luke canan . in pursuit of dolce vita
"he who jumps into the void owes no explanation to those who stand and watch." — jean-luc godard
systems thinker
what started as rebuilding broken teams in fifa career mode turned into an obsession with building systems that win. limited resources, hidden talent, broken systems, dynasties built from nothing. same playbook, bigger board.
my fancy paper from dayton says i learned two fields. what i actually learned came from travel, poker, managing a $10m healthcare equity portfolio, reading the classics, meditation, quantum theory, cold plunging, living abroad, and buying and selling businesses.
today i'm a tech investment banker. the seat teaches independent thought better than the industry practices it. i pitched and created the forward-deployed ai program at the firm because nobody else was going to. it runs now. i want to be closer to the thing being built — operating inside a company trying to change something real, with unconventional wisdom.
nights and weekends: a creator-led group travel marketplace, an ai studio looking to gamify your average operating system, and a community built around purpose.
in whatever's left: exercising, increasing my surface area of luck, traveling to distant lands, type 2 fun, reading, poker, eating well, and connecting quantum physics to things it has no business connecting to.
north star: strip away convention, status, and borrowed belief. find what's true, master the craft, build something real and useful and unmistakably your own. that's art. i'm going to build a company that changes something, then a fund that backs the people doing the same.
i come from a big italian family. probably bigger than yours. i'm grateful for them and most of who i am traces back there.
my parents raised me to travel, which is a polite way of saying they raised me to explore... and then to show other people how. first real test was two months in barcelona. somewhere in there travel stopped being a hobby and became the thing i build around. i find flow in movement.
open threads
- owners who need a better system for running their business. outpost builds the systems that give you time back, make you more money, and make running it more fun.
- creators who want to host trips. flock travel is a marketplace for exactly that. if you have an audience and have thought about taking them somewhere, this is built for you.
- operators, founders, investors, entrepreneurs to think out loud with. especially people working on distribution problems or agentic systems. no agenda beyond the conversation.
- people who collect interesting people. if you're the connector in your circle, i'd like to be in it, and to be useful to it.
any of these sound like you? email me.