First Cheque with Cheryl Mack & Maxine Minter

Day One
  • 0.0 (0)
  • Investing
  • Updated Weekly

First Cheque is powered by Deel & Pear Tree. Founders scale faster on Deel — set up payroll, hire anyone anywhere, and handle visas, HR and compliance in 150+ countries from one platform. Get started: https://deel.com/dayone Pear Tree builds high-performing offshore teams without the agency middleman. Day One listeners get a free team audit + 20% off your first hire: https://dayone.fm/peartree 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 Pre-Seed Winners Before There's Any Data

    May 17

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

    Episode SummaryIn 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. Time Stamps00:00 Intro 01:56 – A brief history of venture stages: how pre-seed became a thing 07:14 – Why round labels are broken and risk stages are a better framework 09:23 – Seed preempts: how big funds are blurring the line between pre-seed and seed 11:48 – Is pre-seed actually riskier than seed? The case that it's not 16:41 – Graduation rates: what the data says about pre-seed to seed conversion 22:59 – Valuation dynamics: what pre-seed rounds look like in Australia vs the US 28:36 – Why Australian founders are leaving for the US at pre-seed and what that means 31:29 – How to evaluate pre-seed companies: inputs over outputs 35:05 – Cheryl's pain framework: frequency, intensity, and willingness to pay 38:28 – Why pre-seed is the best stage for diversifying who gets funded 43:44 – The AI revenue problem: why getting in early matters more than ever Sponsors:First Cheque is supported by our wonderful sponsors:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone ___ Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman. As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs. The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business. As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartree 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/

    47 min
  2. Closing the Gender Investment Gap with Data with Noga Edelstein

    May 4

    Closing the Gender Investment Gap with Data with Noga Edelstein

    Episode SummaryNoga 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. Time Stamps00:00 Intro 02:27 – Noga's first investment: dollar-mite savings accounts in primary school 10:02 – What is Equity Clear and why pipeline data is the missing piece 14:40 – Why closing the gender gap matters now: productivity, economics, and AI bias 19:27 – Pre-seed funding to women is at its lowest ever despite lower barriers to building 24:44 – Why collecting diversity data feels hard but isn't 28:32 – Lessons from the UK: what five years of tracking has revealed 32:02 – Maxine's accidental experiment: when a broken form hid all the women founders 37:39 – How male founders and LPs can push for change by asking simple questions 48:16 – Why funds are missing a trick on sourcing diverse founders 51:32 – Breaking the archetype: leveling the playing field with systemic tweaks 57:15 – Big Cojones moment: quitting law with a newborn to start a company First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. Mentioned in this episode: Deel x PX_Script 2 Deel x PX_Script 1 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/

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

    Apr 19

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

    Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey 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 Mentioned in this episode: Deel x PX_Script 1 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
  4. Why Every Founder & Investor Needs to Understand Open Source AI (Replay Episode)

    Mar 8

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

    Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey 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. Mentioned in this episode: Deel x PX_Script 1 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/

    52 min
  5. How to Pick Your First Market for International Expansion

    Feb 8

    How to Pick Your First Market for International Expansion

    Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey 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. Mentioned in this episode: Deel x PX_Script 1 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
  6. The Australian Venture Playbook for 2026

    Jan 11

    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. Mentioned in this episode: Deel x PX_Script 1 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. What are VC Fund Secondaries?

    11/16/2025

    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/ Mentioned in this episode: Deel x PX_Script 1 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
  8. Why “Boring” Businesses Make the Best Startups (Replay Ep with Matthew Browne)

    10/19/2025

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

    Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey 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:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone ___ Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman. As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs. The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business. As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartree First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. Mentioned in this episode: Deel x PX_Script 1 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
See All (59)

Trailers

About

First Cheque is powered by Deel & Pear Tree. Founders scale faster on Deel — set up payroll, hire anyone anywhere, and handle visas, HR and compliance in 150+ countries from one platform. Get started: https://deel.com/dayone Pear Tree builds high-performing offshore teams without the agency middleman. Day One listeners get a free team audit + 20% off your first hire: https://dayone.fm/peartree 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/

Information

More From Day One

You Might Also Like