Carsify

Jan 2015 - Sep 2015 · 9 mos

Carsify was my first startup. The idea was simple: build an online marketplace for used cars. Think Carvana or Shift, but in Canada, and several years before those companies became household names.

I drove it into the ground. Pun intended.

The Idea

Buying a used car is a terrible experience. Dealerships are adversarial, private sales are sketchy, and nobody trusts the information they're given. I thought technology could fix this.

The vision was to create a platform where buyers could browse inventory, get transparent pricing, and have cars delivered to their door. No haggling, no pressure, no surprises.

What Went Wrong

The unit economics were brutal. Cars are expensive to acquire, expensive to recondition, and expensive to hold. Every day a car sat on our lot, we bled money.

We also underestimated how hard it is to build trust in a market where everyone assumes they're being scammed. Marketing costs were astronomical.

And honestly? I didn't know what I was doing. I was a recent grad with more ambition than skill. That's a recipe for expensive lessons.

What I Learned

Failure teaches you things success never could:

• Unit economics matter more than vision. If the math doesn't work at scale, nothing else matters.
• Capital intensity is a trap. Every dollar tied up in inventory is a dollar that can't be used to grow.
• Know your weaknesses. I was good at the product side, terrible at operations. I should have found a co-founder who complemented me.

Looking Back

Carsify failed, but I don't regret it. It gave me a visceral understanding of what it takes to build something from nothing. The sleepless nights, the constant problem-solving, the emotional rollercoaster.

It also made me a better investor. When founders pitch me now, I can smell the problems they haven't thought about yet. That instinct came from living through my own failures.

Sometimes the best education is the one that costs you the most.