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First Cheque with Cheryl Mack & Maxine Minter

First Cheque with Cheryl Mack & Maxine Minter

By: 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. Economics Leadership Management & Leadership Personal Finance
Episodes
  • Sidecars 101: Why Venture Funds Are Investing on the Side

    Sidecars 101: Why Venture Funds Are Investing on the Side
    Aug 16 2026
    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: 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 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 ...
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    35 mins
  • Eric Ries on What Investors Get Wrong About Governance

    Eric Ries on What Investors Get Wrong About Governance
    Aug 2 2026
    Episode SummaryEric Ries is the author of The Lean Startup and The Startup Way, and the founder of IMVU and the Long-Term Stock Exchange. His new book, Incorruptible, examines why companies drift from their mission once investors and boards take over, and what founders and early investors can do to prevent it.In this episode, Cheryl and Maxine unpack what Eric calls "financial gravity," the force that pulls companies toward extractive, value-destroying behavior even when everyone believes they're pursuing profit. Eric explains why many widely taught governance best practices are actually shareholder-value destroying, and why the earliest stage of a company is the easiest time to build in protections against this drift.You'll also hear Eric break down the "spiritual holding company" structure, using Novo Nordisk's century-old nonprofit foundation as an example of why mission-guardian structures make companies far more likely to survive long term. The conversation covers why founders get talked out of protective provisions until it's suddenly too late, and Eric shares the real story of a startup that took a million dollars from Purdue Pharma to push opioids to doctors, and why it destroyed the company.He closes with his Big Cojones moment: a board meeting early in his career where he expected to be fired for refusing to abandon his unconventional methods, and the lesson that "harder is easier" when you stand for something you believe in.Time Stamps00:00 – Intro04:10 – Eric's first investment: putting his own money into IMVU's friends and family round09:15 – From Lean Startup to Incorruptible: why it's always felt like one continuous project to Eric17:40 – The tortilla company, private equity, and why "pricing power" explains so much bad behavior21:30 – Why so-called governance best practices are often value destroying25:50 – Naming the problem: financial gravity and why our grandparents would have called it corruption30:20 – What founders and early investors can actually do at the earliest stage36:45 – The Olympic athlete analogy: why protective structures only work if built in early41:10 – The spiritual holding company explained through Novo Nordisk's origin story48:30 – Why companies rated for "good governance" have underperformed since 200852:15 – The Purdue Pharma story and how a million dollars destroyed a company58:40 – Big Cojones moment: the board meeting Eric thought would get him firedSponsors: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: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 1Pear 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 ...
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    1 hr and 1 min
  • What Makes a Founder Worth Backing at Pre-Seed? With Ilana Elbaz | GTM at Deel

    What Makes a Founder Worth Backing at Pre-Seed? With Ilana Elbaz | GTM at Deel
    Jul 19 2026
    Episode SummaryIlana Elbaz was employee number five and the first go-to-market hire at Deel, helping scale the company from its early pivots through blockchain and payments to a business she helped grow from zero to hundreds of millions in ARR in just a few years. She's now an active angel investor and runs Deel's global pitch competition, which received tens of thousands of applications this year.In this episode, Cheryl and Maxine unpack how operating inside one of the fastest-scaling companies in the world shapes the way Ilana evaluates founders as an investor. She breaks down her "3-star model" for backing companies (right infrastructure, right team, right timing, read from right to left), why she looks for founders with velocity and speed over founders who claim to have it all figured out, and why the biggest red flag at pre-seed is a founder who narrows their market too early.You'll also hear why she pushes back on founders who insist on enterprise-only or single-market strategies before they even know their ICP, why treating international hiring as a growth problem rather than an HR problem is critical for founders building outside the US, and why Australian founders' instinct to think global from day one is a genuine advantage. Ilana shares what she learned scaling Deel's own go-to-market using the company's own product across dozens of countries, and why staying close to your first hundred customers matters more than shipping a polished product.She closes with her Big Cojones moment: repeatedly landing alone in unfamiliar countries, from opening entities in Thailand to sourcing product in China at 19, with no support system and straight into meetings with lawyers she'd never met.Time Stamps00:00 - Intro04:15 – Ilana's first investment: buying Amazon stock at age 10 and the lesson she learned selling too early09:30 – Why Ilana joined Deel as employee five, drawn in by the labor law and compliance nightmare of scaling internationally14:05 – The 3-star model: right infrastructure, right team, right timing, and why it should be read backwards17:50 – Why founders who claim to have it all figured out should be a pass21:40 – The danger of narrowing your market too early at pre-seed28:10 – Why treating global hiring as a growth problem, not an HR problem, changes everything33:00 – What makes Australian founders well suited to thinking global from day one36:45 – How to answer "what's your expansion plan" as a green flag for investors40:20 – Inside Deel's global pitch competition: 35,000 applications and five investments46:10 – Big Cojones moment: landing alone in unfamiliar countries to open new marketsFirst 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.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/peartreeBrought to you by 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: 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 ...
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    47 mins
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