『First Cheque with Cheryl Mack & Maxine Minter』のカバーアート

First Cheque with Cheryl Mack & Maxine Minter

First Cheque with Cheryl Mack & Maxine Minter

著者： Day One®
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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/Day One® is a registered trademark of W2D1 Media Pty Ltd. マネジメント・リーダーシップ リーダーシップ 個人ファイナンス 経済学
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  • How to Think About M&A as a Startup with Alex Feldman

    How to Think About M&A as a Startup with Alex Feldman
    2026/06/21
    Episode SummaryAlex Feldman is the founder of Tiger and Bear, an M&A advisory focused on tech and services businesses. Before that, he was Chief Strategy Officer and General Counsel at Amaysim, where he ran three acquisitions simultaneously during full lockdown in 2020 and 2021 to build a dominant player that was ultimately sold.In this episode, Cheryl and Maxine unpack how to buy and sell businesses when the world is doing crazy stuff around you. Alex breaks down why today's volatility isn't actually that different from the GFC or COVID, why timing is the single most important variable in any deal, and what the SaaSpocalypse means for tech companies thinking about selling when their natural buyers are struggling.You'll also hear why more than half of Tiger and Bear's recent deals involved European and Asian capital rather than American, why profitable venture-backed businesses are suddenly more attractive to strategics, and what happens when the IPO market disappears as an exit path. For founders who can't raise their next round, he offers blunt advice: never waste a crisis, cut costs to buy yourself runway, and remember that raising and selling are the same activity, you're just selling different amounts of shares.Alex closes with his Big Cojones moment: putting every spare $500 into the stock market during the GFC with no idea where the bottom was, buying Macquarie Bank shares at $30 and riding them back up.Time Stamps00:00 - Intro02:25 – Alex's first investment: going all in on the BHP Rio Tinto merger that never happened06:19 – How to do M&A in volatile markets and why this cycle isn't that different11:50 – Timing for buyers vs sellers: why uncertainty kills deals, not direction13:08 – The SaaSpocalypse: what happens when your natural buyer is struggling18:10 – Why European and Asian capital is replacing American buyers in Australia21:08 – What M&A looks like in the Australian tech ecosystem right now24:01 – When is a company big enough to buy and too small to be acquired28:30 – Mergers of equals: why similar-sized companies come together in downturns38:39 – How to become a disciplined buyer: capital, internal muscle, and integration43:08 – Why the hardest part of any deal is admitting the other side does it better47:54 – What to do when you can't raise: never waste a crisis55:01 – Big Cojones moment: investing every spare dollar during the GFCSponsors: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/peartreeFirst 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 1Deel x PX_Script 2Pear TreeIf you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost. Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business. As a Day One listener, 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.This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/
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    1 時間 1 分
  • How to Think About Equity as a Startup Employee

    How to Think About Equity as a Startup Employee
    2026/06/07
    Episode SummaryAlexey 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 Alexey 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 verbalises: who gets equity, how much, and why you have an ESOP plan in the first place.You'll also hear how he modelled 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. Alexey closes with his Big Cojones moment: proposing to his wife, the most nervous he's ever been despite having climbed Europe's highest mountain.Time Stamps00:00 – Intro03:01 – The three ESOP questions every founder needs to answer05:58 – How to model equity allocation across rounds and hundreds of hires09:10 – Using ESOP as your most powerful recruitment and retention tool12:02 – How walking 200 employees through their equity built culture and trust15:02 – Open financials, shrinking cash balances, and what went wrong along the way17:55 – Why Australia's ESOP ecosystem is still behind Silicon Valley26:48 – Teaching employees to understand equity: the Google Sheet that started at zero29:20 – High salary vs heavy equity: giving employees a real choice32:16 – Common ESOP mistakes founders make and how to avoid them35:03 – Why Australians treat startup equity like monopoly money39:11 – The secondary market problem: why liquidity changes everything for ESOP43:25 – Why your startup career is a portfolio of equity bets46:36 – What angel investors can do to help portfolio companies build better ESOP plansSponsors: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/peartreeFirst 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 1Deel x PX_Script 2Pear TreeIf you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost. Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business. As a Day One listener, 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.This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/
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    50 分
  • How to Pick Pre-Seed Winners Before There's Any Data

    How to Pick Pre-Seed Winners Before There's Any Data
    2026/05/17
    Episode Summary

    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.

    Time Stamps

    00:00 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/
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    47 分
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