Day One®

We're for founders & operators. https://dayone.fm/shows

  1. 5h ago

    Darius Monsef – You're the Number One Consumer of Your Own B******t

    Want to partner with Life After Launch? Explore sponsorship and partnership opportunities at https://lifeafterlaunchpod.com/partner-with-us Darius Monsef has built a color-palette website that grew to millions of users, sold two companies, raised over $40 million for a pediatric healthcare startup, and shut it all down. Twice. He's brutally honest about why. Darius walks through how a joke website for rating color squares became a design resource used by Adobe, how wearing his own branded t-shirt got him into Y Combinator, and how Creative Market sold to Autodesk just 11 months after launch. But the real story is what happened after the money landed: the quiet depression of an exit that wasn't life-changing enough, the $40 million healthcare business that scaled before it had product-market fit, and the moment on a plane, mid-fundraise, when he realised he might be lying to himself and everyone else. He's honest about what it cost to walk away from Brave Care, why he now tells founders to be quitters, and why the businesses that fail teach you more than the ones that limp along for nine years pretending to work. Stick around for his three life lessons: why your health is the input that decides your output, why quitting well matters as much as starting well, and why founders should set goals they can't reach and still call it a win. Time Stamps 00:00 Cold open + welcome to Life After Launch, introducing Darius Monsef 02:16 Growing up in Hawaii, entrepreneurial parents, and the chip on his shoulder 06:48 Building COLOURlovers, the shirt that got him into Y Combinator, and 11 years to "overnight success" 15:27 Creative Market's fast exit to Autodesk, and why the money wasn't enough 21:29 Sightbox, moving to Hawaii, and the depression after doing "nothing" 29:32 Raising $40M for Brave Care, scaling before product-market fit, and the collapse mid-fundraise 40:53 Shutting down Brave Care, then Genie and Rides, and building Pre 50:03 Life lesson 1: treat your health like an athlete's, not an afterthought 55:16 Life lesson 2: be a quitter 59:55 Life lesson 3: push harder than reasonable, then give yourself grace 1:04:33 Closing thoughts + outro

    Darius Monsef – You're the Number One Consumer of Your Own B******t
  2. 23h ago

    Sidecars 101: Why Venture Funds Are Investing on the Side

    Episode SummarySidecars have gone mainstream. Once something mostly associated with larger venture funds, they’re now increasingly common in Australia, with emerging managers using them alongside their first funds and sophisticated LPs increasingly expecting access to them. But what exactly is a sidecar, and why would you use one instead of simply investing directly? In this episode of First Track, Cheryl and Maxine break down sidecars from the ground up: how they differ from co-investments, why LPs use them to double down on companies they’re excited about, and how lower fees and carry can make them attractive to larger investors. They also unpack the less obvious reasons fund managers use sidecars—from getting more capital into high-conviction companies and giving venture-curious investors a way to get reps, to preserving pro rata in follow-on rounds without changing the core strategy of the fund. The conversation gets into opportunity funds, the history of sidecars, and why a vehicle that was once niche is now a standard part of the venture fund playbook. They also dive into the surprisingly complicated world of Australian SPVs, the four main structures available, and the regulatory challenges facing super funds investing in venture. Finally, Cheryl and Maxine look at how the venture ecosystem is evolving, why sidecars are becoming part of the progression from syndicate to fund manager, and what the growing expectations of institutional LPs could mean for the next generation of Australian funds. Time Stamps00:00 – From venture outsider to “everyone is building companies” 01:12 – Why sidecars have suddenly gone mainstream 02:23 – What exactly is a sidecar? 03:14 – Sidecars vs. co-investments 04:12 – The Uber for Cats problem 🐈 05:12 – Why LPs and fund managers use sidecars 05:40 – Doubling down on the companies you love 07:27 – How sidecars can lower fees and carry 08:40 – The paradox of picking winners to average down fees 09:29 – Why sidecars make more sense at growth stage 10:30 – Drafting off someone else’s diligence 11:30 – Follow-on sidecars and pro rata 13:31 – Why competitive rounds make sidecars valuable 14:50 – The admin headache of investing directly 15:05 – Why sidecars can make investing easier 16:02 – The surprising history of opportunity funds 17:25 – When should emerging managers start using sidecars? 19:10 – Why fund managers run sidecars 21:00 – Sidecars, carry and staying disciplined 22:00 – Why sophisticated LPs increasingly expect sidecars 23:10 – SPVs aren’t actually a legal structure 24:10 – The four main Australian SPV structures 25:23 – Why Australia is different from the US 26:00 – The evolution from angel to syndicate to fund 27:08 – The super fund fee problem 28:17 – Should venture be treated differently? 29:11 – The regulatory challenge for Australian venture 30:24 – What happens as Australian funds mature? 31:23 – Why building a fund is still building a company 32:01 – Sidecars 101: did we cover it all? 32:49 – Send us your sidecar questions 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 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. Deel x PX_Script 1 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/

    Sidecars 101: Why Venture Funds Are Investing on the Side
  3. 3d ago

    Benjamin Plummer (Dragonfly Intelligence) on AI's Real Bottleneck, and Why He's Betting on Australia

    Benjamin Plummer has one of the stranger CVs in Australian tech: nine years inside Bridgewater Associates, the world's largest hedge fund, building an AI lab alongside IBM Watson's inventor, scaling a startup he says went from $10M to $160M in revenue in eighteen months as CEO, and now running Dragonfly Intelligence, a firm that buys ordinary services businesses and rebuilds them as AI-native companies from the ground up. This conversation starts with the week ChatGPT tried to cheat its way out of its own safety harness, and what that says about accountability as models get more capable. From there, Ben and Georgie get into why coding has gotten fast while everything around it, deciding what to build, checking it got built right, has become the real bottleneck, why software has spent a decade getting bloated and what an Apple-style, purpose-built alternative could look like, and why locking your business to one model provider is a losing bet. Ben also makes the case for Australia's shot at this moment: not frontier models, but data centers, the application layer, and physical AI, backed by what he estimates is a two trillion dollar services economy that's largely untouched. It closes with Ben's read on who wins and loses as AI reshapes work, and a blunt warning for the services companies still sitting on the sidelines. CHAPTERS 0:00 Cold open 0:51 Welcome to the show 2:16 Sponsor: Deel (pre-roll) 2:36 Hack of the week: the "rambling session" 5:13 Georgie's hack: the NFC nail chip 6:12 When ChatGPT tried to break its own harness 13:14 AI makes coding fast, everything else the bottleneck 15:39 Sponsor: Deel (mid-roll) 18:19 Nine years inside Bridgewater 21:37 Building Elemental Cognition with Watson's inventor 24:26 Scaling Invisible from $10M to $160M 26:06 Why Dragonfly Intelligence 27:59 Spotting "zombie companies" in the AI gold rush 32:10 Why software moats are dying 35:01 Open source, closed source, and not marrying a model 44:26 "Easier to do hard things": Dragonfly's ambition 47:12 The real debate on AI data centers in Australia 52:15 Three bets for Australia beyond frontier models 55:05 Rapid fire: what keeps Ben up, who wins and loses from AI 1:01:30 Outro

    Benjamin Plummer (Dragonfly Intelligence) on AI's Real Bottleneck, and Why He's Betting on Australia
  4. 3d ago

    HealthGPT and What Happens Now AI Is Table Stakes

    A survey of more than 1,800 clinicians across 25 countries found 83% had already adopted AI before their workplace had any governance in place. Healthcare, it turns out, is not just adopting AI. It is being redesigned around it. In the second What the Health Wrap, host Emily Casey is joined by Dr Simon Kos, Global Chief Medical Officer at Heidi, and Dr Janice Tan, GP and General Manager of Clinical Innovation at Bupa, to work through what the fortnight's biggest healthcare stories actually mean. Simon uses Heidi's Pressure Points report to bust some long-held myths. Clinicians are not Luddites; get product-market fit right and they will adopt ahead of their own organisations. Product-led growth is not impossible in healthcare. And the idea that everything must run through a single electronic medical record screen does not survive contact with the reality of shadow AI. Janice agrees, arguing that GPs are among the most innovative professionals there are, and that what matters is not clicks or screens but the value exchange. The conversation turns to where this leaves general practice. Both guests expect voice to become the default way information is entered within two years, freeing clinicians for deeper, more present consultations rather than merely shorter ones. Janice makes the point that scribes save time not to compress the visit but to enrich it. Simon argues that scribes should be commoditised, because they are the entry point to something bigger: infusing evidence and decision support into the flow of care. They also examine what happens when patients bring their own AI into the room. OpenAI's launch of Health in ChatGPT, and the broader move by frontier labs into consumer health, could be the single biggest driver of health equity, filling the gap for people who previously had no care at all. But Simon draws a firm line between consumer-grade and clinical-grade health, pointing to the liability caps some providers attach to their advice and the accountability the medical profession is held to. The regulatory framework for quality and safety is not yet in place, but it is coming fast. Janice explains Bupa's own metamorphosis from health insurer to health organisation, investing heavily in primary and preventive care across medical, dental, optical and psychology clinics, and rolling out AI scribes to its clinicians under strong governance. Simon zooms out to a health system whose old boundaries between payer, provider, acute, primary and consumer care are blurring, driven by digital capability, policy reform and a wave of consolidation. The panel closes on the future of care. They discuss how to equip the next generation of doctors without letting AI become a crutch that erodes clinical judgement, what digital health's US$7.4 billion funding rebound says about capital concentrating into a handful of mega rounds, and why the companies winning big are the ones co-designing with clinicians from day one. Then they imagine the patient journey in 2035, from wellness chairs in autonomous vehicles to consultations that feel, as Janice puts it, more human. GuestsDr Simon Kos is Global Chief Medical Officer at Heidi, the AI clinical documentation company. A physician who practised critical care medicine before moving into digital health, he was previously Global Chief Medical Officer at Microsoft and CEO of Next Practice, and is a long-standing figure in Australian digital health. Dr Janice Tan is a GP and the General Manager of Clinical Innovation at Bupa, where she leads the rollout and piloting of AI solutions across the group's health services. She also advises the RACGP and works to uplift the digital health capability of the GP profession. Chapters00:00 Introducing the What the Health Wrap 00:07 Guest updates: Heidi's global expansion and life in general practice 03:03 The fortnight's five biggest headlines 05:11 Heidi's Pressure Points report: adopting AI ahead of governance 06:16 Busting the myths about clinicians and technology 10:11 Where general practice is heading: voice by default and deeper consults 13:00 Patients are bringing their own AI to the consult 14:21 Health in ChatGPT and big tech's move into consumer health 18:33 Consumer-grade versus clinical-grade care and the regulation gap 23:41 Bupa's shift from health insurer to health company 30:29 Training the next generation without de-skilling 33:43 Digital health's US$7.4 billion funding landscape 35:31 Finding the wedge: co-designing with clinicians 38:46 The 2035 patient journey 42:46 Rapid fire: emojis, surprises and companies to watch Links and resourcesHeidiHeidi's Pressure Points 2026 reportBupa AustraliaBupa's Connected Care strategyBupa to acquire Partnered Health GroupHealth in ChatGPTRock Health H1 2026 funding and market overviewAustralia's ban on genetic discrimination in life insuranceClaude for Healthcare About the hostEmily Casey is the founder of What the Health and host of the What the Health Wrap, making major developments in health technology and innovation easier to understand. The What the Health Wrap is brought to you by What the Health in partnership with Tenmile Ventures. What the Health is part of Day One Network, the podcast and media network from W2D1 Media.

    HealthGPT and What Happens Now AI Is Table Stakes
  5. 5d ago

    How Do You Grow a Marketplace When Both Sides Are Slow? Ishan Dan on RegenX

    Pick My Brain is supported by our wonderful sponsors: 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 Episode Summary Alternative investments can give investors exposure beyond shares and bonds, but most clean-energy projects still come with high minimums, expensive structuring and long, relationship-driven sales cycles. Ishan Dan founded RegenX to help developers make those projects investment-ready and give wholesale investors access at a more practical scale. In this episode of Pick My Brain, Alan Jones helps Ishan confront the hardest part of the model: RegenX is a two-sided marketplace, and neither side moves quickly. Project developers need capital, while wealth managers and family offices need trust, evidence and a reason to pay attention. They unpack how to stop treating both sides as equal growth problems, why one-to-many relationship building can outperform another round of cold outreach, and how a founder becomes the credible industry expert the market needs. Ishan also shares RegenX's fee model, early project pipeline and the regulatory constraints behind raising capital for clean-energy assets. Time Stamps 00:00 – Why RegenX is changing access to alternative investments 01:25 – Welcome to Pick My Brain 02:14 – Ishan's question for Alan 02:54 – From aspiring stockbroker to startup founder 04:40 – What counts as an alternative investment? 05:33 – Making clean-energy projects investment-ready 11:36 – RegenX's first projects and $60 million pipeline 13:13 – The hardest part of raising capital 17:43 – Why two-sided marketplaces are so difficult 24:25 – Trust, relationships and wealth managers 29:06 – Becoming the industry expert 29:43 – Making one side someone else's growth problem 31:34 – Wrap-up Resources - RegenX – https://www.regenx.io/ - Ishan Dan on LinkedIn – https://au.linkedin.com/in/ishandan - Ask Alan a Question – https://speakpipe.com/pickmybrain - More from Alan Jones – https://www.startupfoundercoach.com Pick My Brain is a Day One show hosted by startup founder coach and investor Alan Jones. Mentioned in this episode: Deel x PX_Script 2 Deel x PX_Script 1

  6. 6d ago

    Why "Show Me Your Harness" Beats Any Coding Test: Adam Witanowski, AI Architect

    Most technical interviews still ask a candidate to write a function on a whiteboard. Adam Witanowski says that question is already obsolete, and what should replace it says everything about how AI is changing who gets hired. In this episode of Building Tech Teams, James MacDonald sits down with Adam Witanowski, AI Architect at nib, where he has spent the past several years building the insurer's AI engineering practice from the ground up. They get into why most enterprise AI projects underperform (nobody is measuring the right things), what "back pressure" means for AI-generated code, why Australian salaries can't compete with the US for senior AI talent, and why the technical interview needs a full rebuild. It's a hands-on, practitioner's take on what's actually happening inside enterprise AI teams, not the conference-keynote version. They cover the real dollar gap between hiring an AI engineer in Australia versus the US, why "the whiteboard should come back" as an interview tool, how Adam built his own AI agent to interview for jobs on his behalf, and the testing harness his team uses to check whether AI-generated work is actually any good. CHAPTERS 0:00 - Cold open: the line that explains why most AI investments don't work 0:44 - Who Adam Witanowski is, and why James wanted him on 2:06 - Welcome, and building an AI SDLC from scratch inside a regulated insurer 5:12 - What "back pressure" actually means, and why solo AI coding doesn't scale 10:52 - Startups vs enterprises: re-engineer whole processes, not thin slices 13:24 - Why most companies can't even measure the problem they're trying to solve 17:10 - Software eats the world, and why that makes engineers apex predators 19:44 - Build in-house or buy: the blind spots consulting companies won't tell you 23:57 - Forward deployed engineers, and the rise of the hybrid product-engineer 26:38 - Tangent: his 13-year-old builds an AI auto-aimbot 30:43 - Build, upskill or outsource: the renters, owners and caretakers test 34:18 - What AI talent actually wants beyond a bigger title 38:30 - The real dollar gap: $220K in Australia versus $500K in the US 46:37 - What to actually pay your first AI hire 49:01 - "What you don't measure, you can't change" 51:01 - Redesigning the interview: show me your harness 56:45 - Why the whiteboard should come back 58:38 - Building a harness to test his harness 1:03:46 - He built his own AI agent to interview for him 1:07:28 - Why motivation and taste still beat any technical test 1:12:19 - Apex predator, Jedi, stallion, unicorn: Adam's closing line 1:13:00 - James's takeaway: it's a measurement problem, not a technology problem ABOUT THE GUEST Adam Witanowski is an AI Architect at nib in Sydney, where he has built Prometheus, an integrated suite of agentic AI tools now running in production across the business. He works at the intersection of senior engineering and AI leadership, and has spoken publicly on enterprise AI engineering discipline, including harness design, testing and evals, and AI governance. LINKS Adam Witanowski, NIB · LinkedIn: https://www.linkedin.com/in/witanowski/ James MacDonald, NTP Talent · LinkedIn: https://www.linkedin.com/in/jamesmacdonaldau/ · Site: https://ntptalent.com.au Hosted by James MacDonald, Managing Director of NTP Talent. --- Building Tech Teams is produced by Day One®, trusted partners in the technology space and the production partner behind Blackbird Ventures' Wild Hearts. Sister shows include First Cheque, Oversubscribed and In The Blink of AI. Episodes are cross-promoted across the network.

    Why "Show Me Your Harness" Beats Any Coding Test: Adam Witanowski, AI Architect
  7. Aug 10

    Kirstin Hunter – You're Spending 95% of Your Brain on the Wrong 5%

    Want to partner with Life After Launch? Explore sponsorship and partnership opportunities at https://lifeafterlaunchpod.com/partner-with-us Kirstin Hunter has co-founded a super fund, run a startup accelerator, and now leads Australia's biggest crowdfunding platform. None of it was the plan. She grew up in Tweed Heads folding junk mail for two cents a letterbox, trained to be a doctor, then pivoted through law and consulting before a friend told her the pro bono work she loved was just "the trinkets" propping up a job that made corporations richer. That conversation pushed her into Future Super, where a pitch her co-founders called "absurd" turned into one of Australia's first fossil-fuel-free super funds. She's honest about what came next too: the moment she and her co-founders stopped wanting the same thing, and why leaving felt like leaving a marriage. From there she takes you through Techstars Australia, the funding data project that exposed how badly VCs back women and diverse founders, and how she landed the CEO seat at Birchal, almost by accident. Stick around for the one Revolut stat that makes the case for democratised funding better than any pitch deck could. Time Stamps00:00 Cold open + welcome to Life After Launch 01:14 Introducing Kirstin Hunter 02:16 From junk mail in Tweed Heads to running a $20M student union at 23 09:16 Consulting, "the trinkets," and the leap to Future Super 15:48 Becoming a co-founder and building Australia's fossil-fuel-free super fund 20:39 The co-founder breakdown, and why she walked away 24:54 Techstars, the funding gap for diverse founders, and Funding the Balance 42:27 Landing at Birchal, and the case for crowdfunding 48:06 Closing thoughts + outro

    Kirstin Hunter – You're Spending 95% of Your Brain on the Wrong 5%
  8. Aug 6

    Deel's COO on the AI Agent Writing Its Own Code

    Dan Westgarth has spent 7 years helping build Deel from a contractor invoicing tool into one of the most valuable HR and payroll platforms in the world, and he did it after cutting his teeth as an early operator at Revolut. As COO, he sits across nearly every function the AI conversation touches: finance, sales, engineering, and the sheer operational load of running a company at global scale. In this conversation, Dan gets specific on AI and Ops. He walks through the internal tool that takes a bug ticket, writes the fix, and opens its own pull request for an engineer to review. He talks through what he actually looks for when hiring, and the future of SaaS isn't dead, but there is about to be a lot more competition. We traverse through a funny detour into Dan's own weekend coding habit (his laptop did not enjoy….), a rundown of which AI tool he reaches for and when, and an answer to "what would you build this weekend” Listen for a leading operator's view of AI adoption at scale CHAPTERS 00:00 Cold open, the AI agent that writes its own code 00:46 Show intro, Deel's sponsorship, and what's ahead 02:03 Sponsor break, Deel 02:30 What Deel actually does 03:14 Rapid AI hot takes, finance roles, human oversight, hardware, sports, and the World Cup 09:29 Why Deel keeps winning after seven years 10:00 How the product evolved from contractor invoicing to a full HR platform 11:28 What Dan looks for when hiring 13:06 Leaving Revolut for Deel 14:17 Sponsor break, Deel 14:57 The YC Winter 2019 connection 15:49 Setting targets and building momentum 16:43 Where AI helps the sales team, and where it can't 19:20 Should AI handle your email 21:03 AI meeting assistants, pros and cons 22:53 What makes an A+ engineer in 2026 23:37 Inside DCA, Deel's self-writing code agent 25:55 Breaking into new international markets 28:34 B2C versus B2B expansion 30:16 The cost of not using a platform like Deel 33:01 What keeps Dan up at night about AI agents 33:29 Akai, and scaling operations without growing headcount 36:15 Dan's own weekend coding experiment 37:26 Rapid fire, is the SaaS apocalypse real 39:48 The physical Deel Card and crypto payroll 42:23 What is a stablecoin 43:02 Which AI tools Dan actually reaches for 44:51 If Dan built one AI project this weekend 46:45 Closing thoughts and where to find Dan 47:08 Deel's new Arsenal FC sponsorship 48:41 Georgie's weekly AI newsletter

    Deel's COO on the AI Agent Writing Its Own Code

Trailers

About

We're for founders & operators. https://dayone.fm/shows

More From Day One

You Might Also Like