
Kevin O'Leary Dragons’ Den Canada Deals
Investor and co-founder of SoftKey / The Learning Company
Kevin O'Leary made his fortune building the software company SoftKey (The Learning Company) before selling it. An original Dragon on the Canadian panel, he became known for his blunt, numbers-first style and later joined the U.S. show Shark Tank. He remains one of the most recognizable figures from the Den.
- 12
- on-air deals
- 3
- still trading
12 Canadian pitches have ended with Kevin O'Leary investing between season 1 and season 8. Fashion & Beauty is their most-backed category, with 4 deals. 4 were solo investments, the rest joint with other dragons. 3 of the businesses they backed are still trading.
Deals are attributed to a Dragon only where the on-air record names them. Dragons’ Den Canada does not publish the amount behind each deal, so no investment totals are shown.
What Kevin O'Leary invests in
All Kevin O'Leary deals
Asked C$200KTrend Trunk
Sean Snyder from Hamilton, ON, pitches his online clothing consignment store.
Asked C$30KHoliday Rejects
Chris Cheng, Adil Hooda and Kyle Fitzgerald from Calgary, AB, hope for a Dragon investment in their ugly Christmas sweaters.
Asked C$150KMappedIn
Hongwei Liu & Desmond Choi from Waterloo, ON, pitch their interactive indoor navigation system.
Asked C$50KI For E Mini
This Mississauga, ON, teen hopes the Dragons find stock in his young business.
Asked C$500KThe Law Offices
A Vineland, ON, woman is hoping to collect from the Dragons.
Asked C$150KWoofstock
Marlene Cook from Toronto, ON, pitches her festival for dogs.
Asked C$70KEasy Daysies
A teacher from Maple Ridge, BC, attracts attention for her magnetic schedules.
Asked C$50KDig It Handwear
Wendy Johannson and Claudia Harvey from Toronto, ON, go digging for a Dragon investment on their gardening gloves.
Asked C$150KVantage Wire
Mark Chadwick and Neil Currie from Vancouver, BC, pitch their website that offers real time stock quotes.
Asked C$1MKickSpike
Darrel and Colleen Bachman from Penticton, BC have invented a golf shoe which solves the problem of ruined greens due to spikes.
Asked C$250KTrue North Mortgage
Dan Eisner from Calgary, AB pitches his chain of retail stores that sell mortgages.
Asked C$200KJobloft.com
Chris Nguyen, Lee Liu, Sundeep Mokha and Andy Lai from Toronto, ON try to wow the Dragons with their job board website.
Kevin O'Leary on Dragons’ Den Canada: common questions
How many deals has Kevin O'Leary done on Dragons’ Den Canada?
12 on-air deals, across seasons 1 to 8. Deals are counted where the on-air record names the investing dragon.
What kind of businesses does Kevin O'Leary invest in?
Mostly fashion & beauty — 4 of their 12 deals.
Does Kevin O'Leary invest alone or with other dragons?
4 of their 12 deals were solo; the rest were joint investments.
Are the businesses Kevin O'Leary backed still running?
3 of the 12 are still trading. Each pitch page tracks whether the business is still selling.