Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

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/

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

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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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

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?

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?

In the Blink of AI is made possible by our wonderful partners.

Vanta is the all-in-one solution for startups to become compliant quickly and build a security foundation with ease.

Startup customers get $1000 off Vanta at http://vanta.com/blink

Weekly Substack: https://georgiehealy.substack.com/

Linkedin: https://www.linkedin.com/in/georginahealy/

Instagram: https://www.instagram.com/georginahealytech/

In The Blink of AI is part of Day One, the podcast network dedicated to founders, operators & investors.

Sign up to get your weekly insights into the up-and-coming AI startups: https://dayone.fm/newsletter

Mentioned in this episode:

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In this episode of the Fintech Fun podcast, Chris Titley sits down with Jason Leong, CEO and co-founder of PocketSmith, a bootstrapped New Zealand fintech helping households worldwide take control of their finances.

Jason shares the 17-year journey of transforming PocketSmith from a simple cash flow calendar into a global platform used in 190 countries. He explains the concept of the “home CFO,” why true financial data ownership matters, and how Consumer Data Right (CDR) in Australia is reshaping open banking.

From handling unexpected expenses to tackling bill shock, Jason discusses practical budgeting approaches, the psychology of money management, and how PocketSmith adapts to the evolving needs of budget planners, investors, and digital nomads. He also opens up about the role AI should play in personal finance, cultural differences in money mindsets, and his personal passions for travel hacks and sneaker collecting.

Tune in to discover how you can become your own “pocket smith,” crafting a financially confident future for yourself and your household.

00:00 – 00:14: Introduction to Jason Leong and PocketSmith’s global reach.

00:14 – 01:37: Founding story of PocketSmith, naming the company, and bootstrapped origins.

01:37 – 04:09: The “home CFO” concept and solving the time drain of managing finances.

04:09 – 06:26: Understanding net worth, data ownership, and the rise of open banking.

06:26 – 08:20: Segmenting personal finance users – planners, investors, and digital nomads.

08:20 – 11:35: CDR’s role in Australia, data access challenges, and global integration.

11:35 – 13:11: How Australians think about money vs. Kiwis and the cultural differences.

13:11 – 15:28: Managing financial emotions, reducing stress, and time-saving benefits.

15:28 – 19:40: Evolution of PocketSmith’s features and customer-driven product changes.

19:40 – 23:14: Handling unexpected expenses, rollover budgeting, and financial flexibility.

23:14 – 24:59: Tracking savings goals, budget optimization, and behavior-driven insights.

24:59 – 27:11: Shifting financial aspirations and Gen Z’s surprising money habits.

27:11 – 29:54: The Australian fintech ecosystem, partnerships, and CDR’s progress.

29:54 – 33:21: AI’s role in finance, risks of hallucinations, and cautious adoption.

33:21 – 35:30: PocketSmith’s future roadmap and feature improvements.

35:30 – 42:24: Founder spotlight – Jason’s reflections on life, travel, and sneaker collecting.

42:24 – 43:55: How to get started with PocketSmith and its human-centered approach.

Jason Leong's Linkedin - https://www.linkedin.com/in/jasonleong/

PocketSmith - https://www.pocketsmith.com/

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

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

From surgeon to psychiatrist, Bitcoin investor to billion-dollar crypto brokerage founder, Dr. Prash Puspanathan has lived one of the most unconventional founder journeys in tech. After co-founding and scaling Caleb & Brown into a global crypto powerhouse, later acquired by SwiftX in 2025, Dr. Prash is now pioneering the future of mental health with Enosis Therapeutics, using VR to transform psychedelic-assisted therapy integration.

In this episode of Perspective X, Dr. Prash shares how a single psilocybin experience completely reshaped his worldview, steering him away from surgery and into psychiatry, entrepreneurship, and eventually, crypto. He reveals the parallels between fiscal freedom in decentralized finance and cognitive freedom in mental health, the scrappy early days of arbitrage trading, and the challenges of scaling a white-glove brokerage to serve high-net-worth clients worldwide.

We also dive into the future of psychedelic medicine, why integration is the “real work,” how technology can lower costs and increase access, and why prevention, not just treatment, will define the next era of mental health. From paradigm-shifting psychedelics to building billion-dollar ventures, this is a conversation about liberation, of thought, finance, and human potential.

00:00 – Intro: Dr. Prash’s unconventional founder journey

02:00 – From surgery to psychiatry: psychedelics as a turning point

06:30 – The transformative psilocybin experience and shifting paradigms

10:30 – Understanding psychedelic therapy and integration work

16:00 – Why psychedelics challenge power structures and cultural norms

22:00 – Fiscal freedom and cognitive freedom: psychedelics and Bitcoin

30:00 – Founding Caleb & Brown and building a billion-dollar brokerage

37:00 – Global scaling, high-net-worth clients, and leadership transitions

42:00 – Preparing for acquisition: the 9-month journey to SwiftX

50:00 – Running a dual life as psychiatrist and founder

55:00 – Enosis Therapeutics: VR-powered integration for psychedelic therapy

01:02:00 – Building tools for patients, therapists, and the future of mental health

01:10:00 – The vision for a psychological digital twin

01:15:00 – Psychedelics in the next 10–50 years: from treatment to prevention

01:20:00 – Translating research into real-world impact and future mission

💰 Caleb & Brown – Global crypto brokerage: https://calebandbrown.com

🩺 Enosis Therapeutics – Tech for psychedelic-assisted therapy: https://www.enosistherapeutics.com/

👤 Dr. Prash on LinkedIn: https://www.linkedin.com/in/drprash/

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

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

Mentioned in this episode:

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Frank Greeff, the founder behind a $180M exit and the viral Founders Table series, is back, this time building Kinso, an AI messaging aggregation tool set to change how businesses communicate. Instead of retiring after one of Australia’s biggest tech acquisitions, Frank is diving back into the grind, sharing why momentum and purpose keep him building.

In this episode, Frank reveals the AI hacks that surprised even his engineers, why scrappy MVPs may not survive in today’s fast-moving AI wave, and how personal branding gives founders a hidden moat. Georgie and Frank also dig into what it takes to self-fund after top VCs said no, attracting A+ engineering talent in a competitive market, and why “taste” will define which AI products win.

Plus, Frank unpacks Meta’s $100M AI hires, the rise of deepfakes and how he protects his family, and answers listener questions on planning exits, building AI startups, and navigating AGI, UBI, and the future of work, all while playing a spicy rapid-fire round.

03:20 – What is Kinso and why aggregate business messaging

06:15 – Why Frank couldn’t retire after a $180M exit

10:45 – Hack of the Week: how non-technical founders can challenge engineers with AI

14:30 – Why Frank thinks MVPs can’t be scrappy anymore

18:00 – Building a founding team: attracting top AI engineering talent

23:30 – Meta’s $100M AI hires and how Kinso competes

26:40 – Why VCs rejected Kinso and why Frank’s self-funding

30:50 – Taste as a moat: what makes great AI products stand out

33:00 – How building an AI startup differs from RealBase

36:00 – Planning for exits: documentation and timing

40:30 – Deepfakes and Frank’s “secret password” strategy

43:20 – Rapid Fire: AGI, UBI, future of work, and more

🌐 Kinso – https://www.kinso.ai/

🔗 Frank Greeff on LinkedIn – https://www.linkedin.com/in/frankgreeff

In the Blink of AI is made possible by our wonderful partners.

- Vanta: Vanta is the all-in-one solution for startups to become compliant quickly and build a security foundation with ease.

Startup customers get $1000 off Vanta at http://vanta.com/blink

Weekly Substack: https://georgiehealy.substack.com/

Linkedin: https://www.linkedin.com/in/georginahealy/

Instagram: https://www.instagram.com/georginahealytech/

In The Blink of AI is part of Day One, the podcast network dedicated to founders, operators & investors.

Sign up to get your weekly insights into the up-and-coming AI startups: https://dayone.fm/newsletter

Mentioned in this episode:

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Deel x PX_Post Intro

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

Would you trust AI to help close a multi-million dollar acquisition? That’s exactly what Deeligence is helping lawyers do faster and with fewer headaches.

In this episode of Pick My Brain, Elena Tsalanidis, co-founder of Deeligence joins Alan Jones to pitch her AI-powered legal tech startup. Elena shares how her platform streamlines the M&A due diligence process for lawyers, cutting review time in half while delivering greater accuracy.

Alan and Elena dive deep into B2B SaaS sales strategy, how to stand out in a sea of AI wrappers, and what actually makes a startup defensible when everyone’s using the same language models. They explore how founders can navigate complex enterprise sales cycles, why law firms resist change, and how product distribution (not tech) is the real moat.

If you’re building in legal tech, enterprise AI, or B2B SaaS, you’ll want to take notes.

01:40 – What is Deeligence? AI-powered legal due diligence for M&A lawyers

03:05 – Elena’s background: ex-lawyer, ex-legal tech startup operator

04:15 – Childhood ambitions: politics, drill sergeant energy, and leadership

06:00 – The challenge: how do AI startups prove real product differentiation?

08:30 – Alan on “thin wrappers” vs customer experience as a moat

10:10 – Building trust in professional services: security, UX, and reliability

11:40 – Why distribution beats tech in B2B AI

14:10 – What makes a moat in the era of fast, AI-powered software

16:05 – How deal size affects sales cycles in enterprise SaaS

17:15 – Selling into law firms: why Hobart offices can be a strategic wedge

20:00 – Innovation teams: gatekeepers, champions… or blockers?

22:00 – The danger of general-purpose tools vs specialist point solutions

25:05 – How to respond when clients say “we’ll build it in-house”

27:00 – Why law firms are fast-moving money machines (and hate friction)

👩‍⚖️ Elena Tsalanidis – https://www.linkedin.com/in/elenatsalanidis

⚖️ Deeligence – https://www.deeligence.ai

🎧 More from Alan Jones – https://www.startupfoundercoach.com

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

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

Mentioned in this episode:

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Vanta PMB May 2025_01

Deel x PX_Script 1

Ever wondered what it's like to transition from finance to IT, and from Sweden to Australia? On this episode of the NewyTechPeople podcast, Linda Apostolidis sits down with Margareta Bogatir Studdert, who brings her unique global experience to Newcastle. You'll hear about her fascinating career evolution and the surprising differences (and similarities!) of working cultures across continents.

Margareta explains her exciting work at NGM Group, where she merged two distinct IT support teams and is now leading a major strategic project. Margareta also sheds light on Sweden's progressive policies for working families and women returning to the workforce, which truly set them apart. She'll offer invaluable leadership lessons on cultural adaptability, delegation, and empowering teams to learn from mistakes. Plus, don't miss her thoughts on cutting-edge trends like AI for predictive health and automation, and how NGM is championing women in tech by collaborating with initiatives like Hunter WiSE. Tune in for an inspiring story of career growth, leadership, and the power of embracing challenges!

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

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/

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

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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Dr. Tom Kelly, founder of Heidi Health, is building one of Australia’s fastest-growing AI startups, and he’s doing it differently. In this episode, Tom reveals how Heidi Health transforms messy doctor-patient conversations into medical-grade notes in seconds, why batch transcription beats live, and why trust and time, not flashy features, are the future of healthcare AI.

Georgie and Tom unpack why most B2B SaaS startups may not survive, what not to do as a non-technical founder in AI, and how to build trust in high-stakes industries. They also explore personal branding, attention hacking, agents, and AI's limits in life-or-death decision-making.

Plus, Tom shares a killer AI travel hack and plays Late Stage Startup Bingo, guessing the hottest Aussie AI companies, from Relevance AI to Leonardo.

03:20 – What is Heidi Health and how does it work?

07:30 – Doctors spend half their time on documentation

10:45 – How many Australians have unknowingly used Heidi

12:15 – Does every AI founder need a personal brand?

14:20 – Attention hacking vs. building real trust

18:00 – AI Hack of the Week: voice agents as personal tour guides

20:00 – Gemini’s financial report guessing game

23:00 – Late Stage Startup Bingo: Aussie AI edition

28:30 – The batch processing decision that made Heidi better

31:10 – Why 2% better quality led to 40% more adoption

35:45 – How non-technical founders can get AI-literate fast

40:30 – Should you fine-tune models early on?

44:30 – RAG vs. unlimited context: what comes next

49:10 – The dream of lifelong medical memory

50:50 – Rapid Fire: B2B SaaS, AI agents & Aussie gov support

🌐 Heidi Health: https://heidihealth.com

🔗 Dr. Tom Kelly on LinkedIn: https://www.linkedin.com/in/tomkeykong/

In the Blink of AI is made possible by our wonderful partners.

- Vanta: Vanta is the all-in-one solution for startups to become compliant quickly and build a security foundation with ease.

Startup customers get $1000 off Vanta at http://vanta.com/blink

Weekly Substack: https://georgiehealy.substack.com/

Linkedin: https://www.linkedin.com/in/georginahealy/

Instagram: https://www.instagram.com/georginahealytech/

In The Blink of AI is part of Day One, the podcast network dedicated to founders, operators & investors.

Sign up to get your weekly insights into the up-and-coming AI startups: https://dayone.fm/newsletter

Mentioned in this episode:

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Vanta Ad_BAI Jul25

Vanta Ad_BAI Jul25

Vanta Ad_BAI Jul25

The Australian Information Security Manual (ISM) just got a major update, and not everyone’s thrilled. In this special episode of Secured, Cole Cornford is joined by Toby Amodio (Head of Professional Services, Fujitsu Cyber) to break down what’s changed, what’s missing, and what it all means for CISOs, AppSec teams and public sector security leads.

From the new cybersecurity principles (and why they feel like yak shaving) to the long-overdue expansion of software security controls, Cole and Toby navigate the mess of frameworks, missing maturity models, and babushka-doll-style mappings that have left many teams overwhelmed. They also reflect on what “secure-by-default” really means in a world of legacy codebases, overstretched resources, and one-person AppSec teams.

01:02 – Why ISM Updates Matter (Even If They’re Late)

02:32 – New Principles: Nice Idea, Hard to Implement

04:08 – Yak Shaving and the Complexity Cascade

07:48 – Mapping Mayhem: PSPF, E8 and Governance Overload

10:25 – Losing the Maturity Model: Who Does That Help?

13:46 – Secure-by-Default and the Problem with OWASP-as-a-Proxy

18:13 – Integration, Incentives, and Cyber vs. Business Silos

20:34 – The Talent Gap and Why Code Reviews Still Matter

22:58 – Galah Cyber, Capability Building & Doing AppSec Right

23:57 – Why Buying Tools Isn’t the Same as Building Capability

25:21 – What Red, Amber, Green Tools Really Miss

26:01 – One ISM to Rule Them All… If You Can Implement It

26:52 – Final Thoughts (and a Funding Stick for CISOs)

Mentioned in this episode:

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