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For 12 years, TechTO has been bringing Toronto’s tech community into one room, and last night was one of the big ones. 🚀
The founders behind Jobber, Pluvo, Stay22, and Propel Holdings talked through the hardest calls they’ve made, plus one they wish they’d made sooner. Here’s what they learned and how you can use it.
Read the conditions attached to the cheque
Sam Pillar, co-founder and CEO of Jobber, had a term sheet in hand, and the investors wanted two answers first: “When are you moving up market and when are you moving to the Valley?”
He said no to both. Jobber kept building for plumbers and window cleaners from Edmonton, and today it serves more than 100,000 small businesses.
Every cheque comes with expectations about who your customer should be. Make sure they match the company you want to build.
Teach your buyers before you pitch them
When Vanessa Galarneau, co-founder, CFO, and COO of Pluvo, started selling AI to CFOs, she found that most finance teams didn’t know what an agent was. So Pluvo’s growth strategy focused on teaching them. The team organized free workshops that seat beginners next to advanced users, and it still runs 101 sessions on the basics.
There aren’t many moats left. So, a community built around your business will do more for you than AI agents running outbound on LinkedIn.
Cautious buyers trust whoever helped them understand the problem first.
Give your startup a deadline before you need one
Andrew Lockhead, co-founder and CEO of Stay22, spent 10 years building his first company. When it sold, each of the three founders walked away with less than $33,000. Looking back, he’d rather have shut it down and moved on.
These days, he gives every bet three chances.
Set a date or a milestone
Let yourself push it once or twice
Miss it a third time, and move on
Your time is more valuable than anything else.
The hard call gets easier when you’ve decided your exit point ahead of time.
Profit buys your mission more time
Noah Buchman, co-founder, President, and CRO of Propel Holdings, has watched both funding paths play out.
A company in his space raised US$325 million and shut down when the next round never came.
Propel raised US$4 million from friends and family, got profitable in three and a half years, and didn’t raise again for a decade.
He calls it “purpose needs a paycheck.” Most of Propel’s biggest milestones came after year eight, and profit paid for every one of them.
Even if you plan to raise, knowing your path to profitability means the next round is one you choose.
Every founder on stage last night had a call they wish they’d made sooner. What’s yours? Share it with us, and we might feature it in a future edition.
🎓 “Learning how to use AI is a really good life skill for anything you do in life.” ~ Everest Nevraumont
Everest’s core lessons take about two hours a day. An AI tutor and adaptive apps teach the material, and she’s a three-time Texas State History Champion.
That raises questions parents and teachers are asking:
What does a kid do with the rest of the day?
Who catches it when the AI gets something wrong?
Does learning that fast still teach a kid to sit with a hard problem?
On Nov 10, Everest, her dad, Carly Shuler, co-founder and CEO of Hoot Reading, and Rohan Mahimker, co-founder and co-CEO at Prodigy Education, take those questions on.
📆 Upcoming TechTO Community Events
Nov 3 – What Happens After Dark | TechTO Welcome AfterParty (Ottawa): Be part of the SAAS NORTH AI welcome afterparty tonight and hang out with people building cool things in tech.
Nov 4–5 – TechTO x SAAS NORTH AI 2026 (Ottawa): Join 2,500+ SaaS founders and operators building the future of AI. If you’re still thinking about getting your pass, we’re offering them at a heavily discounted price.
Nov 4 – The Growth Table (Ottawa): Request your spot for a private dinner if your startup has $3M+ in revenue or is venture-backed.
Nov 10 – Future of Education: Impact of AI on Learning (Toronto): Hear how a three-time state champion and her dad use AI for learning, plus Prodigy and Hoot Reading’s founders on what they’re building.
Nov 19 — Humans in the Loop: Building and hiring for AI at Questrade (Toronto): Watch Questrade’s AI team demo a production MCP server live, then talk directly with the Chief AI Officer and the hiring managers building the team.
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