Select Page

It’s 10 a.m. on a wintery Wednesday and I am standing, backstage, in the Dragons’ Den studios at the CBC’s towering Toronto broadcast centre. A camera intrudes into my personal space and an associate producer is prodding me with questions: Am I ready? Am I worried? What am I feeling? I’m trying not to take the bait, delivering instead cheesy sound bytes that I hope will suit their highlight reel. I am sweating slightly, as much because I’m wearing 50 pounds of goalie gear as because I’m about to go toe-to-toe with five of Canada’s most celebrated investors and entrepreneurs.

After the wind-up all morning, including hair and makeup (I’m not sure how much good this does with a mask on), now the pressure is on. The floor staff are preparing to launch me through the cannon that leads me down a mysterious hallway and awkwardly down a flight of stairs into the bright lights of the studio. I’m slightly nervous. I think they’d prefer me to be more nervous.

In truth this is not unfamiliar to me, and not only because I’m an entrepreneur who has pitched professional investors successfully for millions of dollars over the years. Three years previously I had pitched the Dragons on a mobile dating app, Tingle, that surprisingly attracted the favour of Jim Treliving; however the pitch itself never made it to television. That time, I learned a great deal about the process of making the show, and about making my pitch something that would appeal to the Dragons, the show’s producers and, most importantly, the show’s viewers.

That first effort I had resisted producers’ efforts to create a skit or other visual demonstration of our dating app, fearing that it trivialized our otherwise serious approach to reforming the online dating world. I instead delivered a pitch similar to those I’ve delivered to Silicon Valley venture capitalists over the years: I casually introduced our effort, held out some data and showed off the app on a giant-screen television to oohs and aahs from the Dragons. All of this was very successful in conveying to the Dragons that we were a top-notch team building something bound for success. But it didn’t make for compelling TV for the average person.

So for our second go-around I put that pretentious, maintain-your-professionalism approach in my back pocket and pitched the producers on staging a hockey game. Hey, it’s Canada! And my business partner Bret Hedican happened to have won a Stanley Cup during a 17-year career in the NHL. And four-fifths of the staff of our company are hockey players, building a tool called RosterBot, for sports teams. So a little shinny made sense and was a dialogue we thought the viewing audience would connect with. We structured the demonstration to illustrate how RosterBot works—filling an empty slot on one of the teams, finding a spare goalie, etc.

Was I too proud to don all that gear and get a little sweaty flopping around in the studio? Not this time. I even acceded to the producers’ demand that I strip myself of all that gear during the pitch (without a break for wardrobe/hair/makeup!). In short, we were willing to make it more fun, even at the risk of looking a little bit silly.

This slideshow requires JavaScript.

In addition, we leveraged the opportunity in every way conceivable to get our brand across—we gave the Dragons RosterBot jerseys, we wore them ourselves—and we matched those jerseys to the colours of the show.

We also slow-played all the great news about our company, revealing a little bit at a time in the hope that we would be underestimated, and then clobbering those doubts with each revelation. This is a far cry from the way you would pitch a VC, and goes against every entrepreneur’s instinct. But we were there to serve a narrative, and that narrative needed to entertain the audience.

We also offered a more or less “take it or leave it” deal, which is rare on Dragons’ Den; we chose this because we had been valued by professional investors who’d already committed north of $1 million to our company. This came to be the source of much on-screen (and off-screen) consternation for the Dragons. This strategy may not ultimately secure you a deal with the Dragons (and hasn’t for us so far). Then again, if pitching on television is your only fundraising avenue, you have other problems to attend to.

Although I never once nailed my introductory elevator pitch in rehearsal, I belted through it when the pressure was on.  While the producers and crew do everything to wind you up and increase your nervousness, my suggestion is to embrace the anxiety rather than fight it.

After all, it makes for great television. Isn’t that why you’re pitching on a sound stage in the first place?  Here’s the video:

This article originally appeared in Profit Magazine.