David and I worked together for several years. We actually shared a tiny desk together for over a year (oh, startup life!). I can’t believe we still speak, actually.  He is the first person to introduce me to the idea of user experience. Since working together, David has founded his own startup.


What is BlackSquare?

BlackSquare is a slightly different kind of tech startup. Rather than dealing with fluffy bits and bytes, we dabble in the wine industry. Which means we drink less Gin in the office than Wine.

We run Alberta’s largest monthly wine club (WineCollective.ca), a premium flash sale wine portal (Tannic.ca) and a turnkey direct to consumer wine platform for anyone that sells wine (Blackboxx).

What is your background and experience?

I used to be dedicated to sport (started with Speed Skating, and transitioned to Cycling), which gave me an early opportunity to travel the world. During this time I balanced sport with working with computers. I used to do tech support, sell computers, and design/code/write on the Internets. I had my first “blog” in 1995 and thought usenet was pretty neat.

Since then I’ve created and worked at various startups, ad agencies, and ran an online magazine for ten years. I started as a designer, transitioning to a developer, and came full circle finding my passion in user experience and product design. I’m constantly playing with new concepts, and experimenting with technology.

I’m one of those people that always questions why something was built a certain way and imagine on how it could be better. I get frustrated when I approach a building with two doors, and the first one I try is locked! Why do you have two doors? That sort of stuff drives me nuts.

You were a consultant for a long time, did starting your own start up evolve from that, or is it something completely different?

The first time I took up consulting life was rough. I recall one year making $6000, and barely having enough to eat. Then again the last stint I did as a consultant, life was gravy. The only problem with consulting is that it never ends, and I always have an itch to work on products versus projects.

A big drive to working on my own products has come from the fact that I want to have the maximum amount of impact come from my efforts. Most jobs and even some consulting gigs restrain me.

How much time did you put into the experience people have when ordering through WineCollective?

A fair bit, but to be honest the website itself is pretty simple. We have set out to remove the choice when joining (we have five packages). Pick a price point and style, done. Wine starts showing up at your home or office every month – along with in depth tasting notes teaching you about them.

We taste hundreds of wines a month looking to find the best on the market (of which Alberta has an incredible amount of rotating skus). Our goal is to eliminate the dice roll of trying new wines, while pushing you into trying something you might not normally choose on your own.

We only showcase wine that we think are awesome.

Do you get to drink wine every day?


How do you decide what wines will be delivered next?

It’s a mix between seasonality, quality and availability. For example we feature a sparkling wine every December and generally feature heavier reds during winter and brighter whites in summer.

What is your favourite part of founding your own company?

True creativity. Having to make decisions and figure out solutions without any kind of road map is incredibly challenging yet oddly fun.

I used to be excited by spinning out ideas, and now it has lost its luster. Ideas are a dime a dozen, the hard part is actually doing it. It’s the execution that is addictive.

To go a bit deeper I think the largest reward to running my own company is that I’m learning every day. I hope this never changes.

What do you wish you knew before you started?

From my first start up I learned how important it is to have motivated and driven people by your side. I also learned that these people come and go – that’s life.

This time around, I wish I knew how to clone myself. Did I mention we’re hiring?

What’s next for BlackSquare?

We’re expanding world wide, and currently working on expansion to Australia and Asia. I’m excited that we’re disrupting the wine industry, and pushing it into the modern world. We’re growing WineCollective and Tannic, but our main goal is growing Blackboxx as a new global standard for direct to consumer wine sales.

I want to revolutionize how people buy and learn about wine.


If you want to keep up with David, you can follow him on Twitter.