Waterloo  ·  Est. by the people who built it

TheWaterloo Mafia

For over three decades, the most consequential builders in Canadian tech came out of one place. No one owns it. We just decided to make a room — and coordinate a little better.

Sept 11–12, 2026 By invitation only The inaugural retreat
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I  ·  The Premise

Tech is full of mafias. Canadians have just been too shy to name one of the biggest of them all.

PayPal had one. So did Fairchild. A tight cluster of people who built something together, scattered, and then spent the next twenty years quietly seeding everything around them. Waterloo has been doing exactly that — across hardware, AI, fintech, infrastructure, and a dozen companies you'd recognize — without ever stopping to acknowledge it.

No one owns a thing like this, and no one should try. But after thirty-plus years, it was worth coordinating a little better. So we're making a room — no stage, no sponsors, no badge scanners. A small, deliberately chosen group of founders and operators, a campfire, and two days for the conversations that only happen when the conference floor empties out.

The first edition is small by design. Get the room right, set the tone, and let it become the thing people clear their calendar for every year.

II  ·  What It Is

A campfire, twenty people, and no agenda worth printing.

i.

Fireside, not keynote

A fire at the back of the park and roughly twenty people around it. Honest talk about financing in the AI era, ownership, infrastructure, and what's actually BS now — held the way you'd hold it among people you trust.

ii.

Every generation, one room

Zero to thirty-plus years out. The people just starting, the people in the thick of it, and the ones who wrote the playbook — trading notes across cohorts that rarely sit at the same table.

iii.

Pay it forward

Each year the room covers the cabin for a couple of younger founders who couldn't otherwise be there. The mafia takes care of its own — and recruits the next one.

III  ·  The Particulars
When
September 11–12, 2026
Friday arrival, Saturday core, Sunday out — timed to charge up before Waterloo Tech Week.
Where
A family camp outside the city
Rec hall, cabins, and a fire at the back of the park. Everyone clustered together.
The Room
Waterloo Mafia only
First edition stays tight. The broader gathering comes later, once the tone is set.
The Shape of It
Lightly programmed
Catered lunches, a mafia-only dinner, and long open hours. The point is the people, not the agenda.
Contribution
$1,000 – $1,500
Covers cabins, catering, and the wine country evening. Part of it funds the seats we hold for younger founders.
Register
IV  ·  The Weekend

Alright — a little agenda.

FridaySept 11
4:00 PMCheck in
6:00 PMCatered dinner & short welcome
8:00 PMCampfire — introductions
SaturdaySept 12
MorningFree time Optional hike or activity
12:00 PMCatered lunch
2:00 PMFire talks — programming & pitches
4:30 PMBoard the bus to Niagara
5:00 PMWine tasting at Trius
7:00 PMDinner at Trius
9:30 PMCampfire talks
SundaySept 13
9:00 AMBrunch & closing
NoonCheck out

Times are loose by design. The point is the people, not the schedule.

V  ·  The Roster
Founder · Hardware
Founder · AI
Operator · Fintech
Founder · Infra
Wrote the playbook
In the thick of it
Just getting started
Builder · TBD

You know who you are. And if you don't yet — you might soon.

The first invitations
go out soon.

Most of the room is people we already know. But a handful of spots are held for builders we haven't met yet — because the point isn't to keep this small forever. It's to widen the reach, open the door, and pull the next generation in.

Waterloo Mafia · MMXXVI