Operator first. The writing is the residue.
Seventeen years of operating, finally written down.
Thomas Jankowski. Toronto, mostly. Five-time CEO with lifetime P&L above $4 billion across telecommunications, consulting, travel, fintech, media, and healthcare. ICD.D. Most recently ran Canada's largest healthcare marketplace as CEO of Medimap; before that, Chief Digital and Growth Officer at Coinsquare, EVP and Chief Digital Officer at Postmedia, and five years scaling Flight Network into thirty-plus countries with a Phocuswright 35 Under 35 in 2015 to mark the work. A handful of his own startups along the way. HBA, University of Toronto. MA, University of Sunderland. Currently building applied-AI ventures in health and travel under a private holding structure.
The writing on this site is one continuous bet placed in a 2007 MA thesis called Neo-nomads: Between 'Anyware' and 'Anyplace', which argued that non-human agents would become civilization-scale actors sometime in the late 2020s, that discoverability would become an adversarial game against predictive machines, and that the practical mess would live at the seam between people who move and systems that do not. Seventeen years of operating later, the three pillars on this site (AI, healthcare, travel) are not three interests. They are the same bet, finally legible.
The site is the slow archive. Read at your own pace.