Startup Theatre Podcast

Why is government so bad at adopting new technology? And what would it take for New Zealand to build an economy where tech and startups sit alongside our traditional industries?

This week, Serge Van Dam sits down with Wellington Mayor and former Cabinet Minister Andrew Little for a wide-ranging conversation about government, technology, risk and the future of New Zealand’s economy.

Andrew gives an unusually candid view from inside government, including why the public sector is so risk-averse, why agencies gravitate towards large consulting firms and established technology providers, and why Kiwi startups can sometimes find it easier to win government customers overseas than at home.

They also explore Wellington’s opportunity to become a genuine global startup city. Andrew lays out an ambition for 100 new startups a year, more globally significant technology companies, and a city where tech becomes a fundamental part of Wellington’s economic identity.

The conversation covers AI inside local government, the $600,000 council website controversy, legacy technology in healthcare, procurement incentives, New Zealand’s “weightless economy”, and why political leaders struggle to articulate a compelling vision for a modern technology-driven economy.

Plus, Andrew reflects on leadership, failure, resilience, his own technology literacy, what he admires about entrepreneurs, and whether he might ever invest in a startup himself.

A fascinating conversation about what happens when politics, government and startups collide — and what New Zealand needs to do differently if technology is going to help drive the next chapter of our economy.

Startup Theatre is hosted by Troy Hammond, Serge Van Dam and Adrienne Muir.

This episode is brought to you by Maximus — an AI-powered go-to-market agency for B2B companies. Find out more at MaximusGTM.com.

Why is government so bad at adopting new technology? And what would it take for New Zealand to build an economy where tech and startups sit alongside our traditional industries?

This week, Serge Van Dam sits down with Wellington Mayor and former Cabinet Minister Andrew Little for a wide-ranging conversation about government, technology, risk and the future of New Zealand’s economy.

Andrew gives an unusually candid view from inside government, including why the public sector is so risk-averse, why agencies gravitate towards large consulting firms and established technology providers, and why Kiwi startups can sometimes find it easier to win government customers overseas than at home.

They also explore Wellington’s opportunity to become a genuine global startup city. Andrew lays out an ambition for 100 new startups a year, more globally significant technology companies, and a city where tech becomes a fundamental part of Wellington’s economic identity.

The conversation covers AI inside local government, the $600,000 council website controversy, legacy technology in healthcare, procurement incentives, New Zealand’s “weightless economy”, and why political leaders struggle to articulate a compelling vision for a modern technology-driven economy.

Plus, Andrew reflects on leadership, failure, resilience, his own technology literacy, what he admires about entrepreneurs, and whether he might ever invest in a startup himself.

A fascinating conversation about what happens when politics, government and startups collide — and what New Zealand needs to do differently if technology is going to help drive the next chapter of our economy.

Startup Theatre is hosted by Troy Hammond, Serge Van Dam and Adrienne Muir.

This episode is brought to you by Maximus — an AI-powered go-to-market agency for B2B companies. Find out more at https://maximusgtm.com/

How do you build and sell an AI startup in under two years?

In this episode of Startup Theatre, Troy Hammond, Serge Van Dam and Adrian Muir sit down with Jessica Venning-Bryan, CEO and Co-founder of Factor, fresh off the company's acquisition by NZX-listed Gentrack.

Jessica shares the incredible journey from identifying a major problem in the global energy industry to building an AI-powered SaaS platform that was acquired in record time. She also opens up about founder relationships, raising capital, leadership, work-life balance, and why your career doesn't have to follow a straight line.

In this episode we cover:

• How Factor was built and acquired by Gentrack
• The fastest startup exits in New Zealand
• Finding billion-dollar problems hiding in plain sight
• Building AI products for the energy sector
• How to prepare your startup for acquisition
• Due diligence lessons every founder should know
• Why founder relationships matter
• Raising venture capital as a female founder
• Leadership, motherhood, and entrepreneurship
• Why careers should be "jungle gyms", not ladders

• Critical thinking, AI, and the future of education
• What Jessica would build next

Whether you're building a startup, investing in technology, leading a team, or dreaming of your first exit, this episode is packed with practical lessons from one of New Zealand's most impressive founders.

🎧 Subscribe for more conversations with founders, investors and operators building the future.

This podcast was brought to you by Oxygen Advisors

Oxygen Advisors is New Zealand's leading outsourced finance partner for startups and high-growth businesses, providing accounting, bookkeeping, tax, CFO, payroll and revenue operations services to help founders scale with confidence. Learn more at www.oxygenadvisors.co.nz.

#StartupTheatre #JessicaVenningBryan #Factor #Gentrack #Startup #AI #SaaS #Founder #Entrepreneurship #TechNZ #WomenInTech #StartupExit

Sacha Judd, Co-founder and COO of Lume Music, joins Startup Theatre to discuss the future of music, creator monetisation, and building a startup in one of the world’s toughest industries.

We explore why the traditional music industry model is failing independent artists, how streaming platforms changed the economics of music, and why creator-owned communities could become the future.

Sacha shares the story behind Lume Music and the company’s mission to help artists grow audiences, connect directly with fans, and build sustainable careers.

Topics include:

• Music-tech startups
• Creator monetisation
• AI and the future of music
• Independent artists and streaming platforms
• Startup growth and entrepreneurship
• Fan communities and creator ownership
• Building disruptive technology businesses

Hosted by Troy Hammond and Adrienne Muir on Startup Theatre.

Jamie Beaton, founder of Crimson Education, joins Startup Theatre for a wide-ranging conversation on ambition, AI, education, startups, and the future of New Zealand.

Jamie shares his journey from New Zealand student to Harvard and Yale, building Crimson Education into a global company, and why elite universities still matter in an AI-driven world.

We discuss:

• Why top universities are becoming more competitive
• AI’s impact on careers and education
• Whether SaaS is dead
• Why New Zealand struggles with ambition
• Charter schools and fixing education
• Debate, entrepreneurship, and critical thinking
• The future of startups and talent in NZ
• Free speech and modern universities
• What parents should focus on right now

One of the most intellectually honest and thought-provoking Startup Theatre episodes yet.

Hosted by Troy Hammond and Serge Van Dam.

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.