? 33:49 Meta's Llama & the Strategic Logic of Going Open 35:21 Advice for Founders & Investors Building on Open vs Closed Models 39:21 Inside Mozilla Ventures: What They're Investing In 41:31 Prompt Engineering Tips From a CEO (Say Please!) 46:13 The Biggest Brave Moment: Moving Her Family & a 17-Year-Old Dog to Australia 49:20 The Weight of Being CEO & What That Feels Like Resources1) Mozilla Ventures: Supporting startups focused on privacy, AI, and open source innovation. (https://mozilla.vc/) 2) Mozilla Builders Program: Investing in and mentoring early-stage entrepreneurs building ethical tech solutions. (https://builders.mozilla.org/) 3) Harvard University Study: Open Source Software’s $8 Trillion Economic Impact A study on the global economic value created by open source technology. (https://www.hbs.edu/ris/Publication%20Files/24-038_51f8444f-502c-4139-8bf2-56eb4b65c58a.pdf) 4) Anthropic Report on Bias in AI: Research highlighting the impact of bias and the importance of transparency in AI models. (https://www.anthropic.com/research/mapping-mind-language-model) First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

    51 min
  3. How to Pick Your First Market for International Expansion

    8 FEB

    How to Pick Your First Market for International Expansion

    Episode SummaryFrontline’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. Time Stamps03:14 Brennan’s first investment: Mode Analytics and a lawn mowing business in Texas 06:49 What’s changed at growth stage and why “growth” is a different world 08:30 Why AI enablement came first and app layer is finally ready for Series B plus 10:10 The new risk: fast revenue that’s concentrated and not yet durable 14:22 Frontline’s model: Europe seed plus US growth and why it’s unique 15:58 What Frontline looks for: category leaders and a line of sight to a 5x outcome 16:20 The rough revenue range where growth starts paying attention 23:22 The four pillars of expansion: timing, go to market, talent, location 26:00 Timing: the 10 percent pull, exec maturity, and why waiting too long is risky 29:36 Why Europe expansion has to be a CEO level company priority 38:04 Build or buy: why most companies compete into new markets rather than acquire 39:10 Developer community expansion as a new go to market wedge 41:44 Market selection: why nearly everyone starts with London or Dublin 43:56 “Success amnesia” and why you must optimize for learning not quotas 48:28 Relationship driven sales cycles and how Europe varies market to market 52:43 Big Cojones moment: taking a temp Google job and betting on himself 54:26 Doing it again: moving to Dublin in three weeks to help build Google Europe First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

    57 min
  4. The Australian Venture Playbook for 2026

    11 JAN

    The Australian Venture Playbook for 2026

    Episode SummaryAs 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. Time Stamps00:00 – Intro: End of year energy: why 2025 felt different to 2024 03:55 – Election fallout and the government’s “nothingburger” for startups 05:24 – Canva’s secondary and the first real signs of liquidity returning 09:49 – Aussie tech M&A heats up: Canva, Linktree, Jolt, and more 12:09 – The stat that changed the narrative: Australia’s unicorn efficiency 16:14 – The weirdest trend of the year: early stage down, late stage up 18:27 – Tech jobs, data centers, and the infrastructure bet Australia is making 22:52 – Why deep tech and climate are pulling venture dollars again 28:21 – The gender funding gap got worse (and why) 33:09 – Corporate VC is pulling out: what happened to strategic capital 37:02 – 2026 predictions: funding totals, seed pain, and where capital flows next 44:00 – AI bubble risk: tourism, ROI pressure, and the domino effect 47:42 – Hot take: electricity is the next valuation premium 49:00 – Will diversity bounce back in 2026? (vibes, but also logic) First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

    50 min
  5. What are VC Fund Secondaries?

    16/11/2025

    What are VC Fund Secondaries?

    Episode SummaryMax Kausman is the founder and solo GP of Advance VC, Australia's first dedicated fund-of-funds with a focus on secondaries. Advance VC buys existing positions in Australian and New Zealand VC funds—acquiring stakes from investors seeking liquidity and giving new LPs diversified access to mature, validated portfolios across multiple vintages dating back to 2012. In this conversation, they discuss why secondaries won't "save" all of venture (only the top performers), how discounts actually work (spoiler: the average is 30-35% but it's wildly bespoke) and why vintage diversification matters as much as portfolio diversification. Time Stamps02:47 – Max's first investment: lessons as a 14-year-old basketball coach 07:08 – Defining secondaries and Advance VC's unique LP fund focus 09:44 – Why vintage diversification matters as much as company diversification 13:57 – How secondary transactions actually work: the three-way deal between buyer, seller, and fund 19:24 – What Max learned looking under the hood of Australian VCs firms across different funds and vintages 24:09 – Why Max decided on a secondary Fund of Funds (FoF) model 34:16 - Pricing secondaries 42:20 – What discounts actually look like in practice 47:40 – Will secondaries save venture? The truth about liquidity and why it's concentrated in top performers 50:16 – Building Advance VC and the founder journey of becoming a fund manager ResourcesMax Kausman - https://www.linkedin.com/in/maxkausman Advance VC - https://www.advancevc.com/ This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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

    19/10/2025

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

    Episode SummaryMatt 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. Sponsors:First Cheque is supported by our wonderful sponsors:Aussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence. https://www.aussieangels.com/ Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured. https://dayone.fm/galah First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

    51 min
  7. Inside Super Returns: How the Biggest Investors Pick Venture Funds

    05/10/2025

    Inside Super Returns: How the Biggest Investors Pick Venture Funds

    Episode SummaryWhat 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.” Time Stamps01:00 – What Super Returns is, and why it matters for VCs and angels 06:43 – The LP landscape explained: super funds, sovereign wealth funds, and family offices 10:40 – Winners and losers in APAC: India, China, Japan… but not Australia 18:00 – Why Australia needs a better “brand story” to attract capital 19:54 – Hot topic: co-investing and why LPs love it 23:39 – Look-through ownership: why everyone’s just trying to own the outliers 26:43 – Why emerging managers are struggling in today’s fundraising market 33:49 – Family offices having “the time of their lives” in this cycle 34:23 – Mega-funds, evergreen funds, and the $30B a16z raise 39:30 – Will Sequoia and a16z ever lose their dominance? 42:19 – Why APAC liquidity markets matter more than ever 45:30 – The question nobody asked at Super Returns 49:22 – How to actually build LP relationships that work 53:55 – Maxine’s big takeaway: putting Australia on the winners list Sponsors:First Cheque is supported by our wonderful sponsors:Aussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence. https://www.aussieangels.com/ Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured. https://dayone.fm/galah First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

    55 min
  8. How Prosus Ventures Became an “Honorary Australian” Fund | Sachin Bhanot

    21/09/2025

    How Prosus Ventures Became an “Honorary Australian” Fund | Sachin Bhanot

    Episode SummarySachin 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. Time Stamps02:53 – Sachin’s first and most important investment (hint: not a startup) 07:31 – The paradoxical traits of winning founders 10:26 – Singapore vs Southeast Asia: the tale of two ecosystems 18:12 – Why Prosus doubled down on Australia in 2022 28:40 – Tips and traps for Aussie founders expanding regionally 34:44 – When is the “right” time to enter Southeast Asia? 42:11 – The rise of the Australia–India–Singapore innovation corridor 48:34 – Singapore family offices and the art of relationship-driven capital 51:59 – Sachin’s Big Chon moment: learning empathy by building businesses himself ResourcesResources Mentioned 🙋🏻‍♂️ Sachin Bhanot - https://www.linkedin.com/in/sachin-bhanot-15551913a/ 💰 Prosus Ventures - https://www.prosus.com/prosus-ventures Sponsors:First Cheque is supported by our wonderful sponsors:Aussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence. https://www.aussieangels.com/ Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured. https://dayone.fm/galah First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

    58 min
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First Cheque is dedicated to open-sourcing conversations with experienced investors globally. Our aim? To enhance the craft of early-stage investors, from those writing their first cheques to the veterans in the game. Hosted by Cheryl Mack & Maxine Minter, First Cheque is a Day One® show. Day One is the podcast network dedicated to founders, investors, and operators. Tune in for an enriching experience as we uncover the secrets to becoming a skilled early-stage investor. First Cheque on Day One https://dayone.fm/show/first-cheque Sign up to get your weekly insights into the inner workings of early-stage investing. https://dayone.fm/newsletter/ This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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