In this crossover episode of First Cheque and In The Blink of AI, Cheryl Mack (Aussie Angels) and Maxine Minter (Co Ventures) team up with host Georgie Healy to unpack how investors are thinking about AI, beyond the hype. From pitch decks to product demos, they reveal the frameworks and gut checks they use to spot real value in AI startups, even when they’re not technical experts themselves.

You’ll also get a behind-the-scenes look at how Cheryl and Maxine are integrating AI into their own workflows, not just as investors, but as operators. From using ChatGPT to summarise founder meetings, to leveraging Prompt Cowboy and NotebookLM for due diligence and research prep, they walk through real examples of how AI is saving them time, sharpening decision-making, and helping them stay ahead in deal flow. And yes, we finally answer the question: what is an agent… and does anyone actually have one?

02:15 – Are Cheryl and Maxine AI skeptics or advocates?

06:00 – What's actually fueling the AI hype?

10:45 – Are we in a bubble—or just early in the cycle?

16:20 – Valuations, FOMO, and how investors are pricing AI

21:00 – What angel investors should look for in AI startups

27:30 – AI’s biggest red flag: When it all just sounds like magic

31:00 – Are agents real or is everyone faking it?

36:40 – AI in venture workflows: What Maxine actually automates

41:30 – The real power of personal brand in VC

44:50 – How Cheryl preps for founder calls with Google NotebookLM

49:00 – Weekly AI hacks: From flat lays to voice-mode strategy sessions

52:10 – Founder FOMO: Prompt Cowboy, Juno, and other hot startups

54:00 – The case for non-technical founders in AI

58:00 – Are one-person billion-dollar startups real?

😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy

🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/

💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/

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

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Mentioned in this episode:

November 2024 - Galah Cyber

Angel Academy - Best online angel investing course in Australia and New Zealand

Don't forget to check out the best online angel investing course in Australia and New Zealand, Angel Academy. It's fun, engaging, and packed full of insights from experienced investors to help you get started or level up your angel investing, visit www.venture.academy

February 2025 - Angels Academy

Some investor phrases sound helpful. Others feel like a riddle. In this episode, Cheryl and Maxine crack open the language investors use when talking to founders, and translate what’s actually being said behind phrases like “not a fit,” “too early,” or “let’s have one more meeting.”

They walk through the subtle (and not-so-subtle) cues that signal a pass, explain what “conviction” actually means in VC-speak, and share tactics founders can use to get clearer answers during fundraising. You’ll also hear the behind-the-scenes realities of ghosting, deal timelines, internal partner politics, and why “we’d love to stay close” usually means… they won’t.

Plus: a rapid-fire rundown of the weirdest (and most cringe) investor slang, from “due dilly” to “foundies.”

Whether you’re raising your first round or managing investor relationships post-close, this episode helps you spot the signals, ask better questions, and avoid wasting time.

01:45 – “Not a fit”: Why investors love this vague phrase

03:40 – What they mean when they say “you’re too early”

08:30 – “You’re too late”, how stage mismatches work both ways

15:30 – “We’ll circle back” and other signs of a slow no

17:10 – How long does VC diligence really take?

19:15 – Why June 30 is a terrible time to raise

24:10 – Optionality: The excuse behind “we love what you’re doing”

28:00 – “Let the lawyers sort it out”: A red flag or not?

30:15 – The weirdest investor slang (please don’t say “due dilly”)

33:30 – Term sheet vs. side letters: what’s actually worth negotiating

36:00 – Understanding info rights vs. investor updates

38:50 – How to share bad news without burning relationships

45:20 – The shifting goalposts of traction and growth metrics

47:00 – Spotting investor doubts through team questions

48:10 – Final thoughts for both founders and investors

😇 Angel Academy: The most comprehensive angel investing course for Australia & NZ – www.venture.academy

🦘 Aussie Angels: Cheryl’s platform for angel investing – https://www.aussieangels.com/

💰 Co Ventures: Maxine’s venture capital firm – https://www.coventures.vc/

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

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Charles Hudson is the Founder and Managing Partner at Precursor Ventures, a solo GP fund that has backed over 450 startups across five funds, including dozens of category-defining companies led by underrepresented founders. In this episode, Maxine and Cheryl sit down with Charles to explore how he built one of the most successful high-volume venture strategies in the world, all while staying a solo decision-maker.

They dive deep into what being a “solo GP” actually means, how Charles balances scale with intimacy across a massive portfolio, and why trust, not likability, is his north star when supporting founders. You’ll also hear his first-ever investment, the courage it took to leave a top-tier firm to start Precursor, and how he still handpicks every company Precursor backs, often long before they’re obvious.

03:20 – Charles’s first investment: ExxonMobil shares… mailed by cheque

06:50 – What is a solo GP fund, and how Precursor operates with one partner and 14 staff

10:28 – The pros and cons of solo decision-making in venture

12:50 – How Precursor supports 450+ companies (and avoids “orphaned” portfolios)

15:44 – Why Charles shifted from unlimited founder support to intentional check-ins

19:18 – Trust vs likability, and why real feedback matters more than being liked

24:25 – How Charles handles saying “no” to follow-ons, and still earns trust

29:31 – The case for “challenger” VCs over cap-table cheerleaders

32:11 – What Precursor looks for in a founder: not great employees, but great CEOs

36:39 – High volume investing: Why meeting 2000+ startups matters

39:00 – Global allocation: why Charles bet early on African and LatAm FinTech

42:30 – The return of themes (like AI & Women’s Health), and why they can kill judgment

47:52 – When Precursor steps in (and when they don’t): being the “surgeon, not the bandaid”

54:04 – Charles’s biggest Big Cojones moment: leaving Uncork to build Precursor from scratch

56:15 – Why most fund managers are “post-employment” and proud of it

👤 Charles Hudson LinkedIn - https://www.linkedin.com/in/chudson/

🌎 Precursor Ventures – https://precursorvc.com/

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Mentioned in this episode:

Aussie Angels - the preferred fund and syndicate admin platform for emerging managers in Australia

Show Notes: If you’re an investor or keen to write your first angel check, please check out some of the syndicate tickets on www.aussieangels.com

February 2025 - Aussie Angels

Grab your copy of the Dealroom and SideStage Ventures report we talked about on the show with Cheryl Mack and Maxine Minter here - https://www.sidestage.vc/outliers-report-2025

Ben Grabiner is the Co-founder and General Partner at Side Stage Ventures, and the author of a landmark new report in collaboration with Dealroom and AWS. In this episode, Cheryl and Maxine sit down with Ben to unpack the data behind Australia’s rapid rise as one of the most efficient and exciting venture ecosystems in the world.

They explore how Australia produces more unicorns per dollar invested than any other country, what makes the ecosystem so resilient and capital-efficient, and why the next decade might belong to Aussie tech. From funding gaps to founder grit, from global capital flows to angel investor opportunities, this is essential listening for allocators, founders, and emerging fund managers alike.

You’ll also hear Ben’s story, from buying Tottenham Hotspur shares as a teenager, to moving across the world mid-COVID, to becoming a key builder in Australia’s startup ecosystem.

04:49 – Ben’s first investment: £250 in Tottenham Hotspur

06:34 – What makes Australian unicorns so capital-efficient?

09:14 – Unicorn efficiency vs gross unicorn creation: what matters more

13:15 – How Australia quietly matches Israel and India on decacorn creation

14:35 – Why foreign investors see the opportunity more clearly than locals

18:41 – The power of local exits like Afterpay, and how they inspire allocation

21:19 – Can Aussie startups scale globally from home? Or must they go abroad?

23:40 – Why this next wave of operators will be our ecosystem’s secret weapon

25:54 – What global LPs need to understand about Australian venture

30:17 – Why pre-seed funds and angel investors matter more than ever

🙋🏻‍♂️ Ben’s LinkedIn - https://www.linkedin.com/in/bengrabiner/

💳 Side Stage Ventures - https://www.sidestage.vc/

🦘 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/

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Nnamdi Okike is the Co-founder and Managing Partner at 645 Ventures, known for his early, contrarian bets on overlooked verticals and non-obvious industries. In this episode, Nnamdi shares how he leveraged a data-driven sourcing model to identify breakout companies like Squire and Goldbelly, and why seemingly small or niche markets often produce the biggest wins. Maxine and Cheryl dive deep into Nnamdi’s journey from Insight Partners analyst sourcing deals via cold calls, to launching his own fund and achieving a remarkable hit rate, landing him on the Midas Brink List. They explore how he evaluates founder insights, measures market inflection points, and strategically navigates the power law dynamics in venture capital. Packed with strategic insights and candid reflections, this episode is essential listening for emerging investors, fund managers, and founders curious about building defensible businesses in non-obvious spaces.

04:34 – Nnamdi’s first investment during the dotcom boom

06:52 – Defining “non-obvious industries” and spotting hidden TAM

10:40 – Squire: From barbershop bookings to vertical SaaS OS

13:20 – Goldbelly, marketplaces, and the power of founder insight

17:58 – Algorithmic sourcing meets founder conviction

21:30 – What 645 Ventures learned from missing Facebook

26:46 – Building a fund around risk profiles, not just stages

30:34 – Why the power law should shape every VC decision

35:16 – Does 2024 echo 2002? A macro take on the downturn

42:41 – The rise of zombie funds and quiet closures

45:20 – Bootstrapped AI startups and the future of defensibility

52:54 – When vertical AI gets sticky—and when it doesn’t

57:20 – Nnamdi’s Big Cojones moment: from Insight to starting fresh

🙋‍♂️ Nnamdi Okike on LinkedIn – Follow Nnamdi’s updates and insights. https://www.linkedin.com/in/nnamdiokike

💰645 Ventures – A VC firm investing in early-stage, non-obvious software winners. https://645ventures.com/

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Pocket Sun is the Founding Partner at SoGal Ventures, the first female-led, millennial VC firm investing in the future of living, working, and staying healthy. In this episode, she shares how she made her first angel investment at just 24, and how her early bets like Everly Health and Lovevery reflected a conviction in underrepresented founders well before it was a trend. Cheryl and Maxine explore how Pocket launched SoGal’s debut fund, built a deal pipeline through global pitch comps and community, and mastered the art of getting onto oversubscribed cap tables. They also unpack her consumer investing thesis, how she’s navigating fund two with more geographic focus, and what it means to lead recaps and board restructures when the power law turns brutal. For anyone curious about building a fund from scratch, going global with limited resources, or backing change-makers the market misses, this episode is packed with both tactics and courage.

00:00 – Pocket’s first angel check: $1K into an AI startup

05:30 – Angel investing isn’t just for the ultra-wealthy

09:45 – From building a global pitch comp to proving LP credibility

14:20 – Early wins: Everly Health, Lovevery, and chasing allocation

23:35 – “Land and expand”: getting on cap tables and earning super pro-rata

27:10 – Leading recaps and fighting for underestimated founders

35:00 – SoGal’s thesis: The future of living, working, and staying healthy

40:30 – Entering new verticals without prior expertise

46:00 – Pocket’s take on the Vancouver vs. Toronto startup ecosystems

53:00 – Betting on design-led, intentional consumer businesses

59:10 – Why consumer startups often graduate into enterprise giants

01:03:00 – Pocket’s Big Cojones moment: moving solo to the U.S. at 18

🙋‍♀️Pocket Sun on LinkedIn – Connect with Pocket and follow her updates. https://www.linkedin.com/in/pocket

💰SoGal Ventures – A VC firm backing diverse founders in the future of living, working, and staying healthy. https://www.sogalventures.com/

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

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Mentioned in this episode:

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What drives bold decisions, intentional leadership, and the courage to create something entirely new?

In Perspective X, host Pauline Fetaui dives deep into conversations with extraordinary entrepreneurs and leading innovators to explore not just their successes—but the overlooked decisions, mindset shifts, and personal turning points that sparked their greatest breakthroughs.

This show is about the ripple effect of choice: how deep accountability enables us to respond intentionally to life's challenges, rather than simply reacting. If you're curious about the inner journey behind meaningful achievements and how leaders evolve through adversity, this podcast is for you.

Join us on Perspective X, where we move beyond the highlight reel and into the pivotal moments that changed everything.

Launching on the 12th of May, wherever you get your podcasts.

Mentioned in this episode:

Day One sting

Monique Woodard is the Founder and Solo GP of Cake Ventures, a venture fund focused on the enormous opportunities created by demographic shifts such as aging populations, rising female spending power, and America's transition to a majority-minority population. She explains how these macro-level changes expand markets across digital health, fintech, consumer brands, and AI-enabled solutions. Monique also candidly shares her experiences as a solo GP—covering the realities of fundraising, building a unique investment thesis, navigating partnership dynamics, and scaling from Fund I ($17M) to Fund II. Her insights offer a clear blueprint for investors, operators, and founders eager to capitalise on overlooked, high-growth opportunities driven by demographic change.

03:07 – Monique’s first investment: picking stocks at age 20

06:12 – Her journey from rural entrepreneurship to 500 Startups and VC

12:43 – The "Three Layers of Cake": investing in demographic shifts (aging, female economy, new majority)

22:56 – Why geographic focus matters (and why Cake invests only in North America

24:32 – Real talk on Solo GP life: choosing partners, hiring venture partners, and building a legacy firm

30:07 – Raising Fund II: bigger checks, deeper domain expertise, and firm evolution

39:12 – How founders should position their companies in the AI hype cycle

45:24 – Advice for operators: Understanding the difference between investing and running a venture firm

🍰 Cake Ventures – Monique’s demographic‑change VC firm. https://cake.vc🙋‍♀️Monique Woodard on LinkedIn – Follow her insights on venture & demographics. https://www.linkedin.com/in/moniquewoodard

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

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Mentioned in this episode:

November 2024 - Galah Cyber

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In this episode of First Cheque, Cheryl and Maxine sit down with James Tynan of Square Peg to explore why EdTech might be one of the most misunderstood (and underinvested) sectors in venture capital. James recounts his early days bootstrapping a startup in Australia’s tough 2001 tech climate, and the lessons he took with him to Khan Academy—where he witnessed firsthand how technology, when done right, can revolutionise education.

Together, they dive into the massive shifts happening in learning today: how kids are skilling up at breakneck speed thanks to platforms like Scratch, YouTube, and AI tutors; why the “Prussian model” of schooling persists; and where personalisation, assessment, and vocational learning could unlock new investment opportunities. James also offers candid advice for early-stage investors trying to spot the next breakout idea in an era of AI-fueled growth—and shares why stepping away from the “prestige path” (like skipping Stanford) was one of his biggest and bravest decisions. Whether you’re an EdTech founder, an investor, or just intrigued by how fast education is evolving, this episode is a must-listen.

00:00 – Intro

02:16 – James’s first big bet – Starting a company in Australia’s early 2000s “hellscape” and the lessons learned

07:18 – Why MOOCs weren’t the answer – The early EdTech hype, misconceptions about online courses, and how Khan Academy did things differently

11:12 – Assessment as the control point – How exams and credentials shape mainstream education and what might disrupt that model

15:08 – AI’s impact on education – Could personalized, AI-driven learning (and cheating) force schools to rethink how we test knowledge?

18:20 – Kids, dopamine, and the next-gen learning paradox – Balancing entertainment and deep learning, and why “edutainment” rules

24:00 – VC skepticism vs. reality – Why it’s so hard to invest in K–12 EdTech, and where vocational and adult learning might be more promising

32:00 – Rapid AI adoption – From legal tech to healthcare, how ambient tools are skyrocketing and what it means for founders

37:00 – Wedges, moats, and growth – The playbook for AI startups moving from “just a feature” to a sustainable product

42:00 – James’s “big kahunas” moment – Choosing Khan Academy over Stanford and why walking away from “prestige” can change everything

47:07 – Wrap-up – The future of EdTech, AI’s role, and parting wisdom for founders and investors

James Tynan on LinkedIn – Partner at Square Peg and former operator at Khan Academy. - https://www.linkedin.com/in/james-tynan-ba54b93/

Square Peg – The VC firm James Tynan is a Partner at. - https://www.squarepeg.vc/

Khan Academy – Free world-class education for anyone, anywhere.

College Board + Khan Academy Partnership – Free SAT and AP test prep.

Ambience Healthcare – AI for clinical documentation and patient notes.

Harvey AI – Legal AI platform disrupting law firm workflows.

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

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Mentioned in this episode:

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November 2024 - Galah Cyber

Having a clear investment thesis helps you make better decisions, improve your deal flow, and maximise your returns. Cheryl and Maxine break down exactly what an investment thesis is, why it matters, and how to structure one that fits your risk appetite, interests, and long-term goals.

They explore the core elements of an investment thesis, including industry focus, stage, business model, and geography. Plus, they highlight key company criteria investors should consider, from strong founding teams and large market opportunities to traction and defensibility.

Beyond just what to invest in, this episode also covers how to stand out as an investor, build a strong value proposition, and get access to the best deals. They wrap up with an essential discussion on portfolio construction, time horizons, and risk management, so you don’t run out of money before your portfolio has a chance to deliver returns.

If you're looking to sharpen your investing strategy and back better startups with confidence, this episode is a must-listen.

00:00 – Introduction: Why your investment thesis matters

01:49 – Defining an investment thesis: What it is & why it's essential

04:49 – How to break down your thesis into clear categories

05:16 – Industry focus: Verticals, horizontals, and emerging trends

07:05 – Stage focus: Pre-seed, seed, growth—how to pick your sweet spot

08:24 – Business model focus: B2B SaaS, marketplaces, and beyond

10:01 – Geography: The pros and cons of investing locally vs globally

14:29 – Key questions every investor should ask themselves

17:24 – Company-specific criteria: How to create your investment checklist

22:33 – Evaluating market size and growth potential

25:39 – Pain vs pleasure: Investing in painful problems vs unmet desires

29:54 – Unique or niche theses: Second-time founders, alumni networks, and more

33:46 – Access and deal flow: How to attract great opportunities

38:35 – Understanding your personal risk profile & timeline expectations

Angel Academy – Comprehensive angel investing course for Australia & NZ: www.venture.academy

Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/

Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/

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

To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows.

Mentioned in this episode:

November 2024 - Galah Cyber

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