Decisions that shaped my thinking

Twenty moments from twenty-five years. What happened. What decision mattered. What changed how I think.

Early drones

What happened: From 2002 I worked on drone autopilots — Paparazzi, then OpenPilot — years before consumer drones existed. Restricted sensors, weak processors, civilian UAVs still sounded absurd to most people.
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: In 2004 Jason Rudolph and I built Reddog Technology in Brisbane — flat monthly fee for unlimited IT support when hourly billing was still the norm. We standardised on Apple before most corporates would touch it. National expansion within twelve months. International within eighteen.
What decision mattered: Charge for reliability, not breakdowns. Align the provider with the customer.
What changed how I think: Business model design matters as much as product design. I still look for misaligned incentives first.

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Selling Reddog

What happened: After eleven years we sold Reddog Technology in 2015 — a business we had built from scratch into a national and international IT department-as-a-service company.
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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Newcastle Knights private buyout

What happened: I was CTO of the Newcastle Knights and Newcastle Jets. Reddog contracted to the clubs. During the Newcastle Knights AUD $100m private buyout period I was inside a transaction environment — not generic IT support.
What decision mattered: Treat technology decisions as board-level when ownership, capital, and public scrutiny are all moving at once.
What changed how I think: Professional sport taught me that lean corporate teams under public pressure make the same mistakes as any other business — faster.

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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 worked on the Aston Resources journey through its public listing and subsequent merger with Whitehaven Coal.
What decision mattered: At public-company scale, name what is actually being decided before momentum decides for you.
What changed how I think: I saw what scale does to judgment — it amplifies both clarity and confusion.

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 from years travelling through Asia looking for craft and manufacturing relationships. One coffee-shop encounter with bronze cast products in Indonesia became a global commerce business — 500+ SKUs, foundries in Java, export into Europe, America, and Asia.
What decision mattered: Follow the manufacturing relationship, not the ecommerce trend.
What changed how I think: Global commerce is logistics, foundry relationships, and product quality — not a Shopify store.

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Laikim PNG

What happened: Laikim PNG — building tourism and commercial access in Papua New Guinea. I created the business strategy and raised capital, working with Erue Taunao and her PNG tourism expertise. Logistics, government, culture, security. No template.
What decision mattered: Build trust before scale. Relationships before platform.
What changed how I think: The technology was rarely the hardest part. Earning the right to operate was.

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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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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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