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We're for founders & operators. https://dayone.fm/shows
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76
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Recent Episodes
July 6, 2026
Guardrails Are Just Suggestions: Securing AI Agents with Okta's Kevin Akermanis
<p>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 tech.</p><p>In this episode:</p><p>- Why "the business says we need to AI now" collides head-on with the teams who have to make it safe, and why pumping the brakes gets you branded the blocker.</p><p>- The uncomfortable finding from a customer security council: security funding is flat or shrinking while every dollar with "AI" in front of it gets funded.</p><p>- How breaches have quietly become "the cost of doing business", and the apathy that creates.</p><p>- Why the old three-tier architecture has collapsed into the model layer, forcing security all the way down to the data level where it never lived before.</p><p>- The new attack surfaces agents open up, including the hiring bot that leaked applicant data through prompt engineering.</p><p>- Why agents are non-human identities that behave nothing like the service accounts we're used to, and why guardrails are "just suggestions" for something non-deterministic.</p><p>- The fix: valet keys not master keys, scoped and time-limited access, token vaulting and traceability, on behalf of a known person for a known context.</p><p>- The junior squeeze: if entry-level roles get automated away, who backfills the seniors when they retire, and why knowing "what good looks like" still can't be vibe-coded.</p><p>- Where an SMB should actually start: internal first, read-only, inside the Microsoft or Google walled garden, and why Australian buyers care more about MCP than agents.</p><p>Kevin Akermanis is a Solutions Architect at Okta, the digital identity and security company behind Auth0, where he works across the Asia Pacific region on identity, security and agentic AI. Before Okta he spent roughly 15 years at Salesforce across pre-sales and an internal CTO role, giving him a rare view from both the selling and buying sides of enterprise tech.</p><p>Building the team that has to make AI safe? This one's for you.</p><p>---</p><p>Episode Summary</p><p>The business wants AI now. The people who have to secure it are being told to move faster while their budgets shrink. Kevin Akermanis, Solutions Architect at Okta and a 15-year Salesforce veteran, sits down with James MacDonald to unpack what really happens when enterprises rush AI into production: security funding flatlining, breaches becoming the cost of doing business, and a collapsed architecture that pushes security down to the data layer. They dig into why AI agents are a new class of non-human identity that can roam anywhere, why guardrails are only suggestions for something non-deterministic, and the scoped, time-limited, valet-key approach that actually contains the risk. They also tackle the harder people problem: if juniors get automated out, who backfills the seniors, and why knowing what good looks like still beats anything you can vibe-code. Practical, sceptical, no hype.</p><p>Time Stamps</p><p>0:00 The business says "we need to AI now"</p><p>2:53 The real tension: speed vs protecting company IP</p><p>7:22 Security budgets shrink while AI gets the money</p><p>11:28 When breaches become the cost of doing business</p><p>13:42 New attack surfaces and the hiring-bot breach</p><p>18:14 Experience still matters: who backfills the seniors?</p><p>46:39 Agents as non-human identities: scope and guardrails</p><p>55:03 Where to start with AI safely</p><p>57:37 Why the Australian market cares about MCP</p><p>About the host</p><p>James MacDonald is the founder and Managing Director of NTP Talent (Newy Tech People), an Australian tech and engineering recruitment firm headquartered in Newcastle with teams in Sydney and Melbourne. He hosts Building Tech Teams, helping companies up the East Coast of Australia find and recruit the best technology talent. Connect with James on LinkedIn (/JamesMacDonaldAU) or at ntp-talent.com.au.</p><p>About Day One Network</p><p>Day One is a podcast production company and trusted partner in the technology space, producing shows for founders, investors and operators across Australia and beyond. Building Tech Teams is part of the Day One Network, which cross-promotes episodes across a slate of technology and venture shows.</p><p>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.</p>
July 4, 2026
Why Australia Builds More Unicorns per Dollar Than Anyone (Replay) | Ben Grabiner, Side Stage Ventures
<p>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: <a href="https://www.sidestage.vc/outliers-report-2026" rel="noopener noreferrer" target="_blank">https://www.sidestage.vc/outliers-report-2026</a></p><p>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 Maxine sit down with the Side Stage Ventures co-founder to unpack why the ecosystem punches so far above its weight, and why the next decade could belong to Aussie tech.</p><p>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.</p><p>It's why more than 40,000 fast-growing companies trust Deel to move fast.</p><p>Visit <a href="https://www.deel.com/dayone" rel="noopener noreferrer" target="_blank">https://www.deel.com/dayone</a></p><p><strong>Episode Summary</strong></p><p>Ben Grabiner is the co-founder and General Partner of Side Stage Ventures and the author of a landmark report, produced with Dealroom and AWS, on Australia's venture ecosystem. Cheryl and Maxine sit down with Ben to unpack the data behind Australia's rise as one of the most efficient and exciting venture ecosystems in the world.</p><p>They dig into why Australia produces more unicorns per dollar of VC invested than anywhere on earth, how the country quietly matches Israel and India on decacorn creation, and why roughly 40% of local seed capital now comes from overseas, a sign global funds see the opportunity more clearly than we do. Ben explains why capital constraints have bred a culture of doing more with less, why fewer than 30 Australian seed funds made more than five investments last year, and what has to change to close the early-stage funding gap.</p><p>You'll also hear why the next wave of second- and third-time founders could be the ecosystem's secret weapon, what global LPs still need to understand about Australian venture, and Ben's own Big Cojones moment: throwing it all in mid-COVID to move from London to Australia.</p><p><strong>Time Stamps</strong></p><p>00:00 - Cold open: more unicorns per dollar than anywhere</p><p>00:52 - Intro</p><p>04:48 - Ben's first investment: 250 pounds in Tottenham Hotspur</p><p>07:01 - The headline stat and what drives Australia's capital efficiency</p><p>09:24 - Why constraints breed efficiency, and why it's good for VCs</p><p>12:31 - Decacorn creation: Australia on par with Israel and India</p><p>14:35 - 40% of seed capital comes from overseas</p><p>16:24 - What needs to happen to close the capital gap</p><p>20:41 - Can startups scale globally from Australia?</p><p>26:14 - What global LPs need to understand about Australian venture</p><p>28:28 - The rise of second- and third-time founders</p><p>30:37 - Why pre-seed funds and angel investors matter more than ever</p><p>34:41 - Ben's Big Cojones moment: moving to Australia mid-COVID</p><p><strong>Resources</strong></p><p>Ben Grabiner on LinkedIn - <a href="https://www.linkedin.com/in/bengrabiner/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/bengrabiner/</a></p><p>Side Stage Ventures - <a href="https://www.sidestage.vc/" rel="noopener noreferrer" target="_blank">https://www.sidestage.vc/</a></p><p>Australia Venture & Startup Report 2026 - <a href="https://www.sidestage.vc/outliers-report-2026" rel="noopener noreferrer" target="_blank">https://www.sidestage.vc/outliers-report-2026</a></p><p>Aussie Angels - <a href="https://www.aussieangels.com/" rel="noopener noreferrer" target="_blank">https://www.aussieangels.com/</a></p><br/><br/>This podcast uses the following third-party services for analysis: <br/><br/>Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp<br/>Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/
July 2, 2026
Taryn Williams: Building and Exiting 6 Companies and the Cost No One Talks About, where humans sit in the creator economy and AI Slop
<p>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 Model Academy, exiting two of them to international acquirers in 2023. Today she sits across boards, invests as an angel, and advises organisations on AI transformation with Think & Grow.</p><p>In this episode Pauline sits down with Taryn for an honest conversation about what it actually costs to build like this: why and how she runs multiple companies at once, why she loves the 0-to-2-year stage and does not want to be the CEO, and the quieter things founders rarely say out loud, the toll on her relationships and health, freezing her eggs at 35 and what she wishes she'd known about fertility, and the mentor question she still works through every day: when is enough, enough? Plus sharp takes on AI, the creator economy, "AI slop", and whether AI will replace human models.</p><p><strong>Time Stamps</strong></p><p>00:00 - Cold open: "I was 21 when I started Wink"</p><p>01:20 - Welcome — meeting Taryn at South Start, and the snapshot of a serial founder</p><p>04:08 - Scouted at 15: modelling as an accidental business education</p><p>06:21 - Starting Wink Models at 21 — fixing a broken, fragmented industry</p><p>09:04 - Building the first tech product (and the trap of gold-plating instead of an MVP)</p><p>12:21 - Launching The Right Fit and raising capital from Airtree</p><p>17:56 - How big Wink and The Right Fit actually grew</p><p>19:34 - Running multiple companies at once — and stepping fully out of Wink</p><p>22:13 - #Gifted, Notable and Online Model Academy: "every year, birth a new child"</p><p>28:27 - Why it isn't "the Taryn Williams show"</p><p>31:37 - The 2023 exits: running a formal process and the transition</p><p>38:56 - The real cost: relationships, health and never being fully switched off</p><p>43:27 - Fertility, freezing eggs at 35, and what no one tells you early enough</p><p>50:15 - From operator to board chair — breaking the habit of being all-in</p><p>54:17 - Why every founder should understand governance (the AICD course)</p><p>56:28 - In the investor seat: what Taryn backs and the founders she looks for</p><p>59:33 - Advising on AI transformation with Think & Grow</p><p>64:56 - AI, creators and the "AI slop" problem</p><p>69:07 - Will AI models replace human talent in advertising?</p><p>73:32 - Dating, connection and AI: why we've lost the resilience for friction</p><p>80:45 - Tying self-worth to success — the question she still works through</p><p>85:16 - One thing she knows to be true that the world hasn't caught up on yet</p><p>87:36 - Close</p><p><strong>Links</strong></p><p>Wink Models — <a href="https://www.winkmodels.com.au" rel="noopener noreferrer" target="_blank">https://www.winkmodels.com.au</a></p><p>Airtree Ventures — <a href="https://www.airtree.vc" rel="noopener noreferrer" target="_blank">https://www.airtree.vc</a></p><p>Think & Grow — <a href="https://www.thinkandgrow.com" rel="noopener noreferrer" target="_blank">https://www.thinkandgrow.com</a></p><p>Australian Institute of Company Directors (AICD) — <a href="https://www.aicd.com.au" rel="noopener noreferrer" target="_blank">https://www.aicd.com.au</a></p><p>Perspective X is produced by Day One — the podcast network for founders, operators and investors — <a href="https://www.dayone.fm" rel="noopener noreferrer" target="_blank">https://www.dayone.fm</a></p><p>Mentioned in this episode:</p><p><strong>Deel x PX_Script 2</strong></p><p><strong>Deel x PX_Script 1</strong></p><p><strong>Day One sting</strong></p>
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