4 min readSep 24, 2020


Dave Cheung, CTO and Co-Founder of Rafflebox Technologies Inc.

Interview with Dave Cheung, CTO and CO-Founder, Rafflebox

Rafflebox is an online fundraising platform, based in Calgary, Canada, which allows non-profits and charities to run and manage online raffles and 50/50 fundraisers.

Why and how did you get involved with Rafflebox? How do you know the other members?

I met Simon Cusack through a mutual friend, Sufyan Lateef. Sufyan had heard that Simon and his friends had this great idea which was Rafflebox and they needed some help on the technical side of things. I came to a pub in downtown Calgary and met Matthew Broussard who pitched the idea and showed me the slide deck. I thought it was a great idea and absolutely LOVED the branding.

I had originally thought doing an online 50/50 would be a great idea but at the time it was illegal. The rules were changing and Matt and Simon were talking closely with the provincial bodies. I was sold and totally on-board. Later, along with Jamie Archibald, who had built an early prototype, we met again.

On a napkin, we sketched the new draft version of Rafflebox. I remember feeling very excited and eager to help bring that vision to life. Since then, our awesome team, which keeps getting bigger, has worked together to build the version of Rafflebox that you see today and it keeps getting better!

Are there any stories that stand out to you involving Rafflebox?

There’s been plenty! With our first live raffle, we were notified of each ticket sale. Everyone was glued to their phones as each new sale came in. It was addictive and exciting as each new sale came through!

One of our biggest earlier raffles was with Seaside FM, a non-profit radio station in Nova Scotia. They were struggling to keep operating financially. With their big following and presence we were able to raise close to $130,000, half of which went to the station! The raffle helped the station to keep their operations going. How cool is that!?

On top of that, the winner was able to finally buy a car she was hoping to purchase but previously couldn’t afford. The added plus with Rafflebox is that the money given to the winner in Canada is all tax free which equates to a substantial amount of money. The amount of money won can be a life changing amount.

Apart from that, we’ve been running a weekly 50/50 for Fire Departments across Nova Scotia in a communal pot. All sales are tracked back to the referred fire station and they get to keep the proceeds raised on behalf of their stations’ name. The pots keep growing weekly with the last one at over $178,000. The money collected using Rafflebox allows these fire departments to stay operational and helps them provide their amazing and essential public service for all Nova Scotians.

The list of success stories just keeps growing. It definitely brings us joy when we are impacting lives in a positive way. It’s extremely gratifying when you create something from nothing and people, REAL people, start using and trusting the platform. This tells us that we’ve probably done something right.

What is the most satisfying part of the process for you?

I think for me it’s two-fold. The most satisfying parts are being part of something that is innovative. It’s really fun being creative, thinking of new features that help benefit, engage and ultimately allow non-profits to raise more money. It’s rewarding being able to innovate by digitizing something that has been traditionally around for years. Allowing people to fundraise online alleviates a lot of extra work.

Secondly, it’s very fulfilling work to help out non-profits to raise funds and reach funders in innovative ways they otherwise wouldn’t necessarily achieve on their own. Rafflebox is doing good in the world by providing non-profits with funds they dearly need.

With COVID and how things are currently, we’ve been glad that we are able to help groups that would otherwise not be able to fundraise in times like these.

A lot of non-profits rely on casino nights, or working with in person fundraising events such as bottle drives, food orders or a traditional raffle / 5050. With those life-lines cut as a result of COVID and social distancing, groups are moving online. We’re very grateful that we’re able to provide deserving non-profits and charities with a platform that will still allow them to do the fundraising they need to keep going.

Have you ever won anything?

Unfortunately for me, it won’t ever be anything that’s posted on Rafflebox as we have an internal policy that nobody on the team can enter the draws. I’ve won small things here and there, maybe some free gift cards or small prizes at Christmas parties but nothing ever very big, at least that I can remember at the moment.

Contact Rafflebox

If you’re a non-profit or a charity looking to run an online 50/50 or raffle please visit us at www.rafflebox.ca for more information. Happy fundraising!




𝙔𝙤𝙪𝙧 𝙥𝙖𝙧𝙩𝙣𝙚𝙧 𝙤𝙛 𝙘𝙝𝙤𝙞𝙘𝙚 𝙛𝙤𝙧 𝙤𝙣𝙡𝙞𝙣𝙚 𝙖𝙣𝙙 𝙞𝙣-𝙥𝙚𝙧𝙨𝙤𝙣 𝙧𝙖𝙛𝙛𝙡𝙚𝙨.