Moments that changed my thinking

Moments that changed my thinking. What happened. What decision mattered. What changed.

Early drones

What happened: From 2002 I worked on drone autopilots — Paparazzi TWOG (2008, still have it), then OpenPilot CopterControl — among the first consumer boards combining a 32-bit STM32, gyros, and accelerometers. Years before consumer drones existed.
What decision mattered: Stay with hard technical problems long enough to understand them, even when the market does not exist yet.
What changed how I think: I learned when to trust technical intuition on an uncertain timeline — and when to leave because the work no longer matched the goal.

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Engineering and manufacturing

What happened: Years on factory floors and workbenches — large servo builds, robotic prototypes, hardware that either worked or failed in plain sight before I ran companies that depended on it.
What decision mattered: Build the thing yourself once before you outsource the judgment about it.
What changed how I think: Small failures ignored long enough become catastrophic. I saw that pattern first in hardware, then in companies.

Reddog Technology

What happened: Jason Rudolph and I built Reddog from late 2002 — flat monthly fee, unlimited support, IT department as a service before the category existed. National expansion around 2008, international around 2009. Sold to every customer in 2017 rather than as a going concern.
What decision mattered: Align provider incentives with customer reliability — if Reddog bore the cost of failure, reliability became the business model.
What changed how I think: Misaligned incentives explain most IT problems. Business model design matters as much as product design.

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Selling Reddog

What happened: After fifteen years we sold Reddog Technology in 2017 — not as a going concern, but to every customer who bought their equipment and documentation.
What decision mattered: Exit when the model is proven and the next owner can take it further, not when you are exhausted.
What changed how I think: Building and exiting taught me that timing an exit is a decision like any other — it has a window.

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Professional sport

What happened: I was CTO of the Newcastle Knights and Newcastle Jets (2011–2014) — innovation work and the first person brought in to restructure around modern ICT and business systems. Knights: inside the AUD $100m privatisation. Jets: full corporate rebuild.
What decision mattered: Treat professional sport as a complex organisation under pressure — technology as governance, not helpdesk.
What changed how I think: Sport uses the same pattern as mining and finance: lean teams, high stakes, owners, sponsors, media, culture.

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VUID

What happened: Jason Rudolph and I co-founded VUID in 2013 — a real-time ERP platform with 48+ integrated apps on containerised infrastructure. We showcased at Web Summit 2015. Sold in 2016. There was no category for what we were building.
What decision mattered: Ship operational infrastructure people can rely on, even when the market has not named the category yet.
What changed how I think: Pitching something without a category forces decision quality to become the only moat.

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Aston Resources

What happened: I was CTO of Aston Resources and led all innovation work — Maules Creek, A$400m IPO (August 2010), 67.2% shareholder return over twelve months (AGM 2011), merger with Whitehaven announced December 2011 at approximately US$3bn (Reuters).
What decision mattered: At public-company scale, name what is actually being decided before momentum, the market, or the calendar decides for you.
What changed how I think: Scale amplifies both clarity and confusion. Most people only discover which one they had in hindsight.

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Nathan Tinkler period

What happened: I worked with Nathan Tinkler during a period of rapid growth — an environment where decisions compounded quickly and mistakes were expensive.
What decision mattered: In high-velocity environments, the cost of waiting often exceeds the cost of being wrong — if someone is willing to say what the decision actually is.
What changed how I think: My role was never the headline. It was being in the room when the stakes were moving faster than the organisation.

Mongolia, South Africa, and dozens of other markets

What happened: Advisory and operating work has taken me through Mongolia, South Africa, Papua New Guinea, and approximately seventy countries in the past three years — boardrooms, factory floors, and markets where infrastructure and relationships determine what is possible.
What decision mattered: When there is no manual, decide who must trust you before anything else scales.
What changed how I think: I stopped treating international work as travel. It is exposure to how decisions get made under constraint.

Bronze Betty

What happened: Bronze Betty started in 2020 after years searching Asia by motorbike for craft and foundries — a coffee-shop discovery in Indonesia, twelve-hour rides to Java, two foundries, 500+ SKUs, export worldwide. Exit in progress.
What decision mattered: Manufacture where the craft actually lives — own foundry relationships in Java, not white-label someone else’s catalogue.
What changed how I think: Global commerce is logistics, foundry trust, and product quality — not a Shopify store.

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Laikim PNG

What happened: Laikim PNG — founded 2018 with Erue Taunao. I created the business and strategy, raised capital, and provided ICT. COVID paused tourism; we kept building operator and government relationships for when borders reopened.
What decision mattered: Trust before scale — Erue’s PNG relationships and local operators first; platform and capital second.
What changed how I think: In environments with no manual, relationships are infrastructure. Earning the right to operate was the work.

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TStreet capital and pivot

What happened: TStreet had strong IP and weak sales. Eighteen months of runway. The AI wave was about to make their translation technology story harder to sell whether the product deserved it or not.
What decision mattered: Raise on a pivot — translation marketing and support — with a straight story about why the team still mattered.
What changed how I think: We raised at AUD $8m, then AUD $16m a few months later. I should have pushed for the pivot six months earlier.

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Twenty-five years later

What happened: Jason Rudolph and I built Reddog Technology together, then VUID. We sold Reddog in 2017. More than twenty years into our business relationship, he asked me to advise the founders of his next company — an international financial infrastructure business. Details remain confidential.
What decision mattered: Join early when foundational decisions are still open — commercial strategy, operating philosophy, what to build and what to leave out.
What changed how I think: People who have built businesses with you do not come back for frameworks. They come back when the next decision environment feels familiar.

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The acquisition we did not do

What happened: 2018. Client wanted to acquire a USD $85m competitor. On paper: market share, synergies, defensive move. Due diligence was thin. The CEO had already told his team the deal was happening.
What decision mattered: Three meetings later we advised against it.
What changed how I think: Twelve months later the competitor entered administration. I almost let the timeline drive the decision.

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Partnership deadlock before acquisition

What happened: Two equal partners had agreed to sell a USD $120m business. One wanted to renegotiate the earn-out. The other wanted out. Forty-five days to close. They would not speak to each other.
What decision mattered: Restructure the earn-out so both could claim a win without reopening price.
What changed how I think: The numbers were never the hard part. Pride was. Deal closed on schedule.

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The founder who could not delegate

What happened: AUD $40m revenue, family ownership. Every major decision through one person. Growth stalled eighteen months. Two senior hires were packing their offices.
What decision mattered: Name three decisions only the founder could make. Give everything else an owner and a deadline.
What changed how I think: Two quarters later things were moving. I waited too long to say plainly that he was the bottleneck.

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The mandate I declined

What happened: USD $100,000 per month offered. PE-backed CEO wanted me to validate a strategy the board had already rejected twice.
What decision mattered: I said no. I would have been expensive confirmation bias.
What changed how I think: CEO left. They asked me back six months later. I said no again. Turning down work is part of the job.

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Corporate ICT in two weeks

What happened: Tonga Rugby League had no corporate infrastructure — personal phones, personal laptops, no central anything. Mid-season. Travel and admin breaking down.
What decision mattered: One cloud stack. Everyone on it. Fix the rest later.
What changed how I think: Two weeks from approval to deployment. Not pretty. It worked. Some decisions do not need a twelve-month programme.

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Products launched before the market was ready

What happened: More than once I built or backed products the market was not ready to buy — technically sound, commercially early.
What decision mattered: Keep building — but stop pretending the market timing problem is a product problem.
What changed how I think: Timing is not a branding issue. I watch for it now before capital goes in.

Partnerships without exit terms

What happened: I entered partnerships without explicit control and exit terms. Fixed later, at higher cost.
What decision mattered: Write down what happens when the relationship breaks before you need it.
What changed how I think: The conversation nobody wants to have upfront is the one that saves the most money later.

Business is about people

What happened: In Papua New Guinea we were not building a tourism website. We were building trust between people who had every reason to be cautious. At the Knights, during a buyout, the technology mattered less than who would still speak to each other on Monday.
What decision mattered: Ask who has to trust whom before asking what the platform should do.
What changed how I think: I had known this for years. PNG and professional sport made it impossible to forget.

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Where business took me · Thinking

I accept a limited number of advisory engagements each year. Most begin through referrals or direct introductions.

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