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May 21

Learn how to use AI at its exponential with Anthropic's Head of Platform Engineering

Episode SummaryWhen Katelyn Lesse was leading engineering at Stripe, she noticed everything around her shifting because of AI. So she left, and joined Anthropic. Today she leads platform engineering at one of the most important AI companies in the world, which is why we were so thrilled to host her for Anthropic's first ever interview in Sydney. Katelyn does not lead with technical jargon. She leads with a question every builder needs to sit with right now. Are you building on the exponential, or are you stuck on the linear? Most people, she says, are already further behind than they realise. In this episode she shares the exact framework she uses to think about building in the AI era, why your frustrations with Claude are actually signals you are onto something, and what it really means to be AGI pilled inside Anthropic. Time Stamps00:00 Intro 02:53 AI Hack: Using Claude to Pick Wine 03:42 Katelyn's Background and Path to Anthropic 05:32 Why She Left Stripe to Join Anthropic 11:22 What Building on the Exponential Means 11:48 Why Australia Is a Top AI Market 13:05 Is the Claude Obsession Healthy? 15:20 The Framework for Building AI Products 16:38 Why Evals Are Non-Negotiable 18:18 Inside Anthropic's Developer Platform 20:11 What Is Harness Engineering? 25:13 AI Security, Sandboxes and Human in the Loop 29:09 Cloud Managed Agents Explained 31:56 Open Source MCP vs Closed Claude 33:48 How AI Is Changing Engineering Teams 36:24 How to Choose the Right AI Coding Tool 39:12 The End of the Traditional Tech Team 44:30 The AI Magic Moment Everyone Remembers 45:30 What It Means to Be AGI Pilled 47:21 Rapid Fire With Anthropic 49:56 Advice for Developers Building With AI In the Blink of AI is made possible by our wonderful partnersDeelFounders 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 ✨ 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

May 21

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52 min
06/08/2025

How Paul Stovell Built Octopus Deploy to $100M by Ignoring Silicon Valley’s Rules

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey Episode SummaryPaul Stovell, founder and CEO of Octopus Deploy, shares his journey from coding side projects in a Brisbane library to building a $100M+ ARR global business in the competitive world of DevOps. Paul reveals how a relentless focus on product excellence, profitability, and customer value enabled Octopus Deploy to scale without relying on constant investor funding, becoming one of Australia’s most successful software companies. He delves into the benefits (and pitfalls) of building with transparency, why he rejected Silicon Valley’s growth-at-all-costs mindset, and how he structured Octopus Deploy for sustainable, long-term growth. Paul also unpacks the personal challenges of balancing family, co-founding with his wife, and maintaining passion for building, plus why he’s still at the helm despite the inevitable burnout moments. If you’re a founder, operator, or investor curious about bootstrapping vs. fundraising, scaling a product-led SaaS, or maintaining healthy relationships while building an empire, this episode is packed with raw insights. Time Stamps02:20 – Building Octopus Deploy: From Brisbane library to $100M ARR 05:00 – Bootstrapping and turning down a $400K early acquisition offer 08:30 – Co-founding with your spouse: Paul and Sonya’s partnership story 12:10 – Creating a contrarian culture: Remote-first before it was trendy 15:45 – How Australia’s startup ecosystem evolved from 2012 to today 20:30 – Becoming profitable from day one: The mindset behind sustainable growth 26:00 – Facing down Microsoft: Pivoting to survive industry giants 31:10 – Why transparency and building publicly were key growth levers 36:50 – Scaling to 100 employees without losing the original vision 43:00 – Raising $172M from Insight Partners (without needing the money) 50:10 – The realities of taking on investors: How Paul views venture capital 57:00 – Navigating burnout and founder stress while scaling globally 01:04:20 – Hiring mistakes, culture clashes, and leadership lessons learned 01:12:45 – Goal-setting without rigid KPIs: Paul’s unconventional strategy 01:22:00 – Personal life balance: Family, renovating classic cars, and keeping perspective 01:29:30 – What’s next for Octopus Deploy: Staying independent and profitable Resources Mentioned🐙 Octopus Deploy – https://octopus.com 📖 Octopus Public Handbook – https://handbook.octopus.com 📊 Octopus Investor Relations – https://ir.octopus.com 👤 Paul Stovell’s LinkedIn – https://www.linkedin.com/in/paulstovell Sponsors:Perspective X is supported by our wonderful sponsors:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone Perspective X 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 Perspective X episodes and upcoming shows. Mentioned in this episode: Deel x PX_Script 1 Mighty Partners_PX_May 2025 Vanta_PX_May 2025

06/08/2025

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1h 39m
6d ago

Building AI at Scale: Inside Australia's Largest Bank with Blair Hudson

This is a #paidpartnership with Commonwealth Bank Episode SummaryBlair is the Chief Engineer of Generative AI at Commonwealth Bank, overseeing nine to ten teams building the AI platform that powers Australia’s largest bank and its millions of customers. Including me, a Dollar Mite since primary school. His origin story is not what you would expect. He was a self-described hacker who grew up clicking through every system configuration setting he could find on his mum’s school computers after hours. That curiosity took him from building on GPT-2 before ChatGPT even existed, to the heart of one of Australia’s most important institutions. In this episode we get into: The litmus test he uses to spot bad AI use immediatelyWhy context matters more than promptingWhat an AI platform actually is and why your company probably needs oneWhy software engineers need to take more accountability for what they buildThe single security mistake most people are still makingWhy it is absolutely not too late to figure AI out for yourself Practical, candid, and full of things you can action today. Time Stamps00:00 Intro 03:05 What Does a Chief Engineer of AI at a Bank Actually Do 06:02 How CBA Collaborates Across Hundreds of Engineering Teams 08:56 How to Keep Up With AI Tools Without Getting Overwhelmed 12:04 Why Tool Consistency Matters in Enterprise AI 14:56 Why Blair Shares His AI Insights Publicly 17:51 What Being a Hacker Really Means in Tech 20:50 How Blair Hudson Went From Startup AI to Commonwealth Bank 23:59 Why CBA Starts Every Sprint With a Real Customer Call 27:06 Why Over-Engineering Is Killing Your AI Projects 29:47 Where AI Is Actually Moving the Needle in Banking Right Now 32:15 Why the Year of the Agent Was Overhyped 34:41 How to Build AI Fast Without Cutting Corners on Safety 39:28 What Is an AI Platform and Why Does Your Company Need One 41:49 How CBA Handles Shadow AI and Tool Adoption at Scale 45:09 Why Context Is More Important Than Prompting 50:29 The Number One Security Mistake You Are Still Making 52:30 The Easiest Way to Start Using AI to Save Time Today 54:05 Why You Should Never Ship AI Output Without Reviewing It 55:38 Why It Is Not Too Late to Learn AI In the Blink of AI is made possible by our wonderful partnersDeelFounders 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 ✨ 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

6d ago

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1 hr
May 28

You Can. But Should You? | AI and Ethics with Dr Simon Longstaff

"Can does not imply should." That one line from Dr Simon Longstaff cuts to the heart of everything wrong with how the tech industry is currently building AI. The Executive Director of The Ethics Centre and one of Australia's most respected moral philosophers joins Georgie for a conversation that is equal parts grounding and mind-expanding, and one of the most important episodes the show has produced. Simon's path to becoming Australia's foremost ethics expert is not what you would expect. He left school at 16, cleaned toilets on a remote island in the Gulf of Carpentaria, drove ambulances, became a paramedic and fire officer, and was eventually adopted by one of the clans of the Anindilyakwa people. It was at the end of a ship loading wharf that an indigenous elder taught him something about seeing patterns in the world, a lesson he has carried through 35 years of philosophical work and only recently realised had shaped everything. In this episode he unpacks why ethics is not an optional extra bolted onto technology but the foundation it has to be built on, why the pharmaceutical approval model could be the blueprint for governing AI, and why "necessary fictions" mean that CEOs deploying AI are responsible for outcomes they literally cannot understand. He also makes the case that the coming wave of job displacement does not have to be a catastrophe, and explains what ancient Athens and pre-colonial Indigenous life have to do with universal basic income. In the Blink of AI is made possible by our wonderful partnersDeelFounders 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 ✨ 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

May 28

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59 min
3d ago

How to Think About Equity as a Startup Employee

Episode SummaryAlexey Mitko is a partner at Co-Ventures, the architect behind Eucalyptus' ESOP plan, and widely known in the Australian ecosystem as "ESOP Guy." He was around employee number twenty at Canva and one of the early employees at Koala, giving him a front-row seat to three of Australia's biggest consumer tech outcomes. In this episode, Cheryl and Maxine unpack how Alexey designed the ESOP plan that led to roughly $300 million distributed back to Eucalyptus employees, the largest ESOP payout in Australian history. He walks through the three questions every founder faces but rarely verbalises: who gets equity, how much, and why you have an ESOP plan in the first place. You'll also hear how he modelled allocation across multiple rounds and hundreds of hires to avoid giving too much away early, why he personally walked the first two hundred employees through their equity, and why Australia's lack of a secondary market keeps ESOP feeling like monopoly money. Alexey closes with his Big Cojones moment: proposing to his wife, the most nervous he's ever been despite having climbed Europe's highest mountain. Time Stamps00:00 – Intro 03:01 – The three ESOP questions every founder needs to answer 05:58 – How to model equity allocation across rounds and hundreds of hires 09:10 – Using ESOP as your most powerful recruitment and retention tool 12:02 – How walking 200 employees through their equity built culture and trust 15:02 – Open financials, shrinking cash balances, and what went wrong along the way 17:55 – Why Australia's ESOP ecosystem is still behind Silicon Valley 26:48 – Teaching employees to understand equity: the Google Sheet that started at zero 29:20 – High salary vs heavy equity: giving employees a real choice 32:16 – Common ESOP mistakes founders make and how to avoid them 35:03 – Why Australians treat startup equity like monopoly money 39:11 – The secondary market problem: why liquidity changes everything for ESOP 43:25 – Why your startup career is a portfolio of equity bets 46:36 – What angel investors can do to help portfolio companies build better ESOP plans Sponsors:First Cheque is supported by our wonderful sponsors:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone ___ Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman. As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs. The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business. As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/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 Deel x PX_Script 2 Pear Tree If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost. Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business. As a Day One listener, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

3d ago

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50 min
May 14

What AI Is Actually Changing in Cyber and How to Keep Up

Episode SummaryEvery role in cybersecurity is changing fast, but most practitioners are still treating AI like a glorified search engine. In this solo episode of Secured, Cole Cornford shares his unfiltered take on three things on his mind right now: entrepreneurship in a tough market, the growing threat to SaaS product businesses from roll your own culture, and why the cyber industry needs a fundamentally different approach to AI. Cole makes the case that saying "hey Claude" is the least effective way to work with AI today, and that the real conversation has nothing to do with which model you pick. It is about how you interact with it, how you build a harness around it, and how you stop letting third party wrappers make all the decisions for you. He also shares early thinking on an AI course he is building for security professionals, covering AI fundamentals, using AI for security, and securing AI products. Along the way he tackles the rule of three as a framework for prioritising in a small business, why product moats are disappearing fast, and what qualities he is actually looking for when hiring graduates in a market where everyone is cutting them. Timestamps00:00 Trailer 01:01 Chainguard ad 01:28 Intro and today's three topics 02:30 Entrepreneurship in a tough market 04:30 The rule of three and how Cole runs his business 07:00 Why SaaS product moats are disappearing 10:00 Roll your own vs buying commercial security tools 13:30 When rolling your own actually makes sense 16:00 Cash flow warning for Australian business owners 18:00 Why Cole is building an AI course for security professionals 21:00 Models vs harnesses and why most people get this wrong 24:00 How the cyber industry needs to change its approach to AI 27:00 What Cole looks for when hiring graduates right now 30:00 Systems thinking, humanities and the skills that still matter 33:00 Grandma's pot and questioning everything you think you know 35:00 Closing thoughts 🐙 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 Secured 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: Call for Feedback This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

May 14

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29 min
May 17

How to Pick Pre-Seed Winners Before There's Any Data

Episode SummaryIn this 101 episode, Cheryl and Maxine go deep on the fundamentals of pre-seed investing, from how the stage came to exist to why the perceived risk gap between pre-seed and seed is much smaller than most investors think. They break down the history of how venture stages evolved from single rounds to alphabetized series, how seed investors eventually got pushed up the stack, and why pre-seed emerged around 2017 to 2019 as a distinct category. They unpack why PitchBook's definition of pre-seed as "whatever the investor calls it" muddies the water, how seed preempts from larger funds are inflating average valuations, and why thinking in risk stages rather than round labels is a better framework for evaluating early companies. You'll also hear why graduation rates from pre-seed to seed don't support the idea that pre-seed is two to three times riskier, why the Australian ecosystem is sitting on a talent surplus with a capital gap at pre-seed, and why this stage is particularly well suited for angels building diversified portfolios of 20 to 40 companies. Cheryl shares her framework for evaluating pre-seed opportunities through the lens of problem pain, frequency, and market size, and Maxine walks through how to think about return profiles, dilution, and valuation at a stage where there are no outputs to measure. Time Stamps00:00 Intro 01:56 – A brief history of venture stages: how pre-seed became a thing 07:14 – Why round labels are broken and risk stages are a better framework 09:23 – Seed preempts: how big funds are blurring the line between pre-seed and seed 11:48 – Is pre-seed actually riskier than seed? The case that it's not 16:41 – Graduation rates: what the data says about pre-seed to seed conversion 22:59 – Valuation dynamics: what pre-seed rounds look like in Australia vs the US 28:36 – Why Australian founders are leaving for the US at pre-seed and what that means 31:29 – How to evaluate pre-seed companies: inputs over outputs 35:05 – Cheryl's pain framework: frequency, intensity, and willingness to pay 38:28 – Why pre-seed is the best stage for diversifying who gets funded 43:44 – The AI revenue problem: why getting in early matters more than ever Sponsors:First Cheque is supported by our wonderful sponsors:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone ___ Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman. As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs. The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business. As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/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. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

May 17

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47 min
Apr 16

How to Stop Your AI Agents From Breaking with Josh Clemm, VP of Engineering at Dropbox

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey Josh Clemm, VP of Engineering at Dropbox, joins Georgie Healy to cut through the noise and get to what is actually happening with AI agents right now. Josh has scaled engineering teams at LinkedIn and Uber Eats, founded his own AI venture, and is now building Dash, Dropbox's context layer designed to make agents dramatically more reliable. This is someone who has been on the coalface of this technology longer than most. In this episode Josh introduces two ideas that will change how you think about AI at work. Context rot, the reason your large language models quietly get dumber the more information you give them. And work slop, the plausible sounding but completely hollow output that gets generated when AI tools are used without intention. He also delivers the most reassuring reality check of the year for anyone feeling overwhelmed by the idea that everyone already has a fully functioning team of AI agents working for them. They also get into how the index approach behind Dash solves what real time fetching cannot, why the next AI breakthrough might actually come from old fashioned software engineering principles, and the two engineers Josh considers the greatest builders of their generation and why neither of them was asked to build what they built. ✨ 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

Apr 16

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1 hr
May 21

Learn how to use AI at its exponential with Anthropic's Head of Platform Engineering

Episode SummaryWhen Katelyn Lesse was leading engineering at Stripe, she noticed everything around her shifting because of AI. So she left, and joined Anthropic. Today she leads platform engineering at one of the most important AI companies in the world, which is why we were so thrilled to host her for Anthropic's first ever interview in Sydney. Katelyn does not lead with technical jargon. She leads with a question every builder needs to sit with right now. Are you building on the exponential, or are you stuck on the linear? Most people, she says, are already further behind than they realise. In this episode she shares the exact framework she uses to think about building in the AI era, why your frustrations with Claude are actually signals you are onto something, and what it really means to be AGI pilled inside Anthropic. Time Stamps00:00 Intro 02:53 AI Hack: Using Claude to Pick Wine 03:42 Katelyn's Background and Path to Anthropic 05:32 Why She Left Stripe to Join Anthropic 11:22 What Building on the Exponential Means 11:48 Why Australia Is a Top AI Market 13:05 Is the Claude Obsession Healthy? 15:20 The Framework for Building AI Products 16:38 Why Evals Are Non-Negotiable 18:18 Inside Anthropic's Developer Platform 20:11 What Is Harness Engineering? 25:13 AI Security, Sandboxes and Human in the Loop 29:09 Cloud Managed Agents Explained 31:56 Open Source MCP vs Closed Claude 33:48 How AI Is Changing Engineering Teams 36:24 How to Choose the Right AI Coding Tool 39:12 The End of the Traditional Tech Team 44:30 The AI Magic Moment Everyone Remembers 45:30 What It Means to Be AGI Pilled 47:21 Rapid Fire With Anthropic 49:56 Advice for Developers Building With AI In the Blink of AI is made possible by our wonderful partnersDeelFounders 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 ✨ 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

May 21

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52 min
05/04/2025

How Pocket Sun Built SoGal from Angel Checks to Institutional Fund

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey Episode SummaryPocket 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. Time Stamps00:00 – 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 Resources🙋‍♀️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/ Sponsors:First Cheque is supported by our wonderful sponsors:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone ___ Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman. As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs. The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business. As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/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 FC Vanta Ad March 2025_02 FC Vanta Ad March 2025_02 This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

05/04/2025

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1h 5m

Day One®, the podcast network dedicated to founders, investors, and operators.