Kevin O'Leary
Past Dragon · Original panel · 'Mr. Wonderful'

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.

Photo: Philip Romano, CC BY-SA 4.0, via Wikimedia Commons

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

Trend TrunkAsked C$200K

Trend Trunk

Sean Snyder from Hamilton, ON, pitches his online clothing consignment store.

Season 8 · Ep 6C$200K / 20%
Holiday RejectsAsked C$30K

Holiday Rejects

Chris Cheng, Adil Hooda and Kyle Fitzgerald from Calgary, AB, hope for a Dragon investment in their ugly Christmas sweaters.

Season 8 · Ep 10C$30K / 30%
MappedInAsked C$150K

MappedIn

Hongwei Liu & Desmond Choi from Waterloo, ON, pitch their interactive indoor navigation system.

Season 7 · Ep 6C$150K / 10%
I For E MiniAsked C$50K

I For E Mini

This Mississauga, ON, teen hopes the Dragons find stock in his young business.

Season 6 · Ep 6C$50K / 50%
The Law OfficesAsked C$500K

The Law Offices

A Vineland, ON, woman is hoping to collect from the Dragons.

Season 6 · Ep 7C$500K / 33%
WoofstockAsked C$150K

Woofstock

Marlene Cook from Toronto, ON, pitches her festival for dogs.

Season 6 · Ep 12C$150K / 20%
Easy DaysiesAsked C$70K

Easy Daysies

A teacher from Maple Ridge, BC, attracts attention for her magnetic schedules.

Season 6 · Ep 17C$70K / 35%
Dig It HandwearAsked C$50K

Dig It Handwear

Wendy Johannson and Claudia Harvey from Toronto, ON, go digging for a Dragon investment on their gardening gloves.

Season 4 · Ep 8C$50K / 10%
Vantage WireAsked C$150K

Vantage Wire

Mark Chadwick and Neil Currie from Vancouver, BC, pitch their website that offers real time stock quotes.

Season 4 · Ep 10C$150K / 15%
KickSpikeAsked C$1M

KickSpike

Darrel and Colleen Bachman from Penticton, BC have invented a golf shoe which solves the problem of ruined greens due to spikes.

Season 3 · Ep 1C$1M / 10%
True North MortgageAsked C$250K

True North Mortgage

Dan Eisner from Calgary, AB pitches his chain of retail stores that sell mortgages.

Season 2 · Ep 6C$250K / 25%
Jobloft.comAsked C$200K

Jobloft.com

Chris Nguyen, Lee Liu, Sundeep Mokha and Andy Lai from Toronto, ON try to wow the Dragons with their job board website.

Season 1 · Ep 8C$200K / 15%

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.

The other Canadian dragons