Writing and Posts

Writing & Posts

All of my thoughts on technology, leadership, product design, and more, collected in chronological order.

Your customers didn’t buy your software to use your software.

Your customers didn’t buy your software to use your software.

LeadershipExperimentsTech+AI

When generative AI and the frontier LLMs started to become practical, I pushed every team in my portfolio to build an AI feature. I wasn't stressed about what they were building, but I pushed hard to get them all to build something. This wasn't because I thought adding on an AI feature would change the business or even make us money. In fact, we never charged customers for any of them as an added feature. I did this for the sole purpose of forcing people to engage with this new technology.

Proxy Metrics

Proxy Metrics

LeadershipProptechProduct

A long time ago, way back when I still had hair, Microsoft introduced Team Foundation Server and one of the productivity metrics commonly reported on was lines of code written per developer. At the time, it seemed like a relevant metric. More code meant more output, no?

SaaS is alive and well

SaaS is alive and well

ProductTech+AIProptech

A little over a year ago I shared a presentation internally with our CEO, execs and other stakeholders urging action as AI was rapidly accelerating the time to market for new products, creating a threat to incumbents. I outlined several moats I believe we could exploit and I still believe they are valuable space to occupy - for example domain knowledge, compliance capabilities, massive datasets. I did miss one key moat that hindsight allows me to appreciate more fully: Distribution.

2025 - A year of delivery, focus, and foundations

2025 - A year of delivery, focus, and foundations

Proptech

Around this time of year as things wind down, I always end up reflecting on the year and ensuring we have a solid plan to kick off the next year. This year was about doing the hard work that compounds.... Less noise. More outcomes. Stronger products. Stronger teams.

What’s New in the Moodiest Corner of Code Culture

What’s New in the Moodiest Corner of Code Culture

Tech+AIProductExperiments

If you thought coding was just about clean architecture and efficient logic, vibecoding would like a word (preferably in monospace font, glowing in soft lavender neon, backed by a lo-fi beat). What started as an aesthetic subculture blending programming with mood, visuals, and audio has morphed into something weirder, richer, and more creative.

One Down, Two to Go: The Great Ocean Road Marathon

One Down, Two to Go: The Great Ocean Road Marathon

The first marathon in my slightly unhinged “three marathons in under six months” challenge is officially complete. The Great Ocean Road Marathon delivered everything it promised: sweeping ocean views, leg-destroying hills, a mild Antarctic breeze fresh off the Bass Strait, and an almost meditative stretch of road that occasionally whispered, "Why are you doing this to yourself?"