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- Naive ambition isn't a personality flaw. It's the strategy.
Naive ambition isn't a personality flaw. It's the strategy.
$100B+ in assets. 3M+ Canadians. It started with one founder calling every signup himself.
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Michael Katchen stood in a TechTO room 10+ years ago and asked who’d heard of Wealthsimple. Three hands went up.
He started Wealthsimple at 24. No experience in financial services. No track record building companies. Just a question: why is this so hard for regular people?
Everyone told him it wouldn’t work. Five banks. A monopoly on trust. You’re never going to make it.
He tried anyway.
In 2024, Wealthsimple did $20 billion in net new deposits. That’s the first year the company beat one of the Big Five banks on a major financial metric. And earlier this month, Wealthsimple becomes first Canadian FinTech to join SWIFT network.
They now serve over 3 million Canadians on the platform and roughly $100 billion in assets.
At Best Of 2025, Katchen shared three lessons. Not strategy decks. Actual stories.
Hire for resourcefulness. The night of the talk, he got locked in a bathroom at the Wealthsimple office 10 minutes before he had to leave. His chief of staff showed up, jerry-rigged the door open, and got him there. That’s the bar. People who figure it out.
Call your customers. In the early days, his rule: call every signup within 30 seconds. Not a bot. Not a form email. Him, personally. “Hey, this is Mike. I’m the founder. If you have feedback, you have my number.” Your bank will never do that. That’s exactly why he did it.
Do things that don’t scale. He used to show up at offices with bags of lunch and ask if he could do a quick presentation on smart investing. Five people or 100 - 20% became clients every time.
The goal he set in year one: hit $1 trillion in assets in 15 years or less. He still believes it.
“It takes a little bit of crazy to believe you can do something amazing.”
Watching someone say that and mean every word of it will do something to how you think about your own company.
On AI; Katchen, when asked: “If you’re not thinking critically about how it’ll transform your team and industry, you’re already behind.”
His vision: everyone gets a smart CFO in their pocket. Not just people with $75M in assets.
Want to be in that room? Best Of 2026 is April 13. Same energy. New founders.
Toronto Tech Week - May 25-29, 2026
The TTW calendar just hit 165+ events, and we're still announcing our own throughout the week.
Five days. One city. The one week a year when you walk into a coffee shop and the person next to you is probably building something too.
There's an energy at Toronto Tech Week that's hard to describe until you've felt it. Last year, 7,800+ builders showed up across 17 TechTO events. The number that stuck with me: one in three came back for more than one session.
That's not a typical event metric. That's a community number. And this is what we build for.
Our stages featured Brad Feld of TechStars, Avlok Kohli of AngelList, Joanna Griffiths who built Knix into a category, Michelle Romanow from Dragon's Den, and more. Speakers who showed up not to perform but to share what actually worked and what didn't.
Founders crossed paths with investors they'd been trying to reach for months. Builders, operators and investors from FinTech, PropTech, Insurtech, AgeTech, and Mobility came together in curated rooms to shape adjacent pieces of the same future.
That's what Toronto Tech Week does. It collapses the distance between the people who need to know each other.
We're back May 24-29. And I genuinely cannot wait.
3 anchor events just dropped and more are coming! From an Agentic AI session focused on late-stage founders to industry deep dives into FinTech, InsurTech and more, to demystifying the various stages of the startup funding lifecycle from bootstrapping to IPO at our Funding Stage… and a very special keynote I can't wait to share with you all soon.
A week like this doesn't happen without the right partners and supporters behind it. Every partner we work with has different goals. Some want all three (hiring, brand awareness and building customer/partner relationships). Some just want to nail one thing really well. If your brand wants to collaborate and be part of the week (whether as a funding sponsor or a food and beverage partner), I'd love to hear from you. My inbox is open.
Megha Kandoi, GM, TechTO & Peerscale
⏰ More TTW events this week. Subscribe to our calendar so you don't miss the drop.
Quick one: What's the boldest prediction you've made about your own company? Hit reply - one line.
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