Jason Goldlist Ask Jason →

I build things without permission.

But you have my permission to explore — and to ask me anything.

1998·Age 13·A mass-customized clothing line
At thirteen, with an idea and a phone book, I started a clothing line where the customer designed everything.
Anti-brand by name — Uglywear, where ugly people find ugly clothes. Order forms handed out at school; garments sewn by a maker I found in the Yellow Pages.
The Ugly-Wear.com banner: “Where ugly people find ugly clothes!”
Ugly-Wear.com, 1998
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2010·Vancouver Olympics·Deputy Venue Manager
Handed five thousand people to schedule across seventy-seven days, I taught myself to code and wrote the software that did it.
The committee never used it again. It followed the rules. A missed legacy — and the one time the institution didn't bend.
5,000people scheduled across 77 days
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2022·Venue·Co-founder
A fintech, shipped as a tattoo app.
The bet: every payment goes digital eventually, so the opportunity is wherever it hasn't. It started with one customer standing over a fresh tattoo with no way to pay. The partnership between artists and nerds.
100k+tattoo sessions booked · 1,000+ artists worldwide
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2024·Toronto Maple Leafs Baseball Club·Co-owner
There were forty bids. We were the unsuccessful high bidder. So now we own the team.
A 130-year-old ball club, roots in 1895, bought at auction. It started as a dad on a hill at Christie Pits with his kids, thinking if I owned this I could do so much more with it.
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1998 → today
Same move, every time: find an institution running below its potential, earn the right to change it, then ship relentlessly.
I was doing it before I had the word for it.
The record

Everything, oldest to newest. Open any of them.

1998 · age 13 Uglywear →
A clothing line where the customer designed everything. Built at thirteen. Learn more →
2001–2002 EcoChallenge →
An urban adventure competition, designed at summer camp and run in Toronto. Learn more →
2001 Gourmet Gordon →
A 32-role satirical musical, staged, with a fake Hollywood press clipping to match. Learn more →
2004 Fredericton City Council →
Ran for city council in Fredericton. Learn more →
c. 2004 Leadership as Jazz →
My undergrad thesis, typeset and pressed as an LP. "Creativity craves constraint." Learn more →
2007–2009 McKinsey, Africa →
Consulting across Africa. Learn more →
2010 Vancouver Olympics →
Taught myself to code and wrote the software that scheduled 5,000 people across 77 days. Learn more →
2014– TechTO →
A tech community in Toronto. Learn more →
2015–2019 Wealthsimple →
Fintech. Learn more →
2020– Venue Live →
A platform for live events. Learn more →
2022– Venue →
A fintech, shipped as a tattoo app. Learn more →
2024– Toronto Maple Leafs Baseball Club →
Bought a 130-year-old ball club at auction. Learn more →
Ongoing Little League Coaching →
Coaching kids' baseball. Learn more →
Come in

Ask me for something.

You want me to look at your deck.
I'll walk you through what actually helps me help you. It takes two minutes.
Start here →
You want an intro.
If your value prop is strong, go direct — you don't need me, and direct is better. If it isn't, my intro can't fix that. Either way, start with the pitch.
Make the case →
You're building something weird and early.
That's the good stuff. Tell me what it is and where you're stuck.
Let's talk →

Or just come in the front door: jason@venue.live