Day One®

Welcome to the first ever episode of AI Icons, a new thing I'm launching on the show. Here's the idea: the people reshaping tech have stories more entertaining than anything Hollywood is putting out, so in under 30 minutes I'm going to tell you the whole story, the good, the bad, and the ugly, but only the facts. No spin. And at the end, I'll give you my two cents on what actually made them an ico...

Dilip Jacob is the solo founder and CEO of Pitchberry, an AI platform that helps people in high-stakes professions practice the conversations their careers depend on. The idea came from a very personal place: diagnosed with high anxiety, Dilip froze during an investment pitch and went looking for a way to get better. What began as a tool for founders found an unexpected first market in dentistry,...

The business wants AI, and it wants it now. Meanwhile security budgets are flatlining, breaches are becoming a line item, and agents can wander places no one scoped them for. Kevin Akermanis, Solutions Architect at Okta and a 15-year Salesforce veteran, joins James to talk about what actually breaks when you bolt AI onto an enterprise, and why experience is quietly becoming the scarcest asset in t...

Side Stage Ventures and Dealroom have just released the 2026 edition of their landmark report on Australian venture. Grab your copy of the Australia Venture & Startup Report 2026 here: https://www.sidestage.vc/outliers-report-2026 Australia has created more unicorns per dollar of VC invested than anywhere else in the world — and Ben Grabiner has the data to prove it. In this replay, Cheryl and...

Taryn Williams started her first company, Wink Models, at 21 with $30,000 and no roadmap. She didn't stop there. Over the next two decades she built and ran a string of ventures, the talent marketplace The Right Fit (backed by Airtree, scaled to 17,000 talent and 11,000 clients across APAC), The Influencers Agency, the contra-gifting platform #Gifted, the B2B talent business Notable, and Online Mo...

Peter Gostev is head of AI capabilities at Arena (LMArena), the community-based platform where millions of real people vote in blind tests to rank AI models, born out of research at UC Berkeley. Before Arena, Peter was Head of AI at Moonpig and built a large following sharing hands-on explorations of what the latest models can actually do. He joins Georgie Healy from London for a genuinely nerdy,...

The first hire used to be an engineer. Michael Batko thinks that's now backwards — and that's just the start of how AI is rewiring the way you build a tech team. In the first episode of Building Tech Teams , James MacDonald sits down with Michael Batko — who spent eight years as CEO of Startmate backing 240+ startups, and now runs the AI-native venture batko.ai. They get into what actually changes...

Watch this space.

Damian Naughton is the General Manager of ANZ at ElevenLabs, the voice AI company now past US$500 million in ARR, just four years after its 2022 founding. Formerly a regional VP at Slack and an early team member at Sydney's Hyper Anna (acquired by Alteryx), Damian is leading ElevenLabs' new Sydney office and tripling the local team as enterprise demand for voice AI accelerates. In this episode, Da...

Neel Bhattacharya is the founder of LeadTrackAI, a platform built to solve one of the most common and costly problems in sales: leads that go cold because nobody followed up fast enough. After more than a decade in product management across the energy sector, Neel built an AI voice agent that calls a new lead the moment they submit a form, speaks just like a real person, and qualifies them before...

Episode Summary Alex Feldman is the founder of Tiger and Bear, an M&A advisory focused on tech and services businesses. Before that, he was Chief Strategy Officer and General Counsel at Amaysim, where he ran three acquisitions simultaneously during full lockdown in 2020 and 2021 to build a dominant player that was ultimately sold. In this episode, Cheryl and Maxine unpack how to buy and sell b...

Akshay Kothari is the COO and co-founder of Notion, the workspace platform now used by over a hundred million people. Before Notion, he co-founded Pulse, the newsreader app built as a Stanford class project that Steve Jobs name-checked on stage at WWDC 2010 before LinkedIn acquired it. He joined Notion in 2018 when the team was fewer than ten people, and in this conversation with Georgie Healy he...

She raised $4 million just before Christmas, moved out of her marital home inside sixty days, and came back from a two-week break to find an interim CEO appointed and the doors of her own company closed to her. In Part 2 of her Perspective X conversation with Pauline Fetaui, Yas Grigaliunas tells the part founders almost never say out loud: nine months locked out of World's Biggest Garage Sale, wa...

HEO co-founder and CTO Dr Hiranya Jayakody (HJ) started out trying to mine asteroids. Instead, he and co-founder Will Crowe built a way to photograph satellites in space using other people's cameras, pointed one at the International Space Station during COVID lockdown, and got a call from US regulators asking what they'd done. Today HEO runs 7 cameras in orbit and sells space intelligence to gover...

Most people think private messaging is already solved. Chris Fresle is proof it isn't. Chris Fresle is the founder of Just Us, a private messaging app built to prevent image-based abuse. He's a year nine dropout with no tech background, a patent pending across six countries, and a product that uses facial recognition and object detection to make private messages genuinely impossible to screenshot,...

Yas Grigaliunas turned a backyard charity garage sale into Circonomy, one of Australia's most recognised circular-economy companies — years before "circular economy" was even a phrase. In Part 1 of her Perspective X conversation with Pauline Fetaui, she traces the rise: from selling homemade cupcakes at 5am triathlon training and asking herself "how do you raise money without asking people for mon...

Episode Summary Alexey 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 E...

This is a #paidpartnership with Commonwealth Bank Episode Summary Blair 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 click...

"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 produc...

Quinnie Chen is the founder of Profit Plainly, a web app built for solo founders and freelancers who have no finance team, no CFO, and no clear picture of whether their business is actually working for them. Quinnie built it to solve her own problem, after years of running a website and software design business post Canva, she kept reaching the end of the month and realising she had underpriced he...

Episode Summary When 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 le...

Episode Summary In 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 wh...

Episode Summary Every 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 fun...

From policing the streets of Sydney’s King’s Cross to founding one of the world's first enterprise AI companies, Dr. Catriona Wallace has navigated a career arc that defies convention. As one of the few women globally to list an AI company on the ASX, she scaled Flamingo AI to New York and back, all while raising five children and operating on a frontier that barely had a name. But behind the mile...

Tap, beep, done. Australia’s payment experience is one of the world’s most convenient, but also one of the most expensive. Small businesses lose thousands a month in card and scheme fees, while everyday Australians pay hundreds each year just to access their own money. In this episode of Pick My Brain, Gaurav Rana, co-founder of GANI Pay, joins Alan Jones to pitch his mobile-first payment platform...