The obstacle is the way.
Everything I build starts from one belief: my work should serve a greater good and help people get better in the direction they choose. These three missed. Each taught me something I still use.
2014
The Google Billboard
I wanted to bring Google Fiber to Canada, so lower-income homes, and every Canadian, would have another choice for internet. But my résumé was one of thousands. So I rented a billboard across the street from Google’s Kitchener office. It worked: an interview, then an offer. But the job was in Utah, and a few months earlier I’d moved 150 km to be near family. So I said no after investing $5,000, and put a dream to rest.
The lesson: know your non-negotiables before you chase an opportunity, not after it says yes.
Since then: every opportunity gets tested against my longer-term goals and the life I want for myself.
2022
Learnyone
I set out to build an “Uber for the mind”: a platform where people could sell their soft skills and experience as mentors in the gig economy. But it only worked if employers saw it as a need-to-have. So before building anything, I invested $200 in a survey ad in the newsletter of Canada’s HR professional body. Hundreds of HR professionals clicked. But not one finished the survey. If I couldn’t get them through a survey, I’d never get them to hear my pitch. So I walked away instead of investing $100,000 in the build. That $200 saved me $100,000.
The lesson: clicks aren’t commitment. Prove buyers will act before you build.
Since then: every idea is red-teamed and reviewed from three angles (how users fail, how the build fails, how the strategy fails) before I invest significant resources.
2025
Thumbp
I launched shampoo, conditioner and body wash that teach kids how much product to use. A successful US hygiene entrepreneur mentored me, so I adapted his model for Canada. But his model ran on aligned influencers, and Canada didn’t have enough of them. So I went back to rebuild the marketing plan. But while I did, costs rose 13%. So I shut it down, $5,500 in.
The lesson: a growth model is only as big as its niche, and I imported one without testing whether Canada could carry it.
Since then: I size the market before I choose a growth model, not after.
