About

My first computer was a 386 from a garage sale. It cost ten dollars. I grew up poor in the Byron Shire, on the far north coast of New South Wales, and went to Shearwater, the Steiner school, from preschool to Year 12. Hobbies that needed parts were out of reach. Software was free once you had a machine. At sixteen I reverse-engineered the MSN Messenger protocol to write a better Mac client than Microsoft’s. The early web years have the rest, including how I got the school network admin’s password.

My first job out of school was on Easylodge, a loan platform for non-bank lenders, at Equius Finance. Releases went out on a USB stick. In 2010 I started TestPilot CI, which ran the tests for Ruby on Rails apps in the cloud, a few months before Travis CI and CircleCI made that normal. With StillAlive we checked that websites actually worked, not just that they returned 200 OK, and sold it to a SaaS aggregator in 2012. I also built the control plane for a wholesale cloud at OrionVM, wrote the first code at HotDoc, and moved to San Francisco for App.io. I joined as a senior engineer and left as CTO.

In 2014 I flew to New York to interview at DigitalOcean. The whole company, about twenty people, fit on one floor in SoHo. That night they called me back to sign the contract over a bottle of Oban.

A year later I co-founded Flood IO, a load-testing platform. Tricentis bought it two years after launch, and I stayed four years at Tricentis to lead product. Flood kept running at scale after I left: Hotstar used it to simulate the two billion people who streamed the 2019 IPL. After Tricentis I co-founded Airheart, a map-based travel planner. Then came Ensignia, backed by Skip Capital, which set out to prove where software came from and how it was built.

Now I’m co-founder and CTO of Alcova. We build for financial advisers and client advice firms. Our first product, Operator, reads their emails, documents and meeting notes and pulls out the details they would otherwise type up by hand. After years of management, I’m back to building.

John Gall’s law is the closest thing I have to a method: a complex system that works grows from a simple system that worked. I wrote about it in Nature’s Razor.

I live at Jacks Point, just outside Queenstown, New Zealand, under the Remarkables. I try to spend one day a week offline in the backcountry. A neck injury in 2024 stopped me running, so I took up cycling while I recovered. Now I’m running again, on a 20-week half-marathon program with The Mill in Queenstown. The race is on 15 November.

Get in touch

Email is the best way to reach me: ivan@ivan.dev. My code is on GitHub, and I post on X.