『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
エピソード
  • VC Jargons 101: What Investors Really Mean When They Say “It’s Not a Fit"
    2026/09/13
    Episode Summary“It’s not a fit.” “You’re too early.” “Let’s have one more meeting.” “We’re still building conviction.” If you’ve ever walked out of an investor meeting wondering what the hell any of that actually meant, this episode is for you.In this episode of First Cheque, Cheryl and Maxine decode the language of venture capital — from fundraising and negotiations to what happens once an investor is on your cap table. They unpack what investors might really mean when they say you’re too early (or somehow too far along), why “one more meeting” can be a sign they’re sitting on the fence, and when “keep us in the loop” is actually just a polite no.They also get into the weird world of VC jargon — including “conviction”, “due dilly”, “foundies”, “bridgie” and the ever-popular “let the lawyers sort it out”.Once the cheque has landed, they unpack what it really means when investors ask for an update, start asking about runway and burn, want to see revenue hit a certain milestone, or suddenly ask, “How’s it going with X?” They also talk about why regular communication matters, even when things aren’t going well.The big lesson? Founders shouldn’t have to speak fluent VC — and investors could probably do a much better job of explaining themselves.Time Stamps00:00 – Intro: Welcome to VC Gibberish01:20 – “It’s not a fit for us”: what does that actually mean?03:05 – Is it the company, the stage… or the founder?05:00 – The value of asking for honest feedback06:03 – Investors could be clearer too07:09 – “You’re too early”: is it really a no?08:45 – What “too far along” actually means11:05 – “Let’s have one more meeting”11:59 – Why investors ghost13:23 – Sitting on the fence and waiting for FOMO15:00 – “We’re discussing internally” and what happens inside a VC16:41 – When a slow process means you’re not a priority17:08 – Why the “momentum raise” is dead18:35 – The dangers of a June 30 deadline20:16 – What investors mean by “conviction”23:17 – “Keep us in the loop”: the polite no24:59 – When investors want to stay close for the next round25:28 – “Let us know when you have a lead”26:16 – When investors simply don’t have the capital27:16 – Negotiating the deal: welcome to the jargon28:23 – “Val”, “do dilly” and other questionable VC vocabulary30:03 – Information rights vs. investor updates32:01 – Foundies, Cindy and Bridgie32:47 – ESIC, ESVCLP and other acronyms33:40 – “Let the lawyers sort it out”35:50 – The strange two-week period when founders and investors aren’t on the same side36:38 – Once they’re on the cap table36:45 – “Can we get an update?”38:09 – What investors really mean when they ask about runway39:05 – Why you should update investors when things aren’t going well41:26 – When investors don’t want to lead or follow your next round42:40 – “Get to this revenue number and then we’ll talk”43:37 – The moving goalposts of investor benchmarks44:21 – How to benchmark against the best companies instead45:15 – “How’s it going with X?”46:23 – Ask why before you answer47:03 – Please send us your VC gibberish47:50 – OutroSponsors:First Cheque is supported by our wonderful sponsors:Deel: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.Ready to expand your business?Build your global team with Deel at 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 FC_Script 01 - Sep 2026Pear 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 ...
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    51 分
  • Trust Over Likability: How Charles Hudson Built a 450-Company Portfolio
    2026/08/30
    Episode SummaryCharles Hudson of Precursor Ventures has built one of the most ambitious solo GP models in venture capital: around 450 investments over the last decade, with a 14-person team supporting a single investment decision-maker.In this episode of First Cheque, Charles joins Maxine and Cheryl to unpack what it really takes to build and scale a solo GP fund, why he believes partnership dynamics can be one of the biggest risks in venture, and how he thinks about delivering value to hundreds of founders without trying to be everything to everyone.They dive deep into Charles’ philosophy on trust versus likability, why the best investors sometimes need to tell founders things they really don't want to hear, and how brutal honesty can become one of the most valuable forms of founder support. Charles also shares his approach to identifying “underappreciated” founders, why he looks for people who opt into chaos, and what he learned from backing founders who weren't necessarily great employees.Charles reflects on leaving a safe, highly compensated investing job to start Precursor, investing internationally before it was fashionable, why themes can kill returns, and the importance of being early to categories rather than piling into them once everyone else has arrived.Time Stamps00:00 – Intro03:05 – Charles’ first investment: buying ExxonMobil in high school06:15 – What exactly is a solo GP?07:37 – The surprising benefits of having one decision-maker10:28 – The problem with orphaned portfolio companies13:04 – Why solo GPs need to be intentional about founder relationships15:44 – How the “product” of Precursor evolved18:00 – Building trust, setting expectations, and knowing when to step back20:32 – Why honest feedback matters more than being liked23:40 – “It’s you”: giving founders brutally honest feedback25:52 – Trust is a bank account27:47 – Likability vs. trustability in venture capital30:58 – Why Charles backs founders who opt into chaos33:36 – What makes a great first-time CEO?36:39 – How Precursor started investing globally40:08 – Investing internationally and convincing LPs afterwards41:15 – Why themes can kill returns44:12 – Finding venture-scale opportunities outside traditional software45:16 – The challenge of managing 450 investments47:52 – Being a “surgeon” investor: showing up when it matters most52:04 – Charles’ biggest leap: leaving Uncork to start Precursor53:40 – “You pay money to go to work?”55:00 – Why Charles chose to make going back impossible56:31 – OutroResourcesPrecursor Ventures - https://precursorvc.com/Sponsors:First Cheque is supported by our wonderful sponsors:Deel: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.Ready to expand your business?Build your global team with Deel at 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:Pear 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.Deel x PX_Script 1Deel x PX_Script 2This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad ...
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    59 分
  • Sidecars 101: Why Venture Funds Are Investing on the Side
    2026/08/16
    Episode SummarySidecars have gone mainstream. Once something mostly associated with larger venture funds, they’re now increasingly common in Australia, with emerging managers using them alongside their first funds and sophisticated LPs increasingly expecting access to them.But what exactly is a sidecar, and why would you use one instead of simply investing directly?In this episode of First Track, Cheryl and Maxine break down sidecars from the ground up: how they differ from co-investments, why LPs use them to double down on companies they’re excited about, and how lower fees and carry can make them attractive to larger investors.They also unpack the less obvious reasons fund managers use sidecars—from getting more capital into high-conviction companies and giving venture-curious investors a way to get reps, to preserving pro rata in follow-on rounds without changing the core strategy of the fund.The conversation gets into opportunity funds, the history of sidecars, and why a vehicle that was once niche is now a standard part of the venture fund playbook. They also dive into the surprisingly complicated world of Australian SPVs, the four main structures available, and the regulatory challenges facing super funds investing in venture.Finally, Cheryl and Maxine look at how the venture ecosystem is evolving, why sidecars are becoming part of the progression from syndicate to fund manager, and what the growing expectations of institutional LPs could mean for the next generation of Australian funds.Time Stamps00:00 – From venture outsider to “everyone is building companies”01:12 – Why sidecars have suddenly gone mainstream02:23 – What exactly is a sidecar?03:14 – Sidecars vs. co-investments04:12 – The Uber for Cats problem 🐈05:12 – Why LPs and fund managers use sidecars05:40 – Doubling down on the companies you love07:27 – How sidecars can lower fees and carry08:40 – The paradox of picking winners to average down fees09:29 – Why sidecars make more sense at growth stage10:30 – Drafting off someone else’s diligence11:30 – Follow-on sidecars and pro rata13:31 – Why competitive rounds make sidecars valuable14:50 – The admin headache of investing directly15:05 – Why sidecars can make investing easier16:02 – The surprising history of opportunity funds17:25 – When should emerging managers start using sidecars?19:10 – Why fund managers run sidecars21:00 – Sidecars, carry and staying disciplined22:00 – Why sophisticated LPs increasingly expect sidecars23:10 – SPVs aren’t actually a legal structure24:10 – The four main Australian SPV structures25:23 – Why Australia is different from the US26:00 – The evolution from angel to syndicate to fund27:08 – The super fund fee problem28:17 – Should venture be treated differently?29:11 – The regulatory challenge for Australian venture30:24 – What happens as Australian funds mature?31:23 – Why building a fund is still building a company32:01 – Sidecars 101: did we cover it all?32:49 – Send us your sidecar questionsSponsors:First Cheque is supported by our wonderful sponsors:Deel: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.Ready to expand your business?Build your global team with Deel at 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 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 ...
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    35 分
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