John Haber on Confidence, Clarity, and Taking Smarter Risks

John Haber grew up in Montreal’s Notre-Dame-de-Grâce, in a home where learning and hard work were part of daily life. His father was a math teacher. His mother ran a small bookkeeping business. From a young age, he saw how people built things slowly, one step at a time.

At 12, he got his first computer. It was a refurbished Dell from a neighbor. He started building simple websites for school clubs and community teams. He liked solving small problems. Making things easier for people.

That idea stayed with him.

After studying business at McGill, John worked in customer success and product operations. He noticed a pattern. Many companies struggled not because their ideas were bad, but because their products were confusing. People didn’t know where to start.

So he built his work around fixing that.

Today, as the founder of Haber Strategies Inc., John Haber helps early-stage startups simplify their offerings. He works with founders to clarify their message, improve onboarding, and build systems that actually work for real people.

He also spends time mentoring new founders. Many are building their first product. He helps them slow down, ask better questions, and focus on what matters.

Outside of work, you’ll find him playing hockey, hiking in the Laurentians, or trying a new restaurant in Montreal.

He still believes the same thing he learned early on: small improvements can change how people experience something entirely.

Q: You’ve worked with many early-stage founders. What usually holds people back in the beginning?
A lot of people think it’s funding or competition. But most of the time, it’s confusion. They don’t clearly understand what problem they’re solving, or who it’s really for. I saw this early in my career in customer success. People would sign up for a product and then just… stall. Not because they didn’t care, but because the path wasn’t obvious. That stuck with me.

Q: Was there a moment when you realized this would shape your work?
Yes. At MileBridge Software, I worked on onboarding small business customers. We saw churn happen fast. When we looked closer, it wasn’t about price or features. It was about the first experience. People didn’t get to a “first win.” That idea—that early clarity matters more than complexity—has guided most of my work since.

Q: You later co-founded a company that didn’t continue. What did you take from that?
LatticeDesk. That was a big learning moment. We built something useful, but we expanded features before we fully nailed positioning. We were solving problems, but we weren’t always clear about which one mattered most. It taught me to validate the story before scaling the product.

Q: You talk a lot about “soft-tech.” What does that mean to you?
To me, it’s technology that feels quiet. It doesn’t get in the way. It helps people communicate better, understand what to do next, and reduce friction in their work. It’s less about adding features and more about removing confusion.

Q: How do you help founders build confidence in their ideas?
I try to slow them down. Confidence doesn’t come from hype. It comes from clarity. I’ll ask them to explain their product in one or two sentences. If that’s hard, we work there first. Once they can clearly say what they do and why it matters, decision-making becomes easier.

Q: You mentor a lot of first-time founders. What do you notice about them?
They’re usually closer to the answer than they think. But they overcomplicate things. I had one founder who built a full dashboard before talking to five real users. We paused everything and just focused on conversations. Within two weeks, the product direction changed completely—and for the better.

Q: What role did your early life play in shaping how you work now?
My mom ran a bookkeeping business, so I saw how small businesses operate day-to-day. Nothing was abstract. Every decision mattered. My dad, being a teacher, brought structure and clarity into things. I think I carry both of those influences—practicality and simplicity.

Q: What does taking a risk look like for you today?
It’s less dramatic than people think. It’s usually saying no to something that looks good on paper, or choosing to focus on one direction instead of five. Early in my career, I thought risk meant speed. Now I think it means choosing carefully and committing fully.

Q: How do you stay grounded while working in a fast-moving startup world?
Routine helps. I keep one day a week for deep work. No calls. Just thinking, writing, and reviewing patterns. I also spend time outdoors. Hiking in the Laurentians resets things. You remember that not everything is urgent.

Q: What do you hope people take from working with you?
That things can be simpler than they think. Most teams don’t need more tools. They need clearer thinking. If someone leaves a project feeling more focused and less overwhelmed, that’s a good outcome.