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This month’s Together Toronto stage had a founder who rebuilt a closing process she’d lived through, another who turned a no into her first customer, an investor who can tell when an AI wrote your pitch, and a YC alum who got paid before building anything.
More than 300 people were in the room, and these are the four ideas worth bringing back to your startup.
Fix the closing from the inside
When Ankita Sharma bought her first home in Canada, the closing ran on phone calls, email attachments, and names copied by hand between systems. She worked with a law firm to understand why, then built Philer to bring the process online for real estate lawyers.
The law clerks who’d use it worried it would replace them, so adoption stalled. In 2024, approval from the Law Society of Ontario let Philer run closings for homebuyers directly, and it has since handled $250 million in transaction volume.
“A good founder is the one who knows how to recognize it and move past it.”
A “no” is just a translation problem
Construction companies sit on years of project and pricing data that rarely helps them win the next bid. Lylia Djait-Paulien built Tyce to change that, and her first customer came from a pitch that nearly ended early.
A construction CEO stopped her mid-pitch to say his company wasn’t tech-forward
She asked what he cared about, which was winning more projects
She skipped the demo and walked his team through bids they’d already made
That meeting became Tyce’s first paid pilot
When a buyer says no, ask what they’re trying to win and pitch your product in those terms. For Lylia, that meant talking about projects and bids long before AI came up.
Write to investors like a person
Mike Masterson, managing partner at Supermoon Capital, sees the same few mistakes in founder pitches over and over.
Sending an email an AI agent clearly wrote, which ends things before they start
Describing the problem so loosely that he can’t tell what you’re solving
Leaving out why your team is the one to solve it
Not knowing who else is going after the same problem
Each of these tells an investor you haven’t done the homework. A pitch that covers all four in your own words is already ahead of most of what lands in his inbox.
Ask for money before you build
Before writing any code, Raghav Midha and his co-founder took a landing page and sample docs back to the people they’d interviewed. Nine of the first ten said they needed it, and two put down a three-month deposit against an annual contract.
Those two deposits were their first real read on product-market fit.
A prospect can say yes for free, but paying up front shows the problem hurts enough to act. Before you hire or write a line of code, ask your most interested prospects for a deposit, even a small one, and build for the ones who pay. More on this here!
Get the full scoop on each speaker’s story on TechTO’s YouTube channel. Want to be part of the room? Register for next month’s Together Toronto and Ecosystem Showcase.
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