
Almost every market a startup enters now already has competitors in it. Products are faster to build and easier to copy, so a better feature list rarely keeps you ahead for long. What decides who wins is whether the right people pay attention, and attention is a lot harder to buy than it used to be.
The founders on TechTO’s stage and podcast shared three things that work well. They told a story worth following, they made sure it reached the right people, and they stayed with it long enough for it to work.
Your story is the part competitors can’t copy
Jake Karls of Midday Squares sells chocolate bars, one of the easiest products there is to copy. He points out that 15 years ago, a brand could buy attention with TV and newspaper ads. Today people decide what they see, and they tune out a brand that only talks about its protein and fibre. What a competitor can’t copy, he says, is “how we make people feel.”
So he and his co-founders, his sister and brother-in-law, filmed the business from day one, bad days included. That footage built awareness first, then sales, then media coverage, shelf space and, eventually, investor interest.
The hardest stretch came during COVID-19, when Midday Squares lost 70% of its sales. Most of the category cut spending, and Jake’s team went the other way by spending what they had delivering bars to hospitals. It became their highest-growth year.
Know exactly who the story is for
Mahshid Yassaei, CEO and co-founder of Tali AI, built it for a group that trusts each other far more than any startup. Her team made the best product they could for physicians, and because doctors talk to each other, they let word of mouth drive adoption.
For doctors, a colleague’s recommendation carries more weight than anything, and in a tight-knit community, a good story travels on its own.
Stay long enough for it to work
Standing out usually takes longer than founders plan for. Investors will find a reason not to fund you in any market. What matters is your own conviction that you’re solving a real problem for a specific group better than anyone else.
Caitlin MacGregor started Plum (acquired by Phenom in April) early in a crowded market. Investors usually expect a startup to take off within about three years, and hers took longer to find the customers it could serve best. Her team kept going until it did.
In a crowded market, decide exactly who you’re for, then tell those people the real story of building it, hard parts included. A competitor can match your product, but your story will still be your biggest edge.
What’s the part of your company’s story you haven’t told yet?
🎤 Hear Sam Pillar Live on Together Toronto Stage
In 2014, Jobber co-founder and CEO Sam Pillar spent four months pitching investors and came home without a single yes. Nine years later, General Atlantic led Jobber’s US$100M Series D.
On November 2, he takes the Together Toronto stage to talk about what happened in between, and it’s worth hearing from him in person.
Also on stage: Andrew Lockhead, co-founder & CEO, Stay22, Noah Buchman, co-founder, president & CRO, Propel Holdings, and Vanessa Galarneau, co-founder, Pluvo.
Got a question for them? Reply, and we’ll bring a few to the stage.
Select the General Admission ticket type to attend the event.

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