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.

Alexander Fala is the kind of leader who has seen the best and worst of startup life up close, and learned how to keep moving anyway.

In this episode of Startup Theatre, Troy Hammond sits down with Alex, former Vend CEO, Rhodes Scholar, ex McKinsey, and a trusted coach to CEOs across Aotearoa. They unpack what happens when the stakes get real: a capital raise nearly collapsing, lawsuits landing mid deal, revenue shocks that threaten liquidation, and the loneliness that comes with being the person ultimately accountable.

Alex shares hard-earned lessons on board dynamics, making the “right decision not the easy one”, building talent density, sharpening strategy after product-market fit, and why writing is still one of the most underrated leadership tools. They also talk about purpose, identity, and how we tell a better story about tech so more Māori and Pacific talent can see themselves in it.

If you’re building, scaling, raising, or simply trying to lead with clarity under pressure, this one’s for you.

Before the 100th episode of Startup Theatre with Rod Drury, we brought the community together in Queenstown for a live fireside series with founders, operators, investors, and ecosystem builders from across New Zealand.

In front of a live audience, we explored what really happens behind the scenes of building companies – from validating an idea and surviving early mistakes, to scaling teams, raising capital, hiring well, and knowing when to step aside as a founder.

You’ll hear from founders at different stages, SaaS and non-SaaS alike, alongside the people who quietly support the ecosystem every day – investors, advisors, operators, and community leaders.

This episode captures the honesty, humour, and reality of startup life, complete with live reactions, tough lessons, and practical insights for anyone building, backing, or thinking about starting a company.

Moderated by our own Adrienne Muir & Troy Hammond

Fireside chat panel (Founders):

• Rob Stirling – Scannable

• Melissa Jenner – ACTVO

• Heidi Farren – Tourism Innovation Group (TIG)

• Stuart McLean – EverCommerce

Ecosystem supporters panel:

• Peter Fullerton-Smith – Mountain Club

• Alison Meredith – Startup Queenstown Lakes

• Anand Reddy – PwC New Zealand

• Kimberley Gilmour – Sprinklr NZ

Proudly supported by PwC, long-standing champions of New Zealand’s tech and startup ecosystem.

Want a free discovery session with PwC?

Head to 👉🏻 https://www.pwc.co.nz/services/private-business/startup-theatre.html

Special thanks to our supporter sponsor in Startup Queenstown Lakes⁠

A New Zealand insuretech startup thought they’d cracked the US market, until a Fortune 500 incumbent sued them “out of the blue”.

In this episode of Startup Theatre, Serge Van Damme speaks with former Montoux co-CEOs Shelley Cox and Klaas Stijnen about what it’s like to be hit with major IP allegations in the US, how quickly litigation can choke a startup’s ability to sell or raise, and why their realistic options became: fight, sell, or liquidate.

They share the moment they discovered the filing, the impact on customers and staff, the decision to appoint a liquidator in New Zealand, and what’s happening now in the High Court, including the dispute over whether the liquidator can sell assets while proceedings continue.

You’ll also hear practical lessons for founders going into litigious markets: understanding incumbent behaviour, thinking about legal risk as a board-level issue, and why insurance and jurisdiction matter more than most startups assume.

You will hear:

• The moment Shelley found out through an email offering representation, nearly marked it as spam, then googled and saw “FIS versus Montoux” had been filed
• Why a US lawsuit is an incredibly effective way to stifle a startup, regardless of motivation, because defence costs and commercial impact hit at the same time
• What Montoux actually built for life insurers, why actuarial models matter, and what it felt like when they believed they had “cracked it” with major customer momentum
• The three brutal options they had: fight, sell, or liquidate, and why “fight” became financially non-viable fast
• How staff reacted to being implicitly accused of wrongdoing, and what it is like to have no playbook for something this serious
• What liquidation actually means, what a liquidator is required to do, and why the timeline moved so quickly
• The NZ High Court injunction hearing over whether the liquidator can sell assets while the case continues, and why it felt so cold and detached from the humans behind the business
• Hard lessons for founders entering litigious markets: treating legal risk as a board-level topic, reviewing insurance properly, and researching an incumbent’s litigation posture before you enter their space

Startups in the Spotlight: three Kiwi insuretechs going global, PolicyCheck, Simfuni, and Javln.

Sponsor: This episode is brought to you by Vanta. If you are starting or scaling your security programme, Vanta automates compliance for ISO 27001, SOC 2, and more.

Get USD $1,000 off at: ⁠vanta.com/startuptheater⁠

This episode discusses allegations and an ongoing legal dispute. We’re sharing the guest’s perspective and our commentary. Any claims mentioned are allegations only, not findings of fact. Nothing in this episode is legal advice, and we’ll avoid speculating on matters before the courts.