I learn by building. These are things I’ve put energy into over the years.
/ongoing
New Literacies
How do we help kids thrive in a world shaped by AI? I’ve been obsessed with this question for the last few years, and it’s become the work I can imagine dedicating the rest of my life to.
So far: 80K+ words of research on 8 core capabilities, a market map of 140+ products, and ongoing experiments with my own kids. Follow along on Substack .
Piano
I started learning piano in 2024, with a 5-year goal to become a decent amateur. Mostly late-night practice, once kids are in bed. It feels scary sharing progress, but I’m doing it here to force myself to ship.
Angel Investing
I love supporting early-stage founders—especially outsiders with global ambition. 20+ investments so far. Slowed the pace after our 3rd kid, and only invest when I can be unusually helpful. Aim for 2-3 new investments a year.
/building
Things I’ve shipped, mostly with AI.
whereshouldwe.ski
A family ski trip planner. 1,000+ resorts with filters that actually matter when you have young kids: minimum ski school age, walkability, beginner terrain.
AI Chief of Staff
A personal productivity system that makes my digital life legible to LLMs. Reviews my week automatically, surfaces patterns I’d otherwise miss.
/previous
Antipodes (2021-2023) — An investing syndicate I started with some impressive friends , to back foreign founders looking to crack the US. 6 investments, $25K-$250K checks. Currently on hold.
Sweat & Shiver (2022-2023) — Sauna, ice bath, workouts with friends in my garage gym. Mostly an excuse to invest more energy with people I enjoy and respect.
Belgian Waffle Ride (2022) — A brutal, beautiful endurance event: 200km on gravel, dirt, and tarmac. Finished in 11hrs after a few solid months of training.
Baum (2020) — A custom titanium bike from Australia’s best builder. The first version was designed to be the only bike I’ll ever need. Now on its second iteration after an accident in 2024.
RecruitLoop (2011-2017) — Started a company in my twenties. Raised a seed round, moved to SF, built to profitability, exited modestly. Formative in every sense. See: Moving to America , A Personal Transition .
Real Jim Courier (~2012) — A parody Twitter account I ran with mates, tribute to the greatest tennis commentator alive. Got a reply from the sitting Australian Prime Minister (also a redhead).
Australian NBN Project (2009) — Worked on the National Broadband Network strategy at McKinsey. First time I realized most of the value lives at the application layer. Since then, I’ve invested my entire career in tech.
Honours Thesis (2007) — Turned down a grad offer in Brisbane to bet on something bigger. Wrote a thesis, had two papers published ([1] , [2]), and landed a role at McKinsey in Sydney. The first of several bets that got me to California.
[1] Clarkson, Overell & Chapple, “Environmental Reporting and its Relation to Corporate Environmental Performance”, Abacus, 2011.
[2] Overell, Chapple & Clarkson, “Environmental Reporting in the Australian Mining Industry”, Australian Business Law Review, 2008.
Henry Hiace (2005-2008) — A 1990 Toyota campervan I drove across Australia with my girlfriend (now wife). $25 a day, paper maps, unforgettable. Sold it for a profit.
If any of this resonates, the best way to follow along is the newsletter .