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Episode SummarySome 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.
Time Stamps01:45 – “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
Resources😇 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/
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/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.
Mentioned in this episode:
Deel x PX_Script 1
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.
Time Stamps03:20 – 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
Resources🌐 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
✨ Connect with Georgie HealyWeekly Substack: https://georgiehealy.substack.com/
Linkedin: https://www.linkedin.com/in/georginahealy/
Instagram: https://www.instagram.com/georginahealytech/
The Day One NetworkIn 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:
Deel x PX_Post Intro
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.
Timestamps01:02 – 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:
Call for Feedback
Christie Hayward, an apprentice Boilermaker at WesTrac, who bravely moved from Sydney to the Hunter Valley to pursue her passion for metalwork. You'll hear how her mechanical engineer parents fostered her love for hands-on learning, leading her to a career she truly loves. Christie pulls back the curtain on the daily life of a Boilermaker, from welding and fabricating to working on massive Caterpillar mining equipment.
Highlighting WesTrac's strong commitment to women in trades. This is a must-listen for anyone curious about a trade career or navigating a male-dominated field. Christie offers incredible insights into her positive experience as a female Boilermaker, stressing the importance of respect and being true to yourself. Plus, you won't want to miss hearing about her unique hobby as an alpaca breeder and how she channels her trade skills into creative projects at home. Tune in to hear Christie's empowering story of passion, perseverance, and why "having a go" can truly open up endless possibilities!
A few years back, we interviewed over 100 people from Australia's modern and early startup community to pull together a deep 6-part series documenting the origins of Australia's startup ecosystem.
But, the full documentary runs for almost 6 hours.
If you don't have that much time. Here's an AI-generated version by NotebookLM.
We fed it all the interviews that the Day One team conducted, including the final 6 documentary epsidoes and told it to summarise it.
We explore how storytelling transforms compensation strategy in our third conversation with Naomi Trickey, Chief People Officer at Mews. Discover why compensation isn't just spreadsheets and numbers—it's about creating a narrative that builds trust, drives engagement, and makes complex compensation frameworks resonate with employees. Learn how infusing empathy and strategic storytelling into your compensation approach can help navigate difficult conversations and create a more human-centered pay philosophy.
Chapters:
00:00 - Introduction to FNDN Series
01:04 - Meet Naomi Trickey, CPO at Mews
01:48 - Why storytelling matters in compensation
04:47 - Implementing storytelling in compensation strategy 06:41 - Equipping leaders with storytelling tools for difficult conversations
09:13 - Recommended resources for mastering storytelling in business
11:24 - Episode wrap-up and closing thoughts
Connect with Naomi Trickey
Visit https://mews.com/
Linkedin: https://linkedin.com/in/naomitrickey
FNDN Episodes at Spotify | Apple Podcast
Harini Janakiraman and Shams Mosowi are the powerhouse co-founders behind BuildShip, a platform helping businesses automate complex backend and AI workflows in minutes. In this episode, they unpack what it really takes to build a fast-moving AI startup that developers not only use, but love.
Georgie dives into their founding story (from Antler hire to co-founder), their approach to vibe coding with tools like Claude and Cursor, and why product alone isn’t enough in today’s AI landscape. The trio also plays “hit or miss” with popular dev tools like Midjourney, Replit, Cursor, and GitHub Copilot, and they don’t hold back.
Harini and Shams share honest lessons on building for tech-literate users, hiring remotely, and turning branding into a technical moat. Plus: the viral power of great merch, why Shams temporarily moved to San Francisco, and how developers can earn exclusive BuildShip swag by shipping real tools.
Time Stamps02:43 – What makes a great startup partnership work
05:23 – Harini’s AI hack: voice-activated workflows for home and transport
07:21 – Shams’ AI hack: pitch deck evaluator and vibe coding with Claude + Cursor
09:40 – Comparing LLMs: ChatGPT, Gemini, Claude, Perplexity
14:11 – Tech hits & misses: Midjourney, Replit, Cursor, Copilot
21:44 – Where to prioritise capital pre-product-market-fit
24:49 – Is moving to San Francisco worth it for AI startups?
27:43 – Remote hiring lessons: trial projects, red flags, and finding fit
29:54 – Why brand is BuildShip’s moat (and how merch plays a role)
36:11 – How to earn BuildShip merch: hackathons and shipping tools
37:24 – Rapid fire: worst hires, dream users, and impossible customers
40:38 – Social media fails and that awkward “Hey Captain” email
42:07 – Final shoutouts: BuildShip tools, demo challenge, and how to get started
Resources🛠️ Try BuildShip: https://www.buildship.com
✨ BuildShip Tools (vibe-code your backend): https://www.buildship.com/tools
📣 Harini on LinkedIn: https://www.linkedin.com/in/harinijanakiraman/
💻 Shams on LinkedIn: https://www.linkedin.com/in/shams-mosowi/
In the Blink of AI is made possible by our wonderful partnersDeelGlobal 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.
✨ Connect with Georgie HealyWeekly Substack: https://georgiehealy.substack.com/
Linkedin: https://www.linkedin.com/in/georginahealy/
Instagram: https://www.instagram.com/georginahealytech/
The Day One NetworkIn 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:
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
Episode SummaryJames Davie is the Co-founder and CEO of Miyagi, an AI-powered platform helping tech companies run more efficient and engaging online communities. In this episode, Alan sits down with James to explore what it takes to build a startup when you’ve never sold a thing in your life, and why community might just be the next frontier in customer experience.
They talk founder-led sales, credibility building on LinkedIn, and how James is navigating the messy middle between MVP and product-market fit. You’ll also hear real insights into Miyagi’s pilot customers, the importance of owning your distribution channel early, and why building your personal brand can unlock your first 100 users, even before the product is “done.”
This is essential listening for early-stage founders, community managers, and product leaders who know the power of customer engagement, but also know how hard it is to scale it.
Time Stamps01:44 – James’ surprising path to becoming a founder
06:39 – What is Miyagi, and who is it for?
10:30 – The hidden cost of running a community without ownership
12:45 – Founder-led sales when you’ve never sold before
13:17 – Learning to ask for the sale: how James is building muscle
15:54 – Imposter syndrome and credibility as an unknown founder
17:39 – Why LinkedIn alone won’t build your funnel
18:51 – Using small events and meetups as growth channels
21:29 – From attendee to speaker: how to build “expert magic”
24:35 – Becoming a panelist, host, or community organiser
25:58 – Why different roles across the org all touch “community”
26:56 – Founder brand vs company brand: what comes first?
Resources Mentioned👨🏻💻 James Davie on LinkedIn – https://www.linkedin.com/in/james-davie/
🏗️ Miyagi – https://www.linkedin.com/company/miyagi-ai/
Sponsors:Pick My Brain 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.
___
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
The Day One NetworkPick My Brain is part of Day One, the podcast network dedicated to founders, operators & investors.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:
Deel x PX_Script 1
Standard Ledger
Vanta PMB May 2025_01
In this episode of the Engineering Success Podcast, Melinda Sietsma sits down with Peter McKinnon, the managing director of Omnia Wheel. Peter shares his fascinating career path, from co-founding a successful construction company, Mainbrace, to his current role leading Omnia Wheel. He introduces us to the Omni Wheel, an incredible invention that combines the best parts of a fixed wheel and a swivel caster. This means it offers the directional stability of a fixed wheel but can move in any direction, just like a swivel caster—without the typical swivel offset. This innovative design opens up a world of new design possibilities for products and makes things much easier to use, giving you superior directional control and load stability. Peter explains how Omnia Wheel's unique polymer design and manufacturing process truly set it apart from anything else out there.
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryCharles 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.
Time Stamps03:20 – 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
Resources👤 Charles Hudson LinkedIn - https://www.linkedin.com/in/chudson/
🌎 Precursor Ventures – https://precursorvc.com/
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.
Mentioned in this episode:
Deel x PX_Script 1
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