Jonathan Haber grew up in Montreal with a quiet curiosity about how things work. He wasn’t chasing shortcuts or quick wins. He was interested in better systems and clearer ways of doing things. That mindset followed him to McGill University, where he studied Business Administration and began thinking seriously about how technology could improve everyday work.
After graduating, Jonathan launched his first software venture. It focused on helping small businesses organise their workflow and communicate more clearly with clients. The company was modest in size, but the lessons were lasting. He learned early that technology only works when people trust it and understand it.
As Montreal’s tech scene began to grow, Jonathan became more involved with startups. He noticed many founders building impressive tools that were hard to use. Teams felt overwhelmed. Users felt confused. That gap led him to start Haber Strategies Inc.
Through his firm, Jonathan began helping early-stage startups slow down, listen more, and design what he calls “soft-tech.” These are tools built to support people, not distract them. His work centres on clarity, collaboration, and steady growth.
Outside of work, John finds balance through hockey, hiking, and food. Team sports remind him of trust. Time outdoors helps him think clearly. Exploring new restaurants keeps his curiosity alive.
Today, John remains grounded in Montreal’s creative culture. His career reflects patience, empathy, and a belief that the best ideas are the ones that quietly make life easier.
What is your typical day, and how do you make it productive?
My day usually starts early and quietly. I spend the first hour without screens. I’ll review handwritten notes or take a short walk. That time helps me think clearly before jumping into conversations. Most of my work revolves around people, so I try to protect my energy. I schedule calls in blocks and leave space between meetings to reflect and follow up properly.
How do you bring ideas to life?
I start by asking better questions. I write ideas down and let them sit. If an idea still makes sense after a few days, I test it in conversation. I’ll share it with a founder or a team and listen carefully to their reaction. If it solves a real problem, it usually gains momentum naturally.
What’s one trend that excites you?
Human-centred technology. I see more teams designing tools that reduce stress instead of adding to it. Simpler dashboards. Clearer communication. Better defaults. That shift feels meaningful.
What is one habit that helps you be productive?
Daily reflection. I end most days by writing down what worked and what didn’t. It keeps small problems from becoming big ones.
What advice would you give your younger self?
Listen longer before acting. Speed feels productive, but understanding saves time.
Tell us something you believe almost nobody agrees with you on?
Most startups don’t need more features. They need fewer decisions.
What is the one thing you repeatedly do and recommend everyone else do?
Have honest one-on-one conversations. They reveal problems before data ever does.
When you feel overwhelmed or unfocused, what do you do?
I step away from my desk. Hiking works best. Physical movement resets my thinking.
What is one strategy that has helped you grow your business or advance in your career?
Staying local and engaged. Being present in Montreal’s startup community helped me build trust over time. Relationships compound.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early on, I built software that was technically strong but confusing to users. Adoption suffered. I learned that clarity is more important than capability.
What is one business idea you’re willing to give away to our readers?
A simple internal tool that tracks team clarity. Weekly prompts asking, “What’s unclear?” Most companies don’t ask that enough.
What is one piece of software that helps you be productive? How do you use it?
A shared workspace tool that combines notes, tasks, and feedback. I use it to keep conversations and decisions in one place.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
Books on systems thinking. They help me see patterns instead of symptoms.
What’s a movie or series you recently enjoyed and why?
A documentary on craftsmanship. It reminded me that quality takes patience.
Key learnings
- Technology works best when it removes friction rather than adds features.
- Listening early prevents costly mistakes later.
- Clarity inside teams drives better outcomes than speed alone.
- Simple habits, done consistently, shape long-term success.
- Strong communities are built through trust, not competition.