Dragon's Den: Wealthy Barber David Chilton Joins Popular TV Show

Aaron Broverman

Filed under: Entrepreneurship, Television

"Honestly, I owe my RRSP to The Wealthy Barber," confided Christine Liber, the publicist representing CBC who's currently leading me and a few other journalists through the bowels of the CBC Studios and onto the set of Canada's highest-rated entertainment show -- Dragon's Den. (Sept. 19 @ 8:00 p.m./8:30 p.m. NT on CBC)

Sure, Liber's a publicist and right now it's her job to promote David Chilton -- the den's newest dragon -- but that's probably how many Canadians feel who read his seminal financial planning book.

Released in 1989, The Wealthy Barber follows three people in their late 20s as they receive financial advice from Roy, the title character, and must carry out what he proscribes for each of them. Each visit presents a different financial challenge and a different solution from Roy, such as saving 10% of all you earn and investing it for long-term growth. A veritable financial bible, the book has sold over 2 million copies across North America, solidifying Chilton as Canada's own personal finance legend.

With the exception of the release of the book's sequel -- The Wealthy Barber Returns,-- in 2011, Chilton has remained largely absent from the public eye. Instead he lays low, preferring to home school his kids and take on various speaking gigs around the country. Now, he's back, but in the last place anyone would expect this unassuming personal finance guru to show up -- taking Robert Herjavec's vacant spot among The Dragons on the show's seventh season.

Suddenly, Chilton finds himself sparring among established captains of industry for a piece of an emerging business. Most of whom, like Kevin O'Leary and Jim Treliving, have spent their lives building, selling and investing in all sorts of businesses. These are the alpha predators of the business world and when a humble writer from Sarnia, Ontario (who's more known for dispensing advice than writing cheques) sits next to them, one has to wonder what stops him from being eaten alive? It's something Chilton wondered himself.

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"I don't know," says Chilton. "The whole thing was kind of a whirlwind two weeks. They called and said there was an opportunity and an opening and I had mixed reaction initially because I'm very low-key, I really am. I live a very low-key lifestyle and I don't like a tremendous amount of attention -- it comes to you sometimes when you do all the interviews -- but in general, it's not something I've sought out.

The dragons hear over 120 pitches over the course of a 19-day shoot and on the very first day it seemed Chilton had bitten off more than he could chew. "It's very competitive. I was a little surprised. On our second pitch of the whole taping, we got in a heated argument and were fighting over a deal," says Chilton. "It was honestly 20 minutes into the first day and I'm going, 'Holy smokes!' I was a little caught off guard by that."

A veteran of the panel, Kevin O'Leary has been the most outspoken dragon from the very beginning and he says Chilton better be prepared for more of the same if he wants to hang with the big dogs of investing.

"[Chilton] brings attitude, there's no question about it. He's a bit of a kumbaya-er and just loves everybody, so I have to beat him with a stick occasionally. We compete and I crush him like the cockroach he is."

O'Leary may be right. Chilton does love everybody. "I tend to use a fair amount of humour," says Chilton. "I like a lot of the low-tech businesses. So, a lot of the old-fashioned type things that can't be necessarily digitized and aren't too fancy or too dramatic, but still have a great upside."

Whether that makes him a kumbaya-er or not, remains to be seen. "I'm also feeling my way a little bit," Chilton continues. "It's fairly early in the whole process and I think it will take me a while to find my niche, where I fit in and how I juxtapose with the others."

Nobody knows what Chilton is going through better than Bruce Croxon. The Lavalife co-founder was in the same spot just a year ago when he replaced W. Brett Wilson -- the man who holds the record for the most deals on any version of Dragon's Den across the globe.

"I didn't smother [Chilton] with advice. I just said, 'Relax, have fun,' but he's a pretty relaxed kind of guy. He's very smart and very well spoken, so he caught on to it very quickly," says Croxon. "I did tell him, 'Look, you know when this thing goes to air your inbox is going to be a lot fuller. I don't care how busy you were before, you're going to be a lot more busy now, so get ready for that. Roll up your sleeves and prepare because you are going to get a lot of people asking your opinion on things. Whereas, before the show, they might not have cared so much."

Like Croxon, David Chilton won't exactly love all the attention that's in store for him. Still, something drew him into the fray despite himself.

"I love the show," he says. I watch the show regularly. My family loves the show, so you're going to be a little more drawn to the opportunity because of that, but what really clinched it for me was I came down to the rehearsal/audition and I was so into it, I couldn't believe it. I was a little nervous when I first went out. But, by the second pitch, I'm arguing, I'm trying to get the deal, and I thought, I want to do this. You know what else? It's fun and it's something different in my life. For 30 years, I've been involved in publishing and speaking -- I've enjoyed all of it, don't get me wrong -- but it's nice, at age 50 now, to have a new challenge."

One of the biggest challenges was figuring out where he stood among his competitors on the panel. After all, Jim Treliving is Canada's franchise king, owning both Mr. Lube and Boston Pizza. O'Leary never lets people forget he sold his software company to Mattel for US $3.8 billion. Arlene Dickinson has a laundry list of connections as the CEO and owner of Venture Communications and Bruce Croxon has his niche in the tech industry, thanks to starting Canada's largest dating site. With such huge players at his side, what could a mild-mannered writer possibly bring to the table? Maybe he was just a "kumbaya-er."

"When I first got here, during the first block of tapings, that was one of the reservations I had with a few of the pitches. I was competing with Jim and he brought a lot of contacts. I was very honest and I said, 'I don't think I bring the same number of contacts to this,'" says Chilton.

"But, then when I went home and started working on the due diligence for the five, six, seven deals I was involved in at that point, I was amazed at how many contacts I had. When you're around 30 years, and you're speaking as much as I've spoken, you've spoken for everybody: every major pharma-company, all the major retailers and all the major distributors. I started going, 'I know him, I can call them, I know her' and I've started making calls. The fact that The Wealthy Barber has got a good brand -- and Dragon's Den to boot -- opens a lot of doors to a lot of people. So, now I've become a little bit more aggressive. When people bring up contacts, I'm able to say, ' Wait a sec, I do know so-and-so.' So, I've come a long way."

The other dragons have started taking notice -- regarding Chilton as both a worthy adversary and a formidable partner, all rolled into one. He's also very different from his predecessor, Robert Herjavec, who left Dragons' Den at the end of last season with the following statement:

"'I have nothing but the most positive things to say about Dragons' Den -- it was a wonderful experience for me -- but it was time for me to move on. I believe life is about moving to the next challenge. As I always tell entrepreneurs, 'If you are not growing you are dying. It was time for me to grow.'"

"Robert came from a different space," says O'Leary, who remains his panel-mate on the U.S. version of the den -- Shark Tank. "He was very hi-tech, very technology oriented, and David is more broad in the way he invests and that's what I'm learning.

Everyone brings a different style and they have different niches in the kinds of deals that they invest in. So, once you get to know their style and their niche, you know where they're going to compete. You can almost tell which of the dragon's is going to be bidding and if you know that, and you don't want the price to get too crazy, sometimes it's better to partner with them.

This is what we didn't know about David until we saw a few deals and saw how he fit in the pecking order. Did he overpay? Did he underpay? That's what everyone waited to see and learn. I've figured it out. We're half-way through taping and I know what he's doing now. I know when I should partner with him and I know when I should compete against him."

It sounds like The Wealthy Barber is about to get a whole lot wealthier.

'Dragons' Den' premieres Wednesday, Sept. 19 @ 8:00 p.m./8:30 p.m. NT on CBC.