• TechTO
  • Posts
  • TTW Days 4 & 5. The week finished stronger than it started.

TTW Days 4 & 5. The week finished stronger than it started.

Everything that landed Wednesday and Thursday - and what to take with you.

You are receiving the Community Edition of today’s newsletter - upgrade to a Member to receive additional perks and experiences

We told you the bar was set. Wednesday and Thursday cleared it.

The Silicon Valley Playbook for Canadian Founders | Wednesday May 27

SF has a 6-9 month innovation lag on the rest of the world right now. Nobody there is sharing what they're learning. That gap is yours to close.

Founders fresh from Game On's San Francisco immersion shared what actually shifted when they got in the room - what Canadian founders skip, what they overthink, and what they'd do differently now. TX Zhuo (Fika Ventures), Jason Gray (Pioneer Fund) and Andre Charoo (Maple VC) brought the investor lens on what separates the founders they back from the ones they pass on.

Go to benchmark, not to fundraise. And "Fortress Canada" is a revenue problem, not a safety net.

Thanks to gameon and Fasken.

People First, Product Second: A Consumer Deep Dive with Maveron | Wednesday May 27

Some investors chase trends. Maveron bets on behaviour shifts before the market catches on - it's how they backed eBay, Zulily ($2.4B exit), and Flywire. Jason Stoffer broke down exactly how that lens works for Canadian founders pitching US consumer investors.

Michele Romanow was direct: "You can convince anyone to do anything once. People come back and buy a second time because they genuinely like the product." Distribution beats community. The brands winning right now aren't outspending everyone on Meta, they're finding where their customer already lives and showing up there first.

Tyler Handley and the co-founders of Tre’dish brought the founder side - what all of this looks like when you're the one building it.

Beyond the Bubble: An Intimate Chat with Will Hsu and Alex Norman | Wednesday May 27

Will Hsu launched Mucker with no LPs, no documents, no office. Just a website. 150 applications in 4 days. 15 years and 300+ companies later, he sat down with Alex Norman for the conversation he doesn't have on the speaking circuit.

Be contrarian before it's obvious. Different beats better. Interview your VC like you'd hire for the role. And stop spending 80% of your time raising - the money follows the momentum.

"The problem is the problem. You can't pivot the problem. Focus on solving something different - not building something better."

TechTO Summer Social - Powered by Wealthsimple | Wednesday May 27

Packed. Line up around the block. Wealthsimple's money machine sending paper bills into the air, Tre'dish's roulette giving away groceries - waterfront, sun going down, the whole community in one place.

A week of panels, firesides, and market overviews needed a night like this. The co-founder conversation that started over a burger. The intro that didn't need a warm email because you were already standing next to each other.

Thanks to Wealthsimple, Tre'dish, Sage, Motion, and 7shifts.

Market Overview: Fintech, co-hosted with Affirm | Thursday May 28

Canadian fintech founders are too cautious - and it's costing them.

Ricky Lai (Portage) mapped where the capital is actually moving: AI-enabled companies are getting funded at 3.5x the valuation of those without, and fintech multiples are converging with SaaS for the first time. Jane Podbelskaya made the case for embedded finance as the growth lever most founders are sleeping on.

Wayne Pommen closed it out with the line that stuck: stop treating Canada as a ceiling. Push harder, bigger, sooner. The best time to build in fintech isn't coming, it's now.

Thanks to Affirm.

Market Overview: Insurtech | Thursday May 28

"If you're building in insurtech and it's not AI, don't bother raising. Not this year. Probably not next year either." - Christian Lassonde

That set the tone. Then Andrew Ostro and Danish Yusuf showed what surviving this category actually looks like, one Lloyd's contract that took two years, 1,800 broker licenses built from scratch, compliance software nobody else made. The moat isn't the product. It's everything you had to build to keep the product alive.

Thanks to PolicyMe.

The Quiet Part Out Loud: A RevOps Dinner | Thursday May 28

A curated group of revenue leaders closed out the week over dinner and said the things that don't make it into the all-hands. AI hitting faster than teams can absorb it. The real cost of rebuilding mid-growth. The number that looked fine until it didn't. Operators being honest with each other and leaving with a clearer answer than any playbook had given them.

Thanks to Vasco for making it possible.

Toronto Tech Week is a wrap. From builders shipping products that didn't exist that morning to operators mapping where entire industries are going next, this community showed up and delivered every single day.

The energy doesn't stop here. We'll see you year-round.

The regular program is back.

Together Toronto returns July 6 at MaRS. The format that started it all: founders on stage, honest behind-the-scenes stories, the pivots and hard calls that never make the press release. A room full of builders, operators, and investors who show up to actually talk to each other.

TechTO isn't just in Toronto. We're going coast to coast - Vancouver, Montreal, Ottawa, and beyond. Events year-round, communities in every city, and more on the way.

Stay on top of what's coming → luma.com/TechTO-Events

Interested in partnering with us? We're always looking to collaborate with great people and organizations building in the Canadian tech ecosystem.
Reach out → [email protected]

Members get to our signature events for free. That's what the $249/year gets you - free access to every Together and vertical event, exclusive discounts on all member events, and a private Slack where the conversation keeps going after the event ends.



Reply

or to participate.