Posted Monday April 20, 2015


David Chilton is a guy who is very comfortable in the spotlight – and equally comfortable behind closed doors in his modest Waterloo Region home. He’s the embodiment of his own brand – “The Wealthy Barber”, a self-published financial guide, which he pitched tirelessly until it became a smash-hit best-seller. But he’s also a man who spent the best part of several years home-schooling his kids. He’s most recently known as one of the five “Dragons” on CBC’s popular “Dragon’s Den”. But a few weeks ago, he announced that he is leaving the show after three years, giving up that spotlight so he can concentrate on his next big thing – still to be determined.

Chilton leaves “Dragon’s Den” with no regrets, either way. “It’s been a lot of fun,” he told Exchange, in an exclusive interview. But it’s time to go – partly because of the success he has had on the show. He has entered two dozen-plus partnerships with Dragon’s Den pitch-makers – and his approach to those partnerships is quite different from most of his fellow Dragons.

Chilton explains that most of the investors on the show have staff who carry out the due diligence needed once they have made an on-air deal. Not Chilton – he does that entire process, himself (which means he has completed at least 24 due diligence processes in three years), and then he remains involved in a very hands-on way. “I do all my own due diligence,” he says. Once the season is recorded – that happens in the spring – “it takes me about four months.”

This is not because he is obsessive about control, he says. “I enjoy doing it, and it led to better decisions. But I have to admit, it’s a lot of work.” Once the deal is done, with due diligence completed, the project has really just begun. “I work with the entrepreneurs.”

A good example of this is “The Heft” – an auxiliary handle for a snow shovel. Not only did Chilton partner with the inventor; he did the due diligence, he worked with the company, he forged a connection with Home Hardware, and then he appeared in the Home Hardware commercial for the project – which has been so successful that the supplier is struggling to keep up with demand!

Chilton gives full credit to the inventor – who, he says, “has other inventions, as well. He’s a sharp guy.” But the inventor had “no experience in how to get things to market.”

That’s what Chilton brought to the partnership – that, some investment cash, and a home-town connection with Home Hardware. “We traded the exclusive [right to sell] in return for their putting together the commercial.”

He says his biggest success to date, arising from the TV show, has been Steeped Tea – Chilton and fellow Dragon Jim Treliving each invested $125,000 for a 10 per cent apiece ownership of the business. The company has grown by a factor of 10 in slightly more than two years since they invested. “That one’s been a home run,” says Chilton. But he is happy about all his investments: “there’s not single one I wouldn’t do over again.”

Chilton’s very personal, hands-on approach to his investments made it obvious to him, early on, that Dragon’s Den was going to be a limited engagement. “There is no way you could keep up my approach and do the show for ten years.”

Exchange interviewed Chilton on the second floor of a Kitchener gas station building; to enter you have to cross a Tim Horton’s drive-through roadway. Inside, you find Chilton’s office – filled with an eclectic mix of books, athletic equipment, plaques and awards, and a large boardroom table – as well as the offices of the two women who created the huge cookbook and food product business, “Looneyspoons”, and offices for a number of other businesses.

Looneyspoons is the creation of sisters Janet and Greta Podleski; in their early days, they had sought Chilton’s help, believing his success with the Wealthy Barber books would add some expertise to their early efforts to market their recipe books. “I said no for a year… it was my mother who convinced me to get involved. So I said yes.”

He’s no longer involved directly in the Looneyspoons business – but Greta is now his long-term life partner; they’ve been together since 1998.

David Chilton is not your typical Waterloo Region entrepreneur. He’s not a high-tech guy , although “I’ve gotten more and more involved in tech over the years.”

His initial success came from capturing a good idea – “The Wealthy Barber” – and then focusing all his energies on promoting it and accepting every speaking engagement that came his way. Canadian sales total two million.

One of the tougher things about his three-year television stint was the sheer quantity of meetings that his new partnerships engendered. Time once spent on speaking gigs was reallocated to business meetings. “It used to be 90 per cent speaking to 10 per cent meetings; now it’s 60 per cent speaking to 40 per cent meetings, because of Dragon’s Den deals. The time part of it is crazy.”

He says, with conviction, that everything that developed from being a Dragon, “has played out very well. It was never a matter of not enjoying it- it’s a matter of how much time I had to dedicate to it.”

There is one common element in Chilton’s success across the spectrum of his enterprises – his quick sense of humour. He’s a master of self-deprecating humour. Readers, conference attenders, television viewers love it.

To discover this aspect to his ebullient character, you don’t have to look further than his own website. There, you will learn he’s a Laurier grad (economics, 1985), and that he won the award for the highest mark in the country on the Canadian Securities Course. But his bio adds, (and this is pure Chilton): “Cheating was never proven but widely suspected.”

Concerning his Looneyspoons involvement, Chilton says, after five years, “they didn’t need me… I gave them my shares - their fourth book (“The Looneyspoons Collection”) did really well.” Chilton frankly admits that his Looneyspoons’ experience was much more helpful to him in his role as a Dragon. “The Wealthy Barber hasn’t helped me that much,” he says, but the more diverse challenges of the cookbook and food product business “has been invaluable to me. I’ve drawn on my involvement with Janet and Greta ten times more.”

When you start calculating the sums of money Chilton has invested as a Dragon – let alone his other enterprises – it becomes clear that while he may not be a barber, he’s certainly wealthy.

It doesn’t actually show – his home west of Waterloo is modest (he once suffered a break-in, but the thieves took almost nothing, because the expensive furnishings they expected simply weren’t there). He doesn’t like to accumulate possessions. “I’m still in the same little house… I’ll never move. I love it out there.”

He adds, “I’m not a ‘stuff’ guy. I don’t like stuff. I don’t get any joy out of it.”

But he is financially comfortable. He attributes this partly to taking his own “wealthy barber” advice – “investing has been a large part of it,” he says, but then the self-deprecation kicks in, and he adds, “I’ve had a lot of luck…. and I’ve picked the right partners.”

Some of those partnerships are with his fellow Dragons – current dragons Jim Treliving and Michael Wekerle (now a major investor in projects here in Waterloo), and former members of the cast. Chilton says he continues to be in contact with cast members who left the show before he did. “Bruce [Croxon] and I are very good friends,” he says, also mentioning Kevin O’Leary.

It’s hard to imagine the energetic Chilton taking it easy, but he insists that the pace of his life may ease, a bit. “There’s a difference between age 31 and age 51,” he says. “Red-eye flights when you’re 51…” his voice tails off at the unpleasant recent memories. In the past three years, he says, he has spent over 200 nights at the Royal York hotel, in Toronto. He credits his nearest and dearest with tremendous tolerance of his nomadic life. “Everybody in my personal life has ben amazingly cooperative,” he says.

Again, there’s a bit of self-mockery in his assessment, because this is also the man who took time to home-school his children, Courtney and Scott. It seemed to have worked – as young adults, both are entrepreneurs, running their own successful businesses. Chilton is a proud parent. Referring to Courtney, he stresses that “she has asked me for no help.” His kids “definitely have the entrepreneurial gene.”

Chilton does have some hobbies – he reads, he plays some golf, he follows sports (he’s a fan of all Detroit teams), and he spends time with friends. “I still hang around with a lot of my high school friends,” he says. One of those friends is Drayton Entertainment’s Alex Mustakas: “his energy is ridiculous.” You can imagine some other friend saying the same about Dave Chilton.

Chilton continues to be devoted to his kids – while they are independent businesspeople, their offices are in the suite of rooms atop the gas station, near their Dad’s – and he adds, “I see my Mom and Dad most days when I am home.”

But while that kind of leisure time is part of his current operational plan, David Chilton the investor and entrepreneur is not done yet. He’s left Dragon’s Den to open up time to “do a couple of big things…. something else significant.”

He told Exchange, “I’m giving a lot of thought regarding what’s next. I’d like to write, but not necessarily about finance.” And he’s determined that his next big thing will involve less big travel.

He’s firmly rooted in Waterloo Region, and wants to spend ever more time here. “There’s a real spirit of cooperation here. You’re able to call people up and get a meeting with them. They’re always going to sit down with you and give you some time.”

The conversation takes an unexpected turn near the end of the energetic interview. “You know,” says Chilton. “All of this started with me writing for Exchange magazine.” He was a contributor to this magazine in its early days and that, he says, “really changed my life, as dramatic as that sounds. That very much led directly to ‘The Wealthy Barber.’ It all started with Exchange magazine. And we still enjoy it, every month.”

Straight from the Dragon’s mouth!

No one can predict how long it will take for people to stop identifying Dave Chilton as a Dragon. But in some ways, that day can’t come soon enough. Chilton says that he is approached with pitches “non-stop”, everywhere, all the time, “sometimes 15 in a day.” He’s had his exit from a parking lot blocked by a would-be partner; he’s been pitched, a lot, in his least favourite places – airport departure lounges from which there is no escape. He recalls a man who asked, “Dave, would you like to invest in my company before it goes bankrupt?” That’s not going to be one of David Chilton’s next “big things”.

But whatever the next big thing is – it’s going to be worth a story. And nobody will tell it better than Dave Chilton.

Read the full issue(s)

Exchange Spring 2015 Home Edition Exchange Magazine May 2015