Startup Theatre Podcast

In this episode of Startup Theatre, Troy Hammond and Serge Van Dam sit down with Simon Archer, founder of PolicyCheck, to unpack one of the biggest untapped problems in global fintech: understanding insurance.
Simon shares the story behind leaving a successful corporate career to build in the AI era, driven by a simple but powerful realisation. He had already missed one major wave and wasn’t going to miss the next.
The conversation moves beyond the typical startup narrative into something more grounded. What actually happens when you leave corporate? Why most founders aren’t prepared, no matter how much theory they consume, and how building with AI is fundamentally changing how companies are created.
At the core of the episode is a problem most people have experienced but rarely question. Insurance is a promise, yet billions in claims are denied each year because people don’t fully understand what they’ve signed up for . PolicyCheck is taking a data-first approach to fix that.
They also get into:
Why workflow products are becoming obsolete and data is the real opportunity
The shift to lean teams and shared product ownership
Building in New Zealand versus Australia
The reality of incubators in an AI-first world
What it actually takes to build a globally relevant company from NZ
This is a conversation about timing, conviction, and solving problems that genuinely matter.
Links:
PolicyCheck: https://policycheck.com
Simon Archer: https://linkedin.com/in/simonarcher

Is software engineering already dead?
In this episode of Startup Theatre, Troy & Serge sit down with Nik Wakelin the co-founder of Sterling.
They unpack what AI is actually doing to engineering, startups, and how work gets done.
This isn’t the usual “AI will replace everyone” narrative.
Nik breaks down why we’re not seeing job collapse — we’re seeing something far more important: task collapse.
We get into:
• why software engineering is already changing
• what “task collapse” actually means
• why highly capable people are still doing low-value work
• how AI creates massive leverage for builders
• why the best operators will get exponentially better
• what founders and engineers should be doing right now
If you’re in tech, building a startup, or thinking about how AI impacts your role, this episode will change how you think about the future of work.
Startup Theatre explores the real shifts happening in startups, technology, and how companies are being built today.
Checkout Sterling 👉🏻 https://histerling.com/

Building a startup isn’t what most people think.
In this episode of Startup Theatre, Adrienne & Serge sit down with Martyn Bain to talk about the reality of building a global company from New Zealand — and the moments that nearly break you.
From leaving corporate after a defining moment at home, to chasing international deals, to being days away from signing something that could have changed everything… only for it to fall apart.
We get into:
• the moment that pushed Martyn to leave corporate
• why early customers say yes… but don’t commit
• the brutal reality of enterprise sales
• why “signed contracts” don’t mean what you think
• how deals fall over at the last minute
• what it actually takes to build and scale globally from NZ
This is a raw look at the pressure, setbacks, and persistence behind building a real company.
If you’re a founder, operator, or thinking about starting something, this episode will give you a far more honest picture of the journey.
Startup Theatre explores the real stories behind startups — not just the wins, but everything in between.

AI is changing how startups are built.
In this episode of Startup Theatre, Troy Hammond sits down with Toby Cox, founder of Geodde and former Partner & CTO of Paloma (Dovetail), to talk about why he walked away from leading large engineering teams to build an AI startup completely solo.
After years scaling companies and managing teams of more than 100 engineers, Toby is now running an experiment: building a company with almost no team and using AI agents to do much of the work.
We discuss:
• Why experienced CTOs are leaving leadership roles to build with AI
• How AI coding agents are replacing the work of junior engineers
• Whether “solo unicorn” companies are now possible
• How startups can influence what ChatGPT, Claude, and Gemini say about their business
• Why venture capital may not be required to start a company anymore
Toby also shares the thinking behind Geodde, a platform helping companies monitor and shape how their brand appears inside AI tools.
If you're a founder, builder, investor, or curious about where startups are heading next, this conversation explores how AI may reshape how companies are built.
Startup Theatre explores the real stories behind startups, founders, and the evolving tech ecosystem.

John Mitchell didn’t start in tech. He started with a sewing machine in his parents’ basement.
In this episode of Startup Theatre, the Arlo founder shares the full journey from bootstrapped beginnings in Wellington to building a global SaaS platform operating in 70 countries and processing over half a billion dollars in training transactions each year.
John talks openly about:
• Raising his first $1M and then closing just one deal in three months• Hiring mistakes that nearly stalled growth• How Arlo survived when COVID shut down face-to-face training overnight• Why “being found” beat outbound sales• Building a team strong enough to step out of the CEO seat• What AI and vibe coding mean for the next generation of founders
This is a practical, honest conversation about scaling SaaS from New Zealand to the world, navigating pressure after funding, and knowing when to evolve as a founder.
If you're building, raising, pivoting, or questioning your next move, this episode is for you.