Calvin Ho

I hate talking about myself. I’d rather chew glass than post a personal reflection, so this was difficult to do. If you look at my posting history on LinkedIn, you will mostly see company announcements and reposts. I do not enjoy being on stage or speaking in front of large audiences and would much prefer staying comfortably anonymous.

My background is in geology and geography. I would rather be out in nature licking rocks than grabbing drinks with clients downtown. Sales would not have ranked high on my list of dream jobs. But you don’t get to choose what needs to be done when you are chasing an idea.

For over seven years, I worked mostly in direct sales and marketing while building Greenline, a company I cofounded to improve compliance and inventory accuracy for cannabis retailers. That work brought me the success and financial security I have today. Still, I often ask myself:

Why the fuck did I do that to myself?

I think it is because I loved the idea of a new and exciting cannabis industry more than I hated being seen. The thought that I could play a part in something big and help a lot of people succeed in a market that used to be illegal was incredibly appealing.

Also, I was a spiteful 20 year old idiot who believed I could do anything.

That kind of naïve confidence can sometimes work out if you are stubborn enough to follow through. I am currently 31, having sold Greenline and moved into a mostly indulgent lifestyle that revolves around making art and spending time with friends before their lives eventually get consumed by new parenting responsibilities.

Underestimating how hard something will be and starting anyway is often better than knowing exactly what you are signing up for and freezing with indecision.

When my cofounder and I set out to build a system that could handle cannabis inventory and process sales, it seemed simple. It was not. I have never been so wrong in my life.

What I thought would involve tracking price, weight, and the occasional tax quickly ballooned into a massive product roadmap that took years to build. Every province had its own maze of tax rules, security quirks, and reporting demands. It’s like trying to build a plane while it was falling from the sky. On top of that, customer needs kept evolving, shaped by evolving cannabis rules that changed every few months or were left deliberately vague.

If you prefer clean priorities and tidy systems, this kind of project would feel like a nightmare. And in the process of navigating this mess, I’ve learned some important things:

1. Knowing who to listen to
2. Learning how to prioritize
3. Having grace for failure, not inaction

Each deserve to be talked about in detail separately, and none can work as well independently of the others. If I’ve learned anything, it’s that progress doesn’t come from having all the answers, it comes from acting anyway.