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Episode SummaryEvery time you ask an AI to write a song, generate a script, or mimic a creative style, there's a good chance it learned how to do that by consuming someone's life's work, without asking, without paying, and without them ever knowing.
In October 2025, the Albanese Government became the first in the world to rule out a text and data mining exception to copyright law, a landmark win for creators that is now being actively challenged by the tech industry. It's the backdrop to everything Holly and Georgie discuss here.
Holly Rankin, the artist behind Jack River and founder of cultural strategy company Sentiment Agency, has testified before Australian Parliament and become one of the most articulate voices in the fight to ensure the AI economy doesn't get built on the back of stolen human culture. In this episode she and Georgie get into the staggering labour that goes into making a single song, why the "it's too complicated to license" argument from Big Tech is a convenient myth, and what the Anthropic book piracy settlement really signals about where this is all heading. But underneath the policy detail is a bigger question: if we let machines consume and replicate everything that makes us human, what exactly are we left with?
Jack River - https://www.jackrivermusic.com/
Holly Rankin Linkedin - https://www.linkedin.com/in/holly-rankin-3535912b3/
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:
Stripe Startups
For early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe.
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How do AI companies scale this fast without breaking?
Eight figure revenue in competitive markets. Products that double revenue in a single month. Customers who tattoo your logo on their body. Not growth hacks. Not hype. Real traction, earned the hard way.
Brendan Hill sits down with Daniel Slater from Relume, Liam Millward from Instant, and Sally Yu from King River Capital to unpack what actually drives breakout AI companies in 2025. The answer is not building more features. It is obsession with distribution, ruthless focus on speed to value, and teams that move faster than their competitors think is possible.
Relume did not start as an AI startup. It started as an agency. Building websites manually, feeling the pain firsthand, and removing the work that should never have existed. Instant did not find product market fit once. It found it three times, killing products, rebuilding teams, and learning the hard way that revenue without stickiness is a mirage. And from Silicon Valley, Sally Yu shares what she sees across the fastest growing AI companies in the world, why community is becoming the real moat, and why founders with unwavering conviction now win disproportionately.
They talk candidly about churn, mistakes, hiring A players, monthly execution cycles, and why most AI products fail not because the tech is bad, but because the company moves too slowly. This is a conversation about momentum. About earning distribution. About building products people would fight to keep.
If you want to understand how modern AI companies actually scale, and what it takes to stay ahead once you do, this episode is for you.
Oversubscribed is proudly supported by our sponsor Vanta 🦙
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The Day One Network
Oversubscribed is part of Day One, the podcast network dedicated to founders, operators & investors.
Guest Founders:
Relume: relume.io
Connect with Daniel: https://www.linkedin.com/in/daniel-james-slater-13079288/
Instant: instant.one
Connect with Liam: https://www.linkedin.com/in/liammillward/
King River Capital:http://www.kingriver.co/
Connect with Sally: https://www.linkedin.com/in/sally-tech/
Stay Updated:
Listen to the Oversubscribed Podcast on Spotify: https://open.spotify.com/show/6rZ9SajGVXkO8oxuvEHAsk?si=I2yR92GgRZa-Fdqbp8T4bw
Listen to the Oversubscribed Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/oversubscribed/id1848789610
Please note that the content here is for informational purposes only; should NOT be taken as legal, business, or investment advice or be used to evaluate any investment or financial product. Brendan Hill is an investor in Everlab, Relevance AI and A1Base.
About the Host:
Brendan Hill is a Venture Partner at TEN13 and an angel investor in Australia’s fastest-growing startups, including Everlab, Heidi Health, Relevance AI and Instant. If you are interested in finding out more about angel investing, connect with Brendan on LinkedIn: https://www.linkedin.com/in/itsbrendanhill/
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Episode Summary
Consumers lose billions to scams and miss out on trillions in potential savings every year. So what if everyone had their own AI-powered financial assistant working 24-7?
In this episode of Pick My Brain, Alan Jones is joined by James Horan, founder of Phinly, an AI-driven personal finance platform designed to help consumers automate savings, prevent fees, and optimise their financial lives. James walks through his live pitch for Phinly, outlining the problem with doom-scrolling money advice, the rise of AI agents in personal finance, and a bold vision for owning the AI money assistant category.
Phinly connects to over 20,000 institutions, identifies cost savings opportunities, and enables one-tap actions from cancelling subscriptions to switching providers. With early partnerships secured, backing from a global AI accelerator, and a savings-based revenue model, the startup is raising $800,000 on a pre-seed SAFE to scale toward $4.5M ARR in 18 months.
But Alan’s feedback goes deeper than traction and TAM. He challenges James to avoid blending in with every other AI fintech startup in the room. Instead of leaning purely on logic and numbers, Alan pushes for something more memorable: behavioural insights that surprise the audience about their own financial habits. The goal is simple. Make investors go home and say, “Did you know that…?” and have that sentence start with something you taught them.
If you’re building in fintech, AI, or any crowded category, this episode is a masterclass in standing out when everyone else looks the same.
Time Stamps
02:08 – Meet James Horan and his founder journey
03:14 – Lessons from a failed two-sided marketplace
04:28 – The Phinly pitch begins
05:40 – Money advice, TikTok, and the cost-of-living crisis
06:50 – How Phinly works: AI-powered money automation
07:45 – Traction: 20,000 institutions connected and major partnerships
08:30 – Revenue model: percentage of savings and future subscriptions
09:10 – Alan’s first reaction: good foundation, but blends in
11:45 – The power of surprise in a crowded fintech room
12:30 – Using behavioural economics to stand out
14:00 – Stop reading your slides
15:30 – Supporting your story instead of replacing it
17:00 – Bringing emotion into a rational fintech pitch
18:00 – How to create a pitch people repeat to others
Resources
💸 Phinly – https://phinly.com
🎙 Ask Alan a Question – https://speakpipe.com/pickmybrain
🎧 More from Alan Jones – https://www.startupfoundercoach.com
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:
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Welcome back to the FNDN Series, where we continue our deep dive into startup compensation with industry leaders from across the startup world. In our conversation with Carmen Amador, Founder of The Cycle Method and business psychologist, we unpack the critical connection between the menstrual cycle and workplace performance that most organizations are missing. We explore how the modern work environment, built on industrial revolution principles, fails to account for cyclical rhythms and discuss the untapped potential when we understand and leverage the unique strengths that come with each phase of the menstrual cycle. Keep watching to discover why women are twice as likely to burn out at work and what actionable steps both individuals and organizations can take to create more inclusive, effective workplaces.
Chapters:
00:00 Introduction and Warm-Up Conversation
02:30 Guest Introduction: Carmen from The Cycle Method
04:45 Why the Menstrual Cycle Matters in the Workplace
08:15 The Personal Health Journey That Led to Professional Mission
12:00 How Modern Work Structure Ignores Cyclical Rhythms
15:20 The Burnout Statistics: Why Women Are Twice as Likely to Burn Out
18:10 Myth Busting: Beyond Period Pain and Pregnancy
21:40 The C-Suite Framework: CEO, CIO, CPO, CMO, and COO Energies
27:30 Understanding Your Unique Cyclical Patterns
31:15 The Three Layers: Self-Awareness, Adjustment, and Cycle Mastery
36:20 Practical Applications: Sync, Adjust, and Prepare
40:25 The Business Case: Untapped Potential and Performance
43:50 Using Product and Tech Language: Agile Meets Biology
46:40 The Policy vs. Culture Gap: Spain's Menstrual Leave Example
49:30 Creating All-Gender Inclusive Conversations
51:45 Generational Perspectives on Menstrual Cycle Awareness
53:20 Beyond the Menstrual Cycle: Including All Hormonal Experiences
54:45 Conclusion and Final Thoughts
65:50 Beyond the Menstrual Cycle: Including All Hormonal Experiences
68:00 Conclusion and Final Thoughts
Connect with Carmen
Visit: thecyclemethod.com
linkedin.com/in/carmenpsychologist
Resources Mentioned
Oyster - Previous workplace where Matt and Carmen worked together
Culture Amp - People and culture platform
Air Tree - Australian VC company mentioned for menopause-focused initiatives
Canva - Example of inclusive leave policy implementation
Deloitte - Published report on supporting women through hormonal transitions showing 60% higher retention
Research and Studies:
WGEA (Workplace Gender Equality Agency) - Referenced for workplace equity benchmarks
Deloitte Report on Hormonal Transitions - Found 60% higher retention when women feel supported
Spain's Menstrual Leave Policy - First country to offer legal menstrual leave
Concepts and Frameworks:
The Cycle Method - Carmen's educational program and framework
Agile Framework - Compared to menstrual cycle phases
Seasons Analogy - Winter (menstruation), Spring (follicular), Summer (ovulation), Autumn (luteal)
C-Suite Framework - CEO (menstruation), CIO (follicular), CPO/CMO (ovulation), COO (luteal)
Media:
A Good Hang by Amy Poehler - YouTube series mentioned in conversation
More FNDN Episodes:
Spotify: https://open.spotify.com/show/4GeBIeZOKrFxG1oiiPxmiM
Apple Podcast: https://podcasts.apple.com/us/podcast/fndn-series/id1794263484
MenstrualCycleAwareness, WorkplaceWellbeing, WomensHealth, StartupCulture, BurnoutPrevention, HormonalHealth, CyclicalLiving, PeopleOperations, InclusiveWorkplace, WorkplaceEquity, PerformanceOptimization, HRInnovation, DiversityAndInclusion, EmployeeWellbeing, StartupLeadership, WomenInBusiness, CycleTracking, HolisticWorkplace, PsychologicalSafety, StartupBestPractices
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryTracey Spicer is one of Australia’s most respected journalists and the author of Man-Made: How the Bias of the Past Is Being Built into the Future. In this episode, Georgie sits down with Tracey for a sharp, funny, and occasionally jaw-dropping conversation about what happens when we treat AI like neutral math instead of what it really is: opinion written in code.
They unpack why algorithmic bias is getting worse in the generative AI era, how recommendation engines can quietly radicalise people (from Andrew Tate pipelines to hyper-performative “tradwife” culture), and why “move fast” without guardrails is a dangerous blueprint. The discussion also goes into the weird and unsettling frontier of humanoid home robots, privacy risks in always-on devices, and what Tracey learned researching sex robots, including the disturbing ways consent is engineered out of the product.
Plus: why Tracey’s favourite AI tool is Claude, what she thinks about Grok and the chaos machine of X, why we are not getting a four day work week anytime soon, and her case for “regulatory sandpits” to test AI safely before it hits the rest of the world.
Time Stamps01:10 – Tracey’s TEDx “The lady stripped bare” moment and why it still matters
04:45 – Beauty standards, AI filters, and why expectations on young women have intensified
08:20 – Man-Made and the epiphany that sparked Tracey’s AI obsession
11:10 – The AI arms race, speed, and why we are in the “seatbelt era” of tech
14:30 – Digital natives vs critical thinking: the hallucination blind spot
16:45 – Tracey’s AI stack: why Claude is her daily driver
19:05 – Humanoid home robots: convenience vs surveillance
21:55 – Strength vs security: what actually scares Tracey about robots
24:35 – Sex robots and the consent problem manufacturers do not talk about
28:10 – Algorithms as “opinions in code” and how radicalisation happens
33:10 – Removing bias: conversations, perspective checks, and inclusive design
35:00 – Grok, MechaHitler, and what happens when platforms mirror their owners
36:45 – Deepfake porn, consent, and why regulation is finally catching up
38:10 – No, AI will not magically deliver a four day work week
41:10 – Future jobs: law, AI assistants, and why juniors still need fundamentals
44:15 – Indigenous knowledge, language revitalisation, and the full-circle AI story
46:50 – Rapid fire: brain chips, Waymo, smart glasses, and AI “snog marry avoid”
49:55 – What we should do now: regulatory sandpits and real guardrails
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:
Stripe Startups
For early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe.
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AI is starting to change penetration testing, but most people are asking the wrong question. In this episode of Secured, Cole Cornford sits down with Brendan Dolan-Gavitt, AI researcher at XBOW and former NYU professor, to unpack what autonomous pen testing really is, what it can reliably do today, and what still needs humans.
They explore why AI agents are great at scaling the boring parts of testing, like authenticated workflows and broad vulnerability coverage across huge attack surfaces, and why that does not automatically translate to deep, context-aware exploitation. The conversation also gets into the messy parts: AI systems overclaiming “serious” findings, business logic flaws that are hard to verify, audit expectations, and why scope control needs real guardrails, not vibes. From agent traces and validation models to cost curves and creative exfiltration tricks, this episode is a grounded look at where AI helps AppSec and where it can still cause damage if you trust it too much.
Timestamps00:00 – Intro
03:10 – From academia to building autonomous security tools
05:00 – Human pen testers vs AI agents: what is actually different
06:40 – Where AI helps most: boring tasks and low hanging fruit
08:30 – Scale: a thousand targets vs hiring a thousand testers
10:20 – Accessibility, economics, and Jevons paradox
12:30 – Accountability: audit evidence, traces, and “who signs off”
14:40 – Scope control: avoiding prod and preventing out-of-scope actions
16:20 – Safety checkers, overseer agents, and persuasion resistance
18:40 – The cost question: VC money, inference pricing, and efficiency
21:20 – When AI wastes money and why prioritisation matters
23:50 – Failure mode: overclaiming business “vulnerabilities”
26:10 – Validation agents and adversarial peer review
28:40 – The scary clever stuff: exfiltrating files as images
31:00 – What AI finds well: XSS, SQLi, file traversal, hard proof bugs
33:10 – What AI struggles with: business logic and contextual judgement
35:20 – Hype vs skepticism and why nobody has a crystal ball
🐙 Secured is grateful to be sponsored and supported by Chainguard.
Chainguard is the trusted source for open source. Get hardened, secure, production-ready builds so your team can ship faster, stay compliant, and reduce risk. Download your free CVE Reduction Assessment at https://dayone.fm/chainguard
Welcome back to the FNDN Series, where we continue our deep dive into startup compensation with industry leaders from across the startup world. In our conversation with Lachlan Bradford, Community Content Manager at Sked Social and Co-Host of the Funny Business Podcast, we explore the powerful intersection of brand, community, and people operations. Lachlan shares his unconventional journey from cricket academy to lift operator in Canada, bar manager, e-commerce founder, and ultimately to building vibrant communities in the startup world. We unpack the critical lessons HR teams can learn from community building, the importance of authentic employer branding, the power of personal connection over automation, and how to create workplaces where people genuinely don't want to leave. Keep watching to discover how treating your people like community members can transform your retention, engagement, and company culture.
Chapters:
00:00 Introduction and Welcome
01:45 Guest Introduction: Lachlan Bradford
03:20 Lachlan's Unconventional Journey: From Cricket Academy to Community Building
09:15 The Teachers Who Shaped His Approach to Leadership
13:40 From Bar Manager to E-Commerce: Building OB and Co
16:50 Starting Funny Business Podcast During COVID
32:40 The Founder Mindset: Customer Obsession Applied to HR
36:20 Authentic Employer Branding vs Generic Approaches
40:15 The Power of Niche: Speaking Your Audience's Language
44:30 LinkedIn Strategy: Real Relationships Over Automation
48:45 Surprise and Delight: Creating Memorable Employee Experiences
57:35 Creating Workplaces Where People Don't Want to Leave
58:45 Conclusion and Wrap-Up
Connect with Lachlan:
Visit: https://skedsocial.com
LinkedIn https://linkedin.com/in/lachlanbradford
Resources Mentioned:
Sked Social - Social media management and scheduling platform where Lachlan serves as
Community Content ManagerFunny Business Podcast - Podcast for free thinkers and creators hosted by Lachlan Bradford and Robbie
HicksDream Big Social Club - Community initiative founded by Lachlan featuring events, workshops, and networking opportunities
Ways of Working Consultancy - Agile delivery consultancy launched from the Funny Business podcast
People Mentioned:Ben Waterman - CEO of The Resilience Project, former teacher at Cricket Academy
David McKay - Fusion scientist and former Cricket Academy teacher (brother of Australian cricketer Clint McKay)
Mark Worthington - Player Development Manager at Geelong Cats (AFL)Peter Boul - Leadership expert who delivered workshops for the Dream Big Social Club community
Robbie Hicks - Co-host of Funny Business Podcast and business partner
Concepts Discussed:Customer Obsession in People OperationsAuthentic vs Generic Employer Branding
LinkedIn Relationship Building StrategiesCommunity-First Approach to Workplace Culture
Surprise and Delight Employee Experiences
The Power of Niche Positioning in Talent AttractionFounder Mindset for Employee Engagement
More FNDN Episodes: Spotify: https://open.spotify.com/show/4GeBIeZOKrFxG1oiiPxmiM
Apple Podcast: https://podcasts.apple.com/us/podcast/fndn-series/id1794263484
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryEnterprise AI is past the hype phase and into the hard part: scaling what works without breaking security, blowing out costs, or shipping chaos into production. In this episode, Georgie chats with AWS technologist Rada Stanic about using AI as a “study buddy” to renew technical certifications faster, and why tools like AWS QuickSight can generate strong first drafts of strategy docs when you provide the right templates and context.
They go deep on AIOps: the operational discipline enterprises need to deploy agents and GenAI reliably at scale. Rada breaks AIOps into five practical pillars: defining agent intent, identity and security boundaries, policy and governance, observability and evaluation, and managing the rapid model lifecycle as new LLMs drop constantly. The conversation also covers why security questions dominate every enterprise AI project, why data quality still makes or breaks outcomes, and why “RAG” is fading as a buzzword even though retrieval is still foundational.
Finally, Rada shares a sharp concern for the next generation: what happens to junior roles when AI fills the entry level work, and why the pace of change itself may become the next generation’s greatest advantage.
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:
Stripe Startups
For early-stage, venture-backed founders – Stripe Startups is where to start. Enrol in the program and receive access to credits on Stripe fees, expert insights, and a focused community of other founders building on Stripe.
Stripe Ad_Nov 2025_02
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode Summary
If you have to pitch the same product to two totally different audiences, should you use one deck or two?
In this episode of Pick My Brain, Alan Jones is joined by Michelle Chen, founder of Mental Jam, a startup turning real lived experiences of depression and anxiety into cozy, story-driven mobile games. Michelle is preparing to pitch in two worlds at once: to investors who care about venture-scale growth, and to game publishers who care about commercial upside and licensing rights.
Alan breaks down why one pitch is rarely enough, and introduces a simple framework: three decks for each audience. A teaser deck to spark curiosity, a pitch deck to support your live story, and a leave-behind deck packed with detail for later review. They also get tactical about what makes a pitch land: fewer words on slides, stronger emotional delivery in the first 10 to 15 seconds, and building trust by keeping the audience focused on the founder, not the deck.
Michelle also shares the real nerves behind pitching, including stage anxiety and how it impacts performance. Alan offers a mindset shift that helps founders separate their personal fear from the “role” they’re playing on stage, plus practical tips for pitching on video calls. They finish with concrete improvements: shorten the character section, add a clear team slide, and capture customer reactions on video to show emotional impact, not just quotes.
If you’re pitching a product with multiple buyers, fundraising while still building, or struggling with confidence on stage, this episode is a masterclass in making your pitch clearer, shorter, and more human
Time Stamps
02:10 – Michelle’s origin story: from PhD research to startup
04:10 – Why Catalyzer mattered for a migrant founder
05:20 – Two audiences: investors vs game publishers
06:05 – Should you build two pitches? Alan’s answer: yes, tailor
08:05 – The 6 deck framework: teaser, pitch, leave-behind for each audience
13:05 – Ideal slide counts: teaser 3 to 5, pitch 10 to 15, leave-behind as needed
14:00 – Why founders accidentally read slides and lose the room
15:00 – Video call tip: pin the person, not your slides
16:15 – Michelle’s pitch: Mental Jam and Boba Rista
23:15 – Alan’s feedback: scripting, emotion, and the first 10 seconds
26:00 – Handling stage anxiety while pitching
29:20 – Cut words per slide: aim for fewer than 10 words
31:10 – Too many characters: use one or two for investors
31:40 – Add a team slide and show real customer feedback
33:00 – Use video testimonials for emotional proof
Resources Mentioned
🎮 Mental Jam – https://hellomentaljam.com
🎙 Ask Alan a Question – https://speakpipe.com/pickmybrain
🎧 More from Alan Jones – https://www.startupfoundercoach.com
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
Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey
Episode SummaryFrontline’s Brennan O’Donnell has spent two decades helping companies expand across borders, first as an operator at Google and later as a growth investor backing Series B to D businesses. In this episode, Cheryl and Maxine unpack what’s shifted at growth stage in the last 12 months, why the market is still a barbell of “hot or not” deals, and how AI is finally producing application layer companies mature enough for growth rounds.
They go deep on Frontline’s transatlantic model: seed investing across Europe to help founders raise a Series A and enter the US earlier, and growth investing in the US to help companies expand into Europe with a hands on, concentrated portfolio approach. Brennan breaks down the four pillars Frontline uses to drive international expansion timing, go to market, talent and org design, and location plus the biggest traps founders fall into, like trying to launch in too many markets at once or optimizing for revenue targets instead of learning.
You’ll also hear why the UK and Ireland are the default first step for 97 percent of US companies entering Europe, when Europe becomes a CEO level priority, how relationship driven sales cycles vary across countries, and why developer led community building can beat traditional sales led expansion for certain AI products. Brennan closes with his Big Cojones moment: moving to the Bay Area for a temporary Google job with everything in storage, then doing it again to help build Google’s European HQ in Dublin.
Time Stamps03:14 Brennan’s first investment: Mode Analytics and a lawn mowing business in Texas
06:49 What’s changed at growth stage and why “growth” is a different world
08:30 Why AI enablement came first and app layer is finally ready for Series B plus
10:10 The new risk: fast revenue that’s concentrated and not yet durable
14:22 Frontline’s model: Europe seed plus US growth and why it’s unique
15:58 What Frontline looks for: category leaders and a line of sight to a 5x outcome
16:20 The rough revenue range where growth starts paying attention
23:22 The four pillars of expansion: timing, go to market, talent, location
26:00 Timing: the 10 percent pull, exec maturity, and why waiting too long is risky
29:36 Why Europe expansion has to be a CEO level company priority
38:04 Build or buy: why most companies compete into new markets rather than acquire
39:10 Developer community expansion as a new go to market wedge
41:44 Market selection: why nearly everyone starts with London or Dublin
43:56 “Success amnesia” and why you must optimize for learning not quotas
48:28 Relationship driven sales cycles and how Europe varies market to market
52:43 Big Cojones moment: taking a temp Google job and betting on himself
54:26 Doing it again: moving to Dublin in three weeks to help build Google Europe
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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